Episodes

Rob: Welcome to this week’s episode of Startups for the Rest of Us. I’m your host, Rob Walling, in this Episode 536, I believe. I guess I should’ve checked that before I hit record. Thanks for joining me this week. I’m doing a Rob solo adventure. I want to talk through some things that 2020 taught me and hopefully, as you’re listening, it brings up some things that 2020 maybe taught you. Maybe we learned the same things or maybe you had different experiences.

As I was driving across the country, I just drove from Minneapolis all the way to the central coast of California with a car filled with instruments and bikes attached on the back and several pieces of luggage and an aerial rig, if you know what that is, and a dog. It was just me and the dog and all that stuff. I had a lot of time to think. It was four 8-hour days of driving.

Along the way, I was reflecting back. It was almost a mini-retreat for me. I was reflecting back on the year and thinking what are some lessons that I can take away both personally, professionally, and even higher level, just philosophically from what we all experienced in what I think will be, perhaps, one of the worst years on record for a lot of us for quite some time. That’s what I’m going to talk through today.

In true entrepreneurial form, these lessons are positive. I’m not going to belabor the terrible things that happened and then at the end, I have a little section that I’ve just titled Opportunities in 2021. I’m thinking about software entrepreneurs starting new SaaS apps and just trends that I think are going to continue to play out that will need more and better software over the next year or two or three as things panned out.

I have four things to cover today in addition to that Opportunities in 2021. The first thing I learned in 2020 is perspective that startup problems are one thing. That losing an employee, stagnating MRR, high churn, customer flaming you on Twitter really brings you down. It gives you anxiety. It can cause you lack of sleep chew through your mental cycles, but I learned that perspective in all of those things compared to massive wildfires in Australia and California, murder hornets, a global pandemic, massive racial injustice, and even storming the capitol which technically was 2021, put things into perspective for me.

In all honesty, I’ve had a personal reset now with my internal anxieties and concerns about my company, or other companies, or work, life, and professional progress, and just all these things that I think over time creep up on me personally. They start to make me question, and worry, and have concerns about, are we moving fast enough and what happens here, just all the things in your business that you think about. I’ve learned to hold those things just a little bit distant from me in the way that I’m concerned, I’m going to focus on them but I’m not going to let them be on my mind causing me stress 24 hours a day because compared to these other things that were happening in our world, they’re just not that important.

For me, 2020 was a reset of perspective and showed me that having a job where I could work from home and continue to provide for my family and none of us getting sick and on and on. The inconvenience was a rounding error compared to what so many people around our country and around our world have been dealing with. I’m thankful for that reset of perspective that I received over the past year.

The second thing I learned in 2020 is that we can make it through really scary and dangerous things and even when things felt almost hopeless and each of our individual experiences of the year was different. I have memories of gunshots and helicopters flying over our house because we live in Minneapolis, and there were protests, and fires, and all types of stuff that was happening around the time that George Floyd was killed.

Frankly, there’s trauma around that for me and my family. There’s trauma around having to worry about my parents whether they’re going to get COVID or whether we’re going to get COVID. Our friends, who got COVID, are they going to be okay. Our kids are feeling stressed about us. On and on, each of our experiences, I’m sure we have some share, but a lot of us have these individual memories or experiences. I’ll admit that even in those dark times, I remember thinking we’re going to make it through this. This is scary but we will press forward.

I’ve actually reflected back on something I said on this podcast back in either late March or early April of 2020. It was Episode 490 and I’m going to play that clip here right now. I was on the episode with Einar Vollsett and we were talking about things you should be thinking as a founder and as a business owner in this global pandemic as the early days of it unfold. I remember when I said this, I wondered if people would believe me if you as a listener would hear me and believe that I believed it because I did. There was a sense of calm and that was that sense of, we can make it through scary, hard, dangerous things. Let’s cut to that tape here.

Last point, point seven is just reminding you that we are going to make it through this. It feels terrible right now and it is terrible. The health crisis is not something that any of us could even imagine, but things will get better. We will figure this out. While it’s serious and tragic, we need to keep a level head. We need to kind of keep pushing things forward to take care of ourselves, our families, our communities. Again, it comes back to staying mentally healthy and not stressing so much about it, not thinking about it all the time. With little new information or no real new information, it doesn’t help to just think about something all the time. Worrying doesn’t solve anything. That’s something that Sherry and other psychologists have kind of drilled into me over the years. Worry with no new information, there’s no value to it.

While my advice to not worry without new information was easier said than done, I do hope that there was some value in me essentially trying to reassure us that we can make it through these hard things. In fact, we are and we continue to do so.

The third thing I learned in 2020 is that there is always opportunity. This is something I didn’t realize back in, let’s say, the 2001 dot-com bust and the recession that followed. I remember because I worked in tech. I was a web developer at the time and doing consulting and then also working for some startups. I felt like the world was ending. Unemployment shot through the roof, at least in the tech community and it was chaos. I was too early in the workforce to realize that A, this is cyclical, B, usually the best people are employed through the whole cycle, through the ups and the downs, and C, that there is always opportunity. In fact, there can be even added opportunity in big economic bust times. How many great companies came out of 2001 that were almost bootstrapped or just had tiny amounts of funding and then once the economic cycle comes back, these things take off like a rocket.

Similarly, in 2008, how many companies came out of that? In 2020, as the recession hit, what did we see just accelerating? We saw anything dealing with remote work. We saw anything dealing with podcasting, video conferencing. There’s a whole list of online event platforms. There’s a whole list of things that I’m sure you noticed increasing in demand and increasing in MRR. I certainly saw it across both the TinySeed companies and my own portfolio of angel companies. A couple of companies get hit real hard and a handful of companies, just up into the right, doubling month over month, a few months of just crazy growth.

In addition, we started raising TinySeed Fund 2. We were going to start raising it in March of 2020 and we had all the assets and everything ready to start pitching it and this happened. Everything just locked up. We ended up waiting one month or maybe two to start it. But things calmed down and in that ensuing, what has been not quite a year, I guess it’s eight or nine months, we have raised a substantial Fund 2 and are in the process of closing that now.

I’ve watched a handful of startups or even early-stage close angel rounds and start talking to venture capitalists about closing venture capital rounds. Funding was still flowing. There was an initial 1-2 months of uncertainty but after that, there was still opportunity. Even across, again, the TinySeed portfolio, as I look at the numbers, there was one month, six weeks of a pullback and then things kept moving forward. In addition to exits, we just heard from Josh from Baremetrics a couple of weeks ago, he’s still just a handful of months ago, amid arguably tumultuous times.

That ties into my fourth point that doing things in public creates opportunity. You couldn’t look at the pandemic happening and everyone starting to shelter in place and then suddenly build and launch Zoom, or build and launch Tuple, build and launch Squadcast or Castos. You had to be in the game doing something in order to hit it right at the right time and have a product out there that people could just adopt.

Is there luck involved in that? Of course, there was. These founders and others had obviously delivered products that people loved and had growth. They weren’t going up into the right but with the exponential growth that came in a lot of these tools, there was some luck that they were at the right place at the right time. They happened to choose an idea that in this case had such an outlier event as Nicholas Taleb calls it, a black swan event, that is just completely unpredictable. For them, they were in the right place at the right time. This is where that hard work, luck, and skill comes into play.

Did all these founders put in hard work? Absolutely. Did they have some skill and experience to get that product out and to be growing it? Absolutely. Was there luck involved perhaps in the fact that some of these were essentially doubling month over month? There was. But that’s the game. If you aren’t doing things in public, and if you aren’t working hard, and you are putting your skill to work, you’ll never get lucky. If you’re not in the game, no amount of luck will get you to that point of dramatic success. There’s an old quote from Thomas Jefferson that I like to paraphrase, the harder I work, the luckier I get. While I don’t think hard work directly correlates to it, I think there’s a lot of things that are involved. As I’ve been saying, hard work, luck, and skill I think all play a role, in this case, doing things in public continues to create opportunities for founders.

Those are a few things I learned in 2020. Obviously, there are more than that but I wanted to share this with you today. Maybe some of them resonated and I’d be interested to hear if you learned something. You can tweet me @robwalling or post in the comments for this episode which is 536.

Now, I wanted to throw out a few areas that I think opportunities exist in 2021. Frankly, I mean if you look at the TinySeed companies we’ve funded in the first two batches or I look at any of the companies that I see having success in the MicroConf community, or online, or in Indie Hackers, they’re in all types of niches. When you see a list of niches that are growing or industries that are taking off, there is an opportunity there. But there is an opportunity in a lot of places. There’s an opportunity in construction CRM software, like Builder Prime in our 2020 batch of TinySeed and in data for bio-pharma mergers and acquisitions like DealForma which is a batch two company, in online scheduling software, like there are […] SavvyCal which is a batch one company.

Some of these are horizontal. Some are vertical. There’s room to grow in a lot of places but some areas that I see growing over the next 3-5 years are these. Number one, I think there are going to be more freelance and more gig workers than there ever have been. I think part of that is due to the economy. I think part of that is due to people wanting remote work. Part of that is due to people seeing that perhaps working retail or working in a restaurant has been really impacted by COVID.

If there is another thing like this, another pandemic, or another thing that causes work to shut down, people want backup plans. Freelancing sites like Upwork and freelancing management software and ways to pay your freelancers like TransferWise are all things that I’m sure to have gotten just massive booms from this. Thinking about what do freelancers need, marketing, and having freelancers have remained customer-based is tough because they’re price sensitive and they churn and they go out of business because then they get a job. Take it for what it’s worth, but if you can build a business for freelancers, this is a really big market.

That’s why I like what when Dan and Ian are doing with dynamitejobs.com. If you haven’t been to that site in a while, I would check it out because they’re starting that two sets of marketplace but they have the advantage of already having basically both sides of the marketplace filled with their Dynamite Circle online community. I think they’re doing things in public and it’s going to create some opportunity here. I think they’re on their way to finding that innovation. It’s not reinventing something from scratch. It’s not making something completely novel that came out of their head. Let’s take this concept of an Upwork or a Fiverr and put a spin on it that we think is lacking in the market. Much like we did with Drip, where there are other ESPs out there but they don’t do this, and let’s do that better—Derrick Reimer SavvyCal, Ruben Gamez with Docsketch.

There are other e-signature apps out there but how can I put my unique spin on it? How can I get some proprietary traffic channels, and all that? Freelancers are one, obviously remote work. You’ve heard a ton about that. What software do people need for managing and dealing with remote work? They’re going to be more creative, full time and part-time, I’ve been asked in the past two months four times by two relatives and then some old friends from the city I used to live in, I think I want to learn to code, or learn to be a designer, or learn some skill that allows me to work from home on my laptop.

That’s not a surprise because if you were formally working in an accounting office or a legal office or you were going to school to get a degree in something that you were doubting if you’re going to get a job, and then suddenly the pandemic hits, and you realize, I can’t just push paper. I need to be in an office to do my job, or I can’t work at the restaurant like my backup plan. Learning these skills, I think there’s going to be more and more people doing it. What do they need? What opportunities are going to be there? Podcasting’s a big thing. You probably already knew this. You’ve seen the acquisition and the frothiness but it is mind-boggling to me that there continue to be new podcasting apps that are launched that do different things from podcast hosting like Castos to podcast editing productized service like Castos Productions to Squadcast which is the recording a podcast to Alitu. I interviewed the founder, Colin Gray, on this podcast maybe six weeks ago and that is in essence a podcast education but the software is easy podcast editing effectively in your web browser.

What other opportunities are there? I, frankly, could use help marketing our podcast. There are productized services that are doing all types of stuff to help podcasters get recognized, or have better visuals, or have better show notes, or have better editing. They’re out there and I think there continues to be an expansion of new podcasts, but there’s an opportunity to start your own. I know that podcast listening hours have probably gone down now. I think that is going to make a big comeback once everybody’s commuting again. I know not everyone will commute. Some people will stay remote. I still listen to a lot of podcasts. I force it into my day. That’s not going away especially as these cars get the direct podcast integrations, virtual events, online video streaming, maybe online audio streaming events once people are commuting again.

Look at Clubhouse, and isn’t that really what that is? It’s an online audio streaming event. It’s fascinating to think about. I never would have thought that that is the format that people would want. But think about what you’re doing when you’re listening to podcasts. I don’t actually watch a lot of online videos because I can’t background it very easily.

I do listen to a lot of audio—a lot of audiobooks, a lot of podcasts. I think online video and online audio events, that sky’s the limit there, and of course, then mixing that with in-person events as they come back is going to be a big deal. There’s software, there are services, there are all kinds of stuff that needs to be done there. Those are a few, perhaps, obvious areas that I think will be expanding right now and for the next several years. I always struggled with those kinds of niches, or verticals, or spaces because then I would go in and I would often try to create a solution in search of a problem for that audience.

That’s not necessarily the way that I think you should go about it but looking in those spaces and then trying to find problems in them is where I would go. That’s a big thing. I’ve announced a couple of times on MicroConf on Air, I don’t know if I’ve said it on this podcast, but I am working on my next book and it is in essence—it’s not a sequel to Start Small, Stay Small—but it is like the next steps. Start Small, Stay Small focused on these tiny little niche businesses, often with little competition, often having one or two marketing channels. They are really like step one and step two businesses if you remember my stairs step approach. The true lifestyle businesses, true businesses that, hey,  I want to make $10,000, $50,000 a month, just small businesses that will maybe never outgrow that niche.

This book I’m working on now is maybe that next step. If you look at my trajectory of building those small niche businesses and then levelling up to HitTail and then levelling up to a Drip which became a 7-figure app that we sold and obviously, where my life-changing money came from, that’s what this is about. It’s building that million-dollar, multi multi-million dollar SaaS app with our venture capital.

In the book right now, I’m in the section of looking for ideas and how to think about generating ideas for a startup and it doesn’t start with niches. It starts with several different approaches that I’ve seen and I’ve either done it or I’ve seen it in companies that again TinySeed, MicroConf, Startups for the Rest of Us, all these sources than one approach to finding your ideas, to find a problem and then try to build a software that solves that. I have five different ways to find problems.

If you start with what problems do freelancers, or remote work, or creatives, or podcasts, or online videos, what problems are in those spaces and then you can go through these five things of I’m going to scratch my own itch. That’s only if I am a freelancer or I am a remote worker and I have a problem. You can look for a problem at your day job. You can look for the problem of a spouse relative or colleague. You can have a poor customer experience yourself and want to fix that with code and with your app. You can find a problem online by looking at Facebook groups, core threads, private Slack groups, product support forums, and on and on.

Finding a problem is one way. It’s a great way to start. There are other ways. I’m going to run through a few of them here real quick because I have my book up so why not just talk through it a little bit. Translate an existing idea to a new niche. Think about how Ruben Gamez launched Bidsketch in 2009. There was a proposal software out there but he made a proposal software for designers. He niched it down, later he expanded and Bidsketch is still doing very well.

A company in TinySeed batch two called BuilderPrime did this with great success by building a CRM for the home improvement industry. CRM existed, but they really didn’t have it for home improvement contractors. Another way is to go into a large space with hated competitors. That’s what we did with Drip going against InfusionSoft. Xero did this against QuickBooks. Stripe did this against every payment gateway ever. I would say that’s probably more of a step three thing that I wouldn’t do as my first effort but it’s really a fascinating way to dive into it.

There are a few other ways. You can build on your audience or your reputation if you have one. Build on your network. Build a less expensive version of an expensive enterprise competitor. Enter a fast-growing ecosystem that’s like Josh Pigford did with Stripe Analytics, […] did this with WooThemes back in 2008. Of course, you can build on an existing product. This is what Craig Hewitt did with his seriously simple podcasting WordPress plugin. He then built Castos SaaS app on top of that. I realized that’s a lot of information coming at you once. That’s all from a chapter of my book. Once I figure out when that’s coming out, I’ll be sure to let you know.

If you want to be sure, by the way, to be notified or to hear about it, certainly listen to this podcast because I’ll talk about it as we get closer but robwalling.com—sign up for my email list and I will definitely be mentioning it there as we get closer to it. I knew that writing the book would be an absolutely not fun, painful process and it has been that plus some. In fact, with the holidays, and then January, and then TinySeed applications, state of independence SaaS report, I have not touched it in almost two months and I actually feel bad about that. But there’s definitely perhaps a gap in the market for that type of book that I’m writing. I do find that it is easy to get.

There’s a lot of topics to cover. It’s easy to have a lot of content because I’ve been blogging about it for 15 years, talking about it on the show for more than a decade at this point. There’s plenty of words to be written and I will try to keep it succinct as I always do try to make the best use of your time.

Speaking of succinct, I think I should wrap up this episode. I like to do these solo adventures every couple of months, two or three months, and this one’s probably overdue at this point. I actually have an entire other solo episode outlined that I may record here in the next month or so.

If you liked this episode, let me know. I’m @robwalling on Twitter. You can always hit me up directly questions@startupsfortherestofus.com or post a comment on this episode. It’s great to have you here. Thanks again for joining me this week and I’ll be back in your earbuds again next Tuesday morning.

Rob: You are experiencing the next episode of Startups for the Rest of Us. Today, I talked with co-host emeritus Mike Taber. He co-hosted this show with me for the first 448 episodes, and now he comes on periodically to update us on his progress with his own startup, Bluetick.io.

Mike hasn’t been on the show for almost seven months, because he’s had some things cooking in the background that he wasn’t able to talk about. The good news is, Mike’s back on the show today, and he and I have a conversation about what he’s been up to over the past seven months, and things he’s thinking about with his startup, Bluetick, as well as a reveal of what has been going on.

He isn’t able to reveal every detail, but it’s enough that gives you an idea of why he probably wasn’t able to talk about it six, seven, eight months ago. It’s exciting stuff and I’m hopeful for Mike as he moves forward.

If you’re newer to the show and you haven’t heard of Mike before, again, he co-hosted the show with me for the first big chunk of episodes, and now he’s doubling down on bluetick.io, which is his SaaS startup. It’s Cold & Warm Email Followup Software: Personal outreach at scale for your follow-up emails.

With that, let’s dive into our conversation. Mike Taber, thanks for coming back on the show.

Mike: Thanks for having me. How are you doing today?

Rob: I’m doing okay. I’m out here in California. I don’t think I’ve mentioned it on the show, actually, but we decided to take advantage of distance learning for the kids, and since our kids have been in school, this is the first time during a school year we could essentially travel, or live somewhere else temporarily.

As most folks know, I’m located in Minneapolis, which is just a lovely city. We’ve been here for years, and decided to stay. We could have moved away a couple of years ago, but decided to stay long-term. The winters are a bit of a barrier, and we normally do a bit of traveling to warmer climates just for three or four days each month during the winter, now three or four months in a row.

This year, kids are remote, and are on Chromebooks and iPads. We were like, why don’t we just go to the Central Coast of California? We used to have an apartment out here. It was a big could-we-do-that? Pretty soon it was like, yeah, find a more short-term rental and we’re going to spend a couple of months out here in the warmer weather. Although I got up this morning and it was, I don’t know, 39 degrees when I woke up, but the highs are 55–60. It’s like California winter versus the East Coast.

Mike: I will say I would love to get in on this distance learning, so shoot me your address or email, and I will send my kids so we can get this taken care of.

Rob: Exactly, it’s how it’s going on. So your kids are at home too, huh?

Mike: Yeah.

Rob: How’s that been like?

Mike: I’ve become the resident math tutor because apparently, either the kids don’t listen, they don’t take notes, they don’t pay attention, or the teacher isn’t explaining it well. I don’t know what the exact problem is, but needless to say they have a lot of problems with math. I’m not saying that they don’t have a lot of problems with just getting the rest of their homework done, but it’s just brutal. Some of the stuff that they’re doing, my wife’s like, nope that’s all you.

Rob: So you’re the math tutor. I think for us the challenge has not been with specific subjects because they have plenty of face-to-face Zoom calls, Google Meets, whatever. It’s that our kids would wander off onto YouTube and are suddenly backgrounding the teacher, which is exactly what I would be doing if I was in the class. I would want the class recorded so I could watch it back at one point at 8X speed, and that’s at least two of my kids wants stuff faster. Their brain can process it so fast. So for them, it’s wandering.

At home, I have a router where per device just can’t go to gaming websites, block YouTube or whatever. I can just do it all on my phone because I have the eero router. But we are now at a new location and I can’t do that here because I don’t have access to the router, so it’s been a struggle.

Mike: In theory I could do that, too, but a lot of their teachers post stuff on YouTube. They’ll be like, go watch this YouTube video, and the kids are like, I can’t do my homework because you blocked YouTube. I’m like, Dear God you’ve got to be kidding me.

Rob: Here’s how I worked around that: I blocked it on all their devices, and then I have one iPad that is my old one—it’s an iPad Mini—and I have YouTube open on it. When they need YouTube, they come to me and I hand it to them, and then I set a timer or have them sit in the office, watch the video, and then leave. I’ve had them locked down. I’m not saying it’s foolproof or whatever. It’s a pain to get interrupted when they need to, but these are the struggles.

Mike: I’m just going to send my kids to you. We’ve agreed on that, right?

Rob: Yeah, do that. Exactly. Put them on a plane out to California.

Mike: I’m just going to put them in an envelope and just FedEx them.

Rob: Mail them out? Jeez. It’s been 30-something episodes. It was episode 501, the last episode that you were on, updating folks, and that was back in June of last year, so it’s been about seven months. A lot’s going on for you. I mentioned a couple of times in some of the intros for other episodes in the meantime that since you had things going on behind the scenes that basically you couldn’t or didn’t want to talk about on the podcast, and it was potentially exciting things for you and Bluetick.

This is one of the struggles with podcasts. You have to weigh how transparent and open you’re going to be about it, but at this point you’re in a place where we can at least talk a little more about it. Everything’s not finalized so we’re not going to disclose all the details, but there’s been a potential partnership brewing over the past—what has it been—eight months? Do you want to talk people through what that looks like and where it’s at?

Mike: Yeah. It was probably about eight or nine months ago when I was talking to a fellow entrepreneur that I know. He has a couple of different businesses, and the one he wanted to collaborate with me on was basically a CRM that he has for field sales reps. Essentially, what it does is they use either an Android or an IOS app that they put on a phone, and then there’s also a web-based SaaS component to it, and it’s used by them to track their activities. It integrates directly into the CRM system, so that their managers can get the reports.

Things just like talking to their phone with their notes, so they go to a customer, talk into it, and then it just transcribes stuff for them. It tracks the phone calls that they make and receive, and also does email tracking. That’s where Bluetick comes in a little bit because of my background, knowledge, and experience with synchronizing emails. I was able to help out quite a bit with that because they were having some issues. I won’t say very early on because the business has been around for a while, but early on when I started helping them out.

I got a lot of that stuff straightened out. The intent initially was we’ll have you come in and work for a couple of months to see how things work together. Meanwhile, he’s got a couple of other businesses that he owns, and trying to offload those and sell them. Unfortunately, COVID hit, and it really threw a wrench into the entire thing.

Things have stretched on substantially longer than either one of us thought that they ever would. The whole plan was we’ll do this for 3–5 months or something like that, and now it’s double that. We’re looking at 9 or 10 months at this point.

For me, I’ve been helping out with the technical side of things. They’ve got a sales rep, a support person, and a development team that I’ve been working with. I’m basically managing that development team, the support person, and pretty much all of their infrastructure as well, and then also trying to look at ways that Bluetick can plug directly into that.

We’re at the point now where he’s sold the other businesses and is working essentially on this one, more or less full-time. At this point it’s like, let’s actually work together for the 3–4 months that we were going to before, see how things go, and then try and figure out a way to make this work long-term, or is it something that after that 3–4 months, one or the other of us or both decide, this just isn’t going to work and we don’t want to do it, let’s part ways.

Rob: Got it. So it’s a piece of software that is, in essence, complementary to Bluetick. Is that right?

Mike: Yes.

Rob: You can say as much or as little as you know or are comfortable with, but are you talking about a potential merging of the two into a single entity, or is it more like this is going to be a really tight partnership?

Mike: That’s an open question. Neither one of us really knows the answer. It could be one, it could be the other, it could be both. I don’t know, and neither does he. We have to work through things for the next couple of months and see how things play out, and see if there’s a really good fit internally, like directly inside of the app.

Is it going to be a merger, or is it going to be both applications merged together, or is it going to be to keep them separate and we just do a really tight integration? There are implications around all of that based on who owns what, and how the profits are distributed between those two applications, the technical costs and all the other stuff that goes with it. There’s a lot of stuff that’s kind of up in the air right now.

The plan is to just work through things for the next couple of months, see how they work out. Probably the most interesting thing that we started talking about was a way to sell Bluetick to their existing customer base as essentially a done-for-you service.

We’ve already mentally tagged somebody that we know of that is familiar with both products, and would be a good fit to essentially manage those email campaigns on behalf of the sales reps, because the sales reps who are using that CRM are probably not the greatest at putting together email campaigns, or managing them, or anything like that. It would be easier for us to offer that as a service. One, it gets more people using Bluetick, and two, it gets more revenue in the door for Bluetick, but it also gets more revenue in the door for the CRM as well. It gets tighter integration with their existing customer base, and really is more of an upsell to the existing customer base.

I think there are a lot of opportunities and potential there, but we really have to just buckle down and work through those things. This stuff has really started to come together as of a couple of weeks ago, but again, it’s going to be several months before we really know how things are all going to shake out.

Rob: It sounds like everything’s on the table and you’re both on the same page with that, which is probably good. And it sounds like there’s a lot of potential options, which is probably both good and bad.

When I think about selling an entire company—if I was just going to sell it for cash to a buyer—there are enough things to work out there. The moment is like we have two companies and maybe we can partner, maybe we merge them. If we merge, what type of equity does each person get? There’s a lot to be figured out there, so I think that it’s super interesting and exciting.

Obviously, I know more details than you’re talking about on the show and I’ve said it a couple of times, but I’m excited for this as a potential. If it winds up that in essence you do have a co-founder/business partner or whatever term you want to say, I think that could serve you well in this space. I think you have the tech stuff dialed in, I think you’re building a solid product, but there’s always been a lot to do, and getting the marketing engine going has just been challenging with everything else that’s going on.

That’s where having two people working on something allows for just so much more bandwidth, especially if their skillsets are not the same. In this case, that’s true. He’s not a developer, the person you’re talking to. He has a completely different skill set than you, in a complementary way, much like Einar Vollset and myself with TinySeed. He’s got more of the sales, the finances, and working on spreadsheet type stuff, and I’m on the other end.

I’m curious. You’ve been working on stuff for a while now, like you said 8–10 months or somewhere in there, and then you’re talking about now working for another 3 months. What if you get to a point where either one of you or both is like, this just isn’t going to work? Do you feel like you’ve wasted that time, like it’s kind of a wasted, lost year? How are you thinking about that?

Mike: There’s definitely a part of me that wishes that everything had gone substantially faster. I think we’re all like that where we want things to move faster than they do, but I think the whole pandemic really threw a wrench into a lot of things and it just caused delays that neither one of us really had anticipated, expected, or could have accounted for in any way, shape, or form.

If it came to that point where one or both of us wanted to say, this just isn’t going to work out. Would it be disappointing? Yeah, absolutely. Is it still a possibility? Sure, it absolutely is. Would I probably feel like I wasted a lot of time? Yeah, I would. I’m sure that I would feel that way. At the same time, I know that I’ve done a lot of good things so far for that business, and he’s a friend so it’s not like it’s the end of the world. I left him in a good position with a lot of things, and honestly, I overhauled pretty much everything on their entire technical environment.

One of the team of developers that I managed, I think right now is about a dozen people. There’s a lot there. There’s been a lot going on, and it’s been a struggle to keep on top of everything just because there are so many moving parts, not just in that particular product with the two mobile apps, the web-app, all these back-end jobs, AWS Infrastructure, and then I’ve got all the stuff that I’m managing on my side with Bluetick, Azure Infrastructure, Google Audit, and all this other stuff.

It’s been tough and interesting, but let me answer your questions directly. It is a concern or fear that I have, but honestly, what else can I do about it? It’s not a lot I can do.

Rob: Right, it’s an opportunity that when it started to happen, you knew that it has a real potential upside. It has an asymmetric upside because if it works, it could be game-changing for you/Bluetick to partner up in this way. The downside, of course, is that you waste some time. Oftentimes, as entrepreneurs, that’s the calculus that we have to do; figure out is investing this time worth the potential upside? But again, if it works out, could this potentially turn into a business partnership that lasts 5 or 10 years? In that scale or frame of mind it’s like, if that happens, you’ll look back and say, that was a tough time but certainly worth the risk.

Mike: Right, and I can kind of see that now. If it were to move forward and everything were to work out as, I won’t say best case scenario but a reasonably good case scenario, I could definitely see that happening, working out really well. But you’re right. If it doesn’t work out, that sucks. I wouldn’t have called it a complete waste of time either, because I do feel like I’ve learned a lot along the way.

Rob: Yeah, you’ve learned a lot. And like you said, you did help him and his team out, and there’s something to be said for feeling okay about that, just feeling like you made the best decisions you could along the way.

Mike: I can’t think of anything where there’s some additional piece of information that I wish I’d known three months or six months ago. Even last year early on, had I known that the pandemic was going to hit and it was going to cause it to take a lot longer for him to sell his business and come over into this one, would it have changed things? I can’t say that I think it really would have too much. I don’t know. It’s hard to say right now, but I don’t know if it would have made that much of a difference.

Rob: This other software product, is it further along than Bluetick? Is it more revenue? I guess there’s a team working on it, so how could you describe where it’s at?

Mike: That’s hard to answer. It definitely has more customers, more revenue, and a lot more technical challenges because it’s never really been managed by anybody who had an understanding of technology.

The development team that has been working on it for years—we actually switched from one development team to another, and they were in that process when I first started working with them—are the type of people who would do exactly what they’re told but don’t necessarily think ahead.

They don’t have advanced architecture experience and modular programming—all that stuff that goes with it, you would expect from senior developers—it was just handed over the wall like, here you go, we need this done. There wasn’t a lot of consideration given to architectural concerns.

I cut around $25,000 a year off from their AWS bill so far, so I’ve saved them a huge amount of money over there. But if you think about it from that perspective, that number alone is just the savings. I still think there are ways to go with this just by rearchitecting things and changing how things are done, and I could definitely cut the AWS bill by even more.

You can use that as kind of a, I don’t want to say benchmark but a datapoint to say, there are probably ways to plug Bluetick in, and help grow that business as well. Like I said, the lot of the technology sprawls across the mobile apps, the website, integrated into other services, things like that. There’s a lot of upside to it, there’s a lot of potential, and it’s a matter of us dividing and conquering.

Rob: It sounds like it’s further along if you look at business metrics, but it has more technical debt than Bluetick, right?

Mike: Yeah. The technical debt piece, I plugged a tool into it called SonarCloud that just basically analyzes the source code, and that told me that there was about a year’s worth of technical debt associated with just various pieces.

Just by looking at the source code itself, there’s logic that is different between the mobile apps and the web app. It’s been a challenge to wrangle all the technological pieces of it and start fixing them. That’s been my world for the past six months or so, just trying to manage that stuff and get things on track.

I would say by and large, it’s been extremely successful because during that time frame, there was a point where I was told that the number of incoming support requests per day were bordering on 50–60. I’m not sure how much sock I put in that actual number because I just didn’t see a lot of them, but at this point it’s down to a couple a day. It’s really not that hard to keep up with them, but early on you breathe on some things wrong and it fell over. It was just really that bad.

Things are so much better now. I won’t say it’s hands-off because we basically went through a redesign process where we’re completely rebuilding the mobile apps from the ground up, just because structurally, everything was just a total disaster. We’ve done that. we’re just wrapping that up now. We’ll be at a point where maybe within the next couple of days, we could start putting it in front of customers, and having them take a look at it directly. It’s really just a rip and replace of the old version. It does exactly the same things. It just looks better and it functions a lot better.

Rob: That sounds like a challenge. I was going to say, like a fun challenge, but actually that doesn’t sound fun. That just sounds like a technical challenge, to be all factual about it. During this time, were you working full-time, or you had some time to continue working on Bluetick on the side?

Mike: I would probably put it more along the lines of, if you have a full-time job and that was it, and you were trying to build a product on the side, Bluetick was my side business throughout most of this.

Rob: I think we’re all familiar with that. We don’t have to go all the way back to seven months because I actually remember early on, you were pretty engulfed by everything that was going on. You came into the technical situation and were trying to get a lot of stuff fixed. I know that Bluetick was humming along, but you weren’t investing a ton of time. But more recently, or in the past few months, you mentioned to me that you’re considering doing an AppSumo deal.

Mike: Yeah, I’ve been talking to them for a couple of months now. I’m still torn on that, to be perfectly honest. I haven’t pulled the trigger, I haven’t decided to move forward with it. I’ve had conversations with several people who have done AppSumo deals in the past, and one person I talked to said, think of it as a freemium offering. You are using it as a channel to get people in and talk to them, learn about your products, be able to scale things up. You will get a cash injection from it, but don’t necessarily expect or think that you are going to get a lot of them to convert into monthly-paying customers.

AppSumo’s prime offering to most of their customers is they want a lifetime deal. You pay X dollars and you never have to pay for it again, which really puts something like Bluetick in a tough spot because if there are hard costs associated with storage, processing, or anything like that, then it really makes it difficult to offer that kind of thing and come out ahead.

I’ve really struggled with how to not just position that but also to even put it into the AppSumo ecosystem for those reasons. Let’s say that I have 3–5 GB worth of disk space storage on a per-customer basis. If I get a couple of thousand people in really quickly, that could be a hefty chunk of change depending on how much data each of them has. I have no way of knowing what that’s going to be in advance.

Rob: That’s tough. I guess one thing to think about is, I think the majority of AppSumo users will either not redeem the coupon, or will redeem it and then not actually use it. There’s a good chunk that won’t actually consume that much disk space or that much cost. But yeah, you do have to think about this. It is a bit of a gamble.

To give folks an idea, if you’re listening to this, I did have an AppSumo deal way back in the day. I think it was in 2012 with HitTail, and I netted somewhere around $11,000–$12,000. I did another one later that netted about the same.

Ruben Gamez came on this podcast to talk about Docsketch and a bunch of stuff he was doing, and he mentioned on the air that he made about $30,000–$35,000 from his AppSumo deal. I think that’s so much more than mine because: (a) the AppSumo list is so much larger now nine years later, and (b) I think they’ve gotten better at doing the deals.

They pretty much do lifetime-only now. They really encourage lifetime-only because that’s what their AppSumo people like. And I think they know how to price them better and all that. And perhaps Docsketch is just a better fit for the AppSumo audience as well. The things that I pulled out of Ruben and my own experiences.

AppSumo deals are good for your app if it’s relatively low-support, there’s not a ton of onboarding, it’s not complicated—I imagine doing an AppSumo deal with Drip and that would be a nightmare because it’s just a complicated app; there’s a lot to it. Low per-user cost, as you were saying. For Drip, we had cost to send emails, so for the next infinity years, you can have a list of up to 1000 people sending emails. That would have been a cost against us.

And then, usually some type of virality. If your app just has even the modicum of virality, which Drip did have, where you had that ‘powered by’ widget. You had Powered by Drip on the widget, and with Docsketch as an example, Ruben has the Powered by Docsketch. Every document that gets sent out is some type of virality.

Those are three factors that I keep in mind, and have heard from others who were thinking about this. So I hear you. The hard costing is a gamble. If you took $20,000 or $30,000 away from the deal, and then 60%–70% of people didn’t really use it, do the numbers work out for doing this?

Mike: I’ve run them in a couple of different ways, and initially the answer was no. I’ve looked at what things I could change to try and make it work, and there are things that I could do that I believe would address some of those problems, but those are technical things that I would need to change in the product in order to make that happen, to make it work in a way that would be cost-effective for me.

I haven’t done them yet, but I have evaluated them a little bit and said, if I make these changes over here and I produce this cost over there, what does that ultimately mean? I do think there is a way to make it work, I just haven’t mapped out every single little detail. I do have it on my list of things to do to go through that, and I’m probably a quarter of the way through all the list of things that I need to look at and evaluate.

I don’t know how long it would take to do those things—that’s part of what I’m working through—but it is something that I would expect to know within the next couple of weeks. Like what does that actually look like? What would it take if I were to pull the trigger tomorrow? When could those things be done? Would they be done in time? Obviously, they would have to be done in time because otherwise, I would be going bankrupt from it.

Rob: Yeah, and they book way out right now. I think they’re 3–4 months out when you book a deal, so it gives you time to do it. Does Bluetick have virality? Does it have a Powered by Bluetick email footer or something?

Mike: That’s the thing, it really doesn’t. There is stuff that I could put in there, and that would be one of those technical considerations. I could put in the footer of the emails that are being sent out, Powered by Bluetick. I know that they probably would not be terribly happy about that, but if it said that and the AppSumo customers were not paying on a monthly basis, I could justify doing an AppSumo deal where I’m not going to get any additional revenue from them going forward if that were in there and there was that viral component. But there just isn’t right now.

That’s something I struggle with. I agree with you. It needs to be a marketing channel of some kind. If you can’t leverage it into the future with those users, does it really help you? I struggle to say yes.

Rob: I think it will help with short-term cash infusion, and it can help with customer development for sure. You might discover that if you get 1000–2000 new users, you will start seeing usage patterns and perhaps even there’s an industry vertical that uses it and gets a ton of value out of it—mortgage brokers, or realtors, or just something where you’re like wow, this really is the use case for it. So there could be learnings there.

I think the virality thing, maybe talk to AppSumo to find out what they think. I wouldn’t be opposed to adding that Powered by Bluetick link. If that’s a dealbreaker—which no no no, it feels like it would be for me—then if I can do this and put it in what’s essentially a free plan or a lifetime plan, but upgrading to paid removes it.

We had that with Drip with the $49 plan, had a Powered by Drip link, and on the $99 plan there was a toggle to turn that off. That was just part of it. If people wanted it turned off, that’s fine. You just need to upgrade.

Again, I wouldn’t be opposed to doing that or think that it would upset people. AppSumo, the folks that you’re talking to there will know whether that’s a good idea to do or not.

Mike: I haven’t talked to them about that specific piece of it. It’s just something that I came up with as an idea, so it’s something that I still need to talk to them about.

The other thing that I’ve actually considered is when somebody told me, think of them as freemium users. It did occur to me, if I’m already evaluating the things that I would need to do in order to essentially create a freemium version of Bluetick, what would it look like on a grand scale? Could I actually put something like that together and then offer it directly, not necessarily as part of AppSumo, but just directly from the website? Could there be a freemium plan for Bluetick that does have those viral components that would essentially help with marketing?

It crossed my mind. I haven’t really dug into that a little bit, but it is something I’m keeping in mind as I go through and try to make my list of things that I think need to change in order to make an AppSumo deal viable.

Rob: I’m iffy on a free plan with Bluetick. We’d probably need more discussion if we were to actually get into it, but I feel like one of the advantages of doing it with AppSumo is you instantly get exposure to their whatever it is million person list, or 750,000 person list. It’s worth it at that point. But if you’re going to just set up a free plan and let people trickle in, I’m not sure personally that it’s worth the effort there.

Mike: No. I mean doing it in addition to, like here’s an AppSumo deal and then there’s also this freemium version of it. So that’s entry level, then there’s the AppSumo deal, and then there are the regular paid plans. Kind of in-between, that’s more what I mean.

Rob: Yeah, I don’t know. Scaling I think is an issue I would be concerned about, but I guess we already have to be concerned about that with the AppSumo deal, right?

Mike: Yup.

Rob: Anyway, that’s an interesting thought. That’s cool. Next time we chat then, I’d love to hear your thought process about whether you decided to do it or not. I think it’s one of those things that obviously, there’s potential risk. The risk really is that longer-term it costs you some money, or that scaling is just too hard, that it essentially crashes your servers or really brings your service down, which would be a bummer.

I don’t feel like the risk is that you’re chewing through all of your customer base or anything like that. I think AppSumo really does have reach that could be helpful to you and not only in getting people in there, but I remember when I did the HitTail AppSumo deal that a bunch of people signed up through the deal, and then a bunch of people signed up not through the deal.

They just signed up as normal users, and I don’t know why that happened, but people just heard about it. It’s like when AppSumo stomps its feet, their ripples just go far and wide because there’s a million people on that list, and then it just gets talked about. Suddenly, your name is just being bandied about in Facebook groups, in Slack, or whatever. I would expect it to actually drive non-AppSumo signups to Bluetick. That’s the other advantage.

If I were in your shoes personally, I would lean towards doing it because, again, it comes back to asymmetric risk. If it doesn’t work, well that sucks, but if it works, there’s a potential to really expand your MRR in a pretty quick fashion, as well as derive some quick cash that you can use to grow the business.

Mike: The other thing I still have to look at in terms of the numbers is let’s say that I’ve got a bunch of users in from AppSumo and they were lifetime deal users. I’m going to have to eat whatever the cost is for those users. The question is what actually would that cost be moving forward? How many additional customers would I need to bring in as a result of the AppSumo stomp and that ripple effect? How many additional customers could potentially come in that would just completely nullify whatever those costs happen to be? Is the net effect of that positive or negative? My suspicion is that it would be positive and I would lean towards doing it myself, but I still need to sit down and run some of those numbers a little bit more.

Rob: Yeah, given that your price plans are $50 a month, $150 a month, and $500 a month. As an entrepreneur, I am a little bit of a gambler, and I like those kinds of risks. I say that if I were in your shoes, I would do it. I would need to be comfortable with scaling, both technical and support.

That’s the other thing. Recently, folks who do these deals, if they don’t already have at least one full-time support rep in addition to themselves, they often staff up just a little bit because there’s a two or three week period where there are hundreds and hundreds of requests coming in, and you have to be everywhere at once. That would be the other thing. You have to justify that expense as well.

Mike: A couple of different people suggested to me that I hire a support rep, even if it’s only for a couple of weeks or in the initial launch of the AppSumo deal to answer questions and emails, help people through it as needed, and help serve as a filter so that I’m not doing absolutely everything myself.

Rob: On another topic, are we resuming the Startups for the Rest of Us drinking game where whenever we mention the Google Security Audit, everyone takes a shot? Why are you doing this again, Mike? Why would you do another audit?

Mike: I have to, it’s basically an annual audit.

Rob: It’s been a year already. It’s crazy. You have another audit coming up. What do you want to catch people up on what that is or where it’s at?

Mike: I’ve said this before, and I wholeheartedly agree that it’s just completely applicable to this. I either want less corruption or more opportunity to participate. This whole thing is just an absolute, utter scam. It really is. I got an appraised quote yesterday. It was last night, like seven or eight o’clock at night. I just looked at it and like, that’s not going to happen.

Rob: So they did an audit for you last year. This gets people up. Since you tie into Google’s Gmail APIs, that you need the security audit. It was a long-running thing for a year, or a year-and-a-half on Startups for the Rest of Us, where you would come on and update, yeah this audit is a pain in the butt, it’s expensive, and blah-blah-blah.

Eventually, you decide to bite the bullet and do it. You had to negotiate it way down and you got it done. I remember the episode where we celebrated that it was done and all that, and now a year later, you essentially need to do it again and have it updated. They give you a quote and it’s more than the initial audit last year, but you already have everything in place, right? You already have (I’m assuming) a bunch of documents and a bunch of other stuff you need, and that’s all done. How can they possibly justify raising it? Shouldn’t it be maintenance? You know, half the cost? That’s what I would think.

Mike: That’s the thing. That’s what they told me when I first had it done. They were like, if you have this done, in a year if you come back and you use us, then it should essentially be reduced. You won’t have to pay as much the next time because you’ll have already gone through this process once. Of course, fast-forward one year and I ask them for a price quote and they do everything and send me the price quote, and it’s almost double what I paid initially.

I’m like, wait a second. No, hold on. I sent them an email this morning saying basically, this is what I was told, this is what you guys said to me. Essentially, what you’re saying now is that literally everything that we did, we’re just going to throw it all out because it’s all completely worthless, and it can’t be used at all. In addition to that, the cost is double because the work that needs to be done at this point is double what the initial work was, including all that we initially did was worthless. Something’s not adding up here, you need to explain this.

I feel there’s a lot of room for them to come back down to reality, so we’ll see what they say. I’m getting quotes from three different companies, so I’m not too worried about it, but it is something that kept me up at night and made me get up early this morning.

I know that for a fact because when I woke up at four o’clock this morning, it was the first thing on my mind. I’m like, man this sucks, this has already impacted my sleep. I know that I can do something about it, I know that we’re going to be able to figure something else out, but it’s just a pain.

Rob: It’s been a long-running pain. It’s a bummer it comes “so soon.” It just feels like we were just talking about it, but I suppose a year has passed since that. No other updates at this point on, right? You’ll negotiate, you’ll find another vendor, and then you’ll just do it again. You know what to expect this time because you’ve already been through it. There shouldn’t be too many surprises.

Mike: I do talk to other people who have to go through it, so it’s not like I have zero visibility or information about the things that are upcoming, that need to be taken care of. I already have an expectation in my head of like, I need to go do this before we actually get started with the audit.

Right now, I’m just getting the price quotes, but on the side, I’m also looking at those things and saying I need to get this done, I need to get that done. Otherwise, they’ll just come up and say, that’s a fine and you’ll need to fix that before we’ll approve it, so I’m going to have to do it anyway.

Rob: To be continued in our next conversation. Sir, it’s always great to have you on the show.

Mike: Thanks for having me, it’s good to be back.

Rob: It’s fun catching up with you. You and I have only caught up maybe one time. No, that’s not true because we’ve emailed and done some texts. But in terms of voice, we’ve only had one voice call since the last show. It’s good to get you on here and get dual purpose: for me to hear about the ins and outs of what’s going on, and also create an update for the long-running Startups for the Rest of Us fans. Thanks again for coming on. Are you active on Twitter these days?

Mike: A little bit here and there. I check in maybe once a week, or maybe once every other week or something like that. It depends on the week, but I don’t really have a whole lot of time for it. Honestly, I’m starting to come back out of my shell a little bit.

There was that one year period where I just did not touch Twitter at all, and then I started posting a little bit a couple of months ago. I’ve slowly been easing back into something social media but not a huge amount. I’m still not in consumption mode by any stretch of the imagination. I’m starting to slowly unfurl that.

Rob: And if folks want to keep up with us there, they can go to @singlefounder for you, and @robwalling for me. It’s great to have you back.

Mike: Thanks.

Rob: Thanks again to Mike for coming on the show. It’s always a pleasure having him on, and just easy conversation. He and I have had a lot of on and off conversations over the years, so I do enjoy the episodes when he’s able to make it on.

A couple of folks have asked me recently how they can maybe give something back to me or this podcast that’s been running for free for more than 10 years. Realistically, leaving a review or a five-star rating always helps. Also, just a tweet or something on LinkedIn about perhaps how this podcast has impacted you, or just a testimonial of, hey this is a great show and if you’re a founder, you should check it out. We are @startupspod on Twitter.

Thank you so much for joining me again this week, and I’ll be back in your earbuds again next Tuesday morning.

Rob: Thank you so much for joining me for another episode of Startups For The Rest Of Us. I’m really excited about this week. It’s episode 534. It’s a breaking-news episode where I talked with Josh Pigford, the founder of Baremetrics, about his recent sale of Baremetrics for $4,000,000 to Xenon Ventures. Even though the sale was about two months ago, Josh has not been doing podcasts or blogging. This is the first time that I know of that he has come out in public and made comments about the exit. I’m really happy and excited for Josh to see that his seven-year journey of building Baremetrics wound up with that kind of success for him.
I hope you really enjoy our conversation as we dive into the specifics of the purchase price—how much he walked away with, how he is basically getting away with paying almost zero taxes on the proceeds. We talk about what he bought after the exit, how it’s changed his life. Then we look back at the last few years because Josh was on the show back in 2015 and several both exciting and stressful things had happened to him in Baremetrics in the ensuing five years or so. We dig into each one of those.
Before we do that, I wanted to encourage you, if you haven’t gone to startupsfortherestofus.com and have gotten on our email list, there are a couple of reasons to do so. One, every week we send an email with expanded show notes. It’s almost like a detailed outline that is taken from the episodes by our assistant producer. If you go to the website, you’ll see a quick summary with links. But if you are on our email list, you get an email every week with a full-blown outline that includes time codes and just a really fleshed-out version of the episode in writing. That means you don’t have to go through the transcript. If you want to refer back to things, you can get it there.
In addition, if you do sign up to be on our email list, there are two episodes that have never been released on this feed. There’s Rob’s solo episode where I talked about the eight things you must know when launching your SaaS app. The other one is 10 things you should know as you grow or as you scale your SaaS app. I’ve got really positive reviews about both of those episodes. They also come with written guides. They’re like five-, six-pagepage PDF versions of the episodes in case you want to refer back to them or see it in writing. I’d encourage you to check it out, startupsfortherestofus.com, and enter your email.
With that, let’s dive into my conversation with Josh which, in all honesty, turned into a really good, steady-flowing, funny, entertaining conversation. I really think you’re going to enjoy this episode. Let’s dive-in.
Rob: Josh Pigford, thank you so much for coming back on the show.
Josh: Thank you for having me, Rob.
Rob: Your last appearance on Startups For The Rest Of Us was in 2015. It was episode 244. Where we talked about competition, transparency, and funding. We talked about how you had raised, I believe at that point, the full $800,000. Maybe it was only half-a-million at that point. But eventually, you raised a full $800,000 in funding. I asked on the show whether you regretted that at any point, and you said you really didn’t. That you didn’t regret the raise. That at some point, you regretted burning through it a little too fast. Does that ring a bell?
Josh: That’s accurate.
Rob: That’s usually what happens if you burn through it.
Josh: I wish I had not done that.
Rob: That’s the one thing. I am trying to imagine who’s listening to the show who hasn’t heard of Baremetrics. But Baremetrics, you started in 2013 and it was the first, essentially one-click subscription metrics for SaaS apps that worked on Stripe. You just one click, enter your Stripe account, and it gives this gorgeous dashboard of your MRR, LTV, your Churn, all this stuff.
There are certainly other apps that are out there doing it today, but it’s quite a success story in the early days. You and I actually talked about your pretty meteoric growth over the first couple of years. Again, you started in 2013, and we talked in 2015. Since then a ton has gone on.
I’m realizing, I should have had you back a couple of years ago. So many interesting things have happened to you and you’ve done so many interesting things with Baremetrics that there’s a lot of stories to tell here. But realistically 2 ½, 3 months ago, you wrote a blog post called I Sold Baremetrics and that was in November of 2020. In true Josh Pigford transparency, you walked through that there was no earn-out, that the sale price was $4 million, that you personally walked away with $3.7 million in cash. I believe you didn’t pay capital gains tax on that due to the qualified small business stock, is that right?
Josh: That’s correct.
Rob: Which is incredible. For people who don’t know, it’s called QSBS. That is mind blowing because normally you would pay 20% federal, I believe, or at least 18% federal. Then if you have any state tax, you would pay on that. You’re saving yourself between 20% and 30% of that number. What is QSBS for someone who hasn’t heard of it?
Josh: This is basically only really applicable in the US. But what the US government was trying to do was encourage people to hold on to stock in a business for longer periods of time They set up QSBS to say, after five years of holding on to the stock, you can cash out, and not pay any taxes on it—federal, state, et cetera. That requires the states to recognize it which is a classic Alabama fashion. Alabama does not recognize it. I actually end up paying 5% tax on mine which is still better than capital gains.
Rob: Thanks, Alabama.
Josh: That’s right. But otherwise, you pay no taxes on it. That’s cash in your bank.
Rob: Which is incredible.
Josh: It is. That’s one of these scenarios where when I formed Baremetrics as a C-corp that was not anything I had even remotely thought about. I didn’t even know it existed. I set it up as a C-corp because we were raising money at the time. I was like, okay, to do the whole shares-thing, C-corp is the natural entity for that. Otherwise, that would not exist for us.
Rob: If you’ve done an LLC, there’s no QSBS.
Josh: Right. It’s a different story. Honestly, I stumbled upon that by purely just luck.
Rob: You have to hold it longer than five years. The fact that some startups sell before five years and you did hold it for, in essence, about seven years, also opened you up to that. That made it possible. At a certain point, some of these tax benefits make it such that a sale is maybe feasible or not. The question I have is, would you have sold it if you had to pay 30% tax on that number because that’s a much smaller number?
Josh: Totally no, I would not. I remember in 2019, it’s probably April 2019, I had an offer for around $5 million. But it was an asset sale instead of a stock sale. After all that was said and done, nearly 50% of the purchase price would have gone away. I would not have done it then. It’s not worth it. It definitely is a make-or-break deal.
Rob: The thing is, I’ve heard people say, how do you calculate your number? Probably the number that you need to potentially live forever on, so to speak, to retire on. Knowing that people like you and I are never going to not do interesting things, not make things, we’re probably going to make money doing them as we get into later with your woodworking, your Laser Tweets, but just to have that safety of being like, I don’t have to work again.
There’s this rule called the 4% rule that economists studied. I think it was in the 80s and it’s been updated since then. They say, if you have enough cash in the bank, that you can live on 4% of that, then you can live for a 30-year retirement. They ran a bunch of scenarios and most of them worked and some of them don’t. If you sell right now, you put most of it in stocks, and then there’s a huge dip right away, it actually doesn’t work. There’s a timing of events.
Me, I want to be a little more concerned than that because these days, especially right now with stocks at historic highs, I don’t know if the 4% rule is as safe as it used to be. I don’t think it is, personally. But certainly, if you start notching down to a 3.5% rule, a 3% rule, you’d think about, oh, if I had $4,000,000 in the bank, 3% of that is $120,000 a year that you can draw. In essence, that’s your money. You don’t pay income tax on that. It’s already in your bank account, in essence. It’s not a $120,000 salary. It’s more like a $170,000 salary to pull a $20,000 out.
The idea there is a 3% rule. If you had $4,000,000 in the bank, you could potentially live for 30 plus years. In many of the scenarios, people actually had more money left at the end of the 30 years because of just the way the stock market has performed historically. All that said, a lot of people think, Oh, I need $10,000,000 to retire or $20,000,000 to retire. You probably don’t, assuming you’re decent with money, you invest well, you’re not crazy with going out, and buying a Lambo once you get the check. That leads me to my next question which is, did you buy anything in the past two or three months that maybe you’d been waiting most of your life to do? Did you make any crazy purchases?
Josh: The first thing we did was pit off our house. To your point about the 4% rule, that was a big part of our mortgage. It looks like a couple of thousand dollars a month. It’s like, okay, that instantly goes away. All of a sudden, your needs from a cash perspective drop pretty drastically. It’s like at that point, we have no debt. It’s like, okay well, we certainly can live off of the interest of $3.7 million.
Past that, I paid off the house and then bought a Tesla. That was it though. I went back and forth on the whole Tesla thing. We ended up getting a model X which was the most expensive Tesla which I was super happy with. But also, I’m not a big spender. I don’t care to buy really expensive things. I went back and forth on that one for quite a while. But I bit the bullet and I’m happy with it. Everybody loves it, too. That’s what it’s been.
Rob: Yeah, that’s what I found with some larger purchases. We both came from humble beginnings, I’ll say. My dad was an electrician. Mom didn’t work. We always had food, but definitely did not have money for any types of fancy stuff. I’ve always been pretty tight with money. As I started having some entrepreneurial success, we bought a bigger house. As you said, we had a house payment. It was $2,500. I remember being like, oh my gosh, that feels a lot.
Now, of course, it’s like, well, that’s not terrible. Not that big of a deal. After selling Drip, eventually upgrading, my cars were always used beaters that I drove for 10, 15 years. I had a salvage title Buick Rendezvous that I bought for $8,000 in cash from a gas station in Fresno, California. I drove that for 10 years while we were building Drip. It had the side-mirror taped on with duct tape. It just never bothered me. It was just a car.
Then after we moved to Minneapolis, I wanted an all-wheel-drive car with a remote start and heated seat. I’ve never had any of this stuff. I bought a Volvo which is when you hear it, it’s like, oh isn’t that like your grandpa’s car. But no, they’re actually crazy luxury, and they’re really nice cars. It was a big step. Frankly, Sherry pushed me to do it and encouraged me to do it. It was a good move so I hear you on that. Of course, I bought it used because I just couldn’t stand it.
Josh: We were the same way. It was like, I kept looking at like, should I get a used model X or something like that. Then it’s just like, no, we have nothing else. We’re just like, let’s spend tons of money on it. I was just like, let’s just buy it and be done with it.
Rob: Is there any other way you can think of selling Baremetrics and having these last few months to do really, truly what you want with it? Is it a dramatic shift? Do you feel your life has changed pretty dramatically?
Josh: I feel it has changed dramatically from a mental perspective. From a day-in and day-out, what am I doing? I still come up to my home office and do stuff. It’s not Baremetrics. I’m still doing things that probably most people would classify as work. What I don’t find myself doing is going home or leaving my office, and I’m still mentally chewing on whatever it is I’m working on. Whereas with Baremetrics, it goes to say, I would go to sleep worrying about something, maybe an employee had said, or maybe there’s an employee that seems like they’re unhappy so maybe I’ve had this gut feeling that they’re going to leave soon. These things that just occupy your brain space, that stuff pretty much went away overnight. I feel probably mentally freer than I had in the previous seven years.
Rob: I definitely know that feeling. It chews up a lot of mental cycles running a business.
Josh: After you do it for years, you don’t even realize how it’s become the baseline for you. That’s probably the biggest shift for me. It’s not chewing on stuff for days and days.
Rob: You have taken some time off social media, right? Or you had planned to?
Josh: Yeah. I take a little bit of time off. But I think pandemic stuff has made it. Social media can become, for me, some sort of like a social lifeline when it’s harder to see people in person as much.
Rob: It makes it tough. I’m curious, I’m going to ask you as someone who has gone through similar experiences of selling a company, leaving, and having the new owner perhaps make some decisions that I wouldn’t have made. With me, it was a Drip price increase with no grandfathering. That happened very quickly. I was not involved anymore. I sat and watched that debacle unfold. Over the past couple of months, I think that the new owner of Baremetrics has made decisions that you probably wouldn’t have made. I believe there are cancellations you have to call in. There’s stuff. They’re changing flows. How has that impacted you emotionally or in another way?
Josh: I don’t know that it has impacted me emotionally at all. It’s one of these things where, okay, if I have to have an opinion on this, my opinion is I would not have done that. We did not do that while I was running the company. I still would not do it. But I also know that there are different ways of doing things. It doesn’t bother me. Almost what bothers me more is in that particular case where the whole call-to-cancel thing while I’m not involved with Baremetrics. They still were keeping me informed like, well, here’s actually what went down. Everybody was piling on, and the reality was, there’s a lot more to that story than what probably seemed like on social media where everybody’s just piling on, which is always the case.
When somebody posts some angry thing on Twitter, the reality is, they’re not including everything. That was one of those cases where everybody’s piling on Baremetrics. I disagree with the call-to-cancel thing. But at the same time, there’s more to the story here. Baremetrics people just had to bite their tongue and let it pass.
Rob: I didn’t see you getting involved. You were just like, yeah, I’m not going to.
Josh: I didn’t at all because the only way that I said anything about it was I tweeted something about how I was going to write up some rant and then I just decided that I don’t care because that’s the reality. I have an opinion here, but it doesn’t matter.
Rob: That’s it. I hear founders say, I’m starting a new company, and I’m going to hire a CEO to run my old company. I’m going to run two companies at once. Why would I sell? It’s growing. It’s doing well. That’s one of those instances where I’m not saying you should sell or whatever, but there are moments where you are happy that you really are separate from the business, that you’re not, still an owner that a CEO is running. There really is a clean-cut between you and the company.
Josh: I had explored that, too. Let me hire a CEO and I’ll just sit back. But then the whole brain space thing, the whole mental breakdown—we talked about a few minutes ago—you don’t get the break from that. It’s still there because whoever’s running, runs it into the ground, that affects you.
Rob: Yeah. You’re under-diversified. You have literally millions of dollars in cash in this private company that you can’t get out and that’s tough. There’s a lot of risks there. A little bit joke-y but truly but did you buy any crypto with your mad-stacks of cash?
Josh: What we did with the money is we got a financial planner. Planner is probably the wrong word. I meant this financial planning.
Rob: Advisor?
Josh: Yeah. They’re managing our money for us. We basically just put it all with them. They’re handling buying the appropriate stocks and bonds, moving things over at the correct times, and all that stuff. In the same way that I pay a CPA to handle my taxes because I hate taxes and don’t want to try to become an expert on it. It’s the same with the life financial stuff where I can’t simply really wrap my head around it so that I don’t screw it up. I’m going to let somebody else do it.
Rob: Personal finance and investing have been a hobby of mine, a sick twisted hobby, much like entrepreneurship for years. I still manage my own money but I do think there’s a case to be made for getting outside help, getting experts as long as you find someone you can trust. As long as they’re being fairly compensated but there are no hidden fees because that’s something that happens in that space.
Josh: That’s crucial. I remember the first financial advisors that we talked to, I really got a sleazy feeling about him. I would not feel comfortable here and we found someone with whom I didn’t get that vibe with. I think that’s crucial, finding somebody that you feel okay with.
Rob: I want to roll the story back until late 2016. At a point where you almost ran out of money. Baremetrics almost ran out of money. You blogged about this later in March of 2017. How we went from weeks of cash left in the bank to profitable in eight months. The beauty, Josh, you were telling me offline before we started this. It’s so easy to interview you because all you have to do is go back and look at your blog posts and you just tell this extremely open story of what’s going on. You can almost just step from the crisis.
You write a blog about things that are really hard or really amazing wins. Those are the things that are interesting to talk about on the podcast. Almost running out of money and then trying to sell the company, and then selling it—these are all basically bronzed for us in these blog posts that will live on.
Talk to me about this decision in late 2016. By that time you had raised your funding, and I believe you were through it. You burned it. You’re running out of money. What was your thought process there? What was the story? That had been quite stressful. The first is how painful it was for you to sit here and think, I’ve built this amazing company for three years. We’re the envy of a lot of SaaS founders because you’ve been telling your story publicly and then, wow, I might miss payroll next week.
Josh: In 2015, we were on this traditional VC trajectory of okay, we need to get to a million MRR. That’s the next goal. We had raised $500,000. I was coming to the end of that. I was like, okay, we got to raise some more money. We raised $300,000. That was the end of 2015.
As 2016 progressed, we did not have the growth. It’s just a classic startup story of like, you keep raising money, and then you’re not hitting the growth that you thought you would. You’d just start burning through all your cash. Mid to late 2016, we had, in fact, started running out of cash. The financial details of things tend to bore me. I’m in the big picture. Let’s just build a product and see what happens. That’s fun to me, the building things. Managing things and spreadsheets is not fun for me.
That had gotten out of hand for me. I had not paid attention to burn rates stuff as I should have. All of a sudden, I realized, okay, we’ve just got a few weeks of cash left. We got to make some big changes here. I had already gone through the second round where we raised $300,000 more. I was like, man, I can’t do another. Let me go ask for more money from people.
It was either ask for money from people or let’s see if there’s a scenario where we can get profitable and not lay people off. The way that we did that was, everybody on the team took a 15% pay cut. I took a 30% pay cut. From a Silicon Valley perspective, our salaries were not astronomical or anything to begin with. By the end of 2016, we were able to change the graph so that we did not run out of money.
Rob: That’s tough. Did you lose anybody?
Josh: No. We had two people left. I was disconnected from that whole situation. It wasn’t like we had to lay people off or people were like okay, I’m not making enough, I need to leave. There are people who, from 2015 with those pay cuts, they’re still at the company today. All through, I’m pretty proud of how we handled that. But I guess, more grateful for the people who were willing to stick around.
Rob: Yeah, I bet. How was that? Obviously, it wasn’t fun. Did it take a noticeable toll on you? Is that one of the weeks where you maybe didn’t sleep well? Drink a few too many bourbons? How do you cope with that stuff?
Josh: It certainly affected sleep a lot. For me, the stressors with Baremetrics were almost always around the people. A wonderful team, but I always wanted to not do anything that would put the team in some hard position. The fact that we were putting people in our position by asking them to take a pay cut made me sick to my stomach. It was one of those things where, with entrepreneurship, I signed up for the roller coaster ride. I’m aware of the ups and downs. Baremetrics is not the first thing that I’ve ever started. Me, my family—we’re used to some instability when it comes to the financial side of things and comfortable with it, ultimately. But no one I hired signed up for that. It’s tough to ask people to do that. Certainly, some sleepless nights were on them.
Rob: Yeah. I could imagine that. Another interesting point, probably another down point is Baremetrics had a few plateaus over the years. A lot of folks listening to this building SaaS apps have experienced that. Where you’re growing, everything is going great, and suddenly, it’s like, why are we stuck at $30,000 MRR for six months?
People can go to demo.baremetrics.com and they can see your MRR since inception. That’s all I did in preparing for this. It looks like from late 2017 until early 2019, you’re growing a lot faster before then and then you were between $90,000 and $100,000 for 17 months, or 16 months, or something. What happened there? You broke through it. Because I believe right now, Baremetrics is at $150,000 MRR. Obviously, that’s the remedy itself. The first question is, what caused that, and then the second is, how did you figure out how to break through it?
Josh: There’s a number of things. One, there was some technical stuff. We were having to spend a lot of time rewriting things because when you build something, to begin with, there are all these things where you could build this thing to scale up to hundreds of thousands of customers or millions. But then you would never launch the thing because you spend all this time pre-optimizing things.
As is the case with most software, you get to a point where you’ve reached the technical limits of what you originally build. We delayed that rewrite as long as possible. But the 2017-ish timeframe was when we’re hitting the limits here. We ended up spending a ton of time rebuilding the internals. Externally, the customer seed—nothing from an improvement perspective. That was a lot of the plateaus. It was like okay, there are things that people are asking for or wanting but we don’t have the bandwidth to do those things right now because we’re in the middle of this rewrite.
That was a lot of it. Then at the same time, this is about when Stripe starts rolling out their own analytics thing. ChartMogul is probably the most—from a competition perspective—they’re pretty strong and they’ve handled the infrastructure stuff a lot better than we were able to at that time. There’s just all these things that converged and made it really difficult for us to grow ultimately. We only had six, seven people, and all of them focused on engineering stuff. No marketing team or anything like that. It was just a lot of different things that all piled up.
Rob: That had been tough for 15 or 17 months to be plateaued like that. How did you break through it eventually?
Josh: We made the infrastructure changes that ultimately allowed us to do more real-time stuff where previously, your metrics would be delayed by 24 hours. Those infrastructure changes set the groundwork for us to have a more powerful tool. You can do more real-time metrics, you can create all these different segments based on all these different attributes. From an analytical tooling perspective, Baremetrics became a lot more powerful. That was a huge one. As a tool, it lets people do a lot more than they could previously.
Then we started doing these add-ons. We’ve got recover, cancellation insights. There are these different add-ons that make Baremetrics as a tool more powerful. I do believe that product is ultimately what got us through the whole plateau thing. We hired a growth person for a while. That didn’t really work out and didn’t really have any progress there. At least, the entire time I was there, the product, and to some extent, the content stuff drove growth for us.
Rob: Yeah. That’s what I was going to ask was the product got you out of it? Do you think marketing could’ve gotten you out of it sooner? You and I are product people. The expression of like, hey, when you’re a product person, building features is a way to get out of plateaus. But I often think that more marketing could be helpful in those situations. But I’m curious about your take on that.
Josh: I wanted marketing to be this magic pill for us. Especially in the early days, it was product and it was me writing blog posts every single week. That works really well in the early days. But eventually, me writing a blog post every week, I just couldn’t keep up with it. Hiring a marketing person, my hope had been, okay, we can have somebody who can really focus on just marketing this thing and doing the things that I don’t have a skill set for.
For whatever reason, that ended up not really being the case for us on the marketing-hire side of things. I don’t know exactly what Xenon, the acquirer of Baremetrics, is doing on the marketing front now. But the entire time I was there, we never found this marketing channel or set of channels that worked really well for us. A lot of that was just my lack of skill, or maybe it was budget, or willingness to spend money. I never really found it.
Rob: Interest, too, probably.
Josh: Interest, for sure.
Rob: You’re not that interested.
Josh: Yeah. We hired a content marketing person. He was fantastic. If anything, I hired him in January of 2020. He had about eight or nine months where we worked together before I sold the company. In that time, he got that machine going again where it had died off in the previous couple of years with me trying to manage it. I still think content was and maybe still is the strongest acquisition channel for Baremetrics. It was hard to do anything outside of that.
Rob: Yeah. It’s interesting to hear you say, we never really found the channel outside of content and yet you grew a business to almost $2 million in annual recurring revenue. There are many ways to do this. One could argue well with, if we had found the channel over the seven years, it would be a larger business. But it’s also still possible.
Josh: Our friend, Nathan Barry with ConvertKit, was just doing nothing for years almost. He would say the same thing where he’s just at a few thousand dollars a month. Then does almost nothing on the product side, but repositions himself in the product. It just starts growing like gangbusters. I kept thinking with Baremetrics, are we just focused on the wrong people? Is our target market wrong? We just never could find whatever switch to make that happen.
Rob: In December of 2019, you wrote a blog post called I almost sold Baremetrics for $5 million. Leading up to that, I’m guessing, and correct me if I’m wrong but you’re basically, almost six years into this business, it’s growing but maybe not as fast as one would like. Do you feel like you were experiencing burnout? Were you tired of the grind? I guess the real question is what motivated you to start thinking about selling it?
Josh: A lot of that was life timing. I had not been thinking about selling. I certainly had not been pursuing anything and then got an email with a decent offer, relatively straightforward. No complicated stuff attached to it or anything. I was like, maybe this would make sense. At the time, family stuff was rough. There’s just a lot going on that it’s like man, I would love to not have this mental burden of running a company. That started the train down the tracks. Ultimately, it worked out.
Rob: The interested time folks can read that blog post if they want to hear more about how it didn’t work out. That was a bummer. I had to imagine. Obviously, later you sold it and basically got more money because you don’t have to pay taxes due to QSBS because it was a stock sale versus asset. But after that sale fell through, what was your headspace? How devastated did that feel? How did you pick yourself up after that?
Josh: From the time that I got that original offer—that was April and I might have a few months off here—it was August, September when I was like, okay, this is not going to work. At that point, I was so burned out on the process that I had accepted this isn’t going to work out, or at least this time around. I can’t pour more into this. I just need to get back to work.
After I made that decision, I really did not spend much time wallowing. I was just like, okay, well, this is what we got. Let me get back to work. A couple of months later, I hired three people. It was just, let’s go all-in make this happen. I was not as bummed as one would think. But I was probably more so because my nerves were just shot from the whole process and all that falling through.
Rob: I have a lot of respect for that because I don’t know if I could’ve recovered that quickly. My personality is I would hang on to things for months and probably wallowed in the sadness. But it sounds like that really wasn’t the case for you.
Josh: Other than like being bitterly angry at the people who ultimately ghosted us, screw those guys, but other than that, I was ready to get back to it.
Rob: And then in 2020, you launched a new feature. You said you hired people. You launched a new feature, this feature called Intros where I believe you had conversations with investors. It was going to match up potential investors or acquirers with Baremetrics customers who had opted into this thing of, hey, I am looking for funding or I am open to acquisition offers. Here are all our metrics. It’s a natural fit. You had conversations where people said, hey this is a great thing. You built it and it didn’t work. What happened there?
Josh: Of all the things that we had built with Baremetrics, I felt so confident in our research phase of this idea. I had dozens and dozens of calls with ultimate investors because they would be the customer here. We did interactive mock-ups before we wrote any code. We just tried all sorts of things to try to prove the idea before we spent the time to build it.
I felt so great about it. I also had this classic entrepreneur, pie in the sky. This is the thing that’s going to blow it up for us because we’re talking about million-dollar deals here. We’ll be able to make tens of thousands into MRR on day one. That’s the kind of feeling that it had.
We had so many investors who had signed up to be notified when it launched, even outside of all the people I had talked to. Then we launched it and I didn’t get a single paying customer for it. It was such a downer for me and the team as a whole like, where did we go wrong here?
That was probably one of the biggest morale destroyers in the history of Baremetrics. We spent months building this thing. It felt like we were onto something and we got it wrong.
Rob: Yeah. It’s tough. To me, when I think about Intros, obviously, you were going to charge the investor’s side for deal flow, in essence. When I think about it not working, I think well, that makes sense because most investors don’t actually need that much deal flow because they’re giving away money, giving it away in exchange for equity. Still, you’re going to have money and you’re going to invest. Deal flow isn’t as hard as I think people would make out.
If you were just to pitch me the idea, I’d be like, yeah, I’m not sure this is going to work. But the fact that you then did the mock-ups, have the conversations, did the validation, and that all pointed towards it working, that’s the surprising part to me. I just would’ve thought that there would be signals earlier in the process.
Josh: In all my conversations, probably where we didn’t spend enough time harping on this with the investors was the cost of it, or how much they would be willing to pay. Occasionally, someone would recommend, well, how about you take a percentage of the deal that goes through or whatever. We were trying to not complicate it or have a contract signed. We’re now some partial owner in whatever the deal is. There are a lot of different ways you could charge for something like that. We’re just trying to just say, okay look, if we can get you one new deal a month that you, otherwise, would not have gotten, this has got to be worth at least $500,000 a month or something like that. We couldn’t make it happen.
Again, part of that also went down to my aversion to sales-y marketing stuff. It’s like if we had had someone, a proper salesperson handling all that stuff, maybe we could’ve closed some of those deals. After we launched it and could not get people to convert, it was just okay, I don’t know what else to do here because this is so far out of my wheelhouse.
Rob: Right, and at $500,000 a month, it’s more of an enterprise sales process and you didn’t really want to do enterprise sales.
Josh: I did not. It just kills me. It’s not that I don’t think the product could’ve worked. I have seen a bunch of stuff, other things crap up in the past, a year or two since then, from people building similar things like trying to have deal flow and hooking up to your Stripe account and all this stuff. People are still trying it. I was the wrong guy for it.
Rob: That’s the thing I think folks should realize. Validation can work. I will say it does work not all the time. Oftentimes, we validate incorrectly or we make mistakes with it. Sometimes it does give us false signals. Validation is not 100%. But also, when you launch something, a lot of times, knowing yourself and knowing—like you said—what you are interested in, what you’re willing to do, sometimes a product needs something different than that.
As you said, I can feasibly be successful if it has different folks running it. I think of TinySeed and if I were pitching investors and raising money, TinySeed would not be nearly as successful as it is with my co-founder Einar Vollset, who is designed and made for that. It’s more of an enterprise sales process, its relationship, and all that stuff. Much like you, it’s not my sweet spot. In fact, I don’t ever want to do it, ever.
In that case, TinySeed wouldn’t work for me if I had started it on my own. It sounds like interest is a similar thing where it wasn’t in the right place for you. You did wind up selling it for $400,000. It was a year and a half later or something when you wound up getting some cash out of it.
Josh: Yes. I talked about from a moral perspective, how that thing’s failing was such a bummer for everybody. But selling it $400,000, it sort of flipped that over and everybody was really stoked on it. One of our goals for that year when we sold it was to get more cash in the bank. We got profitable after we almost ran out of money. But we were still operating pretty much right at breakeven on purpose. Having just some more cash to the bank to get a little bit more of a buffer wasn’t one of our goals going into the year. Being able to get that buffer in by selling this thing, the leftovers, felt like a win for everybody. I was happy with that outcome.
Rob: To take us forward, two, three months ago, you wind up selling Baremetrics in a true life-changing exit. I asked you before we hit record, Are you going to do the smart thing and take six months off, or knowing you, are you already working on your next thing?
You told me about Laser Tweets which I had seen you tweet about now and again. But I thought it was a hobby thing that you were doing. Folks can go to lasertweets.co and you have a full-on online store here, sir, with their coasters that are laser engraved with people’s tweets. You have a Lil Nas X Coaster set. The first one says, “old town road is literally about horses.” You have this one from Kanye West, well you have a whole set of them. But he says, “I have no interest in working with anyone who is too important, or too good, or too traditional to take a call at 3:00 AM.” Tell me about your maker. This makes sense. Tell me about how this came about and what it’s doing?
Josh: Yeah. It’s super dumb, Rob. In 2018, I got a laser cutter just because, why not. It sounded fun. Then I was like, maybe I should figure out some way to make something with it. Let’s laser etch tweets into woods and see what happens. It was still very much a little hobby thing. In 2019, I made $10,000 from that year. Then this past year, 2020, it’s certainly picking up in the summer. When I sold Baremetrics, I closed the deal by the end of October, early November, which also coincided with the shopping season for holidays.
The second I sold Baremetrics, I instantly jumped into running the laser cutter for 12 hours a day and packing orders all day. This just blew up, man. That’s what I’ve been doing. I haven’t taken a break because I’ve been laser etching Kanye tweets.
Rob: This is the most bizarre ending to a startup exit story that I’ve ever heard. Did you make some money?
Josh: I was looking at it now and I have $20,000 in 2020. I have doubled my growth. This is rocketship growth stuff here, Rob.
Rob: You need to raise funding. I think that you’re onto something here. Oh my gosh, I love it, man. Are you going to continue doing this? It sounds like it has legs of its own.
Josh: I guess. It was certainly not my plan to jump right into it. Right now, I want to see things through. With Baremetrics, for instance, I felt like my role or like my usefulness at the company, my ability to grow it ran its course. I was the wrong guy to keep trying to run the company. With Laser Tweets, it’s like, I’m still the right guy for it. Let me just see what happens. When we doubled sales for the past year, what happens if I double it again this year, in 2021? The first part of it is next year, sell it and be done with it then or something like that.
You’d asked about taking some time off, I don’t feel any desire to start anything new. This is more like, let me just see this through to the end of this thing that I’ve already got going. It doesn’t stress me out. That’s nice.
Rob: It’s nice that it’s so different. So different than running a SaaS app.
Josh: Exactly. I’m avoiding software, building any kind of software like the plague. I just don’t want to touch any software. This is very much not that. It’s handling wood and just like making physical things. That’s almost therapeutic for me, especially because with Baremetrics, it had to work because there were people, families relying on me not running that thing into the ground. Whereas like with Laser Tweets, if it stopped tomorrow, if people no longer wanted Kanye Tweets, fine. Who cares? I don’t. It doesn’t matter. There’s no stress associated with it.
Rob: That’s why I’ve loved watching you over these past seven, eight years since we got to know each other at MicroConf, and on Twitter you’re always doing interesting things. You’re framing them in a way that is both admirable and inspirational to a lot of folks. You make people around you want to build things. You make people want to be entrepreneurial or to do cookie things. I have a lot of respect for what you built with Baremetrics. Honestly, I’m just super happy that this was your outcome. I don’t like to use deserve because it just said a loaded word. I feel like you worked your ass off and you earned some success. Props to you.
Josh: Thanks, man. I appreciate that.
Rob: If folks want to keep up with you, you are @Shpigford on Twitter, obviously lasertweets.co if they want to see the amazing. Dude, you have picked out. Your taste in curating these is amazing. There’s the Elon Musk set. There’s Donald Trump coupled on, Trump sets. I notice Kanye West has the most sets.
Josh: He’s easily the most popular. Followed by Elon. People love some Kanye.
Rob: I can’t stop laughing as I read through these. I love it, man. Thanks again for joining me, man. If you do get the startup bug, I’m curious to see it over the next few months. You’re a maker. You’re a creator. You’ve built multiple SaaS apps. A lot of people don’t know that you had several apps before Baremetrics. But I am genuinely curious to see if it comes back to you. You’re always going to build and launch things. I wonder if you’re going to ever want to do software again.
I have not had the itch to launch production software since we sold Drip. I still build things. I still have packy-hacky ass PHP scripts that I connect to this and that API. I do things and I love codes. I’ve been writing codes since I was eight. But to launch something into production for other people to use, I have not had that desire. I’m, of course, scratching that itch with this podcast, MicroConf, and TinySeed. I’m building interesting things, things that are interesting to me through that. I’m curious to see how, aside from Laser Tweets, you figure out how to scratch that itch for yourself.
Josh: I’m curious as well. I think that the reality is I’ve been building software, trying to make money off of software for the better part of almost 15 years. It’s not like, oh, I’m stuck with Baremetrics for seven years. I’m moving on to something else. I’ve had a career, essentially, in the SaaS world for 15 years. Okay, I feel like I’ve done that. Now, I’m ready to move on to try other things. I get bored. I’m curious what the next few years look like.
Rob: Yeah. Congrats again to you, sir. Thanks for joining me today.
Josh: Thanks, Rob.
Rob: Thanks again to Josh for coming on the show. Thanks so much for joining me again this week and I’ll be in your earbuds again next Tuesday morning.

Rob: Welcome back to Startups for the Rest of Us. It’s me, your host, Rob Walling. Thanks for joining me this week. This is episode 533 of the podcast. Today, we’re talking about life profitability after two exits with Adii Pienaar. I’ll give his full bio in a minute.

He is a multi-time founder with multiple exits under his belt. He has written a book called Life Profitability: The New Measure of Entrepreneurial Success. He talked the talk and walked the walk. He’s been a MicroConf speaker, he’s a TinySeed mentor, and he has lots of experience and success under his belt.

Today we dig into more of the personal side, the life side of building a startup. A lot of what my wife, Sherry Walling, talks about on her podcast, ZenFounder, is the startup family, life, and the balance of those three things. In this book, Adii looks a lot at how to make it all work.

Before we dive into that, I wanted to remind you, in case you haven’t checked it out, the MicroConf Podcast. Every week, we either release an episode of MicroConf On Air, which is our video live stream show—we release that in audio format, or we do MicroConf Refresh Episodes where we go back to a previous MicroConf. We take the talk, pull the audio from it, and then I add an intro to it for context. We put that out on the feed, and we’ve had a lot of interest in this show.

If you haven’t checked it out, just go to any podcatcher, search for MicroConf. It should be your number one result. It’s nice, I subscribed to it myself. It’s a fun reminder, even the talks that I saw in person, which I guess technically is all of them because I’ve attended all the MicroConfs. Even those talks that I saw in person, it’s nice to be reminded and be refreshed on the topics and the ideas that are put forth.

It’s a low investment because it’s audio. Of course, you can always click through the show notes and watch the video if you do want to see the visuals. MicroConf Podcast, if you haven’t checked it out already. With that, let’s dive into my conversation with Adii Pienaar.

Joining me today is Adii Pienaar, the founder of WooThemes—later became WooCommerce and sold to Automattic, the parent company of WordPress—founder of Conversio, an ecommerce ESP that’s sold to Campaign Monitor in 2019. He’s a multi-time MicroConf speaker, TinySeed mentor, TinySeed investor, and he’s appeared on this show once before, episode 467, “A Life-Changing Exit” with Adii Pienaar of Conversio. Sir, thanks so much for joining me today.

Adii: Yeah, Rob. Thanks for having me again.

Rob: It’s an absolute pleasure to have you. You’ve written a book called Life Profitability: The New Measure of Entrepreneurial Success. If folks want to go check it out right now, it actually just dropped today, the day this episode goes live. It’s at adii.me/book. We will include that in the show notes. It should appear in any podcatcher that you’re using today. Coming out in Kindle and physical today, and then the audiobook is out in about six weeks. I have my preview PDF copyright here. Thank you for sending that over.

I’m really fascinated with this concept of life profitability, and I want to dive in today to help flush it out for Startups for the Rest of Us listeners. You’ve been to MicroConfs, you’ve listened to these podcasts, you hear the people that are in this community, and you know that there’s quite a bit of overlap with this idea of lifestyle or of work-life balance, which you addressed in the book. You say, hey, work-life balance is not the answer. We’ll get into that in a little bit. You’re a founder with multiple exits under your belt, so why sit down and write a book about this topic?

Adii: That’s a really good question, Rob. For me, there are multiple answers to it as well. If I were to give you the marketing pitch, part of it is I probably think that in 2021 going forward, we need an augmented version of capitalism. I’m not suggesting socialism or any other kind of model that we had. I’m not suggesting that capitalism itself is wrong, but I think that it’s not always perfect. With the notion of life profitability, I am trying to offer entrepreneurs an opportunity to augment that version of capitalism.

I think that’s part of that be the change you want to see in the world spiel to this. That’s what I hoped for to happen after the book. For me personally, I had much closer ties to the concept. You mentioned that I’ve been a successful entrepreneur in the past. What I know about that journey and what probably resonates with many of the Startups for the Rest of Us listeners here is the notion that it’s really, really hard. Building a business is really, really hard. It doesn’t matter how much you learn, it doesn’t matter how much capital you have, experience, all of those things were really hard.

I’ve mentioned this a few times before. In large parts, building my second business was harder than the first. I know that with more, it doesn’t necessarily become easier. In that personal journey, I almost lost all the things that really matter to me in the world. That notion played a big part in me. Essentially sitting down and realizing that, hey, if I don’t change something in my life, in my business, then nothing that matters is going to be left after all this business or entrepreneurial success.

Rob: It’s interesting you say that. I heard you spoke at MicroConf Europe. I think it was 2017 or 2018, and you were talking about your Conversio journey. This was your, basically, second win. You hadn’t sold it yet, but it was a company that was growing. Most of the talk was focused on how bad you felt, that you were burned out, and that you weren’t having fun.

I remember being surprised by that because I was thinking it’s your second time. We’re usually better equipped with money, with resources, with the mental capacity to know what’s gone on, we’re more resilient, and all this stuff. I’m curious, why do you think Conversio was harder for you than the WooCommerce, WooThemes day?

Adii: That’s one of the questions that anyone can ask me about the book and about Conversio that I have great clarity about. The context there is I can’t just add that. To a large extent, Conversio was much easier due to the success I had with WooThemes. Many of the tactical things were easier. The harder parts were what about me? It was the challenges and the issues I ultimately introduced into the greater equation of building this business and the life I was leading.

The way I now understand that—which is very much a hindsight thing—is in the following way, which is I left WooThemes with this notion that I was a one-hit-wonder. I really wanted to challenge myself again because challenges are what fires me. Money itself has never been a big motivator, challenges are. I wanted to challenge myself again and prove that I’m not a one-hit-wonder, and I can actually build another successful business.

Interestingly enough, at least what I now know is I was only trying to prove myself to myself, which is ironic on its own. It’s part of bringing that awareness and what I’ve had to learn. Hopefully, through Conversio, what effectively happened was two things overlaid. These things happened very soon after each other.

The first thing that happened was Conversio got to a point where we were successful. I think we were probably at about $1.5 million ARR, for example, and I thought to myself, hey, you’ve built another significant business at least. It wasn’t the size or scale of WooThemes or WooCommerce, but it was successful in its own right—just about break-even, growing nicely.

At that moment, the goal of being in this business of proving that I wasn’t a one-hit-wonder evaporated. Shortly after that, just a short couple of months after, we hit a rocky patch where we had to go through layoffs and business was not growing as well as we thought it was, loads of context there. In that hard moment, what I realized was I suddenly didn’t have that North Star, that meaning, that purpose in this business anymore because I’ve done that. That’s where that became a grind.

You’re referring to MicroConf (I believe it was) late 2018—if my memory serves me correct—when I gave that talk. That was me going through that almost rejigging process of reframing the context that I was in. Again, 2018 as a whole year—tactically within the business—was all about taking a screwdriver to every single screw and trying to eke out that 0.1-degree turn to make it a better business. It was a hard year, and that was the context for that talk. That’s why the overall […] that I was, this was so much harder than it was before.

Rob: For context, if folks haven’t followed you in the past or didn’t hear episode 467, when I listen to successful entrepreneurs talk about the world, a lot of them have a pretty unique viewpoint. I often think of Jason Fried as a founder/advocate. He’s always advocating for a cause, whether it’s privacy, bootstrappers, or whatever. I’ve heard someone call me a founder/teacher where I’m going to start companies, and I’m always going to be teaching what I’ve learned. I think of you as a founder/philosopher. Frankly, you’re a poet as well. You have a book of poetry folks can buy. What’s that called?

Adii: It’s called Motion.

Rob: We have a copy. Sherry bought it and so I’ve read through it. You are very much into mindfulness, thinking about the self, being aware, and seeking happiness. You’re like a founder’s body with a philosopher’s mind, or maybe it’s a philosopher’s body with a founder’s mind. There’s some merging of these two in a way that, frankly, I don’t have.

A lot of founders, especially maybe more left-brained founders I would say like I am more of an engineer. I can dip my toe into philosophy, I can listen to it, but I can’t write it. I don’t come up with the concepts. That’s how I feel as I read through Life Profitability. There’s a merging of entrepreneurship and philosophy almost.

With that as an intro, can you just explain? The title of the book again is Life Profitability: The New Measure of Entrepreneurial Success. Can you just give folks an idea or an intro of what Life Profitability is because it’s a term that you coined?

Adii: Yeah. By the way, I totally own and I know you have a cooldown period on domains. Totally proud that I actually own lifeprofitability.com as well, which confirms that I’ve coined the term. Jokes aside, the idea of life profitability essentially comes from firstly, this notion of I don’t think we work to live, and neither do we live to work. You mentioned work-life balance earlier, I also don’t believe that can exist when work is always just part of life.

When viewed from that lens, the idea of life profitability is all around. If you’re an entrepreneur, you should build your business in a way that is profitable to your life. That’s where life profitability comes from. That profitability needs to be more than just literally the financial distributions—whether it’s salary or otherwise—that you get from your business. It truly needs to be ingrained in your whole life.

The book goes through what those various parts of life are. I essentially came down—for me at least and what we proposed in the book—is these concentric circles that start with you first, then your immediate family, your team, your community, and only thereafter that the business itself actually becomes almost the container for all these things.

Really looking at all of those kinds of things in detail and saying, how are the things that I’m doing on a daily basis, whether it’s for my business or just a provisional career, how are those things profitable for the things that I truly value in this world? The converse of that, which I think people often don’t recognize, is the cost of doing those things.

Henry Thoreau, the actual philosopher here, has a great quote. I’m totally going to butcher up. He essentially says the cost of anything we do is life. That is the thing that we ultimately give away. Whenever we make a decision to do something, the cost of that decision is life.

Through that lens, augmenting how you would calculate profitability in a business as well but really saying what are the costs of me doing business here, trying to reframe that, and figuring out, not necessarily change that altogether, but make those incremental changes to shift to greater life profitability.

Rob: I’d like to get into a specific example of a decision or decisions you made to move towards life profitability in your own journey. But first, I want to talk about work-life balance and why in your book, you point out that’s not the solution. What you’re talking about life profitability is different than work-life balance. Can you give folks an idea of how that works?

Adii: The simple version there, Rob, is if we propose this idea of work-life balance, we’re essentially saying that work and life are two opposite things that can balance each other out. They’re two nodes on the same spectrum, and for you to have balance, they have these two […] that interplay between those two things.

The reason I don’t think that works is you’re essentially taking two things and you’re saying that they’re completely independent of each other. I think what all people listening to this podcast know is that if you have a crappy day at work, that spills over into your home life, and vice versa, which means that these things are never totally separate.

If they were totally separate, totally independent, then yes, work-life balance is achievable. But because those things always overlap, there’s always some spilling over of things, I don’t think that’s the key there. Which is why with the book, I’m trying to change that perspective, which I said is all around work just being part of life. Life is the ultimate thing that we’re doing here on this planet and work is always just a component thereof versus this totally separate thing from the lives we’re living.

Rob: Got it. Can you give us an example of a choice you made that was basically moving towards this idea of life profitability in your own experience with Conversio?

Adii: I mentioned earlier that 2018, that tough tactical year we had in Conversio where we essentially had to move too fast to profitability pretty quickly and do so in a shoestring budget effectively after the layoffs.

I remember that towards the latter stages of that year, I was ultimately to do two things. One was to repay parts of the initial founder loan that I put into the business, and the other was to essentially declare a small profit-sharing bonus for the team.

Those two things matter for two separate reasons. The team is more obvious and easier to explain, which is all around building a business in a way that doesn’t just support or empower my life profitability as the founder/entrepreneur but also doing that at least in part for my team members. But that repayment of the loan, which seems very converse to this idea of building and reinvesting or investing in a business was crucially important to me because what it did was diversified some of my risk in the business. It reduced a lot of stress that I had.

I think what subsequently happens is an entrepreneur and a founder that’s not stressed, that’s not anxious in their life is ultimately a better entrepreneur and leader within a team as well. That’s just one of those things that comes to mind, Rob. The reason why that example came to mind was all around how it served two separate groups of people—myself, the team. Almost did that in an almost inception-like, meta-like exponential manner as well by helping me be a better, calmer, more peaceful, or more grounded entrepreneur and leader to the team afterward.

Rob: What you’ve described is a decision that a lot of lifestyle entrepreneurs make. I use that term as a positive. I know Silicon Valley venture capitalists say you just have a lifestyle business, it’s unfundable by us. I—of course, being involved with MicroConf, Startups For the Rest of Us for a decade or more—think lifestyle businesses are amazing.

One of the great pieces of that type of business is you’re in control, you make the decisions, and you can pull up profits when you want. You can really drive the business in a way that fits you, but that helps benefit the team and your customers. You can make the “right decision in your opinion” because if you truly haven’t raised investment or have really just raised a small round from people who are willing to go with you on a journey, you have immense control. You can make the decisions that you feel right about and you feel good about.

Is there a difference between the traditional bootstrapped lifestyle business path and what you’re talking about with life profitability?

Adii: No, there is very much alignment there, Rob. The context here is that I am mostly a bootstrapped founder as well. WooThemes is completely bootstrapped, Conversio raised a single round before moving to profitability. To a large extent, this whole idea of being an entrepreneur stems from one’s desire for freedom. Freedom in whatever way you articulate that freedom. Whether it’s the freedom to work in a way you want, work with whom you want, or work in what you want. It stems from that freedom.

There is that self-expression in that, which essentially says you can build the life you want which is where the term lifestyle business comes into play. I’ll build a business to have the lifestyle that I want instead of being in a corporate gig where I can’t control those things.

The only thing that I’m almost trying to emphasize with life profitability is to truly understand what the things are you really want, what the things are you really value, and to not define those things by traditional measures of success.

It’s actually expanding what that success looks like for you and replacing it with this idea of life profitability. The key part for me here is really doubling down on that original starting point, which was all around I’m starting this business because I have a vision of my future that I want to achieve. Which means that my version of what success looks like for me will always be very, very unique.

Compared to other entrepreneurs, there will be many similarities especially if all of us are bootstrapped, for example. But I for example don’t think that the source of capital is the biggest differentiating factor there. I really think that our unique personalities probably change that equation significantly more than the source of capital does.

Rob: Yes. I have had this conversation so many times where we can say bootstrapped and mainly bootstrapped versus venture-funded. You’re right, you can be a bootstrap founder, run yourself into the ground, and work 90-hour weeks. I’ve seen folks raise $20 million, $30 million of venture capital, and work 8-hour days—it happens—and be happy with their business.

Eventually, they have to perform and everything has to go well. But you’re right, the source of capital is really not how we should be defining these things. Unfortunately, we have fallen into a kind of dichotomy there. What I like about what you said about life profits versus lifestyle business is really figuring out what you as an individual value most.

I’ll tell you a short story. As we’re building Drip early days, I wanted it to make $40,000, $50,000, $60,000 a month. I wanted it to be this amazing lifestyle business that threw off a bunch of cash. Pretty soon, we found we were in the midst of a huge shift in email marketing where there were the MailChimps and AWebers. They were less expensive, no automation, no tagging, and then there were these really expensive solutions.

We could fit right there in the middle and be a nice, usable version that had all the automation. We dove headlong into that. It threw us into a really competitive space, and it was harder than I thought it would be. It was a lot harder than I thought it would be, actually. I hadn’t grown a business that grew that fast before, needing to hire, and just the rat race you can get into.

Segments of your book I actually want to read an excerpt from it right here that really captures what I was feeling as we were growing Drip and as I started feeling a little bit out of control. You say, “Life Profits. In a nutshell, realizing life profits means more lived abundance for every person the business touches. This is the vision, the mission, the strategy, and its outcome. A richer, more colorful life that is so much wider and deeper than a business will look different to every entrepreneur since it’s based on what you value. Making more space for your life when you are used to feeling obligated,” it’s a big word there—obligated—because I felt that every day.

“Making more space for your life when you are used to feeling obligated to give your business your all might feel scary and daunting, but you’re not going to make a drastic change to the way things are right now. It’s important not to do a 180-degree turn here, but instead, begin growing life profits by shifting the way you do things in incremental bits. Within business, there are rules and ethics that must be upheld, but you can play the game in a changed way by differently orienting yourself to it.”

That’s a big gamble and it could be risky. But if you know what you value and you know the road you don’t want to go down, it’s almost a road to unhappiness if you let yourself get pulled. This comes back to what you said earlier, which is don’t value your success by the standard metrics, by what everyone else thinks is a success.

Adii: Exactly right. What the irony of all of that as well, many of us—I definitely have my days where I still feel like an impostor. That impostor syndrome, where it stems from is entrepreneurs archetype lends itself to that because we’re always comparing ourselves to other entrepreneurs and saying, okay, so my business is actually doing okay. Okay, I’m not an impostor.

In saying that, you’re an impostor in your own life because you’re probably neglecting those other life costs that are coming at the price of being this impostor but at least matching up to these other entrepreneurs. That’s the hardest part to figure out for every entrepreneur here is who you really are and what that means for your business. Hence, why I do not propose that anyone makes a 180-degree turn here.

If you’ve got an existing business, dream, or goal, don’t read the book and shift completely here, but really start incrementally thinking about how you can shift that. For anyone reading the book, I purposely went into writing the book. I didn’t want to write here’s 10 steps to life profitability because I don’t believe that those 10 steps actually exist. All of us are so unique, and part of this journey is for us to figure this out ourselves.

The book includes many ideas from my own experience, suggestions, et cetera, for you to help illuminate what those things could be, but I honestly don’t believe that there’s a single blueprint. I also don’t believe, by the way, that there’s a single blueprint for being successful in business, but every year, 100 million copies or whatever of business books sell, proposing that they’ve got the answer for you. Life profitability I don’t think is that because it’s super personalized and unique to every single individual that wants to grow down their path.

Rob: Something that I’ve mentally struggled with over the past few years—obviously, I sold the Drip and moved on—is the Drip years, some of them are great, and then there were times that were just really tough, much like you and pretty much all the founders we know who have done these larger companies and had exits. There are some times that are very, very difficult and the journey is challenging. But for me, it was absolutely worth it. I don’t regret making the decisions that we made to enter the really competitive space, to go after a faster-growing market, to grow the business and to hire. All that, I have no regrets. It turned out great.

What I regret was that my mindset was not right. My mental game—like I often say, more than half of being an entrepreneur is managing your own psychology. I did a poor job of that at times, that’s what I regret. That’s where your book comes in. It’s a level set, it’s a looking internally, it’s saying what is truly important to you, how to pull that out. You actually have worksheets and exercises in the back almost like an appendix that’s basically here are the steps to try to pull these things out of you so that you do know what’s important and that you’re grounded as you do this journey.

The journey is going to be hard no matter what unless you get really, really lucky. There’s just going to be trying times, there’s going to be things like lawsuits, all your servers get hacked, or Russian spammers get in your systems and send things out. Things are going to happen, it’s going to be stressful. At a certain point, you’re going to say, well, I guess we had a good run. This whole thing’s about to collapse, and it’s going to be very, very stressful.

Maybe you almost ran out of cash. I’ve almost done that, you’ve almost done that. All this stuff is going to happen. The difference I see in founders who keep their wits about them, it’s not that bad things don’t happen. It’s that they have that inner groundedness of really knowing what they’re about, knowing where they’re headed with their business and the confidence that this is just the way it goes.

That’s where I feel like your book comes in. It’s a way to find that groundedness for yourself. As you go about this journey, you almost have that armor to these events that are going to happen to you.

Adii: That’s definitely my hope here, Rob. I’m definitely a pro-entrepreneur. I do not want to discourage anyone from being an entrepreneur. I really just want to help them figure out what entrepreneurship means for them.

Two things that stood out in what you said there. The first is yes, we’re grounded when we understand our meaning and when we can pursue our meaning. In those hard times, when we know what our meaning is, our purpose here, it’s a lot easier to never get those hard times. The best way I ever understood that was Dr. Dina Glouberman, she wrote a book. The book is called The Joy of Burnout. She defines burnout as the thing that happens when meaning drains out of the structures that you’ve invested a lot in.

That’s what sometimes happens in business is this thing that we invest so much in and then suddenly we lose meaning. When we lose that meaning, that’s when it becomes harder than it probably needs to be. That speaks your point of that mindset—managing your psychology as an entrepreneur. That’s the first part of it.

The second part that I will just leave with listeners here is that when I have a bad day as an entrepreneur or a bad week where I struggle with my mindset, with the mental or emotional part of being an entrepreneur, what happens after that? Where am I taking that energy elsewhere in my life and probably affecting other things? Whether it’s the people I love most around me. Maybe more irritated or impatient than I normally am with them, or short. Or am I neglecting my sleep, my health in other ways, exercise, or connection with friends? Whatever the case is.

We’re not aware of those things. Even a few words would navigate your personal experience. There are probably others around us or other things, those life costs that accumulate as well if we don’t manage to essentially build a business, run a business, be an entrepreneur in a way that is life profitable.

Rob: You’ve been through two challenging journeys, WooThemes-WooCommerce and Conversio. Something that I told my wife, Sherry, as Drip was—I don’t even remember if it was winding up. It was when we’d hit really hard times. I told her, I’m never doing this again. I’m not starting another SaaS app. This is less fun than I want it to be now. In retrospect, it wasn’t that it was less fun. It was that I didn’t have my mindset together to really play it out the way I should have.

All that said, I moved on from Drip, took six months off, and then started TinySeed. There was a lot of thinking that goes into that. Interested in sharing that with the listeners here, but what I want to hear from you is you did go and start another SaaS app. It’s called Cogsy. The H1 is “Never run out of stock for your best-selling products ever again,” and it’s aimed at ecommerce merchants. You’ve obviously had experience and success in the ecommerce space, both with WooCommerce and with Conversio.

I’d love to hear your thought process post-Conversio as you’re thinking, okay, here I am. I’ve had exits. You can work on whatever you want to work on. You could not start anything. You told me offline you could become a coach, you could become an author/speaker, you could be a full-time investor. You can do what you want. What was that process like for you to say who am I, what do I really value, and I really want to get back in the trenches?

Adii: Firstly, my wife Jeanne has always known that I will probably be doing this again and again. She and I were sitting earlier having a glass of wine and she told me she knows that Cogsy is not the last one. That knowledge is part of our everyday life, which I am an entrepreneur and I will do these things.

I told Mark and Magnus, my co-founders in Woo the other day as well. They chuckled at the fact that I’m doing this again and they pretty much said the same thing which is I’m crazy. When they said that, my answer was very simple—I love the work. It doesn’t matter how hard it is sometimes. I went to great detail earlier in our conversation explaining how tough Conversio was at stages, and how a big part of that hardship essentially created this book as well.

For me, it really came down to knowing bare parts of myself. The most prominent part of why I decided to work on Cogsy was around I like the starting phases of things, and I like holding a team. I really miss a team. I miss post-acquisition after leaving Campaign Monitor. The thing I missed most is my team. Those things are important parts of why I want to do this.

Again, the other part of this is I hope that there is a part of this future with Cogsy that challenges my own life profitability but also allows me to continuously evolve. Because I haven’t totally figured it out. Even as the author of the book, the guy that came up with this term, I haven’t figured it out.

For me, Cogsy is that playground or blank canvass where I can take everything I’ve learned, everything that I understand about myself, just reapply that in a new way, and ultimately continue my evolution and my journey.

Rob: From my end, leaving Drip in 2018, and I took six months off. I was looking around for something to keep me busy. I was hacking PHP on the weekends and tying into crypto APIs just to fool around with stuff. I had a great time doing it, but I almost went down this path of basically walking away from everything—from the podcast, MicroConf, and whatever else. All the brands, all the assets, the world of startups and entrepreneurship.

I thought just a brief moment, what if? Mental exercise, thought experiment, what would it look like for me to just exist in a completely different space? I looked around and I realized, I don’t want to build stuff from scratch because it just takes too long. I have the means, I’m going to acquire something.

I actually got in a conversation with the owner of the second-largest website for tabletop games. I was saying, hey, I think I want to buy this site, talk to me about revenue. We started talking about his numbers and what it looks like to run the thing.

Getting into the tip of a gaming space would be fun because it’s a hobby. I do it with my kids and I really enjoy it, but what I realized within even weeks of thinking about this avenue is that I would be leaving behind a huge piece of myself. Almost something that I’d taken for granted because I’ve done it for so long.

I’ve been thinking about it for 20 or 30 years. I’ve always been enamored with entrepreneurship. I’ve been writing about it for 15. I’ve been podcasting about it for 10. This is the thread of my life, this is the through-line. I realized I value freedom, purpose, and relationships. You hear me talk about that a lot. I would have left behind a huge part of my purpose and a part of my legacy if I were to do that—and a part of freedom, purpose, and relationships. I love having relationships with founders. They’re just super interesting people. I find them fascinating.

It was a thought that for a moment like, oh, but I could just start over, and wouldn’t it be easy? But I had to dive into myself. I had to be mindful, I had to know myself, know who I really was to say this—Startups for the Rest of Us, MicroConf, this community, this ecosystem, it was the moment that I doubled down on it and said, I’m going to be doing this for the rest of my life.

It’s one of those things in my life that I don’t think will ever go away now that I’ve had the moment to reassess and think. For me, what is life profitability right now? It’s not abandoning everything I put into the world so far, not that it wouldn’t live on or whatever. I think there are such a big point and such a big part to asking yourself, what is it that I really want? You wanted to do another SaaS app, and that’s the path for a lot of founders.

You see Ruben Gomez is on his second, you see David Cancel has done five of them. That’s a path for some, and others go more of the teaching route or the author route. As you said, you can be a keynote speaker, some people become investors, some people gather folks and build communities. Figuring that out about yourself is the point of everything we’re talking about here.

Adii: Exactly, Rob. In anyone’s next steps here—in my next steps, there’s only going to be a single common denominator, and that’s going to be me. I mean, businesses can change, ideas can change, people get divorced, families change, people move countries. All these things can change, but there’s going to be a single person on that journey that’s going to be the only present and that’s going to be yourself. That’s why it’s important to really know who you are because that’s how you can constantly adjust to the next steps you’re taking.

For me, maybe Cogsy is my last SaaS app or last software business that I build myself. Maybe, there’s going to be a new chapter in the future. The idea of life probability acknowledges that whereas life naturally evolves. That’s the way the universe has always worked, and the key is just to stay in that mindfulness. Stay aware of when those energies change, when the things you want change, when the definition of your life profit changes, and then readjusting the next steps that you take from there.

Rob: If you folks want to check out the book, they can head to adii.me/book. It is $0.99 this week on Kindle and you have physical copies as well. As I said earlier, it will be out in audio in about six weeks.

If folks want to keep up with what you’re up to, you’re Adii on Twitter. It’s a great four-letter Twitter handle there. As we were chatting, when you said lifeprofitability.com, I just typed it into the browser just for kicks. You have a podcast. I didn’t know you had a podcast. We can plug it here, Life Profitability podcast. Is this the first podcast that you’ve hosted?

Adii: Yes, it is.

Rob: How are you enjoying it?

Adii: I have my good days and I have bad days, Rob.

Rob: Very cool. Folks, that’s where to find Adii. Thanks so much for coming to the show, sir.

Adii: Thanks for having me, Rob.

Rob: Thanks again to Adii for coming back on the show. It’s always a pleasure talking with Adii. I’ve known him for many years and I have a lot of respect for what he’s built. Thank you for joining me once again this week. I look forward to coming at you in your earbuds again next Tuesday morning.

Rob: You guessed it, it’s another episode of Startups for the Rest of Us. This is episode 532 where I had the pleasure of sitting down with someone I’ve admired for a long time. His name is John Warrillow and he has written a couple of books—now three books—on selling companies. It’s not SaaS or startup specific, but I really respect John’s experience building and selling his own companies. His first book, Built to Sell, had a pretty big impact on me as we were going through the experience of selling Drip.

I was honored to get him on the podcast today. He is a big name in the M&A space, and his book was just released last week. It’s called The Art of Selling Your Business. We effectively just talked through a few pieces of advice John has, and I asked him questions about all types of stuff. He has such a myriad of experiences. It’s a really good conversation even if you’re not selling today. The thing I like too is he’s not selling services. He’s not saying you should sell your business or here’s how to do it and now pay me to broker you. He’s not a broker. I just really appreciate that aspect of what John does.

Before we dive into that, we have a new podcast review from Tax Podcast Fan in the US, and they say five stars, “The OG SaaS podcast. I’ve been listening to this podcast off and on for at least five years. So much actionable wisdom.” Thank you so much. We have 875 worldwide ratings, not all have reviews but I would love to get to 1000 ratings. If you haven’t clicked five stars on the Apple Podcast or whatever podcast you use, I would really appreciate it.

If you haven’t heard, TinySeed batch three applications are open. They’re open for about another week from today from when this episode goes live. If you run a SaaS company, bootstrap SasS, that’s at least doing $500 a month in MRR and up, you should apply. If you’re interested in getting mentorship, advice, and being in a batch experience where you’re in the trenches with other founders, as well as the funding we offer and unfettered access to myself, Einar Vollset, and other knowledgeable SaaS folks, I would encourage you to apply. Head to tinyseed.com/apply.

Also, if you feel like maybe you’re not ready yet, we are going to be running another application process later this year. We raised TinySeed’s second fund, and it allows us to start funding more companies because that’s been the issue to date. We get more quality applications for good businesses that we’ve been able to fund based on the first round of funding we raised. Tinyseed.com if you’re interested. With that, let’s talk about The Art of Selling Your Business.

John Warrillow, thank you so much for joining me on the show.

John: Good to be here.

Rob: It is a pleasure to have you, sir. I think I mentioned this to you. I came on your show Built to Sell Radio a few months back. I think I mentioned it on there that your first book about selling companies called Built to Sell: Creating a Business That Can Thrive Without You was something that I read multiple times as I was going through the exit process with Drip.

Then I stumbled upon Built to Sell Radio and I thought is this going to be the typical kind of fluff around selling a company where they don’t dig into real stories? I was blown away by how much information that you’re able to convey and how helpful your examples are on Built to Sell Radio because they’re real companies. You interviewed, in my memory, services company and there are some tech companies, but there’s an awful lot of physical products.

It just feels like it’s not these Silicon Valley—I sold Instagram for a billion dollars in a week—stories. What I see is the more true look at what it’s like to sell a company. Do you hear that a lot?

John: No, but it means a ton for me to hear that from you. You’re absolutely right. We try to interview the real entrepreneur. Our sweet spot is a deal that’s $1 million to $20 million of value, they’re life-changing events for the entrepreneurs who experience them, and they will never show up in the headline. That’s the sweet spot for us.

We try to unpack those. We try to understand the pitfalls to avoid, the mistakes to avoid, and some of those successes. You are an incredible example of that when we had you on. It was one of the best-rated episodes of all time. I’m grateful for you to be on our show too.

Rob: Absolutely. As we are recording this, you’re launching your book this week. This will go live next Tuesday. Last week, in essence, your third book in your trilogy about selling your company is available now. Honestly, I have a preview copy. I’m going to buy the audible. I got an audible alert today. I’m going to go buy that version, but folks, seriously, you can have a Kindle version for $10. You can go to Amazon, any local bookseller, and Audible for an audiobook if you want to check it out.

The book is titled The Art of Selling Your Business, subtitled Winning Strategies and Secret Hacks for Exiting on Top. The way you framed it to me—I hadn’t realized there was a trilogy. I had read Built to Sell, as I said, and I had noticed you wrote a book called The Automatic Customer, which is about getting subscription revenue.

I never read that because we run SaaS companies and that’s built-in for us. I didn’t realize that you were then going to make a capstone, The Art of Selling your Business. Could you talk through a little bit? I’m guessing a good chunk of the audience has heard of or has read Built to Sell because it’s popular in our circles. How is The Art of Selling your Business different from maybe the other Built to Sell or the other two?

John: Yeah, sure. Built to Sell is how do you build a valuable company structuring so that is not dependent on you personally. The Automatic Customer is all about recurring revenue. You’re right, for a SaaS company, that’s old news, but for a lot of businesses, that’s a new way to think. There’s nothing faster that will take you from a multiple […] to a multiple of revenue when you go to sell your capital and then have recurring revenue, which is the subject around The Automatic of Customers.

The thing that is really interesting is I often—not these days given the pandemic—get asked to speak to entrepreneurs. When I talk about either The Automatic Customer or Built to Sell, oftentimes, the questions the audience has at the end of my speech have nothing to do with my content. They’ll be like, yeah that was great. I really appreciate recurring revenue itself, but what I really want to know is how do I avoid an earnout or that was great but what’s an escrow?

I realized that there’s a real appetite among entrepreneurs to know some of the knots and bolts, the best practices, the hacks for selling a company—the actual transaction itself. That was the idea. It’s really build, accelerate, and then this last book, The Art of Selling Your Business but harvesting the value you created. That’s the back story.

Rob: Very cool. I think one of the reasons I was drawn to Built to Sell, originally—and your writing in general—is not only was it referred to me by multiple people, but there are so many books written by people who have never done it. That’s okay, but it’s more of a journalistic approach.

Prior to writing your books, you started and exited four companies including selling one to a public company. Then you went and wrote your book, you started your podcast, now you’ve interviewed hundreds of founders in-depth about real exits, as we’ll continue to say—the $1 million to $20 million, which is a vast majority of what companies will sell for, I’m guessing on this earth. It’s like the $1 billion exits are just the outliers.

Listeners, if you’re listening to this and you’ve never heard of John or his books, he is both a practitioner and now someone who has a broad range of knowledge around this—obviously having written three books and done these interviews.

I think I want to start with a question of, if a founder is listening to this and they’re thinking, should I sell my business or when is a good time versus a bad time to sell? How can a business owner know or think about when is the right time to sell their company?

John: Right now, a lot of people are asking that question because the pandemic has caused a lot of founders to suffer. In the SaaS world, it’s a bit different. Technology, in many cases, is swamped through the pandemic relatively unscathed. But the old school economy has been crashing, in particular, a lot of service businesses. That’s caused a lot of business owners to want to sell, they want to get out. Of course, the business itself is not always in great shape.

The counterbalancing force, I think, right now is that interest rates are so low. The biggest majority of deals that get done in this space we are talking about today are funded by private equity groups. They run on basically good debt. They run on good debt terms. When a private equity group can get debt cheap, it accelerates their appetite to buy businesses.

Right now is a funny time because, on one hand, you think it’s a terrible time to sell your business. On the other hand, given low-interest rates, it’s actually a very good time. You’re seeing M&A markets reflect that. I think it’s a unique time in history too to be thinking about this topic.

Rob: In the conversations I have both with founders I’m invested in and listeners of this podcast, MicroConf attendees, and such, I have heard that there are definitely a lot of transactions happening. Maybe, to your point earlier, SaaS was lucky because SaaS is still growing across the board, and in some cases has been accelerated by the pandemic.

John: Not to state the obvious, SaaS company, you can still use it at home. It’s a big deal. As good as it is right now for a SaaS company, I think we run the risk of writing it over the top. Have you ever had Rand Fishkin on your show?

Rob: I haven’t yet but Rand is a friend of mine. He’s an investor and mentor in TinySeed. He was going to speak at MicroConf last year, but obviously, we postponed it. I’m invested in his company, so yes, I know Rand very well. Love his book.

John: Yeah, you would have read Lost and Founder. It’s a great book for any SaaS founder. It is required reading. I had Rand on the show, and I had him tell the story of when Brian Halligan from HubSpot came and tried to acquire SEOmoz. Have you ever heard of this story?

Rob: I have. You want to tell it here because it’s really fascinating.

John: Yeah, because it speaks to this idea of writing it over the top and when’s the right time to sell. Halligan comes to Rand. Rand has built SEOmoz software, SaaS business—something around $5.4 million in ARR, annual recurring revenue. Halligan says we want to buy your business. We’re going to give you an offer of $25 million of cash and HubSpot stock. Rand, in his mind, he’s heard this number four times top-line revenue, and he’s on the way from five to what he thinks that year is going to be $10 million in annual recurring revenue.

He’s like four times ten is 40, and here’s Halligan’s offering me 25. Long story short, Rand turns him down and instead takes a venture capital round and the VCs get him to launch a bunch of products in unrelated categories. Long story short, those products failed. Rand actually goes through a period of depression where he’s actually removed by the board by the venture capitalist. The […] venture capitalists often invest is they used preferred shares so they’re guaranteed preferred return.

I interviewed him after this all went down and I said, what’s your stake in Moz worth these days? He’s like, I don’t think it’s actually worth anything because once the VCs get their preferred return, there’s nothing really left for us. I said, wow. He’s like, what’s worse is I’ve got to spend the bulk of the rest of my assets—the cash that I have—on elder care for my grandparents. I said, out of interest, what would that offer from Halligan now be worth given the increase in HubSpot stock? He said it would be worth close to $200 million.

Rob: Oh my goodness.

John: Anyway, I don’t mean to be the bearer of bad news, but it’s an indication or an illustration of writing it over the top when a glib answer to the question when’s the best time to sell? It’s when somebody makes you an offer because, at that point, you’ve got negotiating leverage. You’re not courting them, they’re courting you. You can use that to your advantage, but there is the risk of writing it over the top meaning not selling when someone offers you a reasonable good sum for your company.

Rob: That was definitely something I was concerned about back when we were running Drip and building it. It was growing quickly but there were a lot of competitors. The stock market valuations of public SaaS companies were climbing, climbing, climbing and it was about seven times revenue. Then it got cut in half in January of 2016, which is right around the time there were a lot of people sniffing around at that point.

It was down to 3.2 or something of revenue, and suddenly that became a multiple that potential acquirers were going to base their offers on. Not to say you wouldn’t negotiate against that, but that was an instant justification of SaaS isn’t worth this much anymore. I remember thinking uh-oh, did we ride this over the top? We’ve had this sustained growth of the stock market and of the economy. At that point, it was from basically 2009-2016, seven years. It starts to feel a little long. We’re even further into that now.

I know that I’ve predicted five of the last two recessions, but I do as a startup founder. If you get that offer, it’s tough to walk away. If there’s an offer for enough money, you never have to work again, you really have to ask yourself do I want to walk away from that? And at the possibility of doubling that in the next year or doubling them in the next two or three years because there’s just always a risk.

I don’t think you and I want to be the sky’s falling about it. Anytime an offer comes by, you should sell blah, blah, blah. But what we see in the movies or what we read on TechCrunch of it sounds like every company gets an offer every few months, and that’s not the reality that I’ve experienced. Would you agree with that?

John: I agree 100%. You’ll get those fishing letters from brokers who say, I’ve got a buyer that wants to buy your business. Those are usually not true or disingenuous. You’ll also get a lot of fishing letters from private equity groups and those are sourcing agents. They’re just trying to get a proprietary deal. A prop deal is where the acquirer has proprietary, unique, or exclusive access to buying your business. It’s a recipe for making sure you sell your business for much less than it’s worth. They are bad actors out there who are trying to, essentially, prey on your naiveté or your ignorance about the process. You will get those letters. Those are different from a genuine, large, recognizable company that comes to you and says look, we’ve seen what you are doing and we want to buy your business.

In your case, Leadpages came to you. That’s a very different conversation than a chop shop that’s just basically cranking out letters that basically swipe out the first name of the person. You can quickly discern those by asking and responding thanks for your interest. Tell me, what specifically about our business did you find most compelling. Most of the time they’ll stutter because they have no clue what your business does.

Rob: It’s a mass cold email. I think that’s a good point to raise, and piggybacking on that, let’s say I’m a startup founder. I’m a SaaS founder. I’m doing $1 million, $2 million, $5 million and I do get an email from a company that—whether it’s private equity or whether it’s a strategic, potential acquirer—are probably much bigger than me. They probably have done this a lot more times than me, and they, in my mind, have more leverage. What’s the best way that you would advise a startup founder to try to gain leverage when negotiating with a player that is so much larger or more experienced than they are?

John: Piggybacking on the last comment, I would definitely say getting multiple offers gives you that leverage. I’m reminded of James Murphy, I interviewed him for the show. He developed something called Viviscal, which is a hair loss treatment for women. It turns out, women lose their hair for different reasons than guys do. He developed this hair loss treatment. He became this huge success. Got Reese Witherspoon to endorse it. Got it to $50 million in revenue, not totally ARR but annual revenue, and he went through the process.

He got 12 bidders for the company, and the best offer at that time was I think €103 million, they’re based in Ireland. The 12 offers were perfect because that gave him great leverage. He played one off the other, threw a whole process, and got down to two offers both of which were then increased their offer to €130 million. And then of course he went through a second round of playing one off of the other and ultimately got €150 million from C&D, the ones who own Trojan condoms along with a bunch of consumer packaged goods.

The moral of the story is he never would have been able to gin up the offers that much had he not started with 12 really good ones. He’s a tiny company relative to C&D, but it was the recipe he needed to punch above his weight.

Rob: How does one do that? I’m imagining you get this email and it’s like I guess I should start a conversation. Are you willing to sell? And typically, what I did—and the advice I’ve heard—is you play hard to get. Of course, you can always reply with everybody has a price type thing but you don’t want to act too eager like I’m really looking forward to it. What is your first response to an email like this as a founder?

John: To an email from a potential acquirer? Like legitimate you vetted that you think are real?

Rob: Like you recognize the name like Facebook. Facebook Corp Dev emails me and says, hey we’re looking for a strategic acquisition in your space. I know they would never do that upfront, and there’s a bunch of code words that they use about partnerships. But when you get to that point, how do you interact with that from the start to try to balance hard to get but also wanting the process to continue with the conversation.

John: I think there’s no harm in having that conversation with a strategic acquirer, and I think going into that, what you’re going to want to do is arm yourself with an entire bucket full of what questions. What questions, of course, are open-ended questions that elicit the creativity of the person you’re asking the question of.

If I was going to a meeting with Facebook Cooperative Development, I would have 10 or 20 questions that start with things like what was it that you found in my company that you were interested in? What do you think the strategic fit is? What do you think some of the barriers would be?

Basically, what you’re trying to do is dominate the conversation. You’re trying to get them talking 99% of the time. The reason you use what questions is they are open-ended and force an answer, and you keep control. Just like a good salesperson in a consultative selling context would never let the prospect take control of the conversation, equally, you never let the cooperative development person take control.

You want to be on the offensive. When I say offensive, I’m not talking about you talking. I’m saying you pushing them to keep talking. That’s the way you’re going to take much more information out of them that you’re going to give to them. The idea of getting suckered into (if you will) a proprietary deal or a prop deal—which is what these strategics call it when you start negotiating with them independently—means you’re going to give up a lot of negotiating leverage.

I think it’s okay to have that conversation. You just don’t want to give up too much information. Information in an M&A process is valuable. I’ve got a crude analogy in the book, it’s like a striptease. I know it’s terribly crude and not very politically correct, but in essence, the selling of your business is somewhat like a striptease. Where the information about your company—your ARR, your net churn rate, your whatever—that’s all your clothing. You want to leave it on but undress in a very strategic tantalizing cadence, which is designed to maximize your attractiveness in the eyes of an acquirer.

It’s all done very deliberately. I had someone ask me recently. Someone’s looking at acquiring our business, should I share my QuickBooks login information with them? And my answer was, no, that’s a little premature. Again, information about your business is very precious. It’s to be doled out or dripped out (to use your word) very slowly and deliberately.

Rob: Yup. And get an NDA before you give MRR. That’s always my typical advice to founders. Why would I give my revenue to someone without having some type of NDA signed?

John: An NDA is going to be a good proxy for interest because acquirers don’t like signing NDAs because it exposes them to liability. If you’ve got a tire kicker, someone who’s just sniffing around your company to get competitive information, they’re unlikely to want to sign an NDA. Whereas if you got someone genuinely interested, they’ll sign an NDA.

Rob: You mentioned earlier a proprietary process where basically you don’t have other bidders. You don’t have a competitive bidding war in essence that you set up. I know that there are folks who run these processes. My co-founder with TinySeed founded a company called Discretion Capital, and it does sell-side processes for SaaS companies. They’ll contact a bunch of private equity, they’ll contact a slew of strategics, and they run that process to create a bidding war.

When you said that the guy (I forgot his name) who’s selling earlier had a dozen offers, that is crazy. That’s amazing to have a dozen offers. Is that what he did? Did he run a process himself? Did he get help to run a process? How does that usually look like? Because it sounds, for me, I’m not big into spreadsheets, the MBA stuff. I’m a startup founder who’s building a business. It sounds complicated and, frankly, a little scary to me. How does that work out?

John: Dan Sullivan, the guy who […], talks about these things being who problems not how problems. What I mean by that and what Dan means by that is that these things—finding multiple bidders for your company—is something that we as a founder think is our job and actually, it’s not our job. It’s an M&A professional’s job to find and acquire for your company. That’s what they do.

Instead of trying to figure out how to do it yourself, I would—in all cases—hire an M&A professional. That’s not what I do for a living, so I say that without trying to sound you can’t hire me to do that. I’m not trying to make a commercial for me. But I think they are worth their weight. They’re going to create competitive tension for your deal.

I think the only exception to that, I interviewed a guy—Peter Kelley—and he built the SaaS company for online auctions of used cars. It’s not a sexy business, but it’s basically an auto trader for used cars. Where if you’re a car dealer, you can buy your inventory on this website. The competitors in that space, there are three giant, old school auctioneers that own that space. They are old school. The big car goes on the conveyor belt and the used car dealers sit there with a pencil and paper and write down the specs and make an offer. It couldn’t be more old school.

All three of these giant auctioneers had approached Peter about buying his company. Peter, for a variety of reasons, decided it was time to sell. In that case, he just went all three and said, okay, you’ve expressed interest. Make your best offer. He knew who they were. He did not want to run an auction because he was afraid that if he told BMW and Ford about his business model, they would create competitive auctions. He wanted to keep it very, very close to these three companies. He was very sure they already wanted to make an offer.

That’s a fairly unusual circumstance. In that case, you might run your own process. But again, in almost all other cases, I think an M&A professional is going to really pay for themselves by creating this competitive tension.

Rob: I would agree. I think that’s a mistake that a lot of founders make, myself included, of we start our company and you’re doing everything. You can learn things quickly and you feel like you’re doing really good at learning and picking up new skills. This is a skill that is not something you can learn easily.

In fact—I’ve said this many times—when we sold Drip, one of the first things I did as it got serious was to hire representation, essentially. A broker who acted as an investment banker, an adviser on our side because he had done dozens and dozens of deals—tens of millions, hundreds of millions—and just knew what was standard and knew when to talk me off the ledge. It’s a very emotional process, as a lot of people talk about. That is one thing.

Same thing with me. I’m not selling anything either. I’m not a broker. It doesn’t matter to me if folks hire a broker or an adviser to do this. But I think it’s as you said, worthy of gold, not only for the advice that you get but for the mental side of things. The reassurance that I’m at least going about this. It’s like would you sign the contract without a lawyer reviewing it? You’re going to hire a lawyer to do stuff. Why would you construct a deal without someone on your side who really knows how to construct deals well?

John: Yeah. I think you’re hitting on it right with there’s a very practical reason. This is what they do, this is their job. There’s also that emotional reason where they act as that foil. Think about you pounding your fist on the table asking for an extra half-turn multiple extra whatever. The next day, you’re reporting to that individual. You burnt all that relationship capital being just a jackass in the negotiation and now you’ve got to sum up, put your tail between your legs, and say, please, can I have some more budget to do X, Y, or Z?

I think you want to insulate yourself. The good broker can play both good and bad cop, by the way. They can play bad cop. They can insulate you and they can pound their fist. They can also do the opposite. They could be the good cop. When you’re pounding your fist and frustrated with something, they can communicate that frustration but in a much softer way to the other side.

When we’re recording this, I think today Rob—by the time it airs, it’ll be a couple of days ago—is the 12-year anniversary of Sully, if I’ve got it right, landing the plane on the Hudson River. Do you remember that?

Rob: Yeah, I do.

John: I think it’s the anniversary, and I think it’s the perfect analogy for a SaaS founder selling their company. Sully had done literally everything there was to do in an airplane, Sully had done in his 40-year career. He’d flown the first seat, left seat, right seat. He’d gone through terrible turbulence. He’d done everything. He was, in fact, the trainer who trained other younger pilots. He had never in his 40-year career had the opportunity to land a plane on the Hudson River. One-shot, huge stakes.

The same is true for a lot of entrepreneurs, right? We’ve been running our company for, in many cases, decades. We could talk all day long about marketing funnels, hiring employees, and NDAs. But when it comes to the mechanics of selling, it’s just not something you practice every day.

Rob: Yeah, indeed. You may do it once or twice in your life, but there are people who’ve done it 20, 30, 40 times. If I have a marketing campaign, I buy some google AdWords, and I accidentally leave it on or I get low clickthrough rates, I might burn tens of thousands of dollars, depending on the scale. If you sell your company poorly and you don’t negotiate for things that maybe you should, you can leave literally millions of dollars on the table. That’s why this is important.

John: I interviewed a guy, Kris Jones, have you ever heard Kris in the show? He ran an affiliate marketing program called Pepperjam. Do you know Kris?

Rob: I haven’t heard of him.

John: Good guy, and I interviewed him on my show about this idea of leaving money on the table. He gets a call from my Michael Rubin who was the Founder of GSI, sold to PayPal—a huge, multi, multi-million dollar deal. Michael Rubin calls up Kris and says, come down and see me. I’m intrigued by this company, Pepperjam. What are you guys doing?

Kris goes down and he’s expecting a one-on-one meeting with Michael. Instead, he walks in on Michael’s office and there are his chief financial officer and his chief counsel flanking him. Without even exchanging, hi, how are you? Michael says to Kris, what do you want for Pepperjam? Kris is like, I was expecting a conversation here. Michael repeated. He’s like, what do you want for your company?

Kris blurted out a number, feeling on the spot. Rubin turned to his chief counsel and his CFO and said okay, I think we can get a deal done. What he was communicating to his lieutenants was, don’t pay a penny more than the number Kris just said. Kris, upon reflecting after being put on the spot, he says, I probably should’ve answered that differently because I put a ceiling on which I’m never going to sell beyond. It’s just one of the mistakes we make when acquirers approach us and say what do you want for it? We’re under no requirement to answer that question. In fact, I think answering it is usually a mistake.

Rob: Right. That’s good advice. There’s something else in your book that I’m really intrigued by. I like mental farmworks, I like rules of thumb, and I feel like this 5-20 rule is an interesting rule of thumb and I never heard it anywhere else. Do you want to tell people what that is?

John: Simply put, the 5-20 rule means that a company that is going to acquire your business is likely going to be between 5 and 20 times the size of your company. Now, that’s not always going to be the case. Clearly, Google makes acquihires all the time, and they’re thousands of times more. But it’s a rule of thumb, and it means that the most likely acquire for the companies, I think in our community—and I say that your audience if you will—they’re likely not going to be Google, Tesla, and Facebook. It just doesn’t move the needle for them.

But most likely to get an offer from a private equity group. Someone rolling up SaaS companies together because they’re generally in that space, and you’re going to be a material acquisition for them. But it’s also not so big an acquisition that it’s going to put their company out of business. As you look out on the landscape and say, who’s most likely to buy my business? You might throw Google, Tesla, and Apple on your list. But realistically, it’s probably someone slightly smaller, again, between 5 and 20 times the size of your company.

Rob: Nice. I like that. I think it makes sense. What you said, use the phrase acquihire and most folks have heard that. But that’s different than what we’re talking about. We’re talking about selling your company and getting a really great multiple on revenue. That’s to strategic or private equity, and there’s a whole process that goes on there.

Acquihire is when there’s a really small team—oftentimes just the founders—like you said, Google or Facebook comes and says, we like the tech you build. We’re probably going to kill the tech, we just want you to come work for us. They give, typically, it’s a lot of stock. You might get a half-million or a couple of million dollars in public company stock. Is that how you describe an acquihire as well?

John: That’s exactly right. Really, they’re BATNA, Best Alternative To a Negotiated Agreement—in other words, their plan B—is they’re going to hire a recruiter from […] or some fancy recruiting house and they’re going to go hire for your people. They’re just doing the math and say, okay, to get a CEO, I got to hire a recruiter, a head hunter, and it’s going to cost me $100,000. And then I got some VPs, that’s going to cost me $80,000 each. It’s $600,000. Give them some stocks and yeah, you’re right. Kill the tech, we just want people. That’s an acquihire.

Rob: I want to ask you if there are any—evil tricks is maybe a strong word—worst practices like a Fortune 500 or private equity group might use to prey on a more inexperienced founder?

John: There are tons of them, that’s why I dedicated a whole section of the book to the things that acquirers do that you need to look out for. I think probably the most damaging is something called re-trading where you agree to a price for your company at a letter of intent stage. When you sign a letter of intent, you’ve got to sign a no-shop clause, meaning you’re not going to continue to negotiate with anybody else—like getting engaged, you agree not to see other people.

At that point, the leverage in the deal goes from you as the seller having most of the negotiating leverage to now with all in the hands of the buyer and they know that. Re-trading happens when they use that leverage to manufacture reasons to lower the price they offered you at the LOI. That’s an evil trick they use because, first of all, they know they’re probably dealing with someone who’s going through this the first time. That you’ve probably told your employees, you’ve told your spouse, you bought the ski house in your mind, and you’re now very emotionally committed to selling.

They just say, well, we’re going to drop our price by 10%. You say, why? And they say, well, that’s just our decision. You have very little recourse. In a letter of intent, it’s usually non-binding, meaning they can walk away, you can walk away. But if you do walk away and go back to the other people you had at the table before, they’re all going to wonder what they found in due diligence. What’s lurking in your closet? What skeletons do you have that they found? They’re going to take a very skeptical view of your company if you say, yeah, we were going to do a deal but it fell apart. They’re going to just really highly scrutinize you.

Re-trading is a fact of life. It’s one where you can defend yourself against it, first of all, by hitting your numbers. If you have numbers that you put in a plan that you’ve shared with an acquirer, during due diligence, you got to hit those numbers. Equally, there’s illegitimate re-trading, which is the one I’m talking about where it’s done for no other reason other than because they can.

Rob: That’s crappy. You talk about that a little bit in Built to Sell, and I had heard of folks doing that. Luckily, I’ve had cursory involvement in dozens of exits where either a founder just gives me a phone call and says, hey, I’m thinking about selling and we talk about it. And I haven’t heard that happening, but obviously, that’s rough. I would have a tough time working for that company. I would feel like I got screwed.

John: Again, you’re emotionally so far deep into the process. I just did an interview on the show, I don’t think it’s gone live yet when we talk. But it describes a two-year selling process where the acquirer made an offer, they both mutually signed a letter of intent, and then the acquirer couldn’t come up with the money. They drag them out, drag them out, drag them out for nine months, and then they bailed and it went on.

That happens and it’s a dirty underbelly of the world of acquisitions. The other one that comes to mind around tricks that big companies use is tying your earnout to something that is completely out of your control or so outlandish that you’re never going to hit it. An earnout, of course, is where you get some cash upfront and then there’s a future payment. It’s less common in a SaaS business. Many of your listeners, hopefully, will be able to avoid an earnout. Some of them, especially those in the service business would certainly have to deal with an earnout.

One of the classic tricks is to tie an earnout with thresholds that you have to hit along the way in order to unlock the budget to hit the next gate. I’m reminded of a guy named Rod Drury. Rod started Xero, the cloud-based accounting platform that you’ve heard—a big competitor of QuickBooks. Before he started Xero, he actually created a company called Aftermail, which was a way to archive email and it was a very successful company. Built it up, sold it for $45 million. That was the headline number.

But it was actually—after we unpacked it on the show—$15 million of cash, the rest in an earnout. Rod, as you can imagine, he’s a young guy, he sells his business for $15 million. This is life-changing money. It blew his mind. He had trouble getting back in the driver’s seat. He had trouble hitting his first gate, which would’ve unlocked the budget to help him hit the earnout. Anyway, six months later, he bailed and walked away from whatever it is, $30 million, that he stood to gain if he stuck it out for three years.

But what he realized was, he’d signed up for this thing that he had no chance of hitting because he needed six months just to sober up and unwind from the sale, which he just didn’t give himself. He missed the first gate, and then it’s impossible to reach the next.

Rob: That is something that I tell founders. I was actually talking to a founder literally right before this call with you and me. He has an offer, and it’s a life-changing—never have to work again—number. We were talking about what that means. The advice I often give is when you sell the company—if you do have an earnout and you still have to work—it gets a little easier because you can breathe easy like wow, I’ve taken a lot of risks off the table. But it’s tough to keep your head in the game. I think that’s pretty common.

John: Did you have an earnout with Leadpages? I can’t remember.

Rob: Yeah, we did.

John: How was it?

Rob: It was relatively short. They were very reasonable and we also negotiated pretty hard to keep it short. For us, it actually wasn’t bad at all. I don’t know if we got lucky or it was the judgment that we did. We chose to sell to Leadpages rather than some other interested acquirers because I did trust that they were going to treat us well and they did. It wasn’t based on any of the got […] numbers. There were no milestones that I felt uncomfortable with, if that makes sense. In the end, it was definitely a good decision for us. No regrets there.

John: That’s fantastic. If you could get your earnout tied to something other than earnings, it’s ironic even the name earnout. But if you could get it tied to a goal like a topline revenue, even then you’ve got probably a little more control. The problem with tying an earnout to your earnings is, of course, once you’re at the vision of another company, you lose control over your financials. That gets done by head office. They can oftentimes graft other expenses under your P&L because head office expenses. It just gets messy trying to control the expression of profit when you don’t control it anymore.

If you have to deal with an earnout, getting it tied to something more like revenue or in your case, launching of a feature. That’s way, way more in your control.

Rob: Yup. As we wrap up, three years ago, if a founder were to email me and say, hey, I’m thinking through this exit. Maybe they have no offers, maybe they have an LOI, whatever it is. If I have time, I always jump on a 30-minute call just to chat with them, just to give them some moral support and talk through the mental process. But I also recommend that they listen to at least a few episodes of Built to Sell Radio just to get their head around how it might be, and I recommend a few books. It used to be Built to Sell and Finish Big by Bo Burlingham. I really like that book. I read it multiple times as well as we were exiting.

Now, I’ve added two more to that list. There’s one called Before the Exit by Dan Andrews. And you actually interviewed his co-founder, Ian Schoen, on the show many years ago. They had a cat furniture and valet podium business. Before The Exit: Thought Experiments For Entrepreneurs is a good one. And, as of today, I’m adding The Art of Selling Your Business. Again, if you’re thinking about selling your business or even if you’re not, this is a no brainer. Just spend $10 or $20 and get educated.

Obviously, John, you’re a wealth of knowledge, and I really appreciate you taking the time on the show with me today.

John: Thanks, Rob. It’s great to be with you.

Rob: Thanks again to John for coming on the show. It’s interesting, I know that I talked a few times during the interview about how you should just go out and buy the book even if you’re not thinking of selling a business. I really mean that because this is the type of thing where I’ve gotten to the point where for a $10 book, $20 audiobook, or one Audible credit, however, you think about it, it’s not the cost of it.

The real cost is the time that you have to invest because we have these big lists and we have so many priorities. I’ve read through The Art of Selling Your Company and I know that anything that John Warrillow puts out is going to be of that high-quality bar that it’s going to be worth your time at some point.

His way of thinking around negotiation. I love the 5-20 rule. There’s just a lot of nuggets in his brain that he has put in his three books, frankly, that it’s one of those that I think is a good thing to just have. It’s good knowledge to have in your back pocket as you’re running a company, even if you never plan to sell. Thank you for joining me again this week. I look forward to talking to you again next Tuesday morning.

Rob: Welcome to this week’s episode of Startups for the Rest of Us. As always, I’m your host, Rob Walling. This week, I talked with Colin Gray, the founder of The Podcast Host and Alitu. It’s a really interesting conversation as I follow Colin from his days of building a hobby project in podcast hosting, to hiring a freelancer to start producing shows, then starting to create educational content, creating courses, and finally building a SaaS app on top of that. Very much a stair-step approach in action.

But before we dive into that, I want to let you know that TinySeed batch three applications are open as of yesterday. You can head to tinyseed.com. If you run a SaaS app with revenue, I’d really encourage you to apply. You can head to tinyseed.com to learn more about the funding, mentorship, and guidance we provide in our year-long remote accelerator program.

At tinyseed.com you’ll see an Apply Here button, and it typically takes people 10-15 minutes to apply. It’s not a huge process. I would love to connect with you and learn more about your company if you’re interested in potentially being part of TinySeed batch three.

On a separate note, I wanted to mention that I often get contacted with private questions of folks who don’t want to appear on the podcast. It’s things like, hey, I’m thinking through an exit. Potentially, I have an acquisition offer, some interest, or I need to potentially fire a cofounder—pretty tough things that you can’t have on the air.

But one that I do get relatively frequently—and I think it’s because I’ve been so public about growing Drip and then selling it—is should I sell my company? Should I think about selling my company? What does that entail? Or even, I have an offer, I have someone sniffing around and I’m thinking about selling. What should I do?

I’ll tell you, I receive these emails and it is such a life-changing moment. If there can be such a huge swing from selling for net profit versus selling for revenue, knowing how to do that, what to put in place, and how to go about that process. It’s almost a public service announcement that if you’re a SaaS app and you’re doing at least seven figures in ARR, in my opinion, you should not sell for net profit multiple. You should be selling for a revenue multiple, and these days those multiples are pretty healthy.

You can listen back to the interview I did with David Newell of Quiet Light Brokerage, it was 20, 30 episodes ago. I was saying, if you’re doing $1 million, maybe get 2-3X, and I believe he came back and said no, it’s like 3-4X maybe 3-5X. If you’re doing $5 million or $10 million, the multiples are even larger.

It’s something that I think there’s potentially some confusion. I think if you’re doing six figures in ARR, you’re probably going to sell for a net profit multiple. But once you get into the millions, there are so many buyers, private equity strategists that are willing to pay healthy prices, life-changing money, never having to work again for money.

Frankly, if you’re thinking about doing that, I would encourage you to reach out to me. Drop me a line. You’ve had an offer, you’ve had someone sniffing around, or you’re thinking about doing that, I’m always happy to at least at a minimum have an email conversation about it. Sometimes I’m able to jump on a phone call, and I know people who do the sell-side representation of SaaS apps and maximize that value.

There are a couple of founders that have asked me for advice and I’ve essentially laid out the options as I see them. There are brokers, there is the sell-side representation, there is sell-side SaaS representation much like Discretion Capital, which was founded by Einar Vollset, my cofounder with TinySeed. Depending on where you are, what you’re thinking, and what you want to do, there are ways to maximize that value.

Maybe I’ll do a whole episode, maybe I’ll get Einar on here at some point and talk about how to maximize that value. We have chatted about that on the podcast a bit, but in my mind, it’s just very important that the value you build in your company. If you’re going to exit, be deliberate about it because it can be the difference between selling for $1 million and selling for $5 million, if you sell it well and you run the right process.

I’m just extending an open offer. This is the type of thing I’ve been in the business of helping founders for almost 20 years now. In the business, I mean doing it for free effectively through the blog and the podcast, and mostly free through a $20 book. It’s important to me that founders don’t get taken advantage of and that as founders, it’s so hard to get that base hit and to make that multimillion-dollar business. When you exit, I want you to get the maximum value of it.

If you’re not going to sell, that’s cool too. Run the business, be proud that we can bootstrap, and make these amazing, amazing life-changing outcomes for ourselves. But before you make a permanent decision like selling, I really want you to check out all your options. Look at the landscape and certainly feel free to reach out to me anytime with such a big decision as that.

With that, I’d like to dive into my conversation with Colin Gray, the founder of The Podcast Host, which is a great educational website about starting podcasts and the SaaS app, Alitu. Let’s dive into my conversation.

Colin Gray, thank you so much for joining the show today.

Colin: It’s a pleasure to be here. Thanks for having me on.

Rob: Today we’re talking about Alitu, which is your SaaS app. Your H1 is really simple podcast editing for people in a hurry, and it’s software that helps people edit their podcast. You built this actually on top of an info product audience that you had built. So thepodcasthost.com is your hub. That’s where you put out your podcast, your videos, and a lot of blogging and written content. Then you sell courses or you sell membership on there as well. It’s very reasonably priced by the way.

I was clicking around, looking at one of the courses thinking, I want to get this. You have your Podcast Host Academy. It’s like $225 a year, US. I was thinking, I might do it just for this one piece of it. Do you really get all the courses for that?

Colin: You do. Funny you mentioned that because something is going through my head at the moment to raise that price.

Rob: I was thinking about that actually too. For me anyway, I’m in a different place than I was 10-15 years ago, but I was like that seems incredibly reasonable for everything you have here.

We’ll go through the timeline of how you built that, but in essence, today, Alitu is—after two years of the launch—doing about $45,000 a month in MRR, that’s US. Although you launched the podcast host 10 years ago, we’ll cover this, but it kind of feels that you got really serious about it in the 2014-2015 range and then started thinking about software. Of course, like everything, it’s a bunch of false starts. You built something and eventually, it took you almost two, three years when you’re thinking about it to launch it.

Something I do want to touch on is you have this relatively big audience on The Podcast Host already. The people who knew trusted you. It took you six months to get to $3000. I think it’s $3000 US. I’m kind of doing some on the fly conversions here from pound sterling, but it took you six months to get the $3000, and it took you a year to get you to $8000. That had to have been a little tough. Was that a struggle emotionally to have built that audience and to feel like you should just be able to launch something and have everybody buy it and then to take a year to get to that MRR?

Colin: It was, absolutely. I mean at that point, we had a few thousand visitors a day. It was a lot of people visiting the site. I’ve got a good mailing list as well. I thought it was great at the time, probably 5000-6000 I think at the time. I was expecting more, certainly. That first couple of months of launch, I thought we could get up to a few hundred, at least that was my aim certainly.

That first year was tough. I mean, it was all funded through the other sites. The main site, the content site was doing well. That kind of kept my spirits up, but it was quite a few hardpoints that first year for sure.

Rob: Yeah, I can imagine. We’ll dig into that a little later because I do like to touch on this topic of should you build an audience. I can attest that it’s great for info products and that it’s a lot less useful for SaaS. I think you’re probably an example of that. I had no idea—before we started talking—that that was actually your experience. I think it’ll be fun to do that.

For folks listening, when we save the content side, that’s thepodcasthost.com. That’s the videos, the blog, and the course. Then Alitu is the SaaS app that helps folks do the editing. In November of 2010, a decade ago, you launched The Podcast Host. It was a hobby project that you launched—it was podcast hosting for your own shows?

Colin: It was. It was one of those scratch to an itch things where I was running a bunch of podcasts for a university. That was my job at the time. I was a learning technologist working at a university. We started a bunch of podcasts to help teach students. The name was Podcast Host at that time was horribly unreliable at the top at that time.

In fact, one course that was about to run, I had the course starting on a Monday morning and we had to deliver the podcast as a part of it. The whole podcast hosting site went down on a Sunday night and didn’t come back up again until the end of the week. That was the last straw. I ended up just building a WordPress site and setting up podcast hosting myself on there. That’s how it started. That was why it was called The Podcast Host—an unimaginative name.

Rob: That’s so interesting, but you’re not still hosting podcasts today. How long did you do it and why did you kill it?

Colin: It was about a year and a half I did it and I ran that as a sideline. It grew up to about 150 or so podcasts at the time. I killed it because, at the time, there were a few incumbents there. I mean they haven’t been running for that long. It wasn’t that big of an industry at the time, but it just felt almost already that it was commoditized.

The prices were really low. It was a really low monthly fee, but the support was huge. Partly because the tech was pretty undeveloped at the time actually. It was hard to run a podcast back in 2010 still. I always got a lot of questions around the gear, around the distribution, all that kind of stuff around the hosting. A lot of that hadn’t been solved necessarily at the time.

I’m sure if I’d grown a team around it and got a lot more support around it, I could have done something with it. It felt like really hard work at the time. I’m not usually averse to hard work, but it felt like hard work I wouldn’t enjoy. That’s pretty much why. I thought the content would be more fun. There were other things I wanted to do more.

Rob: I wonder if it’s a question of timing because obviously with new startups, Castos, Transistor, they’re obviously having success, part of that due to Covid. But I think that there is and probably was room for a podcast host. It’s interesting to think that perhaps you were a few years too early.

Colin: Yeah, there absolutely was. I mean looking at the other companies that started around that time and a few years following that, I think probably if I’d been more technical if I’d been a developer, I certainly could have started to build some solutions to solve those problems people are having. The distribution problem and stuff like that, but it just wasn’t the direction I wanted to go.

There was so much customer support I remember that really clearly. We get a lot of customer support through Alitu. For some reason, I enjoy supporting people through the Alitu process—the creating, the editing, I didn’t enjoy supporting people through just the basic distribution, the basic getting their podcast out there. There’s a strange little difference there I think.

Rob: That was the first couple of years. Then you were writing about podcasting. I’m imagining you’re starting to build some SEO traffic, a little bit of an audience. You start this hosting, you shut that down, it’s probably sometime in 2011.

In 2015, as things were building for you, you took on a freelancer to start working on producing shows for clients. You essentially launched like a productized service that helped produce podcasts. That ran for the next five years. That ran from 2015 up until just a few months ago. I think you said you stopped taking clients maybe a year ago, but it ran until then.

What’s the story there? Did you use that revenue to fund everything else, was it a shiny object, or was it a valuable thing, and why did you eventually decide to sunset that?

Colin: It was really valuable. It did a couple of things for us I think. The first one was that it gave me the excuse to take somebody on a staff member because it was paid work. I could obviously see the return for his time. I took on Matthew at the time. Really his first job was to help with that production. We put it out to our mailing list, to the website, and really started advertising it and got on about 5-10 clients right away on a weekly basis. It was just a monthly fee we started with. That gave me the confidence to take him on.

I don’t think I could have done it otherwise. But strangely enough, that only ended up taking up maybe 1-2 days of his time. The catalyst for growing the rest of what we do was to help Matthew give me the content. That gave me so much more capacity to create bigger, greater blog posts, do more research into what we should be writing about, covering, running a podcast with him for ourselves as well.

The client work gave us that in the first place. Really, we got up to a decent MRR itself. It did complement the income of the podcast quite a bit, but it was more the kind of confidence I think to start taking on staff. Once you’ve taken on one, taking on the next was so much easier. Having that little impetus to start really got us going.

Rob: Yeah, I can see that. Then why did you decide to shut it down in the end?

Colin: Scalability essentially. We did enjoy it. We do miss that work actually. I talked to Matthew about this all the time. We always talk about trying to take on some more exciting big projects for clients because it’s pretty fun making those stories for people and working with people to get their story out there. It just takes up so much time.

For the last project that I did, I actually worked on a project directly—the narration, all that kind of stuff. That was just last year. I got to the point where I’d spent two days scripting and narrating a show and realizing how much more value I could have gotten out of that time working on Alitu, working on the marketing for it. While we love that work, it was just not scalable for what we wanted to do. It just wasn’t giving the value to the company that my time should have been given.

Rob: I know what you’re talking about. In fact, now that I am able to work a lot on projects that I want to work on, I have circled back to doing that kind of work. That’s what TinySeed Tales is for me. It’s my ability to sit there, script, and produce a show because I don’t need to focus, grow, and push so hard like I used to on the SaaS apps I was growing. It makes a lot of sense, but I enjoy it. I’m doing that out of choice.

TinySeed Tales, there’s a business purpose to it, but frankly, we started doing it because I really wanted to. I totally get that feeling of man, this is fun, but how do I justify spending two days when I could have grown MRR, launched a new feature, or done some SEO or whatever.

Colin: To an extent, it’s worth it in a way because we created a show at one point called Hostile Worlds, which was a fun audio drama thing around space. Matthew and I created that, that was almost a portfolio piece. I feel like when you’re in a space like ourselves when it’s creative, it’s quite a reputation-based almost that you have to have something good to show that you know what you’re talking about. Especially when we are the creating app—we’re not hosting, we’re not just purely technical. We’re the creating, the creative editing production app.

I think having that behind us and our portfolio does help. I think it was definitely worthwhile, but it was just something to move on from.

Rob: In 2014, 2015, you told me you were running eight different businesses at once, and that it wasn’t as glamorous. Richard Branson runs eight businesses, but let’s just say he has staff in place to manage them. I’m imagining you’re running around with your hair on fire.

The question I want to ask you is between 2007 and probably 2011-2012, I did something similar where I had about 10, at any given time. It was between 8 and 12 different businesses running, but a lot of them were these small websites that were effectively on autopilot until something happened to them. A lot of them were based either on, display ads, or SEO.

They had traffic on autopilot and the conversion rates were consistent. They would generate between—the lowest one is probably doing about $600-$700 a month, and the highest one was doing in the $5000-$7000 a month range. I packed those all together and that was my 4-hour workweek in essence. I worked literally 10 hours a week for a pretty long time.

It was because the businesses didn’t require a bunch of staff—I had some virtual assistants but they were very task-based folks. They didn’t require a lot of staff, they didn’t require a ton of support, they didn’t require a ton of marketing or new features, and I wasn’t trying to grow any of them. I was focused at the time on writing my book and starting MicroConf, and the podcast and stuff.

If any of those had needed to grow, if I was trying to build or grow 8 businesses at once, or 10 businesses, that would have been insanity. For me, it was a lot of autopilots, bouncing around working on what I wanted to do. With that context in mind, in 2015 you’re running eight businesses. Were you trying to grow and launch eight businesses at once, or were a lot of them kind of running themselves?

Colin: Yeah, the former. Definitely trying to grow. I mean, I would have loved to be in a situation where they were making a minimum of $700 and up to a few thousand. This was the time when I was trying to get out of my full-time employment. Around that time, in 2014-2015, I was still doing a Ph.D. Actually, that’s what I was trying to get out of. I was thinking of what I was going to do next.

My approach actually, I had a few like that. I had a few passive businesses, which were content-based, SEO-based. In fact, Alitu we can get into slightly where the story for that came because I bought Alitu as a business directory. That was what the domain was. It was a business directory, alitu.com, which I then repurposed later on. My approach was more I found people who knew the subject, who had the expertise, and I was the technical person behind it.

One example was my brother actually. He crafts beer, runs bars, distributes beer, and so we set up a beer box business. Sending out boxes of curated high-quality craft beer, and it was a subscription-based business. We started to run that. That was one of those experiments for example, and there were a few others like that as well. None of them got to above maybe $1000 MRR apart from The Podcast Host. That was the one that took off. It was the one that could have separated itself from the pack.

I was glad by the end of that year to quite a lot of the other ones that never got past a few hundred. It was a tough year certainly.

Rob: That’s the advice I give to folks—when they ask, should I start two businesses at once or three, or I hear them say, I’m working on these three businesses—is always do one at a time. You can own multiple businesses, I don’t think you can grow multiple businesses at once, because of the focus that it takes. Unless you are in that Richard Branson situation where you have a bunch of budgets and you truly have GMs, or CEOs, or someone who just has the owner mindset.

But if you have task-based or project-based people, you’re going to be doing too much management. It requires too much of that entrepreneurial drive in order to actually grow small businesses where you’re spinning most of the plates. You don’t have all the support.

Colin: I do agree with you that it’s very hard. It’s near impossible to grow that many businesses certainly, even two or three simultaneously. But I do think back to that time and think I didn’t know The Podcast Host was going to take off. It wasn’t at a living level at that point. The other ones didn’t look promising and they could’ve potentially worked. I do see it as a bit of an experiment and worthwhile almost spending at least 3-6 months on that experiment, even if it’s going to be a very, very tough six months.

I’m glad I tried them all. I don’t regret not starting those other ones, which I think I would have otherwise because we had a lot of conversations around them. I didn’t know The Podcast Host was going to work. It’s a tough decision, and you’re absolutely right. You have to make a choice sooner rather than later. I do sometimes think that over-focusing can be slightly dangerous. I’m not sure what the exact […] there but there are definitely different paths.

Rob: I think that’s a helpful sentiment to think about not wanting to limit too early because you don’t know what’s going to take off. In April 2016, you started coming up with ideas to help your existing audience and you want to do something in software. What was that switch, not even away from, but in addition to the content and everything that you’re giving your audience you wanted to make a software play? I’m curious to hear about not only why you made that decision but then how you went about coming up with the idea for Alitu?

Colin: The main reason was competition actually, honestly. It was becoming really hard to sell education and content at the time. For products in our area, there were a fair few people coming out with different courses. There were a fair few people actually starting or running software products and giving away what we would consider a paid course for free as a lead magnet for their software. It was becoming difficult to generate a decent income through that software. I could see that just getting worse and worse in the future.

I wanted to create something that just happened more of a mote. Something that was more difficult to copy. I considered a few different things. We considered the hosting side of things again, considered a few different approaches. Really, the editing was the part that we were asked about all the time.

To create content, we’ve got a bunch of different ways that we ask people questions to get ideas for our blog posts, for our podcast, and all that kind of stuff. The one question that always comes up is how can I make editing easier? How can I make podcast editing take less time and be less technical? I don’t have to worry about what is compression. What’s equalization? What’s normalization? I don’t care about these terms. I just wanted to sound good.

I just thought I’m sure there’s a way to automate this because it’s quite procedural in a lot of ways. Thinking back to our podcast production days, a lot of this, we actually set up templates for people’s shows. It’s actually quite easy to do it week by week. That was what started it. It was that competition side of things, the mote, and scalability as well. Just be able to think about how we could get something that could get thousands of users on here because education just isn’t going that direction for us.

Rob: Right. You’re making some money but not as much as you want it, and I think scalability is often like you said, the big thing people seek in software. That’s spring 2016 and you started inviting testers, I am assuming beta testers. It wasn’t until August 2017, about 15 months later, and then I guess you were actually inviting them in January 2018. That’s like more than a year and a half later, almost two years later. You eventually launched it to paid users in June 2018. It’s like 27 months. That’s a really long time. It feels wrong to me on paper. Did it feel that way to you? Why did it take that long?

Colin. It did. It did feel that long. I think a big part of the problem was I was a non-technical founder trying to bootstrap a software company. I had some income from The Podcast Host, but I didn’t want to take on five developers all at once. I wanted to build it in a way that is sustainable. I wanted to build in a way that was definitely validated so that I wasn’t putting $50,000 into something that doesn’t actually work. I say it felt like a long time and it did feel like a long time, but it never felt like too long. It never felt like too long. It actually always felt like we were moving at a decent pace.

I remember the first four or five months I worked with one backend developer to build the technical prototype. It looked horrible. It was just a terrible interface. It wasn’t designed to be a good interface, but it was to showcase the backend technology, to show that we could do decent processing, bunch all the clips together, add some music with some fades. That took about five months, but there was so much progress. Seeing these little things—the fades are working now, that’s great. The music is fading into the voice, it sounds brilliant. This is happening every time without me having to do anything.

Going into the design, that was another few months. I always felt like a bit of progress every day. Then actually implementing those designs. It always felt like a long time, but I was never in an enormous rush because I didn’t want to ever go unprofitable. We actually never did. We never went unprofitable through the whole thing. I always funded it through The Podcast Host income. I was happy to go at the pace that it went.

Rob: That’s really nice. It’s like a stair-step approach. It’s like your step one and two businesses were The Podcast Host. It’s essentially an information product course that you are selling and you’re bringing in traffic through SEO and content marketing. That allowed you to buy out your time so you didn’t have to work full time for anyone else. To own your time, to invest in a little bit of revenue on top (it sounds like), a little bit of excess to then hire one developer to work on it.

It’s a nice approach. It takes you a lot longer to get there but you can do it profitably. You do it on your own terms. I think just given that amount of time, you have a high likelihood of eventually finding something that’s going to work.

That’s interesting. So you launched in the middle of 2018. You have this big audience, we touched on this earlier. You had a mailing list. You had prime people, and yet you’ve launched to (in essence), after six months you only had about $3000 in MRR. After a year, you had about $8000, you gave me pound sterling, but I’m converting to US dollars, about $8000 after a year, about $12,000 MRR after 18 months, which was right before COVID.

When COVID hit, presumably you had a really big spike because I know a lot of remote communication and podcasts stuff happened. That was obviously a big boon. But even after 18 months, you were around $12,000 MRR but you have this big audience. What’s the disconnect there? Do you think that the audience—a lot of people are aspirational and want to buy an info product or a course that they may or may not implement versus buying a tool, using a tool, and paying for it every month is such a different ball game? That’s my hypothesis. I’m curious, you lived this first-hand, what happened there?

Colin: I think the biggest disconnect in the whole thing—I think of them as two parts. I think one part was that we had to be in marketing the education to our audience a fair bit. They enjoyed our content certainly, but we had tired them out a little bit of the time potentially. More than that I think potentially was that I had slightly underestimated or maybe heavily underestimated how specific the audience was.

We’ve been creating general podcast content on our blog. This may apply to many other areas too. I hope it’s useful, but certainly, I thought we were creating general podcast content and we had a general podcast audience. It turned out that actually the content we are creating, the most popular stuff was actually quite technical.

We were writing about gear. We were writing about software. We were writing about recording, editing, and all that kind of stuff. The people we were attracting—I believe looking back on it—were actually quite technical people in the first place. They were DIY podcasters, which we’re really happy to come in and play around with all the gadgets and the gear. Those people are far less likely to pay $28 a month for something that takes away their technical troubles because a lot of them quite enjoyed playing around with that stuff. I think that was the biggest disconnect in the early days.

I realized that only about 6-12 months in. That’s when we started creating a lot more content that focused on the audience that I hadn’t reached at all before, which was more the businesses, more the entrepreneurs, the solo founders, the people that are trying to grow a personal brand. Therefore, they don’t care about the technical stuff. They don’t care about how to edit, all the terms, and all that kind of stuff. They just want it done for them.

I think that was a big part of it that I hadn’t realized actually how specific or how niche our audience was until we tried to sell them something that was on the opposite end of that niche.

Rob: Once you create that content for the more (as you said), the solo founders or the business people, do they find you via SEO on a monthly basis where they stumble upon an article, they read it, and they go; or have they become part of your audience? When I say audience I mean they’re subscribing to your list, they’re following what you do, and they’re sticking around.

Colin: For sure that latter one. They’ve become part of our audience now because I’ve always been good at the funnel state of things. That was something that always really interested me. I find it quite fun. It’s kind of a game to figure out how to give people content they really want, they’re interested in. How to give them something else they’re even more interested in—sign up to the email list, then get on to the first products, maybe a few dollars, that kind of stuff. I really enjoy that, and as we start to create content that attracted far less technical people. I could see them coming in asking us questions.

It’s always a really engaged audience, I find podcasters. They ask you lots of stuff. They get in touch all the time. They’re not afraid to get in touch and ask for some freebies. We started building that funnel up. They were definitely on our email list. These days actually, I would say we have a good balance.

We still cater to the technical people. We still love rating gear reviews, software reviews, but we do a lot more around just general growth. How to grow your podcast, how to launch a podcast, how to make it sound better without much work. They definitely joined our audience over time. Now that is the main lead generator for Alitu.

Rob: During the last couple of years as you’ve been growing this, was there a time when it was so slow that you thought about shutting it down or that you have a lot of mental or emotional distress around it?

Colin: Do you know what though? It was never the times where it was slow that made me want to shut it down actually. Like I said, I always felt like we were making progress. I always felt like we were making something great with Alitu. I love the interface. I use it for my own shows. I was a big part of the development around it. It was to make my own production easier too. I was always quite happy with that. I’ve always been very careful with the money we spend on it as well. We’ve recruited slowly.

I had impatience in the early days, but I read a bunch of stories. I probably heard on your own show as well, Rob, and elsewhere around people talking in years. At various points, I used to think in months. We’ll get this done by this month, this done by this month, but then you hear the stories of really successful big companies. They all talk in years. We did this in 2018. We did this in 2019. It made me slow down my speed and be happy with that slower pace.

It was good because that never overwhelmed me—the speed of growing users actually. It frustrated me potentially because you’d always want more users, obviously. The points when I actually felt almost ready to shut it down are when we’ve had troubles that caused a bunch of customer support.

For example, one of our biggest mistakes was changing our interface in a way that I thought would really help users. I knew it would help me. It was the way I thought, and we changed the interface in quite a big way at one point on the editing screen. The outcry was absolutely crazy. It turned out that more than half of our users much preferred the old method, and we had weeks and weeks of repair and thinking through how we compromise, do we compromise, and all that kind of stuff?

It’s times like that where I think, do you know what? I write the content. We get affiliate income through that. We get sponsorship. All of that is completely passive. I don’t need to deal with customers. I could go back to that, but I do love helping people in that way—helping them in the podcast easier. That gets me through, but certainly, it was always that rather than the growth speed that almost made me want to give up.

Rob: It’s a healthy way to look at it. I have verbiage in both the intro of Startups for the Rest of Us from time to time, as well as MicroConf on-air that says, we want to build ambitious startups, but we think in terms of years, not months. And as such, we play the long game and don’t burn ourselves out by working 90 hour weeks or something to that effect. That plays into what you’re talking about is you see Josh Pigford from Baremetrics who just sold Baremetrics, yesterday actually. I think it became public. That was a seven-year journey for him.

Even Drip, which seemed really fast, from the time we broke ground on code was three and a half years. That was three and a half years to sail, to exit. That was one of the faster stories that I’ve heard about something. The fact that you’re two years in, I have to imagine that—while obviously, COVID has been a catastrophe for the world—the acceleration of your growth over the past four or five months has to have felt like you’re on cloud nine. Is this one of the most exciting times of running this business?

Colin: Yeah, for sure. We’ve taken on another four staff in the last three months. We’ve taken a part-time support person full time. We’ve taken on a full-time marketer for the first time. We’ve taken on a community and social marketer as well and another developer as well to help us with our audio side of things. That’s exciting, but I am at the moment thinking—absolutely, the extra income has helped us do that but we could hire more. I do think we have a little bit of space to hire more.

Right at the moment, I just think the unpredictability is so high over the next 6-12 months that I’m definitely leaving up a bit of wiggle room in our income. I don’t expect to grow as fast. I mean we doubled in three months. It was actually crazy. But I do not expect—in fact, the growth has already dropped a lot compared to that. We’re still growing steadily, but certainly not that fast. I think it may slow down even more over the winter certainly. I’m leaving a lot of wiggle room, but it has been actually brilliant.

Rob: Did anything break at the seams when you doubled in three months? Was there support tickets falling on the ground? Did any of your tech have any issues?

Colin: Yeah, support tickets were certainly taking longer than we thought. We had a little bit of scalability. It wasn’t even so much actually the infrastructure scalability. It was more of our capacity to troubleshoot. One of the reasons why it is worth going slow, certainly with ours, is that audio is so unpredictable. We deal with so many different types of audio files, so many different types of recordings, and we’re always working on improving how we clean up files, how we deal with different files.

We only have one developer who is a real audio expert in that sense. It was really his time to troubleshoot twice as many little audio nickels, little audio […]. That was our biggest trouble, which is why we took on another audio developer. There were definitely a fair few issues. We’ve got past most of them though, thankfully.

Rob: You’ve obviously had a pretty amazing success. Even though it may sound like it was a slower start given that the large audience that you had back in 2018, being at $45,000 MRR after two years is amazing. Most SaaS businesses we know about never make it that far.

I’m curious if you’ve ever thought—did you build the right product? Because Alitu is editing software, but you could have, in 2018, decided to launch a hosting company. You could have decided to build a podcast recording much like Squadcast or Zencastr. There are a lot of different options for you, a lot of different roads or paths for you to have gone down to serve your podcasting audience. Have you ever sat and thought, did I build the right product, or could I potentially have more success if I had gone down one of these other paths?

Colin: For sure, I have, and I think I did. I think I built the right product for me. I think I’ve heard you talk about the product founder fit? Was that your concept?

Rob: I think it was someone else, maybe Justin Jackson, but I even think someone had said it before him. He’s just done a lot of writing on it. I’m definitely familiar with it.

Colin: Well, I’m sure I’ve heard of it through yourself certainly. I think that is important to me actually because like I said, I tried hosting years back. I just didn’t enjoy the support, the customer questions, the stuff that came about around that area. Editing, production, creating is the stuff I love. That’s why I created The Podcast Host in the first place, the website. I think I could have created a hosting platform. I could have created a recording platform right at the start, but I think certainly with hosting, I don’t have the aptitude for that to compete in what is quite a commoditized space.

There was already a lot of competition there, for example. There’s always room for more for sure, but I enjoy the uniqueness of Alitu. When we started it, there was nothing else like it on the market. Even now, there’s nothing really doing exactly what we do, and I really enjoy that. I really enjoyed the feedback we get when people get in there and suddenly they can edit in such an easy way. They can create this vision that they have in their heads without all the stress around learning things like Audacity and stuff like that. It’s something that gives me so much satisfaction and I love it. That’s what keeps me going.

Like we’ve talked about, there have been more than a few hardpoints. It’s been a slow growth. I could’ve given up many times, but that’s what keeps me going I think. It’s just that feedback. It suits my aptitude to create a product that helps people create.

Rob: That’s really cool to hear actually. It’s like a life vision or mission that you have, and it fits so well within that, it sounds like. It brings you joy to be working on this particular SaaS app, which I think is pretty unique. A lot of people enjoy what they’re doing. I’ve enjoyed building my SaaS apps, but I don’t know if it actually fits into my personal and professional vision in a way that Alitu fits into yours. Congratulations on that, and frankly, congratulations on all your success.

If folks want to keep up with you, you are @colinmcgray on Twitter or @thepodcasthost on Twitter as well as thepodcasthost.com. Colin, thank you so much for joining me today.

Colin: Thanks, Rob. It was great fun. Cheers.

Rob: Thanks again to Colin for coming on the show. If you have a question for me or a future guest, please send it in to questions@startupsfortherestofus.com. If you include a link to an audio file that will go to the top of the stack. I hope your 2021 is doing better than our collective 2020 went. I do hope to see you at an in-person event, maybe at MicroConf, or maybe another startup event here in the next 12 months. Thanks so much for listening. I’ll talk to you next time.

Rob: Thanks for checking out this week’s episode of Startups for the Rest of Us. It’s episode 530. I’m Rob Walling. Every week, we cover topics relating to building and growing startups that are ambitious but sustainable. We know that starting a company is hard. More than half of being a startup founder is managing your own psychology, and that so much of this journey is making difficult decisions within complete information where the right answer is impossible to find through math or data. That is one thing that makes it so hard for us.

It’s great to sit down once a week to think about this, to hear from other founders that are going through it, and to just feel like we’re not alone in this journey. This week I sat down with Derrick Reimer. You may know him from The Art of Product podcast, and he’s the founder of SavvyCal, which is a competitor to tools like Calendly and YouCanBook.me.

Derrick and I take on a bunch of listener questions this week including how to make good decisions on a dev team, whether we have regrets about selling Drip, the effects of web scraping on your business and how you can potentially block web scraping, how much of your journey and success can you share with family and friends, and more.

Derrick and I have known each other for almost a decade at this point. It’s always a pleasure to have him on the show. I think we have great chemistry, and it’s just really comfortable when we sit down on the mic together. I hope you enjoy our conversation.

Derrick Reimer, thanks so much for joining me today.

Derrick: Yeah. Thanks for having me back on the show. Always a pleasure.

Rob: I know, man, you’ve been on several times. For folks who don’t recall, you are the co-founder of Drip that you and I built together and exited in 2016. You had founded a little side project called Codetree that you built up to (if I recall) about $4000 MRR. We talked on this podcast about how you sold if $128,000, right around the time we sold Drip as well. I think you sold a car, a house when you moved here.

Derrick: It was a mass liquidation event, yeah.

Rob: Now, you are working on SavvyCal at savvycal.com, which is online scheduling. If people used Calendly or YouCanBook.me, it’s a similar tool, and you’re getting some good traction with that. If folks want to hear your journey, they can head over to artofproductpodcast.com. Excited to dive into some questions today?

Derrick: Yeah, let’s do it.

Rob: Yeah, I’m stoked. The first question comes from colin@thepodcasthost.com. Take it away.

Colin: Hey, Rob. It’s Colin here from the podcasthost.com and our SaaS product, which is alitu.com—podcast maker. My questions around the SaaS we’re building is the team that we have now, which is growing—we have five developers now on the team. I’m asking about decisions.

We’re starting to struggle with decisions because we have more than just one or two people, we started to have—now and again—disagreements, and not in a bad way. We’re having good discussions around these, but one person will believe we should go one direction, one person believes we should go the other direction. We’re reaching an impasse more often than we used to.

I’m wondering how teams—development teams in particular—should think about decisions when it’s not a black and white decision, there’s no one right answer. This technology has these pros and cons, this technology has those pros and cons. How do you decide? How do you decide which direction to go? What decision to make? I’m curious how you do that on teams, especially […] ones. Thanks for all the content you do, and looking forward to your answer.

Rob: Interesting question. Since I know a little more about Colin’s business, I want to give some background. He and I have actually spoken. I’ve interviewed him for this very podcast. The interview just hasn’t come live yet. He runs a SaaS app in addition to educational stuff for podcasters. His team is relatively small, and he’s not a developer. Just as […] any of that is relevant. I think he said in the voicemail that four developers, five developers—still a relatively small team. What do you think about this topic of making decisions in a dev team?

Derrick: This is a really interesting question because it can get tricky when you have a number of developers on a team who each bring their own varied experience to the table and have their own preferences and certain libraries that they prefer to use. Obviously, we have to contend with this kind of thing at Drip. For the longest time, we were very, very small. It was just me and a couple of junior developers. I got to kind of just call the shots on the foundational pieces of technology that we’re going to use.

I guess, my first piece of advice is someone should be in the leadership position on what the core values are and what the types of technologies you want to use. It really helps to establish some guiding principles. An example being, are we willing to use libraries that are brand new, or are we looking for a certain amount of time that they’ve been around and battle-tested? Do we value a good amount of documentation? Is the library actively maintained? A lot of people on the team already know how to work with the underlying technology, or is it some language that only one person knows and they’ll be the bottleneck on maintaining it?

Considerations like that are practical things you can use to guide technology decisions. Another good exercise is to encourage folks to try to craft a thoughtful pitch for it. And in writing, it’s probably a good way to do it. Just organize your thoughts. If we’re at an impasse and we’re trying to figure out which library to use, state your case and roll through some of those guiding principles that the team has. Does it check those boxes, and use a little bit of persuasion to try to advocate for the piece of technology you want to use.

Rob: I agree with all those points. When I’m thinking about it, there has to be a hierarchy. This is why that exists. While it’s not a dictatorship in terms of I make all the decisions and everyone listens, it shouldn’t be like that. There should be helpful conversations. You can vote if you want. But ultimately, this comes back to who’s responsible for this. Who owns this area of the company?

When I think about having a dev lead, a tech lead, a development manager, or whatever title you want to imbue on them, they are ultimately responsible for the uptime of the app. If it goes down, they should get paged at 2:00 AM in the morning—they or whoever else is on call. That should be shared around. They are the arbiter of these decisions ultimately. I love and I loved healthy discussions we used to have at Drip—both pre-acquisition and post-acquisition. When it was just a handful of us, to when we had an engineering team of maybe 16 or so when we left.

There were spirited discussions, but ultimately, it would come down to a couple of options that made the most sense. And then sometimes, there was just a decision made by the manager or made by one of us, if it percolated up. In Colin’s case—as the CEO or founder, I don’t know (as a non-developer) if he wants to be the ultimate arbiter. But technically, he is the owner of all of it. He is the person who would make the decision if a tech lead didn’t know what to do or whatever.

But realistically, if it’s within the wheelhouse, it’s in the discipline that your developers are experts in, then I would have that senior person be making those decisions. Have its responsibility, its ownership, and it’s the freedom to make the decisions such that they are willing to own them later. If you use a cutting edge, brand new library, know that that has risk, per your comments. Maybe it gets abandoned, or maybe they do a 2.0 update where the entire API changes like a lot of the JavaScript and VC frameworks did back in the day.

There’s a balance here. If every decision is a bunch of conversation and even arguments, something is broken. That’s not how it should be. In general, there’s usually a pretty obvious choice or maybe two. And in general, if you have a team that wants to do the best thing and is keeping the mindset of building an app for the next decade. We need to build stable, maintained components—whether it’s an open-source or not—libraries, and this and that. Oftentimes, there are usually one or two obvious choices based on the language or the tech stack that you have. There’s a leader (so to speak) in the space.

Derrick: Yeah. Encouraging a mature mindset around technology. I’ve seen this among developers as they get deeper into their careers. The first couple of years you’re a developer, you really are in the experimentation phase. You like to pull brand new things off the shelf and play around with hot new technologies. I’ve seen many startups make this mistake where they’re like, we’re going to use RethinkDB for this thing because it’s a really hot, cool, new database. And then come to find out it’s a nightmare to DevOps to keep it up and reliable is a nightmare. It ends up being just an albatross.

I think the more mature developers, oftentimes, become inherently skeptical of shiny new things and tend to—all things being equal—go with the simplest architecture or the simplest technologies that are battle-tested. Even just laying that out is this is something that we, from a practical standpoint, want to do and then try to hold things to that lens as much as possible.

Sometimes you’re going to have to take some risks and choose something where you’re not totally certain that it’ll pan out. But hopefully, most of the time, when you’re making these decisions, it’s a pretty straightforward one.

Rob: And part of that is to use boring technologies. If I were to build a SaaS app again, God forbid that ever happens, I’m only joking. But I would need someone to convince me pretty hard to not use either Ruby on Rails over Postgres or Python Django. They just work, and I like HTML that just gets spit into the browser. I know that some people really like their spinny things like the MVC framework in your browser. It loads it, but that bugs that crap out of me. I’ve just seen too many issues with that over the years.

Yeah, it’s getting more mature, and of course, apps built-in that are doing great and there are pros and cons. But for me personally, there are some tried and true technologies that over time, of course, is Ruby on Rails 10 years from now the choice? Probably not. Technology just doesn’t tend to have that arc. It does get outdated. But I get a look at that maturity curve and pick the things that’ll work.

Derrick: Yeah. One more note on that too is if you’re looking at the Hacker News crowd and a lot of people who are working at really large companies like Google, Facebook, Fortune 500 companies, or whatever where there are large dev teams, you’ll see those types of organizations that are at high scale using a lot of microservices, being a polyglot organization where they just have 10 different programming languages in the mix, and you choose the best tool for the job.

That’s good for the stage that those companies you’re at. But if you’re a bootstrapper trying to just get your initial version of your product off the ground, you do not want to be mimicking what those teams are doing. Because they’re implementing things so that they can scale it up to a team of 500 engineers handling a crazy, high volume of scale. You’re going to be a long way off from that. Like looking to funded companies to see how to build your business, it’s also risky to look at funded companies and large organizations to see how to organize your tech stack too.

Rob: Yeah. On this note, Colin didn’t specifically call it out, but there’s obviously a difference between development and technical—technology choices and product choices. When I say product, I mean which features do we build, what do they look like, what’s the user interface, what’s the user experience of them, and how do we technically architect them? Maybe the technically architect part, that probably actually goes in the first bucket that Colin already raised.

Your product decisions, I think maybe a little different because oftentimes, technology decisions, as we’re saying, it’s like, there are one or two kinds of obvious choices based on your stack. With product decisions, there’s not. What should we build next? I don’t know. It’s anybody’s guess.

With a product, especially at an early age when you’re small and growing, I think you need one, maybe two product people, and they have the vision of where it should go. They take in all the feedback. Again, it’s either one person if you’re the product CEO, or it is two people like you and I did where we’re co-product leads.

As you expand, you get to 100-person company, 200-person company, you do need a specialist in different areas. Typically, you break it up by an area of the app or break it up to the API in the web app, and this and that. There are different product owners there. But at that early stage, I do think you need fairly opinionated people to not let the app just be whatever the customers request next you build.

I don’t think most developers have product skills. It’s a totally different skillset. Writing code, architecting, and building a feature is a skillset. Scaling and all that stuff is a skillset. Let’s say in 2008, I had learned that really well when I was a senior in all those things. I knew very, very little about actual product thinking. About what to build, what not to build, how to build things, user experience. I didn’t even realize that I didn’t know that skillset, I didn’t realize it was a separate skillset.

In your mind, as a leader, whether you’re the CEO, the founder, or you’re the product owner, product manager (so to speak), I would not leave it to a developer. Unless they have this experience or they’re really sharp and you think they can learn it. I would not leave it to a developer or a team of developers to decide what features to build next.

All right, thanks for that Colin. I hope our thoughts were helpful. The next question is from Will Johnson. He says, “You might have spoken about this and I missed it, but I was curious. Now that a few years have passed, do you ever regret selling Drip to Leadpages?” We sold it in July of 2016. It’s a little over four years now. I’m curious. You and I have talked about this, but not for quite some time. It was a few years ago. We were grabbing beers chatting about it, but I am curious to hear your thinking about it.

Derrick: Still, I think my answer back then was no, and I think my answer is still no. I haven’t woken up and said, oh man, we shouldn’t have done that. I’ve had time to reflect on it. Reflecting back on my experience, we obviously started this, and there were just two of us. Then we grew the team very slowly pre-acquisition, and we took on a lot of ambitious challenges in building Drip. It started out very simple and then it became this full marketing automation platform. It was a ride of a lifetime building it. It was a lot of fun. I loved working with the team that we had. I have a lot of fun memories from that time.

But I also realized that I was starting to get burned out pretty completely by the end because the journey morphed from let’s figure out how to build this really powerful product that is really in line with what people are requesting. There was a lot of energy behind that, and it started to slowly become overtaken by the scaling challenges that we had.

We built such a powerful product. I like to laugh about this that we get ribbed by the engineering managers who ended up taking over the engineering team from us at Leadpages. And they’re like, you guys built a product that’s way too powerful. We need to put more guardrails in place because allowing people to segment or whatever became a nightmare. I had to spend a lot of my time just figuring out how to re-architect things and keep the app from not falling over during that tale end time. We were in the thick of that around the time that we got acquired.

To me, it felt like the right point to entertain the strategic acquisition that we did. I don’t think I could have done that for many years longer. Something big would’ve had to change. We would’ve had to either raise some funding and hire some really experienced engineering leaders who had scaled something like Drip before. I was definitely bumping up against the edge of my capabilities. I didn’t have any experience doing it. I was just figuring out how to do it as we went along. It would’ve started to continue to burn me out if we had kept going at that pace.

Rob: Yeah, I’m in the same boat as you. I can’t think of a day when I’ve woken up and thought I wish I was still running Drip. The adventure was amazing, and the journey was incredible. It was growing fast. Could we have waited another year and sold it for more money? Yeah, almost certainly. But there are these certain windows that you get. You don’t get an acquisition offer that comes along where someone is serious about it willing to pay a strategic premium. That doesn’t come along every day.

To be able to accelerate earnings is really what it was. It was to take years and years of any potential net profit we could generate and just accelerate that to the point where it’s like, okay, now we’re able to move on to the next thing. I was in a similar boat as you in terms of I was struggling with burnout for different reasons—probably the same reasons. It was just running all and too many things. There was a lot of stress—a lot of stress on both of us. We totally could’ve done it.

If we didn’t have acquisition offers and we’re still running Drip, it would be wildly successful and it would be doing a lot of ARR, millions and millions. But when I see that path, it’s like that would’ve been cool, but we’ve also gone these other paths now. Those have been really fun.

What’s interesting is I didn’t think I was going to enjoy the post-acquisition time as much as I did. When we were still working at Drip/Leadpages, obviously, there were some things, it’s like we’re part of a big company now. There were things I didn’t like. But I really enjoyed our team, and I really enjoyed having the resources for the first time to hire super senior talent and to scale-up servers.

It wasn’t infinity money, but it felt like that. Given that Leadpages have raised $38 million in the venture, and we came from very cash-strapped—that it really felt like a different game we’re playing all of a sudden. I learned a tremendous amount about that type of business, about that side of things, and about hiring when you have more resources about what money can do. These days, again, if I were to start another SaaS app, I would either fund it well myself or I would raise around really early. Because I can absolutely now see how money changes things and where I would spend it to get there faster.

I think 10 years ago, I remember saying, I don’t know what more money would do for me. I hear people say that. That’s cool and that’s valid that you don’t, but there’s almost always a way that more money gets you there faster.

Derrick: I agree. That was a really fun time. I think that’s also another reason why I can’t say that I regret selling Drip to Leadpages. The question was like, in general, selling Drip and then also selling to the people that we did. Unfortunately, I hear a lot of acquisition stories where people hate their time at the company as they’re doing there or not or whatever the arrangement is. That was not my experience.

We retained basically the entire team for a while, got to grow it, and work in a cool office in downtown Minneapolis with a bunch of really smart, creative people. That was really fun too to get to play around with extending the vision for Drip while we were there in directions where we had more resources to actually throw behind it.

Rob: If there’s anything you could say you regret about anything, I remember when Drip—after you and I left—they have made different choices. They were redesigning the app towards the end. They changed the color palette, they changed the logo. After we left, they did a pricing upgrade or pricing change that made a lot of people mad. They’ve done other stuff. I don’t regret it in terms of I wish I still owned it so that we could undo that or whatever. But it was a little bit sad for me to see that happen at the time.

And to feel like oh man, that’s a bummer that they went and did that. But at the same time, look what we’re doing now. We’re doing fun stuff. I’m working at TinySeed, MicroConf, and this podcast. You’re doing Savvycal. I’m not the type of person to run the same app for decades. It just wouldn’t interest me.

The Drip ride, I was doing the math on it. From the time you broke ground a code until we sold it was three and a half years, and from the time we really finished the slow launch until we sold it was two and a half. It felt a lot longer than that, to be honest. It felt like at least twice that long. I think that’s the sign of a journey that the candle that burns so brightly burns half as long. It feels like that was a very intense journey, and I don’t know how long either of us would have wanted to be on that train.

Derrick: Totally.

Rob: Thank you for the question. I hope our musings were helpful, insightful, or informative. We haven’t talked about that in a few years. It’s kind of fun.

Our next question is from Dave Lara, and the subject is the effect of web scraping on my business. He says, “I’m a software developer who’s debating between native and web or a combination of the two.” When he says native, do you think he means a native mobile app or a native desktop app?

Derrick: A little bit further on his question I think he says mobile, actually.

Rob: Cool. “It sounds like it is virtually impossible to prevent web scraping without degrading the experience for legitimate users. So basically, if I want to create a collection of useful original data on the web for my real users to enjoy, am I just to accept that the data I spent time and money creating will be stolen? That I will have to invest in tools to mitigate this theft and potential for crashing my site from the stress, or do I look at a closed native mobile environment (there you go) where scraping would be more difficult and just avoid the web altogether?

The more I look into this, the more a native mobile app sounds easier than fighting with scrapers on the web despite the reduction in users this would cause. Am I looking at it the wrong way?” What do you think?

Derrick: This one I found a little bit tricky. I think he’s omitting some details for the sake of protecting his intellectual property probably. I don’t know exactly what the nature of the business is. To me, my assumption is that he’s aggregating some kind of data. He’s pulling together a data set that others would potentially want to just harvest, and instead, he’s selling access to it.

My first reaction was that putting it behind in a native mobile app is just another more aggressive tactic (you could say) for fighting scrapers. Ultimately, if a bad actor wants to steal data that you have explicitly said is not allowed to be used in this way, then it’s a losing battle. If there’s a will there’s a way is my first reaction. I think stopping ethical people who are entertaining violating your terms of service should be pretty achievable if you make it clear what the boundaries are for using the data in what ways.

If someone is an unethical actor and they want to get your data, whether it’s taking screenshots from a mobile app or sniffing network traffic to figure out what your network API endpoints are for getting that data into the mobile app or whatever. I think you may have a hard time still stopping them even if you went into a native environment.

My initial reaction would be that this (to me) doesn’t sound like something that should necessarily cause you to make a huge technical decision that would maybe harm your ability to grow the business just because some bad actors may want to try to steal data.

Rob: I kicked this email over to Chris Dokomajilar. He’s the founder of DealForma, which is a TinySeed batch 2 company. DealForma is, in essence, a business that has proprietary data that they sell to folks in the biotech and pharma space. I said, have you thought about this? Is this an issue for your business? Because his business is doing well, it’s growing. They sell to enterprise clients. If someone had his data, that is the real value of what he’s providing.

He said, “Here’s our approach, and here’s how I think about it. Number one, only paying customers can access their data. Number two, trial users are limited to only those that we let in, and that’s after a call where we’ve made some progress towards closing a sale. I know this won’t apply to everyone or at scale. Number three, we make it easy for paying customers to export data within reasonable limits so they can get work done, but not so much that they’re dumping out all the data. Trial users cannot export.

Number four, disabling text highlighting within the data limits the amateurs. Number five, seed the data with unique and obvious wrong data, which we can refer to if we really need to claim copyright infringement—as long as it doesn’t affect real usage. And number six, terms of service protect against it.”

He goes on to say, “Keeping the data up to date with new info and new updates on old events makes any one-time data output stale pretty quickly.” And then being selective about customers helps too. It gives them more value on the entire platform over just the data. There are no guarantees, as he’s saying, but that’s how he’s thinking about it. You can check out dealforma.com if you’re curious more, and I appreciate Chris weighing in on that.

I agree with you, if someone really wants to do it they can do it. I know that places like CrunchBase, which a lot of people try to scrape, are pretty hard to scrape. They use a lot of JavaScript frontend, and of course, it’s possible. But man, I think between using some best practices like anti-scraping best practices—it’s never going to be possible, but to make it difficult without going way outside spending hundreds of hours building something custom. There have to be libraries and GitHub that help you do this.

And number two, having rate limiting. I think that’s a big thing right. If your data is paged and most normal users are going to page through it at human speed. But you can often tell—just by the rate they’re hitting it—if they’re hitting it in an automated fashion. There’s rudimentary advice, but that’s the step one where I would think about.

My guess is it’s a problem you’ll have eventually, but it’s not the first thing I’d be worried about. I’d be worried about are customers willing to pay me for this? Can I build a business to $5000, $10,000, $15,000 a month—whatever your goals are. There are way more important things to be worried about. Personally, I would not make the decision to go mobile-only if this is the only reason. I don’t think this is enough of a reason to not build a web app.

Derrick: Yeah. Drip was obviously subject to a lot of potential abuse from spammers. We had to, over time, build up a moat of defenses against all the different ways that people tried to misuse the system. At this point, it sounds like you’re early on enough in your own business that it’s not totally clear what the attack vectors are potentially going to be for someone who wants to really try to do harm to your business or steal value.

I would try not to make too many upfront assumptions about that because it’s going to be really hard to know what are the ways that people are actually trying to do that if at all, or maybe this won’t even be an issue.

Rob: Thanks for the question, Dave. It’s an interesting one I don’t think we’ve had before—all the hundreds of Q&A episodes we’ve done. That was a fun one. Hopefully, that was helpful for you.

Our next question is from Evan G, and his subject line is huge growth in a year. Should I jump ship from my full-time job? He said, “Hey, Rob. I reached out a few months ago about a migration tool I built that was seeing about $3000 a month in one-time sales. I’ve since modified the product a bit and figured out how to also sell it as a monthly subscription tool.” I think Mike and I talked about this one. We were trying to figure out if a one-time migration tool could be sold as a subscription, but obviously, he hasn’t been able to do that.

He said, “Here, we are getting close to finishing out the year, and I just hit $100,000 in gross revenue with $1500 in MRR with 40 customers. If you remember from last time, which I’m guessing is unlikely, this product has massive platform risk. I built a feature of a product.” So in essence, it moves data from one product to a competitor (I believe). If that competitor basically built this, then he’s saying he would be out of business.

“My passion is entrepreneurship and I love this, but I also know what my revenue could literally end tomorrow if the product just released my feature. I stay in touch with the product manager over there as they currently appoint people my way. Nonetheless, the risk is there, but I feel like I’ve built an audience that I’m exploring and building new products for. If I’m going to make more money on this project than I do at my full-time job, is it time to quit and pursue this thing further?

I have a 5000-person email list of potential customers, some of which I’ve already started chatting with about a new product, but part of me is scared too. I have a wife and a kid I support, and frankly, I’ve gotten used to having two income streams. I’m going to make over $200,000 this year between my full-time job and side project. Maybe not life-changing, but still a lot of money in my opinion. Would love some advice on stuff you would be thinking through whether to make the jump or not.”

He also has a follow-up, but let’s dig into that. What do you think, sir?

Derrick: Well, that’s the classic decision point that a lot of us bootstrappers end up going through. I mean, it very much comes down to what is your own tolerance for risk. How much money do you have in the bank? If things were to go sideways, are you comfortable with that?

In my mind, I put myself in this category. I think I tend to be a little too risk-averse sometimes. I try to remember that with the skillset that I have—and I think you’re probably in a similar situation where you have a very marketable skillset—what’s really the biggest risk if you do make the jump? Will you be unable to get a job within a couple of months, or do you think you have a high likelihood of being able to put your skills to work on the job market if needed?

If the answer is, yeah, I think I could probably get a job given my network and my skills, then this might very well be the right time to double down on your own independent business. But I think it is a very personal decision.

Rob: Like you, I in the past have also been a bit more risk-averse than I should have been, and I wish that I’d taken some leaps that I hadn’t. You want to talk about regrets, it’s not selling Drip, it’s staying working a full-time job too long or it’s not doubling down on things and taking bigger bets with different amounts of money that I had at the time.

I think it does depend, Evan, on your comfort level with this. Risk tolerance is one thing. When I see this type of platform risk, it does concern me a bit. The way to get away from platform risk is to build this for a bunch of platforms, to have five platforms each generating $100,000. And then if any one of them shuts you out, you still have a good chunk of money.

I actually see this with a lot of Shopify apps. Between Shopify, BigCommerce, Magento, and WooCommerce—even those that do move out to each of those platforms—Shopify is just the 900-pound gorilla. You’ll see an app with 80% of its MRR coming from Shopify—a thing that could get killed by platform risk. That’s something that you got to figure out how much I believe is going to happen.

In addition, do you think if they want to build this that maybe they would just acquire you and you get a nice multiple on this? I think that’s something we talked about in the last episode. My take, I don’t want to give someone else advice because I think to Derrick’s point, we don’t know how much money you have in the bank. But if you’re able to save a good chunk of this and if you quit your job and everything went south tomorrow, you could live for months on your savings, then really it’s that question, what is the worst that can happen? The real worst.

Even if we went back into being in a recession, you’re a software developer with skills, what do you do? You get a job, you build this out. If the platform risk killed this overnight if they suddenly built it, I don’t think your revenue would go to zero instantly. It would go down, but you have traffic, you have leads coming in. Maybe there are things you do a little better than if they were to try to build it in-house. And then how long would it take you to expand it to other software packages to diversify?

There are a lot of ways. There’s often that thing, it’s that fear of oh my gosh if this happens then we’re done. I remember thinking with Drip, it’s like oh no, the Russian spammers sent all these phishing emails through Drip one Sunday night. We got blacklisted all of our IPs, and I remember wiping my hand saying, well, we’ve had a good run. But you know what, we were fine. It sucked for a couple of days, then we got de-blacklisted, and everything was fine.

These things that seem catastrophic—don’t get me wrong, there are some things that really are, but most of them are not. As savvy entrepreneurs, one of our biggest strengths is figuring out creative situations to things that just seem insurmountable at the moment. When I hear us talking, we both are probably trying not to give him direct advice, but it’s like we’re both leaning towards you should probably just do it. Is that what we’re saying?

Derrick: I think so. That’s probably what I would say.

Rob: Yeah. Making $100,000 from a one-time-use tool is pretty cool. He had a follow-up question as well, which I actually like and I don’t think we’ve ever talked about on the show. He said, “Do you share your successes with family and friends? I officially hit a $100,000 in gross this year and I feel like I have no one to share it with besides my wife, and yes, that’s a great person to share with. However, I have close friends and family, and to them, I don’t want to tell them I made all this money because I don’t want to sound like I’m bragging. I just want someone to be excited and pump for me. How do you share your accomplishments with others?”

I like this question because I know that I encountered that as I would build apps and I got HitTail to $20,000, $25,000 a month. It’s like I’d never seen that much money in my life, and I couldn’t tell that to a lot of my family and a lot of friends. And I actually remember telling it to a friend and a month later, he has to borrow money. I was like, oh man, that sucks because then I have to be like well, I don’t really loan money. I mean, it was just a […] situation. I’m curious what your experience has been, Derrick.

Derrick: Similarly, the way I think about this is most laypeople don’t really know how to interpret SaaS metrics. Most people don’t know what MRR is then you tell them. Well, it’s monthly recurring revenue. Especially if they’re not entrepreneurs, if you tell them—I’ve experienced this on both sides.

I’m celebrating 1000 a month. I just had that celebration recently with Savvycal, and to certain people who don’t know any better, they’re like sorry, is that a good thing or a bad thing? That’s a low number. And then on the flip side, if you reach these various milestones—$10,000, $50,000, or whatever—sometimes if people don’t know they can just think now you’re rich. Are you going to buy a private island?

Personally, I enjoy sharing it most with a mastermind group, advisors, or people who are in the same space playing the same game and know what these different milestones actually mean. And then with family and friends, I do still like to try to celebrate milestones. I think that’s really important for mental health and to give people a window into this crazy hard endeavor that you’re doing. But I usually try to abstract it a little bit.

Maybe I’ll say, now this business is paying my living expenses or something like that instead of an actual dollar amount. Because if people don’t understand the dynamics of a business and if you say a big number, it’s not all pure profit, or whatever, it just helps from muddying the waters a little bit. That’s how I approach it with friends and family.

Rob: I like your point about sharing with other entrepreneurs. I actually emailed back and forth with Evan a little bit, and that was the advice I gave him. You really should have a mastermind or a group of people that you talk to regularly who just get what these things are.

I remember telling a friend, Drip hit $40,000 of monthly revenue. The guy was like, that’s how much I make in my day job in a year. I was like, yeah, but it’s not all going into my bank account. Again, it’s that weird thing of, so your business has half a million dollars a year and there’s three or four of you working on it. Wow, that’s a profitable business. It can get weird. I didn’t share a lot of stuff along the journey with outside people who like yourself—you, Phil, and I were in a mastermind. I’m sure at times I said big numbers, but you guys at least knew what the context is there.

Evan, I think if you’re looking for other people to share it with, I like your way of obfuscating the exact thing. Hey, it’s paying my living expenses. Your next thing is it’s buying me a private yacht, it’s buying me the second private jet, and an island in Hawaii. So then you’re obfuscating, they don’t really know how much it is. I think that’s cool. I think that’s a nice way to do it if you’re wanting to share with other people.

And then obviously getting together with entrepreneurs. It’s the MicroConf community. If you went into MicroConf Connect and you said I hit $100,000 and posted the screenshot—$100,000 in a year—people would be like bravo, man. Way to go. No one would be like wow, you’re rich or can I borrow money? It’s a great milestone to hit. Thanks for sharing that with us, Evan. I appreciate it.

All right. I think we’re going to do our last question here. This is from Mike Needle, and he says, “First off, thanks for all you do with the bootstrap startup community. I’ve been listening to you for several years now, and your consistency helps push me forward. I’m currently building uption.io.” The name is cool when it’s written out, but saying it on a podcast, it’s like how is that spelled? It’s not upshon. It is uption, and H1 on that is joining a mastermind group focused on reading personal development books.

So Mike describes it as a platform to join temporary book clubs/masterminds centered on a specific book with the focus being on personal development and business topics.

“I went back and listened to episode 167 of Startups for the Rest of Us from January of 2014 on starting a mastermind, and I’m curious what you think has changed in the past almost seven years? What advice do you have on how to curate masterminds for others? And finally, what book titles would you have loved to read and discuss with others?” Several questions in there, sir. Do you want to just pick one and go?

Derrick: Sure. I think you can probably speak better to what has changed from your previous episode about it, but I guess I’ll just speak generally about a couple of things that I’ve noticed out of my mastermind groups in the last few years that have been really positive.

A couple of qualities that I look for or try to cultivate are varying degrees of experience. When there are a couple of different people at different levels in their business, but not too far away from each other, but close enough where if someone’s further along, they can still remember when the people who are not quite as far along were in that phase and can still offer advice that they can draw from their own experience.

I think it’d be hard for me to be in a mastermind group with Jason Fried because he’s been running this multi-million dollar business now for many, many years. The problems he deals with are far different than the problems that I’m dealing with. I think being close enough but having someone there to pull you up. It’s nice to be the person in the middle position too if there’s someone who’s not quite as far along as you. It can help you to solidify your own thinking and way of strategy around business if you’re helping strategize with someone who’s not quite as far along as you.

Masterminds where you can have complete transparency, a high degree of trust. Usually, the ones that have lasted the longest for me are ones where we’re actually friends too, it’s not just business. We have a strong personal rapport with each other. We would get along outside of the context of just talking about business and really trust each other a lot.

And then finally, my favorite element of a mastermind is when they function as an extension of my founding team. Because I’m doing the solo founder thing, and it’s really nice to have a co-founder. If you don’t, if you can lean on your mastermind group in the same way—in a lot of the same ways that you would as a co-founder, at least to talk through hard problems that you’re dealing with. That’s a major win.

Rob: When I think back to what’s changed, it’s not much. When we launched MicroConf Masterminds, which you can check out microconfmasterminds.com, which is a matching service we do to get folks together and linked up. There were two episodes about masterminds, pulled out a lot of that content, and turned it into a guide—maybe it’s two guides. I forget if it’s one or two, but it’s how to start and run a mastermind. It’s an eight- or ten-page ebook that you can download for free at the MicroConf website.

When we looked through it, it was pretty much timeless stuff. It was how to arrange it. There are a couple of different formats you can choose from. A lot of what you just said was communicated in there. I don’t think I have any big takeaway of like oh man, we’ve innovated so much on this model and it’s so different. No, personally I like three-person masterminds. I think four is starting to get big. I think two is fine, but it’s not enough people. There are nuances and personal preferences, but I don’t think a ton has changed.

His second question was what advice do you have on how to curate masterminds for others? I think it’s providing that introductory guide or ebook of this is what a mastermind is. This is our opinion about what they are and this is how. Perhaps you pick a format. You can get opinionated or you can say these are the two or three your group can choose from, in terms of always doing hot seats or just doing round-robin every time. That’s a nice thing when you do have three people is you do an hour, everybody gets 20 minutes. That tends to be plenty of time.

Or when it was you, me, and Phil drinking in my kitchen, it was three of us. Each person gets 45 minutes and two are so tired at 11:00 PM trying to pry ourselves out of there. Those are some of the fun ones. I have good memories.

Derrick: Those were the days.

Rob: I think curating masterminds for others is just about trying to pick people who, like you said, are near each other in the journey. Although with a book mastermind, I mean it’s more of a book club. I don’t know that you necessarily need to be as close in the stage of the journey as you are if you’re going to meet week in week out or month in month out and really talk about your companies.

Derrick: Oh, no. I guess I was going to say that just came to mind when you were saying that book masterminds. I suppose curating those probably involves—if you’re doing a deep dive on something very specific. If it’s general business advice, then that may be generally applicable. But if it’s very specific, then trying to pull the other people who are struggling with that specific thing. If you’re doing a deep dive on the paid acquisition or something than if you’re diving into something about, and obviously trying to pull together people who are actively working on that problem and not just theoretically. It’s probably more of a chance for success.

Rob: Yeah, I’m curious. This is an interesting experiment. I don’t know that I’ve heard of someone doing this before. I’m curious to see how it turns out. His last question is what book titles would you have loved to read and discuss with others? I assume he means back in the early days maybe. I don’t know that I have any off the top of my head. Start Small, Stay Small, of course.

Derrick: Of course.

Rob: I remember reading and really liking The Personal MBA back in the day, but that is a lot of generalized knowledge and less applicable to actually getting off the ground. I’m having trouble thinking of others. There was one that was a copywriting book. It was like the ultimate sales letter and the ultimate sales machine. There were some really tactical ones, but I don’t know that those are as interesting because they’re just a little dry and it’s a lot of tactics. Do you have any? Do you have any thoughts? Do you have any books you would wish you could have read through with a book club?

Derrick: Yeah, probably a couple. I think if it’s a group that’s earlier on in their journey, but even this is applicable to people who are further along and still doing customer interviews. I think The Mom Test is a book that I talk about all the time, and it’s just a framework for how to talk to customers in a way that will actually be useful and not give you biased data. I see that mistake being made over and over again because it’s just so hard to do. That book is really tight, really actionable, and it crystallizes my head the first time I read it. I felt like, man, this should be on the reading list for any founder who’s trying to validate a market and get a product out there.

I also really like The Traction Book too. It’s one that I return to all the time.

Rob: That’s a good one by Gabriel Weinberg and Justin Mares. That’s a good one. Did I ever tell you the story? I sketched out this idea in—I don’t even remember what year it was, but I wrote it all out and I asked Ruben Gomez about it. I said I want to write a book. There’s no book I know out there about SaaS or startup marketing, and I want each chapter to be a marketing approach. I want to give an active, like a real case study of me doing it or someone else doing it and it’ll just be a big buffet. Just a big list of marketing approaches so people could go to it and pick from it. He’s like that’s a great book. You should write that.

I don’t know what happened. I either bought HitTail, we started Drip or something, and it’s like who has time for that? When they came out with it I was like, yes. It was not, oh no. It was, I’m so glad someone wrote this. Whether it was me or not, it’s just such a good book. It’s such a good idea, and they implemented it well. They went to experts who knew each of the areas, interviewed them, and then gave ideas and stuff on how to get it accomplished.

Derrick: Yeah, really good. They’ve got a framework you can follow if you want to run through an exercise to try to distill down some to test first, different traction channels. And then it also, for me, just serves as a reference. If I’m needing to brainstorm, I want to come to spark some inspiration for how to grow the business, I will just often return to it and thumb through it and usually spark some inspiration.

Rob: That’s a good one, and I’m glad you thought of it because I was trying to think. There were books that were impactful on me like the 4-hour Workweek back in the late 2000s. Maybe back in the day, I would have liked to talk about that. I was really, really early in the journey. I think it was 2007 when I bought it, I’m maybe misremembering. But I think the only app I owned was a .net invoice at the time, and so I was applying some of the hiring a VA overseas and learning some of that outsourcing stuff. That would have been fun back in the day, but I definitely wouldn’t want to do that today. It wouldn’t really apply.

Derrick: Yeah. I also got to give a shout out to Dr. Sherry Walling’s book, Entrepreneur’s Guide to Keeping Your Sh*t Together. That’s probably a good one to do a book club on, honestly, because it’s probably a lot like exploring your own psychology that you can dig into a little bit with other founders. It might be a bit therapeutic.

Rob: That’s a good point actually. That would be a really good one. I already jokingly plugged my own book, but I agree because I think a lot of founders go through tough experiences. I mean, you and I on this podcast have just been like yeah, we were kind of burning out. Yet, you and I never sat down and talked about that. I should have probably gotten a therapist yet at the time just to vent and think of how to make things better. It blindsides you. It catches you off guard, and maybe you don’t even realize it at the time. I think having that book knowledge in your head and being able to discuss it would be good.

Well, sir, it’s great having you on the show. If they want to hear from you every week talking about what you’re up to on Savvycal with your co-host Ben Orenstein—Art of Product in any podcatcher, and it’s the artofproductpodcast.com if they want to see your show notes as you say at the end of every episode.

Derrick: Exactly. It’s become a trope now.

Rob: Yeah, and you are @derrickreimer on Twitter. We’ll of course link that up in our show notes.

Derrick: Awesome.

Rob: Thanks again for coming on, man.

Derrick: Thanks for having me.

Rob: Thanks again to Derrick for coming on the show. If you have a question that you’d like to hear answered by myself or a future guest, send it to questions@startupsfortherestofus.com. I’ll be doing probably one Q&A episode a month, assuming there’s enough question volume, and so far there has been. If you send a voicemail, you can send it as a Dropbox link, a Google Drive link, or however else you want to get that to me. Those go to the top of the stack. Thanks again for joining me this week for episode 530, and I’ll talk to you again next Tuesday morning.

Rob: Welcome to this week’s episode of Startups for the Rest of Us, I’m Rob Walling. Every week on this show, we dive deep into topics that relate to building ambitious startups. These are not startups that require us to work 90-hour weeks, sacrifice our life, our relationships, our health in order to build a great company, and a business that can change our lives, and change the lives of those around us. We focus on bootstrap and mostly bootstrapped startups, those that are highly capital efficient, but still want to be ambitious, still want to build interesting things, and we want to have an impact on the world.

This week I had a really interesting conversation with John Howard of Slingshot. He initially connected with me through MicroConf connect. That is our Slack channel. It has more than 1600 founders and aspiring founders. It’s microconfconnect.com. We connected there and he was asking me some pressing questions and I said look, I don’t do consulting, but I’d be happy to have a conversation with you if we can record it. If it’s good, we’ll put it out as a podcast episode. That’s what this conversation is. It’s John explaining how his business works and it’s not just a straight ahead SaaS, there’s some SaaS-ish elements, but he’s dealing with physical products as well. You’ll hear me just try to dive in and kind of get my head around his business and then try to explore options for him.

He was specifically wondering if he was missing anything on the pricing front. We looked at his pricing and kind of tried to analyze it and look at it from different angles, and figure out what other type of options he has. But before we dive into that conversation, I got a couple emails with feedback on episode 525 which is where I read on-air an email that I had sent about 15 years ago around the time that I acquired DotNet Invoice. It was to a friend of mine who was asking to be a cofounder.

I got a couple pieces of feedback on that episode. The first is from Ralph and he says, I really enjoyed the episode where you read your old email. I’ve listened to 124 episodes of Startups for the Rest of Us to continuously back to 415 and I’ve cherry picked some older ones. I’d already heard about your purchase of .net invoice, how you made mistakes, etcetera. However, hearing it again from the viewpoint of the ghost of startups past rather than you looking back from today, brought home the distance you’ve covered in that time and that others could do the same. I particularly liked your analysis of why you were seeking a cofounder and why the friend you approached would have been wrong.

Another piece of feedback comes from Daniel and he said I like the episode this week, but I’m in the group that would completely disagree with you about a business plan. To cut in here, in the episode I talked about how my friend suggested we should create a business plan and that wasn’t something that I wanted to do. I didn’t think it needed to be done for this little product. Back to Daniel’s email. He said, obviously you caveated that point heavily and said that they’re good for some people and not others. However, I challenge you to take that further. Just an idea, but why don’t you debate that with one of your regular guests? I’m sure one of them would take the opposite side. It could be of use for anyone starting out to hear both sides of the discussion. Best wishes and happy holidays.

Thanks for the suggestion Daniel, I may take you up on that. In fact, if you have been a guest on Startups for the Rest of Us and would like to come back on and discuss business plans with me, I’d be happy to do it. I think that this stance that I take is I believe in having a marketing plan and I believe in having a budget. A marketing plan can literally be a one page Google doc with bullets in it or a Notion doc and the budget is usually just a spreadsheet that gives me some idea of how I’m not going to run over. That is my “business plan.”

The business plans that I was seeing you create with the software just seemed like a lot of extra headache, and work, and guessing. Maybe we’re using different words for it or maybe Daniel or others feel like even for a product that’s doing $500 a month, or you think it’s going to make $1000 a month that you should actually create a full on business plan for it.

I think I’m just more of a lean thinker than that or maybe I also don’t love a lot of process and creating a lot of documents that I think don’t have a lot of value to me. That is my style and I do tend to keep stuff in my head until it needs to come out. I might write a quick document that is describing the direction we’re headed, but I know that other folks want more detail, and I do think it’s kind of an interesting way to think about it. I don’t think it’s one size fits all. Anyways, thanks for the feedback. I really appreciate it. Now, let’s dive into my pricing deep dive with John Howard of Slingshot.

John Howard, thanks so much for joining me today.

John: I appreciate it. Thanks for having me on.

Rob: Absolutely. I’m pretty excited to dig into pricing for Slingshot. You hit me up in MicroConf Connect. To folks who aren’t in there, we have more than 1600 founders and aspiring founders now in our Slack group, so microconfconnect.com. You DMed me and you said, hey, I heard you gave some pricing advice on a recent podcast. You want to chat? I was like, well, I’m busy. I got stuff going on, but if you’re interested in perhaps coming on the podcast, we can have a pretty good conversation about it. I appreciate you taking the time to do it.

John: It’s so awesome and I appreciate it.

Rob: If folks want to check out what you’re working on, it’s useslingshot.com and your H1 is, your easiest swag campaign ever. Quality branded swag, a custom merchandise store for employees and fans, and worldwide fulfillment. Where you stand now, you’re the only employee, you’re the single founder. You do have, you told me, many contractors who are doing design, or development, or fulfillment, or just filling in all the gaps that you can’t handle on the day-to-day basis as a founder. Do you want to give folks an idea of where the business stands? Whether you are willing to share revenue or just some type of size to give an idea of the stage? It is December of 2020, and you launched it in January. It’s about a year old, but I’m guessing you have worked on it for quite a bit before then.

John: Basically, 2019 is when I launched it. Actually, it was January 1st.

Rob: It’s almost two years, got it.

John: Yeah. Totally different model that was working pretty well. We had about 10 clients on that model month-to-month. It was a unique swag store that give away points and you can transfer those points and be like, hey, you did something great, or the KPI, or the birthday, or start date. I’m really fine, but we knew it was one of the things that wasn’t a requirement at a company though. We’re still trying to build that really fun product market fit for the necessities and it’s hard to do.

Then Covid hit in March. When that hit this year, every single person quit except for one. We’re still trying to build up that market and find out what that was. Since then, I’ve met a lot of smart people since then that helped me guide my way to the true product market. We now have an awesome platform that as of now we’re going to hit around $200,000 by the end of this year in revenue.

I still am the only employee and I’m wearing a billion hats as my wife knows. Other than that, I am able to really export. People that actually physically know that I pay for fulfillment in some warehouse, and I pay people for marketing, and to help me out in building new product releases, but allows me to really focus on sales, client relationships, and et cetera. We’re doing really well. It’s a totally different change but still in the same vein that we are giving away great swag to people who deserve it.

Rob: That’s the thing, your background is in design and UX, and if folks want to check you out on Dribbble you have John Howard is your username and you actually started an agency called Black Airplane which is at blackairplane.com that you exited about 4-5 years ago. You sold it to someone who could level it up. The logos on the homepage of that are Coca-Cola, McDonald’s, Home Depot, The Weather Channel. I mean those were I’m assuming many clients that you closed. Are you the double threat of an amazing designer and also an enterprise sales person?

John: That would be a little braggadocious for me, but I appreciate that. I look at things more for the user experience side and that’s what has given me an ability—I’ve always wanted to start a business. I think that was my first love. I lost my job at an agency that I worked at. They forced me into, hey, why not start an agency? You love business and you love doing design work. That was the love story there and because of that, I put all my effort into making that happen. That was Black Airplane. I did not do any development there, it was really just design. We ended up working with some really amazing clients as you mentioned some of those. Coca-Cola being one of the most recognizable here in Atlanta and because of that, I kind of handed that off.

At one point, I really wanted to go build a product company. Especially working with products all the time, people who are doing products, it just keeps you energized. I handed it off to people much more formidable to me to be building an agency in building that up and they’re just doing a tremendous job. They made it now the whole gamut of design and development. It’s really grown, there’s about 18 people now. When I left it was two people and we had eight contractors, so big change.

Rob: Good for you. That’s cool to know when to hand something off, when to let it kind of take wings and give it to someone who perhaps can take it to that next level if it’s not something you want to do. I’m curious then, so you are running this agency, the description on the homepage is we’re a digital product design and development firm in Woodstock, Georgia. We’re on a mission to make sure no digital experience gets left behind.

You obviously have the chops whether your own design skills or through the network of contractors or employees that you worked with to build full on digital products, web and mobile, whatever. Why start something with a physical component? Basically, you started a product that allows other brands to launch their own swag campaigns or swag shops versus just going and building a software product, a SaaS, or whatever because you obviously have the skill and experience to do that.

John: Yeah, I’ve done that before. If I could show my rap sheet of how many things have failed, I could give you a long list. I’ve done a lot of that work. They made minor successes here and there, but I’ve learned a lot along the way. I had just been really fascinated with the physical and marrying the digital world to a physical product. I think I’ve really been obsessed with that for a long time. What got me excited about it was at Black Airplane, we did swag. I don’t know how the swag looks now there, but it’s always been great. We never slapped our websites and names. We were about people’s swag. It gave them really great swag. Every single time, people would brag on something we had.

I used to joke that people would wear the Black Airplane swag out to the park or on a date. They wouldn’t rip the sleeves off and cut off their grass, it wasn’t one of those types of shirts that you hated, or hats, or whatever. It was really nice stuff. I saw that people got really excited about that. I just felt a relief. I’m really obsessed with your experience. I want to build this product and platform and marry that experience of getting something from an employee, or colleague, or boss, and then receiving that in your hand physically seeing that side of things as well. Both of those things got me really excited.

Rob: That makes sense. The companies that I’ve launched and pretty swag for, I always took that same tac. Especially at several of the Drip shirts, I had a professional artist, he actually is a comic book artist, to design this character called Drippy who, rest in peace, Drippy was retired after the acquisition. I remember telling the designer, I want this to be something that could appear in a store like in Urban Outfitters, or some store that someone might see. Obviously, I wanted branding, and perhaps a logo, and maybe at a tagline somewhere on it, but it’s not this big prominent thing.

John: Right. You’re not walking around here with your billboard, that’s not the point of it.

Rob: Exactly. You decided to launch this, I know we want to get into pricing, but I just have so many questions because when I look around the internet, I see this is a solved problem in my opinion as an outsider. Printfection, spreadshirt.com, printful.com, swag.com, activeimprints.com, axomo.com, I literally searched for 45 seconds and I found those. I guess the first question is, are you crazy for entering such a crowded space? The second question is, how are you different from them? Because I know you’re not crazy. From your past, I know you’re an enterprise salesperson, a designer, and a gifted business person. I know you wouldn’t enter the space and be $200,000 of annual revenue by accident.

John: Great question. I think those are fun to kind of pose. I don’t usually get those in sales calls because people are calling me for that reason. They don’t want to deal with it. I think that the question usually originally I thought, people just love giving away swag, we have the point system in place. The reason we killed that is we thought the people wanted to give away things. We thought that was the […] and we wanted to give away great swag and they wanted a platform to do that and the avenue to really reward people.

I think they still do, just nowadays, it’s just overwhelming. People ops is really the general term. There are so many that are involved. I started out with more people ops demographic I was trying to reach, but a lot of people try to get away things or something for themselves, they’re just too busy. They don’t want to do any of that.

Even the things like Printful and Printify, I recommend to people all the time, so that if their budget doesn’t get us, they want to do DIY solution, go set that up. You got to set up your website, your location, you got to generate terms, and set up your little call to action pages, and go print stuff, talk to vendors, and all that. I go on and on because I want that to feel heavy, because it is. Even with the Printify or Printful solution. You’re having to go set that up for yourself and get that running.

The quality is not there, you can’t print in multiple locations. You don’t get the same quality of shirt and hats, you can’t do things that are super custom and unique. You’re bound by two things. One is the uniqueness of the campaign and the main one is 90% of why we sell it because it’s just too much work to go to ship things out to ship stations, setting it all up to get it all running, the full gamut of the campaign.

Our differentiator now is not based on, hey, we do really great swag. That’s a given. I don’t even sell that anymore, right now it’s basically like, you don’t have time to do this. I know you love your people, we thought we’d solve that for you. Now what we’re going to do is take everything off of your hands. All you got to do is get excited about rewarding your people.

I think we keep people in that excited ethereal place when they’re working at a job which they’re pressured to perform and they want to go home and not think about this stuff. They just want to get excited about their people. When you remove all the other burden off of them, it frees them up hourly monetarily to go do a really, really great job at that. The fact that they also track campaign usage to again on Printify and Printful, you can see how many things are sold, but you can’t tell the conversion rate of people that did something because of that movement.

We actually track that. We have extremely high conversion rates on our call to action pages of people that willingly got something free and then chose to do another action for their company. That’s how we’re different. We really alleviate time and then we track the actual conversion rates on your swag campaigns.

Rob: I want to touch on a few points there. One, you mentioned people ops, for those who haven’t heard that term before, it’s the new term for HR. Human resources is becoming less and less of a term that’s used. People ops are the folks who are helping you manage your people typically at a larger organization.

The second thing you mentioned is people will get something for free and then take another action for your company. I think there’s two questions there. One, are you right now focused on let’s say larger companies? I’m in Minneapolis. I think of Target, Best Buy, General Mills, these are large Fortune 1000 maybe even 500 companies. I forget who’s in the 500 at the given time, but those are large companies and they may want to give away a bunch of swag for free to their employees.

I guess the first question is, is that more the type of client you’d be looking for versus I think producer Xander and I who work on MicroConf together, we have talked at different times about setting up a MicroConf swag shop where the swag wouldn’t be free, but we’d probably sell it at cost. We want people to wear it, but also we can’t lose $10,000 giving stuff away for free. I guess the first question is those are the two things I think of when I think of a swag shop. Are you focused on one over the other?

John: Right now, they’re all giveaway campaigns. That’s the primary sponsor revenue earlier. All of that is attributed. Actually, 95% of that right now wants to keep things outside of that or attribute it to a giveaway campaign. We did start with the internal employees. It’s people who, hey, do you want to give away things to your employees? That area is just too small and people already really focused on doing that anyway. A lot of them realize, if I gave away things to people external from here, I’m already doing that through advertisement and setting up ads. My conversion rates are usually .1%-4% on a high print ad.

Power campaigns right now that we’re tracking are converting, again, the conversions are all subjective, but converting on they got something free and then they did something with it are around 20%. It’s extremely high because you’re giving them something free and they’re going to do another action after that, but that’s where we’re at now.

We are also going to start focusing on launching a new product called […] that’s going to focus on the same. We’ll do all of this for you, we’ll save you all this time while you focus on your brand, but you can actually sell your products. We’re really working with people that know their brand very well, that know they can make money off the products they sell.

Rob: Got it. I want to dig into that action then because I’m not sure I quite understand when you say, they’re running ads to give stuff away. Again, just come back to Target or Best Buy, they wouldn’t run Facebook ads to say, get a free shirt that says Target on it or free Best Buy swag. What am I missing there?

John: For sure. Yeah, they would more run ads to give away something free like a document or a PDF and hope that you convert and give your email address or something, but you are not proactively doing anything from there. I’ll give you three examples of what we do. Basically, if Best Buy were to say, we want to run a thank campaign and spend all of our money on giving away swag. It could be small or large, it doesn’t matter, but something really unique and cool we’ve had done for Best Buy. We want to give that away free.

What happens is these people get code. Maybe they attended an online conference, maybe they went to something physical, a booth at Best Buy, but they did something. When they get this code, they go to put it on the internet which is Slingshot. We have a site setup for them. After that, we have a page where they can either cool down—basically a celebration page that says, your product is on the way, we have some information there.

What we can do is we can set up a custom call to action that happens on that page. That means, we already got them excited waiting for the free thing. They did that first. We didn’t ask them for something before they gave them something free. After that, because they’re at this high and getting excited about something, we then ask them to do a call to action. Three of those to give you an example, recently, to make it really quick, that’s one. They would’ve made a post about the beta of Illustrator. They want people to post and further talk about the beta after they got their free product, it’s just a tweet button. You basically tweet it, edit it the way you wanted to.

We also have one where you can fill in Glassdoor reviews. This is after 60 days of being an employee in certain companies. This company had the call to action where you say here’s your free item. If you love to do this, we have an optional thing as well, would you post it? Go to Glassdoor and leave a review for our company.

The third one, you want to ask two questions after you use their product. They give you something free, after you’ve been using a trial of the product. This conversion page, the call to action page after, again, it’s optional. They’re able to say, here’s a few questions I can fill in and submit this. It just helps them along. They get free stuff from that. The conversion rate is really measuring after the excitement, after they got the free item, will they fill something out or do an action.

Rob: Fascinating. This is like a whole ecosystem. This is something I really have not been exposed to. I’ve seen swag shops for conferences or companies. Back in the day, I was a Microsoft MVP in asp.net. It just means that you pass some certifications and you become an influencer in the community and then they nominate you and you get a bunch of free software.

John: New swag, yeah.

Rob: They give you I think I got $100 credit at their company store. I could software and I could get other stuff. I’ve been exposed there and I’ve obviously been exposed through MicroConf, or Drip, or the companies I’ve started to extend our brand and everything. This is a completely different thing that I have not seen before. We have trial users, give them something and then ask them a question, or we’re going to ask for Glassdoor reviews, or as you said Adobe illustrator wanting beta users to tweet about it.

John: Right. That was done really fascinatingly well. We’ve tested it and made the collection basis nicer, mobile, make sure it’s something really easy and simple they want to do. We always negotiate the complication with clients, because they want to always ask more, or do something more, and we have to say no, or put it before the form. We want to ask them this before they get something free.

We always thought that again, you want genuine responses. We measure genuine responses to getting something free, and then voluntarily choosing to take action after that. We’re truly like MailChimp you can measure mail, why can you not measure swag campaigns the same way. It was a little different there, but why can’t you do that? We kind of have been pitching that back and forth ourselves. Building something that is measurable in the same way with swag.

Rob: I often say when someone’s launching a new product, if you’re going to compete with existing competition which most of us these days are, I say, look you should own a unique position, you should own a traffic channel, or you can be cheap. Those tend to be the three things. There’s always like, be careful with the cheap, because unless you truly have a competitive pricing advantage, then you’ll just become a commodity, and blah, blah, blah.

For you again, competing with these other things that kind of do—again on the surface, it all seems to be the same for me, but as I’m digging I’m like, you actually are differentiated. Are you essentially, you’re a full service, high quality, high priced version of these things? You have the CTA aspect, the call to action aspect built-in. Is that what makes you different than other options I would look for?

John: Yeah, I think that’s really the main one. Basically it’s nice quality swag. We made everything really high quality. There’s no effort from you at all. If we say the easiest swag campaign around, it truly is. All you have to do is go, I want to give out codes today? We’ll take care of the rest. It’s that easy. I want to start a new campaign off this in the exact swag from last time because I want to extend that. You could do the same thing and then afterwards, you’re going to measure it.

It’s really that cyclical like, just getting excited about giving away things and wow, there’s an option here where I could measure that as well and it’s going to show me that. That’s where you get excited more. You’re going from people ops now to really talking to a lot of marketing people. We started out with people ops and marketing. They are super excited about it, they have so many ideas that we can force them to drill down which marketing people have these challenges, drilled down into one call to action. If you want to start a different campaign to test out like an A/B test, you can do that. But really, one call to action you can get them to do after coming off this hive and something free.

Rob: That’s what I was going to say. The call to action piece almost seems, aside from the full service which I think is great, because it raises the price point and makes it easier for people to get onboard. The call to action piece, is anyone else doing that? Tying a post swag call to action where I signed up, I selected the shirt or the hat. I love the hat that I just got from Adobe. That’s going to be now shipped to me and now of course I’m willing to tweet about it. It sounds like you have all that built into your system. Is anyone else doing that?

John: Not that we’ve seen in that way. I have seen other swag stores that have some kind of plug in that says, can I get some feedback? But it’s usually disrupting. I’m user experience centric. Everything’s got to be easy. Everything built into our platform is extremely easy. We tied in to Google. I think they naturally grab all your information. We don’t store any information, your payment information, our call to action for our stores that’s coming out for the payment stores. If you want to sell swag, it’s super easy. It’s all one click.

Everything is UX centric, so because of that user experience, I haven’t seen anybody really marry them up in the way that we have. They’re just people using plugins on wordpress stores that are very heavy, or  themes, or whatever it is. Even Printful and Printify which are our competitors in the manufacturing space, we don’t even mind that people send us their swag. They have other people that use swag from outside of here because they get it from somewhere else or they prefer a different vendor. We don’t mind it all, we just take it on. We still charge the fulfillment fee for the package and set them up on the call to action as well.

Rob: Got it. That’s the thing where you’ve innovated here from what I can see and why I now understand how you’re different. You’re going after marketing leads or folks who actually want to get to a call to action and they’re going to do it through swag. Because that’s the thing, marketers are used to spending money to get things. They’re used to paying writers for SEO, they’re used to paying SEO consultants to help with it. They’re used to paying for ads to drive people to places. Spending money on marketing to get a tweet, or to get a survey answer, or to get a Glassdoor review, that’s nothing new. You’re just providing this whole other thing as a service.

John: Right, incentivizing stuff they already do, bringing it together, that’s really what we’re doing.

Rob: Okay, we’re 20 minutes in and I have a picture. I really need to understand that, because if we start to talk about pricing from the top, I would have dug into why aren’t you $99 a month plus X of fulfillment like Printfection or Printful, but that’s not the value you’re providing.

John: We’ve been there.

Rob: Exactly. Talk me through that. I’m sure you’ve had many pricing models before. Maybe don’t go through all of them, but you could briefly touch on this is how we’ve evolved and where we are today. Then you and I can kind of bat around what’s working, what’s not, and just figure out if you’re on track.

John: For sure, we’ll talk about that. I’ll make a really brief, back when we started in January, 2019, a year ago, that was when you bought points. You pay for the points up front basically. Whenever something was done, you get a one off of print. We didn’t use Printify Print, but we used a local vendor with really high quality swag, but you could buy the points and you paid a monthly fee of $99 a month. It was really nice, it was great.

Again, all these people went away during Covid, so our new model, we started out still doing the monthly fee and every time we’re having these conversations with people that are already paying a ton of money, they’re like, why am I paying monthly if I’m going to be doing new campaign with you all the time? We ended up charging —instead of doing the monthly fee of $99 or $299 with some of our clients, we ended up staying at $99 per campaign that we set up, up in the front. That’s basically three months of what we used to charge up front, it’s built in and we know they’re going to be re-upping.

Almost every client we’re working with now has a new campaign coming out every couple months. They’re re-upping or rebuying into that campaign process. They’re paying that $99 each on a one A/B campaign page set up.

Rob: Okay, which seems inexpensive to me. You’re essentially doing enterprise sales with larger companies and we talked about Adobe, that lead time to close that deal was not 15 days. I can assure everyone listening that it was months and months. If it’s $99 to set it up then where are you making your money? Because I know that your margins are pretty good, we talk a little bit offline in advance. Where do you make your margin then?

John: To give you a back-story, Adobe for someone like that, working with those types of company, it took me almost 10 hours to get on board it, of me filling out things to make sure I was set up to even allow us to get into their system. They have to approve you with this big group of people. To get into their system that’s really hard in the first place, enterprise sales are extremely hard, but once we’re in, the lead times are not very long. We really have been setting up campaigns for a lot of the Adobe. We work with almost every Adobe team now as well.

With the Adobe team, things didn’t get set up within probably 10 days, 30 days max to get paid for that. We charge everything up front so we wait on invoices to get paid before we’ll start a campaign. That’s one way we don’t take on the scary parts, so we’re trying to bootstrap. We worked that out early on. We’re making our money based on the margins inside of the campaign itself. That’s actually for the Swag and then to fulfill that Swag. Our campaign profit margin is around 35% to 40% off of the actual amount. Basically, they’ll send us the amount, we’ll then go buy the Swag, get all that done for, you don’t have to worry about it. We make about a 35% to 40% margin there, and then it’s $350 right now per package to send those out. All that are bundled up into one package price that they pay for to start a campaign.

Rob: Got it. I’m imagining this campaign since they’re pre-buying shirts, hats, mugs or whatever. This is thousands of dollars, if not tens of thousands depending on—I mean they’re placing an order with you. They’re saying we want 100 shirts, 100 hats, 100 mugs or maybe it’s 500 each and then you say okay. That’s $8000 or $12,000. Is that the idea?

John: Yeah. What we end up doing too, it’s around $6000 on average, around $5800, we’re calculating per campaign that’s launched. That doesn’t mean you have other ones who are tiny. We work a lot with tiny companies as well. Those are probably around 20%, 80-20 rule. We do work with a lot of small companies as well that run smaller campaigns. The cool thing about that is we’re not changing how much we charge for the swag that they’re purchasing. There is a minimum entry to even jump into a branded campaign.

The cool thing is we’re really pushing people to buy five agnostic items, so sure that you’re going to have to always re-up and buy new smalls, new mediums or new larges that’s a property of the swag closet. We do still order those items and people pressure us to get those types of items. They really want it, they really want that certain item, but really we’re sneaky people to think it can be reused for new campaigns over and over again. Maybe they’ll buy something new. This year it’s going to be the sticker, the hat and the socks or whatever it is. Next year, it’s the socks and this. They can always having to campaign running with existing swags or really pulling from that at all times.

Rob: That would probably exclude MicroConf from doing it because we would be looking for a print on demand solution, such that we wouldn’t want to come up with let’s say $5800 to basically populate your—because I assume you have a warehouse and you’re doing all the fulfillment. That would make less sense for us given that we have no idea what the demand is because we’re not thinking in terms of campaigns. This isn’t as much marketing, I want a call to action for us. We truly just would want a swag store to extend our brand and run it at break even. I mean that’s accurate, right? It’s not necessarily a fit for the model that you’re looking at.

John: Yeah. Thinking of MicroConf, everybody that I know that’s in that group that I personally know as a DIY person. They’re sending everything up. They’re chaining it all together. There are no code solutions. Slingshot was built with no code, almost everything is. We’ve got some custom code in it but 90% of Slingshot is built on no code. We’re doing that, making this much with having a no code solution is play. Because of that, I think a lot of people want to chain together their own stores and their own brand and put their logo wherever they want, but you’re very limited on what you can purchase. Sometimes people don’t care. Again, if it’s brand awareness like I know MicroConf and I just want to get something from that field made by what I get from them, it doesn’t really matter.

If it’s you choosing, you being Rob, what items you want to go out to these people, the one off solutions where we restarted, it was really great. You’re hoping that people have great brand awareness. You’re hoping that they could generate that. With people giving away things, there’s always a demand. They can always give away or run a new campaign. There’s always a need to get a new call to action or return on investment for something they’re giving away. Just because the buy ins are a lot higher there, with our new store, we’re really focusing on companies that know where they’re at with their brand and want to move to a new solution where they can focus more on their brand and worry less about running everything else.

Rob: How are you finding these new marketing customers? Because it feels to me like this is almost a new—this is something I haven’t heard of before of using swag truly as not just brand awareness but as a marketing assets that I’m going to give this away in order to get the call to action, the tweet, the survey, that glass door responses. I can’t imagine anyone searching for this. If I’m in marketing at Target, I’m not searching swag to give away so that I can get someone to tweet about Target. That’s a challenging position for bootstrappers to be in because you often want to fill demand.

That’s the easiest way to do it. There’s already search demand. There’s people seeking and I can either run some ads or I can do content or SEO and I can get in the way of that traffic channel. It wouldn’t seem that you’re able to do that. How are you finding new customers and then we’ll actually talk about pricing? I promise.

John: That’s fine. The cool thing is when I even asked you for pricing is like I know where I’m at but I want to make sure I’m not in the wrong place. He might have another opinion that yours, as smart as you and just be helpful, which is the reason for that. Aside from that, like you said, it’s not easy. There’s a lot of not training I would say, but there’s a lot of people—the eye-opening moment that you had 20 minutes into the call, I have to make that happen usually within 5 minutes of the call.

I always schedule calls for 15 minutes to force that reaction, our demo is only 30 seconds to show the actual platform. When I do that it’s really like how do I plan the phone call before that, it’s really writing about it a lot, talking about some of our success. I’m not an influencer by any means, but I do work with a lot of enterprise companies who know that if John’s seeing something in this area of your experience, I’m going to at least check it out and trust it.

I have a great group of advocates on my side that help me extend my voice and reach because I’m a transparent guy. I’m open about everything. I’m always reaching out to someone as did to you. I did that to get him on this call today, but as you said I reached out. I was hoping I could get your ear up. I think of the whole thing as like I made a lot of relationships that way.

I’m not really doing traditional marketing and sales right now. We are working on setting that up. Right now, it’s very much word of mouth, through LinkedIn, talking about different ways that people are looking for things. No, they are not finding us organically searching through that, but the cool thing is everybody that filling out these calls to actions and claiming swag is coming through our domain to do so. The volume is ridiculous. If you look at our stats, our volume is just people passing through. We’ve had quite a few people come through that goes, I love this system. Can I talk to you about this?

Rob: You have a viral loop there?

John: Yeah. That is built in. I’ve been doing that for 10 years and making sure that’s in place when we launched. That’s built in so I don’t have to spend a lot on marketing right now to do that.

Rob: That’s interesting because I think as we talk about pricing, one thing in the back of my mind that’s a little disconcerting is that you’re not on subscription. If you don’t have repeat buyers, the fact that you said that Adobe—you’re working with most of the departments, probably means that you’re just getting new projects constantly and that is what’s going to make or break this business. Because if you had to find a new Adobe or just a new client every month or every week or whatever to fill your pipeline and keep your revenue, this is a grind, this is a sales business.

The beauty of SaaS or subscription or recurring revenue is that you don’t necessarily have to do that constantly and you can build this flywheel. Your flywheel is not going to be subscriptions, it’s going to be reorders in essence from these larger orgs. Has that been the case so far, most of the companies you’re working with are coming back and doing more and more campaigns?

John: Yeah. Even at Adobe, their departments or divisions or what they call them internally but a lot of people really did know someone else that works there is 21,000 I think people that work there now, latest count. A lot that I work with have heard it, I heard of Slingshot used here but I don’t know who you are. I don’t know this other person but has heard of it. A lot of the people, we are relying right now on re-ups. They are doing that because they’re seeing the value there. We were able to show them statistics.

Getting a new organization like that set up, that’s monumental. That’s why I stopped and said right now we’re working on having some new organizations that are that large that have different groups that can break out. Really tell one another without knowing who started it, tell each other about the product and service. We are reliant upon that being new campaigns and banking on that right now honestly.

Instead of the month to month, which seems to me—when I talk to people, it seems to be almost like you’re charging us month to month, but already charging us a huge amount for the campaign project. We talk about building that in so it covers us for a few months just to create somewhat, not predictable revenue, but built in revenue from that. We’ve gotten away for the month to month subscription altogether. Definitely, I thought about reintroducing—I don’t think I have the right platform to reintroduce that yet, that makes sense not to say it during a sales call.

That’s why I’ve been really stagnant on whether we should do this or not. Right now, we’re killing it, but I don’t know how long that will last without at least some kind of predictability month to month.

Rob: Right. It doesn’t seem to me like the subscription is going to work given this current marketing campaign. You call them campaigns because they are marketing campaigns in essence. That’s why I was confused when I looked at your home page. I’m like, why is he calling a swag store a campaign? Because again, I’m coming from the MicroConf mindset of we would just want a store that’s open year round and you could come and buy a shirt at cost or maybe if you attend MicroConf, we send you a coupon code where you get it for free. That kind of thing wouldn’t be a campaign and so that’s how you’re differentiating. You’re talking about marketing campaigns.

When I think about how marketing campaigns are thought about, they have a budget and they have an ROI that if we pay $5 per tweet or at $10 per Glassdoor review, or whatever that may be, maybe $50, then that’s a success. Back in the day, if I could pay $100 per new trial at Drip, we were minting money. When I think about writing a check for $6000 as you’re saying the average price is $5800 for a campaign, you’re right, the $99 a month seems superfluous. To get us all on the same page then, you charge this upfront fee to manufacture and a warehouse the merchandise for this campaign and then you charge a per package fulfillment charge. I think you said it was $3.50.

John: Right.

Rob: Okay, is that it? I mean that’s basically your car pricing if I were to come to you from Target, so that you’d be like, alright, how many mugs and other things you want to print? It’s $5000 or $10,000 plus this fulfillment fee, does that kind of summarize where you’re at?

John: Yeah. We want to be one packaged price. We do break it down so you’ll see things like a line item because people need that to take it back to their teams because every team works differently. It is all one package price at the end of  the day is all you’re paying.

Rob: It’s enterprise sales. I mean it reminds me a little bit of custom software back in the day or even not back in the day, you’re running Black Airplane which was custom UX. That’s what this feels like. The advantage you have right now is that no one else is doing it. Is that right? I mean it’s essentially a green field and you can price it within reason where you want it to be?

John: Yeah. There’s somebody that can always come up with something competitive. I’m not excited about that but I do look forward to beating them, it’s the competitive nature in me. Really, once they talk to us, they’re going to get that same experience at scale always. It’ll always be scalable. I think it could be our next big challenge, can we always scale the experience that the person on the other i.e. in this case you would receive every time you engage with our team?

Like you said, it’s very much like Black Airplane it was an agency world. I’m used to selling to enterprise companies that they invest in. The cool advantage I think here I know there’s other things like Printful, and Printify, etcetera. There’s a million of them that exist. You’re having to piece those together, but most people who are sending swag out to the void and they’re paying for that. They just do it like it’s natural. I got a startup, I have a company or a new niche. I’m going to buy a swag for the whole company. We’re just helping you measure that and make it meaningful.

I think that’s really the advantage that every time I talk to someone, it’s completely unique. It’s like wait I’m already doing this, but you’re going to help me actually do this, do something with it and make it mean something. I think that’s what keeps people’s eyes really wide. They’re not really paying a premium when it comes to we bought the swag, we went to the post office, we had everybody’s addresses and we shipped all the stuff out to them. We have to store it all down at our swag closet. Even in my LinkedIn, I said I’m saving you from your swag closet and save your sanity or something like that.

It’s being cute by playing on it. It’s a lot. People don’t always use the swag, they always do that for printouts, they get really great stuff but actually it’s something that people will use that you can measure against for an ROI.

Rob: Got it. When I hear your pricing, it seems to make a lot of sense. The fulfillment cost, I’m used to it. That’s what FBA, Fulfillment by Amazon does. That’s what any warehouse is going to charge you. They’re going to charge you a monthly storage fee, which it sounds like you’ve baked into the campaign costs, so it’s all one line. I know it’s line items but it’s all one big price. They charge storage and they charge fulfillment and then of course the actual payment to USPS, or UPS or FedEx or wherever you’re shipping. All that feels like it makes sense to me.

When I think about pricing, your set up fee is $99, should that either go away or should that go up, especially for the first one? I would be thinking there and I would be thinking about your margins on your large quotes or just any quote. Have you had complaints about we quoted $5000, that’s too much. Can you build an extra 10%, 20%, 30% margin in there, given that you are not a commodity at this point. That you really are something that is value add, someone would have to chain together all these other services in order to do it.

You’re already charging a premium price, can you charge a bit more? Those are probably the only two areas that I think of, is that set up fee or effectively just raising prices, building more margin into your quotes.

John: As we move and I work with great ops people. I say this, I mean, to my dearest heart, I love working with people that are super, super focused on just loving on people. That’s just the way I’ve always done business, sounds cheesy but you’ll see my point on everything, like love on people first, everything else will follow. I want to make sure that the people I’m working with are focused entirely on their people, not just their campaign, but in that vein of thought.

As we move further away from people ops and focus more in that marginal area people ops to, hey, introduce me to your marketing team leader, CMO, or whatever at whatever organization. They’re going to want more measurability on this. As we get more into measurability, which we’re doing a great job now as new pieces are coming out at the end of the year, there’s some really exciting things. They’re not going to be heavy. I don’t want the product to ever feel heavy. When they see this, it’ll be one of the things they can look at and say, you know what, there’s absolutely ROI here. It’s measurable and we can actually spend more money. That’s where I think I’ll be more comfortable even increasing margin there.

Right now, the balance is probably about 40-60, 40 being people ops, 60 marketing reps that we’re working with. I want to be careful to not just be inundated with ROI, measurability when some people just want to give away something for free and just do that, because that’s the company they are. Even in Adobe, it’s about split now, the half of people we’re working with, most of them, can you show me the measurements? It’s awesome. I wish we could see more numbers.

Somebody said the other day, more numbers it’s better for me. The more I can see, it’s better. I think we’re in the middle of figuring out what that is. I don’t think we’ll ever lose people ops, but I want to make sure the experience is top of the line, which is right now that the third page is optional. It’s completely optional if you want to measure or not. 90% of our campaigns are  measuring right now.

Rob: As I think about it, it’s like you’re in a good spot in terms of not being commoditized once someone understands what you do. I think you can go up market into larger campaigns, in which case, as you’re doing now, you’re charging a big lump sum to make it worthwhile, to do the enterprise sales process. If you go up to $20,000, $30,000, $50,000 campaigns, that all plays out. It’s more enterprise sales and it doesn’t seem to bother you. A lot of people don’t like it, but you seem to be good at it and doing it.

You are leaving room below you for someone to come in and do a print on demand version of this exact same thing at, let’s say, $99 a month price point. Obviously, they would have to build a lot of the margin into either that monthly fee or more likely the fulfillment and the production itself. They’ll charge on that on the t-shirt print or on the mug print.

I don’t necessarily think you should bother with that. You’re a single founder. You’re having success and I think where you are up is going to be amazing. I think if someone were to compete with you, they would probably start in that realm, going after the folks who maybe can’t afford the $6000 or $10,000 up front, or aren’t confident enough in it and almost want a test bed of print on demand approach to do more one of things. It’s a higher unit cost obviously but it’s a lower upfront fee.

John: I think to just pretend I was to do that and if anybody were to listen to this in the future, if I was to that, that’s where I would start as well. I would come up with let me piece together our WordPress theme and then put together something on the end that asks for some information or get a plugin or whatever in the front end, do Printful or Printify or whatever it is. Even those on demand prices, they’re on demand for a reason, talk about quality but they’re on demand for a reason.

You’re paid to get something on demand, but you’re still paying a premium when you look at the prices for those items. They would have to build in a lot of margin to make that work. Everybody I worked with, which is again, the power of negotiation—I’m not saying I’m the expert of all experts in this area, I’m not. I’ve been in a lot of great relationships over the last—I’m 37 now, but over the last 10 to 15 years and because of that I’ve been able to work my margins way down. Even when I say margins on my prop, but even larger campaigns that are running with lots of items, we work with a lot of small companies to pay pretty much the exact same amount aside from the fulfillment fees that they would, almost exactly if they were to run externally.

Now, it’s going to be, again, tough depending on who you go to, but they’re paying pretty comparably to that, unless they go to a vendor like a print shop and work with them, they’re not going to get their margins down. Even if this person we’re competing or I was competing against myself, the reason I didn’t go that route is because there are not really a lot of margin to make there either, unless you’re charging some pricing.

I actually worked with local vendors to get their prices way down, so that I can go and compete with the one off with way better quality, way better options, unlimited items you can choose from. We work with almost every company brand out there. Because of that, it is competitive but they’re going to struggle as well in trying to create margin there.

Rob: Yeah, and that’s the challenge of dealing with physical goods and especially custom physical goods is that doing one versus 100 is ridiculously expensive. In fact with Drip, we’d print 100 t-shirts at a time and I believe the cost, I went directly to this printer that I had a good relationship with and it was like high quality print, high quality shirt, $7 or $8 a piece and then we had a poly bag for $1 and then shipping was nothing. It was so inexpensive.

We went and looked at print on demand because I didn’t want to have a box of t-shirts in my garage, per what you’re saying. I believe the print on demand for comparable quality is about $21 or something in that realm. That’s what you’re saying and that’s where if you build a SaaS app, we forget that when you’re building software, unit economics really are much less relevant and obviously you’re in a position where that is perhaps the most. It is a competitive advantage given what you’ve discovered.

I appreciate you coming on the show today, John. I don’t know how helpful it was for you, but it certainly was pretty interesting to me to dig into this world and then to see that connection tie into marketing calls to action because that’s of course been my life for 15 or 20 years.

John: I love Drip. I think when I talked to you originally, I didn’t even know what startup I was doing, but I talked to you about four, five or six years, I don’t remember. You were at Drip, we talked through—I think I wrote our you on Twitter and we ended up talking for a while after that on email. It was super nice that you reached out. I was super surprised that hardly anybody does that. I’m like, I’m going to be that same person. Now, when somebody reaches out to me, I do my best. I can’t do it now but let’s go meet somewhere or talk somewhere or go sit down. Even when I sold my agency, everybody came out of the woodwork that wanted to start an agency and do the same stuff and say like, there’s not really all these secrets.

Today, when you’re telling me, this is helpful or not, it is. I think it’s easier to talk to someone else and get it out to someone else about an echo chamber of yourself when you’re a solo founder is extremely important. It’s been a privilege to even be on here and talk to you.

Rob: Yeah it’s been great and you know as a single founder, I would recommend, I’m sure you’ve heard me beating this drum for years, but mastermind group. Having two other founders who you talk to twice a month, who are in this essentially with you, even though they’re not your spouse, significant other or cofounder but they’re on that journey is something I really recommend for single founders, having been on that journey and felt the loneliness of that.

John: It was heavy in some days.

Rob: I know, I’ve been there. If folks want to keep up with you on Twitter, you are @useslingshot is your company and @howardcjohn and of course useslingshot.com, if they want to check out what you’re building. Thanks again for coming on.

John: I appreciate it. Thanks again.

Rob: Thanks again to John for coming on the show. After we recorded, he actually Slacked me. I believe it was the next day and he said, kind of random, but I was thinking about our conversation the other day and I do think a monthly fee could be at play if it adjusts their fulfillment cost. We charge $350 per item currently and if it allows them to set up unlimited events, since currently we charge $99 per event. It might be interesting to our higher volume clients. That’s the kind of thinking I was trying to get out with John, is there a benefit that you could give them in exchange to have some kind of monthly fee. I think that’s a great idea.

John, I hope you’re able to maybe test that out and certainly you can report back by writing in the questions at startupsfortherestofus.com. You can hit me directly in MicroConf Connect or maybe we’ll follow up with you in six months, bring you back on the show and see how things turned out. Thanks again for showing up this week, the last week of 2020. May 2020 soon be in our collective rear view mirrors, thanks for listening this year. I’ll talk to you next week.

Rob: Welcome back once again to Startups For the Rest of Us. This week’s episode was quite a challenge, I have to admit. The show must go on. Mike Taber and I attempted to record a live episode on MicroConf On Air’s live stream, and we got through it. But the number of technical challenges that were involved was ridiculous, failure after failure. I’m very thankful to editor Josh.  He was able to clean the episode up, that it sounds mostly seamless, although there’s differing audio quality at different times due to streaming and buffering because we were not recording in Squadcast as we normally do.

Obviously, this episode will feel a little different. It is live, and sometimes I believe my AirPods connected and then disconnected so I was on my non-podcast recording mic on and on. I hope you enjoy this episode today where Mike and I ran through our 2021 predictions.

Mike, in the original draft of Star Wars: A New Hope. What was Luke Skywalker’s last name?

Mike: Starkiller.

Rob: Nailed it. In this episode Startups For the Rest of Us, Mike and I talk about our predictions for 2021. This is Startups For the Rest of Us Episode 528.

Rob: Welcome to Startups For the Rest of Us, the podcast of developers, designers, and entrepreneurs be awesome at building launching, and growing startups, whether you’ve built your fifth startup, or are thinking about your first.

I’m Rob.

Mike: And I’m Mike.

Rob: And we’re here to share our experiences to help you avoid the mistakes we’ve made. What is the word this week, sir?

Mike: I have some big news to share. I am officially moving to Canada.

Rob: Are you really?

Mike: No. April Fools’ Day? It’s like March 3790th, but April 1st is going to be right around the corner. I figured I’d spring one on you.

Rob: Oh my gosh. I thought you were serious. I was like, congratulations, sir. All right. What’s going on now? What’s the word this week?

Mike: Not much. I’m just trying to wrap up the end of the year and get things all straightened out for next year. Mostly a lot of paperwork at this point and getting things together to have ready to send off for tax season. It’s just wrapping up last-minute implementations, and sales, and stuff like that.

Rob: Are you going to get a tax refund or are you going to pay?

Mike: I have no idea. I don’t usually find out until March, April timeframe, something like that. I have no idea.

Rob: Cool man. Let’s dive into reviewing our predictions that we made in December of 2018 for 2019. We never did make 2020 predictions, but these are basically for two years ago. You want to run through your head. We each had four predictions, and you can run through yours, and give yourself a rating of 1-5 on the accuracy, five being most accurate, and then I’ll do the same.

Mike: Sure. The first one was that a global downturn would be in full swing and I was off by one year on this. I don’t feel like I was. I don’t feel like I should get credit for it, but at the same time, it was only off by a year. It does feel 2020 is a global downturn. I’d probably only give myself maybe 2 ½ on this one. I’d probably lean towards a lower score, maybe 1 ½ or two instead, just because I was off by the year, but it’s not to say it didn’t come true.

The second one was esports leagues getting a TV channel aside from Twitch. You’d told me that apparently, that already existed so, five.

Rob: You have predicted something that had already happened.

Mike: Yes. It’s like a reverse Nostradamus. My third prediction was something bad would happen with Tesla, SpaceX, or Elon Musk. I have to say, in retrospect, looking back that there were some tweets that his behavior got more and more outrageous. Then he was essentially forced to step down as the chairman of the board by the SEC, and they fined him $20 million or something like that.

Rob: But that happened in September of 2018. We recorded this in December. This was months later. You were predicting something even more.

Mike: Oh, I don’t think that happened until the spring though. It was February of 2019.

Rob: Elon Musk stepped down as CEO and stepped down as chairman and this is September 19th, 2018 in nytimes.com, three months prior. You were predicting something more would happen. I vaguely recall.

Mike: I thought there was some other stuff that came out afterward, in the spring of the following year, where they came out, and fined him, and did a bunch of other stuff, but I could be wrong on that so that’s one.

Rob:  I don’t remember him getting fined after that. Aren’t the stock prices all up? I don’t know, man. I would think this is a mess as well. I just don’t know if anything could happen.

Mike: The article I was looking at said that he had tweeted something out, it was a picture and it said, “4000 Tesla cars loading for an SF in Europe.” He tweeted out on February 19th, 2019. After that his general council resigned and then all this other stuff. There was a bunch of stuff that happened afterward. I give myself a three on that one.

The last one was Amazon will overtake Apple in terms of market cap. I was pretty far off on that one. And that would be a one, maybe a zero. It was within the realm of possibility, but certainly, I don’t think that it happened.

Rob: All right. Let’s see if we can get through my four predictions here that I made again, back in December of 2018 for 2019. The first was that cryptocurrencies would have ups and downs, but there would be no major boom in 2019. That was still bullish long-term. Now, we’re having a big boom in 2020. I would give myself a four on that because there was no boom in 2019, and there is a boom right now. The bullish long-term thing remains to be seen, but I’ll give myself a three or four. I predicted 2019 would be the year of AR, augmented reality, and I would give myself a one or whatever the lowest score is on that. I remember being like no air is going to take off, and there’ll be a headset, and we’ll be doing it.

Like every prediction with technology, it’s probably five years early. There would be a Facebook antitrust suit brought against them. An antitrust suit brought against Facebook. I predicted that for 2019, and there would be a rise of a new social network as a result because they would either get broken up or get handicapped by it. For 2019, I get a zero but for 2020, that just happened two weeks ago for those watching in the future—Facebook antitrust suit. It’s funny how the timing works out. And then I made a bold prediction that Twitter would be acquired, which it did not happen so that is an absolute fail.

You and I have never really had good track records with these. It’s kind of tough, especially the bolder. You want to make it bold so that they’re fun to talk about. The bolder they are, the less likely they’re to happen in the next 12 months. A lot of our predictions, I bet if we went back, a lot of them happened eventually.

Mike: Sure. I don’t think people are going to be predicting things that are just not even within the realm of possibility, but eventually at some point, sure, they could all happen.

Ben: Cool. With that, sir, let’s dive in. Let’s see, we each have five predictions for 2021 and why don’t you kick us off with yours?

Mike: My first prediction is based loosely on current events, but I believe that commercial office space real estate will never recover. That’s going to be a function of these large businesses that have sent everybody home for long stretches of time. Whether initially, they thought it was only going to be a couple of weeks, and then they realized it was several months, and now it’s stretched out in some cases to six months, a year, or two years at this point. They’ve realized that they don’t need those big office spaces. They have these big buildings and places, whether they’ve either purchased it or rented it, and they’d come to find out and realize, hey, we can make this work and we don’t need these spaces. We can have all our workers at home and we can cut a lot of expenses by doing so. In some cases, they’re cutting millions of dollars by being able to do that and they’re making it work. Knowing that they’re able to survive without this office environment, is going to encourage them to continue down that path, and they’re just not going to come back. There are certainly some who are going to, but for the most part, that stuff’s gone away, there’s still going to be a lot of services—real estate for salons, phone repair, and retail, and things like that—but the actual office space stuff, that’s gone. I don’t think it will ever come back.

Rob: Bold prediction, sir. What’s funny is, as you talk and say these companies have realized they don’t need the office space, they can be remote, does it feel to you finally like catching up. What was the bootstrap, the MicroConf community has been doing for a decade? Because we didn’t have the money to hire talent. You couldn’t afford to hire talent in a major city so we always hired remote. It’s like, oh, you’re getting here too now.

Mike: I feel it’s hearkening back to my consulting days where I would go into a company and they’d say, oh, this can’t be done or we can’t do it this way. And I asked the questions, why not? But because I’m an outside person, in some cases, they would just obliterate it as no, that’s completely a non-starter, even though I’ve made it work at other companies. There are other cases where they’re like, oh, that’s a great idea. Why didn’t we think of it? It’s just like, it wasn’t you didn’t think of it or nobody’s talked to you about it. You just didn’t believe it until you actually saw it. That’s more of it than anything else.

Rob: I agree with that. My first prediction is that privacy concerns will continue to transform email marketing back to what it used to be, which was basically, spray-and-pray. Obviously, over the past 15, 20 years, if you think way back to early days of constant contact around 2000, you get some open rates and some click-through rates, but a lot of people didn’t pay attention to them and you just had this list that you sent a broadcast to, and you didn’t do any type of tagging or behavioral based email.

You didn’t write anything specific for different segment, and then over the next 10, 12 years, that became a thing. Marketing automation and the tagging, and everything became a thing as Infusionsoft, Marketo, Pardot, Drip, and then Mailchimp added them in a Weber added out of that type of stuff. But the privacy concerns with tracking pixels in essence, inside emails is becoming more and more of an issue.

This year with hey.com with the Basecamp guys putting out Hey and saying, we’re going to block all tracking pixels. I believe they’re going to shame people in the app who sends tracking pixels. There’s kind of becoming this backlash about it. While certainly I don’t think every email client will do that instantly—much like Not Provided started happening in Google, and much like SSL everywhere became a thing—there’s a movement towards essentially blocking a lot of the good metrics that an email service provider can get from email broadcasts or an email automation. Once you lose a lot of that stuff, you will start to lose the helpfulness of the tagging. It’s not that you can’t have any automations, but it’s going to set email marketing back in five or 10 years.

Mike: My second prediction is related to government regulations on big tech. There’s a couple of different things that will fall under this umbrella for my prediction. This is almost a two-parter and the first one is going to be an over attempt by the government. I’m going to lump a couple of them together like in the United States federal government, the European Union, or maybe even as I doubt a state government would have the ability to do this, but they’re going to attempt to break up at least one of the big tech companies and my money on that would be on Facebook. But Amazon, Apple, and Google are all there on the cross areas, but Facebook is probably the one that would end up being targeted if any of them won.

My second prediction under regulations is that governments are going to actively crack down on the gig economy. Essentially, people who are doing side jobs or they’re stringing together multiple side jobs in order to either make a living or make extra money on the side, those types of people, the government’s going to look at those and say, not only are they very high at risk for getting COVID or other things, but the problem that the government’s going to look at and see is that those people don’t have any healthcare, or health insurance, or have low access to it. They’re not treated well. They’re not paid well and therefore, need to be productive.

The governments are going to crack down on those things and put legislation and regulations in place, and not just talk about it. They’ve talked about it before. They’ve tried to do things like the California state government has tried to do things, but no one’s ever made a concerted effort. And that this year is going to be the year that they do that.

Rob: It’s already happening. I guess there’s a lawsuit against Facebook and Google. Lawsuits from 40 something states and the federal government. Are you piggybacking on that and saying the results of that lawsuit will be that they try to break one of these up.

Mike: Yeah. There’s a difference between suing them and then trying to get them to change their practices. We’re going to go that extra step and they’re going to say, no, what you’ve proposed is not acceptable. We want to break you up. Similar to what they did back with Microsoft, and then Microsoft did all these different things, that never actually came to happen. But they’re going to push for that hard enough that it’s going to get to that point where that’s on the table as a potential resolution, whether it happens or not is a different story but it’s going to get to that point where it is pushed and it is openly on the table and everyone’s talking about it.

Rob: It’s on the table already. The prediction to be bold would be that it will happen. People are already mentioning it. The first news article I read was, “Could they be broken up?” And that’s the first thing that folks are saying. I would also say that Facebook and Google have a suit against them and Apple doesn’t yet. My opinion is Google, Facebook, and Apple are monopolies. Amazon is not a monopoly in anything. Maybe Kindle is the only one I can think of. Can you think of another thing they’re a monopoly in? Because they don’t own enough of the ecommerce market to be a monopoly.

Mike: There are spaces in the ecommerce market where they are doing things that are more monopolistic, such that they own the platform, and they’re allowing people to sell the fulfillment by Amazon. I believe that they’re using some of that data to decide what products that they should offer as white label Amazon products, and they’re using sales data that they shouldn’t. That came out a little bit, it was at least alluded to in some of the congressional testimony this past year, but it was never concretely confirmed one way or the other. There are definitely arguments there.

Rob: I hear that. The white label stuff you’re mentioning is anti-competitive, but I don’t believe it’s monopolistic. To do an antitrust suit and to try to break up a monopoly, you need to find evidence that they are a monopoly. Now, they could be sued, I believe, for anti-competitive practices with the white label stuff, but it’s just such a different game. With Walmart, and Target, and Best Buy, and all these other retailers, Amazon has the majority of the market. They don’t have that 90 something percent penetration that Google does, or Facebook does, or whatever Apple has.

Mike: The monopoly behavior is where they have access and visibility to sales data for their competitors directly in the platform that they’re selling on. That’s where it becomes abusive, a monopoly platform.

Rob: It’s anti-competitive. Monopoly is a very specific definition. It’s where you own almost all the market and no one else can compete. Frankly, Walmart is competing. Shopify stores are competing against Amazon, but anti-competitive is not right what they’re doing, but it’s a different name.

I don’t know that you can bring an antitrust suit against them. It’s just interesting because I’m in the same book boat where Facebook, Amazon, Apple, Google. These are all huge companies, they must be monopolies but I only think three of them are. I don’t think Amazon is, and knowing Bezos, he’s a pretty smart guy to have not done that, that they’ve gotten this big without being a monopoly in any space. They have Amazon AWS and the Google app engine, and Azure are both good solid competitors of that. Again, Kindle is the one I can think of where they just own the vast majority of that market but anyway, a good prediction, sir.

My second prediction is that in 2021, in-person events will happen but adjustments will be put in place, whether it’s social distancing early in the year, or masks being warrants—just all this stuff that we’ve seen around. Then as we get towards the end of the year, less and less of that stuff will be needed.

Mike: Cool. My third prediction is related to healthcare. There’s going to be a major breakthrough in nanotechnology. Obviously, there’s been a lot of advances with the COVID vaccine but this is going to get to the point where it could be something like an implanted chipset that is intended to go mainstream. I don’t believe it would go mainstream next year but I do think that somebody is going to come out with something where the intention is to do that. It might also be something that is much more, I’ll say specialized. It could be an artificial organ, an artificial one that has not been developed yet. Maybe pieces that would augment your liver, or maybe a replacement kidney, something along those lines.

It could also just be something that’s a little bit more simplistic that is for either monitoring or diagnosing ongoing bio functions. It could be used for surgery or for postop care or something along those lines. In those cases, it obviously wouldn’t be mainstream so much as it would be specifically for hospitals or surgery centers where they can just put this in you and implant it and then use it to assist them with whatever it is that they’re doing. People will be terrified by this whole idea because they’ll be like, oh my God, Bill Gates is trying to microchip us.

Rob: Only some people will be terrified by it and there’ll be people who are totally willing to do it. I like that prediction. We got a prediction from the chat, from Ken Wallace, he says, be bold. Predict that 2021 is the year of universal basic income, UBI, Mike. I don’t think it’ll be a thing in the US. I can totally imagine some countries in Europe giving it a try in 2021.

Mike: Yeah, I definitely could as well. It’d be a long time before something like that happens in the US but Europe is definitely a lot more progressive and from that standpoint, I could see them doing them.

Rob: I’m not read up enough on UBI to have too much intelligent thought on it. But my third prediction is that funding in the startup space in general will—and especially in the bootstrapper space—will continue. It’s de-stigmatization as more founder-friendly options continue to show up and continue to expand. It’s interesting. When was it that I predicted it, but it was something about that there would be more bootstrappers raising funding. This was three years ago and it was before I started TinySeed, I’m pretty sure.

I was just seeing that Indie.vc was around and then revenue-based financing started happening with the SaaS capitals and the Ladder capitals. It just made sense that more people who maybe wouldn’t have wanted to go venture track five years ago would potentially want to do the falsity fund strapping route, or just the raise one small round to go to profitability or do revenue-based financing, or just do the non-venture track, any of those options, it’s not binary anymore. I can bootstrap, I can do one round, I can take money from TinySeed, I can take money from Indie.vc, I can do revenue-based financingc—if I get to the point where that makes sense—or I can take venture, this whole buffet of options.

What it feels to me, it hasn’t happened with everyone, but there is a de-stigmatization of funding, whereas funding used to come with a lot of strings attached—loss of control, can’t sell my company, I got kicked out as a CEO, I have to put up with these venture capitalists breathing down my neck, and this board, and blah, blah, blah—and all those things. Poof. If you want to take funding from certain people under certain circumstances, none of that exists anymore. There are different constraints but the optionality that founders have especially bootstrap SaaS founders have these days are tremendous. 2021 basically continues that the stigmatization process.

Mike: I would agree with that. That’s a good prediction. My fourth prediction has to do with movies. Specifically, the Marvel cinematic universe is going to somewhat fall off a cliff. It’ll be subtle at first and then people are just going to be like, yeah, I’m not into this. The reason specifically for that is that they’re getting into the territory of going in and pulling out some of their second-tier characters to draw them to the forefront, which I agree with that as a general strategy and thing that they should do because there are lots of characters that are probably less popular. But because they’re less popular and people haven’t heard of them, there’s going to be a lot less interest in those.

Iron Man is an obvious draw but there’s a lot of these other characters that they’re pulling out like Dr. Strange where some people like, I don’t even really know who that is, I’ve never heard of that person before, even if they’re peripherally involved or knowledgeable about comic books and things like that. I just think that a lot of those characters are not going to be nearly as big a draw and it could result in them scaling back what they’re going to be doing in the future.

I’m a little, I don’t want to say concerned, but I do think that what they’re going to find is that following is ramped-up for the longest time until the last couple of Avengers movies, and then it’s going to fall off a cliff, and they’re not going to quite know what to do with it. They released the new Star Wars solo movie and then it didn’t do as well as they had hoped it would or thought it would, and then they’re going to pull back on the reins.

Rob: That’s a bold prediction and I hope that doesn’t happen—

Mike: I hope it doesn’t either.

Rob: —but it is a prediction. That’s the thing, man. One example is Moon Knight, anyone who didn’t read the comic was like, Moon Knight? Who’s that? But he’s slated for a movie or a show or something coming up. I remember, when they did Iron Man and Captain America, Iron Man always had a comic but he really was not prominent—he was fine—but he was not that prominent the way he is today where it’s like, no, Iron Man is one of the leaders of the Avengers, and even Captain America. I remember I was like, this movie is going to be terrible, and then I saw it and I was like, I cannot believe how good that movie was. I can’t believe that they made such an amazing, compelling story from that character.

I hear you. I appreciate the boldness of your prediction. I hope it doesn’t come true. I know they’re already doing several Marvel TV shows in Essence or streaming shows on Disney+, and that’s basically what Star Wars has gone through. If you heard, they did 10 Star Wars announcements a couple of days ago, or it was last week, I guess, and I believe seven or eight of them are essentially streaming—eight seasons of streaming shows and only two of them are films, which is fascinating.

Mike: It’s fascinating, but also, them hedging their bets and in such a way where they’re not betting everything on this massive movie offering, and they’re spending hundreds of millions of dollars, and they may ultimately spend hundreds of millions of dollars on a particular storyline, but by doing it through their Disney+ platform. That’s the thing. They’ve got all these different channels and ways to distribute it where they can put it as a TV show—it’s less effort, less money, less production costs, all these other things that go into it—and then they can essentially gauge the margin market but also build interest in that storyline.

When it gets to a certain point and they can say, oh, this justifies having an actual movie, now, we’ve amassed the interest. As opposed to they come out with a new movie for this character nobody’s ever heard of—it’ll be like John Carter. They’re like, oh, wait a second. What? Who’s John Carter? What are you talking about? Unless you’ve ever read those books, you would have no idea and it’s not an interesting story.

Rob: I hear you there, sir. Speaking of that, we’ll get back to startups in a second. Are you watching Amanda Lauren?

Mike: Yeah.

Rob: Do you like it?

Mike: Yeah. That’s good so far.

Rob: It’s really good and I’m stoked on it. Alright, my next prediction. My fourth prediction is that VR will become mainstream.

Mike: You just ripped that off from one of the listeners.

Rob: I got an Oculus Quest 2 about three weeks ago and it is a consumer level, it’s about a $300 headset, you don’t need a computer to run it. It just connects to your wifi, and then you get on your mobile phone or your iPad. It is amazing. The kids love it. It $300 and it just works. You just plug it in and it works. I mean, you don’t have to plug it in, it’s completely wireless, and it’s such a leap and a bound from, oh, I need to go out and get a windows PC that’s all beefy.

Frankly, we bought one about a month ago, and within two weeks Cherry’s like, oh, we should have two because you can do a bunch of cooperative games with them and stuff. I can easily see us just picking one up every quarter next year because a lot of the co-op games go up to four people, and I’m not saying Oculus—it’s the only one I’ve owned. I’m not comparing it to other things. I’m just saying if they can build a headset this good for $300 and sell it for $300, where are we headed next? Where is the $199, $99 headset? The experience of it is amazing. It truly is game-changing. Certainly, if you’ve never done VR, it’s a trip, and even if you have done it to sit and be able to play it for 60, 90 minutes and go into the VR world is, it’s like we’ve seen in the movies for 30 or 40 years, but 2021 is the year.

Mike: Tube-related anecdotes ones. I remember seeing a VR headset from 20 years ago. It had this like little hockey puck thing that you had to hold, and you could move your head up, and you can see everything. It was like these little LCD screens in front of you, but this was back—it was literally 1996, something like that. It was ridiculously early, not nearly as good as what they have today.

But the other somewhat related anecdote is when I was a kid, I actually wanted to be a science fiction writer. One of the ideas that I’d come up with for a storyline was in the future, there’s a future where people are not fighting wars anymore. They’re basically fighting with these virtual reality simulators where they’re almost in this giant robot or something like that, and they’re battling each other for control of different territories, but they are augmented in such a way that it becomes real. When you shoot at somebody, it’s not just a laser blast. There are physical sensors and stuff built into the suits stuff that the people had to wear, and you could literally take physical damage from somebody shooting you inside of the “simulation”. Then there are backstories where people do nefarious things and sabotage other people’s suits and stuff like that. I never really fully published anything or came out with it but that was the idea I had a long time ago.

Rob: I like that kind of stuff. Alright. Oh, that was the VR Oculus, so we’re on to your fifth and final prediction for 2021. While we do that, it looks like we have a little more in the chat. Ken Wallace said, my Mandalorian prediction, Grogu goes to the dark side. Oh, is this a spoiler? Grogu goes to the dark side but comes back after destroying the Darksaber. Zander’s note, I still refuse to call him by his name.

We have a prediction, he says, next JS GraphQL and Tailwind CSS will become extremely popular. I think that’s already happened, hasn’t it? They all seem super popular to me. I keep hearing about them, but I guess it depends on what we mean by super popular.

Mike: If they get websites, we know they’re going to hold.

Rob: Right. Cool. Can I have in here your fifth and final?

Mike: Yeah. My fifth and final prediction here is that we will discover definitive proof of extraterrestrial life. I don’t know what exact form that’s going to take, whether it’s going to be Mars or some comet, or an asteroid going by, but that’s the prediction here. There’s a lot of scientific discovery going on right now where people are trying to pull back that information from outer space. They’ve even recently sent a rocket out to an asteroid that was going by planet Earth and brought some of the materials back. It took three or four years or something like that to get it. I don’t know if they’ve analyzed it yet or not but they do have other ongoing things going on. We’re going to get something.

Now, does that mean that we’re going to see proof of little green men? No, that’s not necessarily the case. It could very well just be single-celled things. But the idea there is, it’s not just particles from Earth that ended up in outer space because they were on a rocket or something like that or a spacecraft, and then we find them elsewhere, it’s that they are actually extraterrestrial in origin, so off of anywhere, whether it’s Mars or the moon, something like that,

Rob: That is a bold prediction, sir. I like that.

Mike: I had to go with one that was off the wall. I felt like if you’re going to do predictions, you may as well go all in at some point.

Rob: It’s Babe Ruth colonist shot. My fifth and final prediction is that in terms of the world and COVID, everyone’s predicting, oh, it’s the middle of the year, and then not to the end of the year. I’ve heard people say like, it’s going to be five years until everyone feels back to normal, or the end of 2022 until things are back. We’re going to get back to normal a lot faster than we think, at least within our home countries. I know traveling internationally is going to be different because different countries are handling things. But as vaccines roll out, as we get herd immunity, I think the cases are going to drop faster. I also think people’s comfort level and a lot of people’s desire just to not be cooped up and to go out and go to in-person events or go to movies or go to concerts.

The desire to go to those things is there, and there’s pent-up demand now. The moment—I know several people—the moment they get cleared, when they have that second vaccination, they want to go and do all the things. I’m probably one of them. I’m not an extrovert and yet I want to go work at coffee shops again. Minnesota opened up for a while and we’re back closed again, but we were doing those things, but I still really miss just being able to get out. It’s going to happen fast. I’m an eternal optimist on this front, actually.

Mike: You’re doing a lot of projection there because I’m on the other side of the spectrum, I almost got a t-shirt that literally said when this is over, I still don’t want to see some of you.

Rob: I have that 2020, 0 out of 10, would not recommend a shirt with the zero star.

Mike: I read the 2020 Dumpster Fire t-shirt.

Rob: Yeah. I have a few of them. Well, man, those are our predictions. Can we get to revisit those in just about a year?

Mike: And see if any of us gets above three, four?

Rob: Yeah. If we get more than one, three, that’s probably the goal for next time. The theme music that we couldn’t play today, but it was edited in post, is an excerpt from We’re Outta Control by MoOt, and that’s used under Creative Commons. Obviously, you can search for Startups in any podcatcher and subscribe to us, and always head to startupsfortherestofus.com for a full transcript of each episode. After this is cleaned up, it’s going to be nice and tight. Thank you so much for listening. Mike and I will see you next time.

Mike: Take it easy.

Rob: Welcome to this week’s episode of ‎Startups For the Rest of Us. I’m your host, Rob Walling. It’s Episode 527, where Courtland Allen from Indie Hackers joins me. We talk about moving from agency to SaaS. We talk about equity splits. We talk about the best cities for bootstrappers and more.

Before we dive into that conversation, ‎Startups For the Rest of Us has 890 worldwide ratings across 48 countries. Our most recent review is titled Inspirational. “Longtime listener, I run a portfolio of SaaS apps, three built from scratch, and one acquired recently. I learned a ton from this podcast. Very grateful.” That’s Danielle0412 from the UK. Thanks so much for that review, Danielle. If you haven’t left us a review or even just a rating, would appreciate a five-star rating. I’d love to push past that 900 worldwide rating mark on our way to 1000 in 2021.

Thanks again for joining me. Let’s dive into our listener questions that I answer with Courtland Allen. If you haven’t heard of Courtland, you should check out indiehackers.com. It’s a great online community for people building online businesses in order to improve their life. There’s a range of SaaS and info products and all types of things, indiehackers.com, as well as the Indie Hackers podcast, Courtland is the host of that. It’s an excellent interview and topical new show that many of us listen to every week. I’m a fan. Let’s dive right into our first listener question.

Courtland Allen, welcome back to ‎Startups For the Rest of Us.

Courtland: Rob, thanks for having me.

Rob: It’s always great to have you, Sir. I’m excited to talk through some listener questions today. We have a nice stable of things ranging from splitting branding, to business structure, to co-founder equity, stair-stepping, all that stuff. Are you ready to dive in?

Courtland: Yea, I’m ready to. Sounds like a lot of good stuff.

Rob: As usual, we always start with voicemails at the top of the stack. We’ll roll our first question from Dustin Overbeck, here.

Dustin: Hey Rob, my name is Dustin Overbeck and I run a web design agency called Town Web. We are a web design and hosting agency for municipalities all across the United States. I’ve been running this for 13 years. We have more than 550 customers, and we’re in about 35 different States. I’m getting ready to build a SaaS app that would be sold specifically to the same customers that I currently have for the web design and hosting part of things, but also to other municipalities who are not currently web design customers of ours.

I’m curious to know if you have any input on other web design agencies that entered the SaaS space because my question is more about branding and business structure. When I’m looking at the numbers for the SaaS app and the price points that we could sell to in the market that we can go after, I feel that this SaaS business could be 10-15 times bigger than what we currently have for the web design and the hosting side of things. I’m leaning towards, yes, we should have a separate brand for the SaaS product. I’m curious if you know of other agencies who have done that same thing, or if they entered the market with the same name as their agency. Although we do have a good brand known in the municipal web design industry, the brand that we can come out with for the SaaS app could actually be more exciting and maybe even more memorable to those potential clients that we can go after.

The other question is about business structure. If it’s going to be as a separate brand, should it be a completely separate business? I know there are inherent costs when you have two separate businesses because you’re now keeping track of two different books, two different tax filings. But if the second business could be 10-15 times bigger than the first business, is it worthwhile to have separate businesses? Thank you for any input.

Rob: Thanks for that question, Dustin. Courtland, you have thoughts?

Courtland: I do. I’m looking at his website now, Town Web. This is pretty cool. This whole idea of having an agency to build websites for the super-specific niche of municipal websites. This question really is about branding and this way he phrased it—should we start a new brand or go with their old brand. I would separate your identity from your brand. Their name and their logo are what I would classify as their identity. It’s Town Web, this cool American eagle looking thing going on next to it. But then your brand is more so your reputation with your customers. What do your customers actually think about you? You can’t change your reputation except slowly over time, but you can’t get rid of it either. You can get rid of your identity and then people can’t connect your identity to your reputation, and that’s bad if you have a good reputation.

When I look at this, on one hand, you could change your identity. You could have a completely different logo and name, but preserve your reputation by simply contacting your customers through sales. I presume when they do this new SaaS tool, they have 550 customers for their previous agency. They could just email these people from their previous identity, using their old email address, and say, hey, this is so-and-so from Town Web, the agency you’ve come to know and love. Then boom, your reputation is cemented because it’s already there. They already know you. You can say, we’re working on this new thing, what do you think, blah, blah, blah. Do you want to hop on a call? You’ve got your reputation preserved, which is your brand, and you can transfer that to your new identity with these few customers that you start with.

Even if his new business ends up being 10-15 times bigger than his old business, which is a pretty bold prediction, you’re still going to start probably by doing things that don’t scale. You’re still going to start with these sales calls and these cold emails probably, and they’re probably going to be towards your old customers. It’s worth preserving a reputation there and just making sure they know who you are and getting a good start there.

Rob: I like the way you’re thinking about it. The way I think about it is 37signals in Basecamp, that’s probably the best example. 37signals was their design agency, it was the company name because Signal v. Noise was their blog name, and then Basecamp was the product. And you knew that 37signals built Basecamp, and you trusted 37signals because you’d read their blog, or their books, or whatever.

That’s how I think about it, which is what you’re saying here is you have Town Web, it has a brand, it has an identity. Personally, in their shoes, I would not name the SaaS app Town Web. I would have them be very separate. He didn’t specify what it was going to be, but it’s XYZ Tool by Town Web. You can easily have that which is where you can borrow your brand equity. It’s much like the state of independence State of Independence Saas report by MicroConf.

We lend MicroConf branding to this new thing, but it still is able to have its own identity. Because to your point, you’re going to start with older, existing customers, and so having that brand is important, having the relationship. When you get up to new customers, I agree with Dustin when he says, we could do something more exciting. We could come up with a cool name and a cool logo and even develop its own identity.

Personally, if I were doing this, maybe you launch 1, 2, 3 SaaS apps. Now, you need three different SaaS apps over the course of 10 or 20 years. You don’t want them tied to the agency. If it becomes literally 10-15 times the size, since SaaS apps by nature are more profitable than agencies, my guess is much 37signals did, much like Mailchimp did—because they were an agency before they launched email marketing software—they wound up shutting theirs down. I’m sure that’s not Dustin’s plan right now. And I’m sure he wouldn’t go into it saying, I’m going to shut it down. Shut down, or sell it, or somehow walk away from it. Because if you get a SaaS app doing millions of dollars a year, suddenly things are really annoyances. I’ve been there. I’ve had many businesses and when one gets big it’s, oh, this is what I should be focusing on. With that in mind, I would hate for the two to be coupled to the point where you lose optionality.

Courtland: Another business that comes to mind here is Wildbit, which also started as an agency, and now they’ve got a host of different products. Go to wildbit.com and see, here’s the company that owns the different products. But you can also go directly to those products. Each of which has its own unique brand, it could get very confusing. Town Web, it is an agency, but then they also have a product called Town Web. Now it’s two different things. Now they’re stuck in the situation where they have one website that’s trying to cater to two different customers—one case of product and one case of service. Then, you’re also right, what if they want to launch more SaaS businesses in the future, it’s just going to be confusing. I like the idea of having separate brands and you can just manually transfer the reputation from your first brand to your next brand by getting in contact with your existing customers.

Rob: Exactly. Likewise, his second question was about business entities and whether you should separate them. Look, if you were not a super legitimate web agency that had the budget to do it, in the early days you could say maybe we keep them under the same corporate umbrella, and maybe just save on the $500 or $1000 a year, maybe it’s $2000 a year of bookkeeping and tax filings. But given that you are a legitimate business from the start, if I were in Dustin’s shoes, it would absolutely be a separate entity.

Whether the SaaS product, whether that’s an LLC or an S corp, C corp, whatever you want to do, I would form this thing, I would keep separate books, I would put a trunk of money into it, essentially angel investing. Whether Town Web puts that money in, or you put that money in personally, give it enough budget that you can build and support it. You can always fund it more later, but you maintain that because that is essential if it goes under, you can then have losses against it, which you should be able to write off. If you ever decide to sell it someday, I know that’s the last thing you’re probably thinking about, it should be separate. Because if it’s tied in expenses, and credit cards and bank accounts are all tied into an agency, it’s just a mess.

While it feels maybe a little overkill in the early days—I got to have a second tax filing and yes, you do have to probably go through Stripe Atlas to get a separate entity—there are some duplicate things I just don’t think you’re going to regret. You could always merge them later. It’s easier to merge things than it is to pull them apart. In fact, I went down this road. I had an umbrella company now called Start Small, LLC and it owned several small products that I owned and I would just slowly pile them on.

It owned my half of MicroConf and my portion of all these things, and then Drip initially launched under there. As Drip got bigger and bigger and started employing all of us and becoming just a more legitimate company, I was like, this should be its own Corp. I eventually did have to fork it out basically and pull it out of this LLC that owned all this other stuff. It was painful. It wasn’t totally undoable, it turns out it was the right decision because within a year we got the acquisition offer. We sold it. It would have been an absolute nightmare to try to go through a sale with shared books, shared expenses, because an acquirer wants a clean break. They want to know that this Corp owns all the IP and that everything is clean. Thank you for the question, Dustin. I really appreciate that.

Our next question is from an anonymous question asker. It’s about co-founding an app, what percent equity split he should think about. He says, “My business coach came to me with an idea for a SaaS app that he would like me to build and handle the technical side. He would handle the marketing side of things. We would be bootstrapping so no initial investments. I offered that I would build the app, handle the features, maintenance, upgrades, and support for 40% of profits and 40% of any future sale of the web app. Is this a fair number? Bouncing this off a friend, they said it might be too much and they were thinking it should be more like 10%.

I usually recommend co-founders split things 50/50 when I’m asked this question, but my business coach brought the idea to me and he’s approaching retirement, so I reduced it to 40%. I’m not sure I would want to spend the time to develop it for less than 40% equity since I could use the same time to work on my own SaaS that I’m currently building. My business coach has no experience with SaaS or web apps so I expect to bring a lot of knowledge on the product side, on the technical side, and that will even cover some of the marketing optimization, SEO, building an email list, et cetera. In my opinion, this has a pretty good chance of success. The business coach knows the founder of a similar SaaS in another niche that has 200 plus users at $50, a month and is still growing.” So that’s like $10,000 MRR. “Thanks for all the great content over the years.”

Courtland, what do you think?

Courtland: Tricky topic. I’ve had some bad co-founder fights in my past, over equity actually. I think a lot of it really comes down to not exactly the number that you named, but the process that you use to get to that number, and how much you and your co-founder on the same page about that. It can be easy to throw a number out, it can be easy to say, oh, let’s be 50/50 now. But if you haven’t thought about why you’re choosing that and you haven’t specifically agreed with your co-founders on why you’re choosing that, later on, it opens up just a lot of space for unhappiness, disputes, and misunderstanding. If it comes down to that, you want to be able to say, look, this is what we decided on and here’s exactly why we’re changing this now.

The first thing I would do rather than just say it needs to be 50/50, maybe a small discount because it’s the other person’s idea, I would say the way you split your equity should be based less on equality and everybody getting the same and more on contribution. If your level of contribution later on is different, it might arouse some resentment and some tough conversations down the road. Some of the factors that are important to me like your level of experience and effectiveness, and how much time you plan to spend on this, it sounds like the question asked to who has another SaaS business that they’re going to be splitting their time between. Does their partner also have another thing going on? Are they going to be full-time on this? That’s a huge factor.

Joining later means taking on a little bit less risk, which means that can affect your equity. The more risks you’re taking on, the more equity you should probably get. Contributing to the idea means you’re at more risk because it’s your idea and you can’t go to someone else. Writing code is a pretty effective major thing to do. You should think about what is the other person going to do in their role, and how’s that going to shift over time? These are things that are difficult to predict.

What I would do is I would start by sitting down with my potential co-founder and saying let’s come up with some framework that takes as many of these factors into account as we can possibly predict, and then agree on that framework. And then have a completely separate conversation after that, where you plug in the values and the numbers into this framework and you see what that spits out.

Rob: You want to know their contributions in a number of different ways before you talk about equity.

Courtland: Exactly. Because there’s so many different ways that things can change over time. Some of that is protected by vesting your equity but a lot of it isn’t. If somebody decides that they’re going to start working only half time instead of full time, that’s something that happens quite often due to life circumstances. How do you want to play that in terms of equity, if your equity was decided with the assumption that you would both be full-time on this thing, plus a range of other different activities? It’s good to just be open-minded and open-eyed about this stuff and try to, as best as you can, look into the future and predict what might go wrong and how we can pre-handle it so that when it actually happens, it’s not this big surprise, and we don’t have to figure out what we’re going to do from scratch.

Rob: I like that you brought up vesting, for sure. I think that’s the number one thing I would have is that both of you should be vesting such that if one person walks away, they don’t take their equity. I liked your point about full-time that if you are both going to be full-time, which doesn’t sound like you are, but if you’re planning to be 40 hours a week each, if someone drops to 30 or 20 hours, if you’re working at a startup and you have stock options, typically you stop vesting when you go part-time. That’s something to think about.

The biggest question I have is you’re bringing the technical side and you’re bringing marketing, SEO, building an email list—a bunch of the marketing side. What is your co-founder bringing aside from an idea? If he’s approaching retirement, as you say, how hard is he going to work on this and for how long? There are maybe yellow flags in my mind, are you both committed? That goes back to your questions, Courtland, of have you talked this through? Have you sat down and said, you’re going to retire in two years, are you going to work on this after this? Or is your plan that you want to build this up and sell it in two years? In that case, what should our vesting schedule look like? Should I maybe take on more of it? Maybe this is more of a side project for you, or is it a side project for me? Everything you’ve raised, it fits into that.

He had a sentence early on that says, I would do maintenance, upgrades, and support for 40% of profits and 40% of future sales, the future sale of the web app. We should just be doing equity. Why wouldn’t you just take equity, which in essence would be profits and sales? You can have phantom equity and all that but if you were giving this much to it, I’m just not sure if that’s the right approach. But later on, he does mention equity, which is easier to vest than phantom equity that may be an aside. But you’re right, there’s a lot of details here that make it an it-depends scenario.

Courtland: When you’re working with a co-founder, this shouldn’t be a super tough conversation to have. If things go poorly, there are things that are stressful later on, there’s going to be a lot of other harder conversations to have when things are on the line. At this point, if you only have an idea, and you haven’t gotten started, really nothing’s on the line. No one’s sacrificed a lot. Ideally, when you work with a co-founder, it’s somebody you’ve worked together with, how you deal with conflict resolution, you have shared values, and you want to test that stuff as early as possible. Presumably, this person hasn’t worked with a co-founder before, but having this conversation upfront and just being straightforward about it, it’s a good test because if this conversation goes poorly when there’s nothing on the line, maybe this isn’t someone you want to work with.

Rob: As the developer, your work is front-loaded. It’s easy for the two of you to have a conversation and for you to go spend four, five, or six months building a product only to come back and find your co-founder has lost interest. Or your co-founder maybe can’t deliver on what they promised. Maybe they don’t have the connections and maybe they can’t do sales. What is he bringing to the table? And what can he be doing hour for hour, if you want an even split or close to it, while you’re writing code? Because we know there’s a lot of things you can do. You can be out having validation conversations, customer development, you can have input on the product, you can be taking pre-sales, you can be writing articles, you can do marketing, landing pages. I know you said you have most of that knowledge, but having an idea and being a subject matter expert in a space is fine, but that’s not even table stakes to me for an even split if you’re going to go spend hundreds of hours building and marketing a product.

Courtland: Agreed. It’s one of those things where early on having the idea seems very important because there’s literally nothing else. You might think, oh, this person should get 60%. But the more sweat equity you put into things, the longer you sit there and toil, and write code, and work as the months and years pass, the value of the work that you’re doing increases relative to the value of that idea. If this person isn’t actually contributing a lot in that domain, which so far isn’t necessarily proven that they have, or even can, whereas it’s probably pretty proven that you are a developer who can build things, you were just taking on a lot of risk as a developer in that situation.

Rob: Thanks again for the question. I hope our thoughts were helpful. The next question is from Franco and he’s talking about the stair-step approach, the first step. He says, “Thank you for all your awesome content. It helps motivate me and helps me power through even at the beginnings of a path to a software centered business/life.

My question for you is where should I look when trying to take the first step to make something the world can use and appreciate. Thankfully, the SaaS sector has been growing and gaining traction, but for those of us who are beginning from scratch in the industry, it’s become increasingly hard to take that first step, mainly in my own experience because every niche has been saturated and the expertise needed to start something has increased as well. Hopefully I’m wrong and you can tell me or anyone who is in the same place, where or how we should approach this problem. Thanks for the podcast. I’ve been listening for about half a year and I even enjoy the old episodes from years ago.”

Thanks for the question, Franco. I’ll just add one sentence here. I don’t think every niche is saturated. I do think the smaller and smaller you go, there are opportunities. I wrote an entire book on this. Courtland, what are your thoughts for Franco?

Courtland: I liked that you said that because the entire idea of there being a staircase and Rob, you’re the expert on this, is that the first step is the smallest step. It’s the easiest step. You should always be thinking, what is the smallest thing that I can do to get started, to get my momentum going, to get a couple of wins under my belt, and then parlay those wins and the advantages you accrue to take the next step. When you’re looking at it from that point of view, it doesn’t matter if a space is saturated because if you’re looking at it that way, you’re looking at the tenth or the eleventh step on the staircase. You’re trying to be focusing on the first step where you pick such a tiny niche, or such a very specific problem, or something that’s so straightforward that it doesn’t really matter that there are other bigger players in the space later on.

In my opinion, if you were in a particular situation or you’re not even sure what industry you want to go into, what problem you’re going to solve, one of the best steps you can take is just to do some research. Take a look at what’s out there, what problems people have. I, myself, favor an approach where you look at the intersection of things that you’re interested in and things where people have valuable problems to solve as evidenced by the fact that people are spending a lot of money there.

I have a friend who started a business in the recruiting space. She was very passionate about applying for jobs to become a software engineer, and how terrible that was, and how fake the process was. Something that was recently on her mind and she cared a lot about, and she thought she could do a much better job. It was an industry where companies spent a lot of money on recruiters, on hiring software engineers, on all sorts of different activities there. It satisfied both requirements. It took her a month of just looking around at different things to even just figure out that’s the problem that she cared about, and that’s where she started. She started off by writing.

Writing isn’t that competitive, lots of people are writing. But it doesn’t matter how saturated the writing space is, people will still share your blog posts on Twitter if they’re well-written. They can still be indexed on Google. I would look toward picking a problem first. Then I would look toward maybe even doing something very lightweight, maybe info-related or content-related, where it doesn’t matter what the competitors are doing, and where you can have some real quick wins before I worry too much about jumping straight towards building a SaaS in a competitive space.

Rob: Yes. This is where I invoke the ‎Startups For the Rest of Us drinking game. We all do a shot because I say a stair-step approach to bootstrapping, which Franco brought up. He raised the issue of where I should look. Obviously, these one-time sale products with a single sales channel—like a WordPress Plugin, or a mobile app, or Shopify add-on, or an info product, as you said, or any type of app store, makes it ThemeForest—any of these things make it pretty easy to get started with not a ton of marketing knowledge needed. Imagine if you launch a WordPress theme on ThemeForest, or you do adopt a WordPress plugin, or you already launched something, every niche is not saturated.

Saturated is even a strong word because you can always compete, but maybe when you’re still playing high school ball right now, and the miners in the majors, people are just better at what they’re doing. They have more experience, they have more budget, and they have more history doing it.

I do think that you want to take more of the Start Small, Stay Small approach, which is to look at smaller niches that are underserved and just cut your teeth at those, and you build up experience, you build up a little bit of revenue, you build up your skill set, you build that tool belt, and then you can go essentially build off from there. I do think a lot of people make the mistake of wanting to build a SaaS app which is awesome then we all aspire to do that, but trying to do that as your first step is a real challenge.

Frankly, if you know a programming language, if you’re a mobile developer, I would probably start thinking about launching something in mobile. But if you’re PHP or Pro, I’d probably lean towards WordPress. When you look at all the B2B app stores and just do a Google search for them—there’s Salesforce, and Shopify, and I don’t know, there’s got to be dozens of others, I know there are Photoshop add-ons—you can do just on and on and on. It’s just finding something and picking it and taking a shot.

Courtland: I like some of the stories that have inspired me recently from just founders that I’ve talked to on Indie Hackers. I talked to Tara Reed who is in the education space. She’s been teaching founders to build businesses without code. Her path for getting started was really simple. She gave a talk somewhere where she talked about how an app that she was building didn’t use any code. People are interested and they’re like, how does she do it? She said, oh, I’ll teach you, just pay me $900 and I’ll let you know. She got 10 students who paid her, and she taught them, and then put out the call, hey, it went really well. I could teach more people. And she had 50 or 60 students sign up for that one. Then after that, she grew by reaching out to influencers in the space and doing Instagram takeover ads of their Instagram pages, or Twitter takeovers. You’re just going to pay them to advertise to their audiences.

Again, she just started very small. She wasn’t like, I need to go up against Lambda School or any other code school, day one with a slick website. It was just one-on-one sales, a very small number of students. Almost any education business can start that way if you’re willing to charge enough for what you’re teaching.

Maybe one other example would be Kristy Lawrence, who did start with a SaaS app called Plan. She spent eight or nine months developing relationships with influencers on Instagram—talking to them, getting to know what their challenges were, getting to know what their problems were, getting to know what would be valuable for them in the space, commiserating because she was an influencer herself, and sharing tips and tricks.

By the time she had her SaaS built, she had a pretty long list of people who not only would be her users, but who could promote it to their followers, and their audiences, and could help sell it. She ended up making $10,000 or $20,000 in the first week of her SaaS business existing. But that’s because she didn’t start by just starting to code. She started by talking to lots of people one-on-one, which is something you can always do regardless of how saturated the space is.

Rob: I love it. And just between you and I, since no one else is listening, I’ve started work on another book. Have you ever written a book? It is so painful.

Courtland: I haven’t, but Stripe keeps trying to get me to write one with Stripe Press.

Rob: It never gets easier. This is the fourth book I’m writing. Sherry and I had a bunch of podcasts. Essentially, she took an inroad into the second so it’s 3 ½ books, but it’s still not getting easier. The point of that is, though I obviously have a whole section on finding an idea. It’s looking for your advantages and it’s solving a problem, which is what you’ve just said. I have this huge list of things, which is to scratch your own niche. That’s what most people quote and it’s become famous because Basecamp said it for years. But then that went away because we all scratched our own niches. It’s not that it doesn’t exist, but it’s how many bug tracking tools, how many project management tools do we need.

I have all these other startups that I’ve seen, whether it’s through TinySeed, or MicroConf, or hearing on Indie Hackers, or an interview on this show. People encounter a problem with their day job. People see a problem of a spouse, or a relative, or a colleague. People have a poor customer experience and realize they want to build an app that makes it better. People find a problem online by going to a core thread or being in Facebook groups, you can translate an existing idea to a new niche.

There’s proposal software, but there’s no proposal software for designers, or there’s no proposal software for this or that, so just niche something down. You can find a large space with a hated competitor like Drifted with Infusionsoft and Xero did with QuickBooks. You can build on your, if you have an audience reputation, build on that. If you have a good network build on that, so on and on. Any of these is almost individually a thought experiment.

Each of those things, I just rattled off. Again, those will be in a book out sometime next year, maybe, but there are so many ways. Each of them, there’s no path. There’s no blueprint for this part. There’s no one, two, three-step. Once you get to product-market fit, and you have customers, and you start having channels at work, it is extremely repeatable. Usually, there is a pretty solid blueprint of how to go from there up, how to go from there, to a million, to 10 million, or whatever.

There are all these paths and everything. But in these early days, it’s much more you have a compass, not a map, and so you’re just kind of wandering and trying to take in thoughts and see what resonates with you and see there’s a product founder fit and there are all these things. But there are a lot of ways to get there. Don’t expect that anyone else’s approach will definitely work for you. Look at a lot of different approaches.

Courtland, I like that you brought up the folks that you interviewed on Indie Hackers because those are just two examples of people who kind of found their way. Maybe it sounds like they almost did it accidentally, maybe they didn’t. They just kind of took it one step at a time in these very small increments and built it into something pretty impressive.

Courtland: I’m a big fan of being very deliberate about ideation. It’s a very tall order to sit around and wait for inspiration to strike you in the shower. But if you’re going through the world, and you’re deliberately looking for problems, and you get your antenna up. Whenever you see somebody complain about something, wherever you see somebody pay for something, whenever you see somebody asking for something, you evaluate that problem. You’re just going to get a lot more sort of shots on goal. Most of those problems won’t be something that really resonates with you.

But if you’re just absentmindedly, hoping a problem comes to mind, almost none of them will turn into anything. Often, if you just start with something that’s not great, building that you’ll encounter lots of other problems that are burning, that may be you need solved or you see other people need to be solved, that can get you to where you want to go. There is no tried-and-true blueprint or roadmap, but there are a lot of things you can do to massively increase your chances of having a good idea to start with.

Rob: For me, one of those is having a notebook and taking notes, as you said, every time an idea comes around or someone mentions a pain-point and just adapting that over time. My best ideas never come in flurries, they never come instantly. They almost always come and are refined over weeks, if not months. I have a list and list of ideas that I’ve had since probably 2008 or 2009 in notebooks. Now, a bunch of them have been built and I can check them off the list. I don’t need to do those, but the new ideas, the idea for Drip came over weeks and it wasn’t just a simple thing. They evolve.

Cortland: I’ll say one more thing on that, which is the cool thing about taking notes, the way that you’re doing it is it helps you escape this recency bias. Whenever we get a new idea, we just get super excited about it, it’s the best thing ever. A lot of that excitement is because it’s new. If you let your ideas simmer for a while, like four to six weeks, four to six months, sometimes ideas that you are really excited about it turns out that you’re not that excited about. Some of these ideas that you’ve written down, you’ll be excited about for years. Those are the ideas that actually have legs, that actually resonate with what you want to build, and that might have some merit like on a structural strategic level as well. Keeping a running log like that is so great because it can help you make better decisions instead of just impulsively choosing what the product of the day, whatever got you excited about this week.

Rob: Yeah. I have a 48-hour cooling-off period on registering domain names. We’ve talked about this, how many domain names do I have. Ian has shown from Tropical MBA, calls it the Boulevard of Broken Dreams. That’s his GoDaddy account because I used to register a domain. Look, great idea, register the domain. Now, it’s like two days and then if I still like it, I’ll register the domain.  I’ve written up entire SaaS apps or business ideas and come back to them a week or two later. And I was just like, what was I thinking? This is a terrible idea. That’s good, it’s good to see it with fresh eyes.

So thanks for the question, Franco. I hope that was helpful. Our next question is from Kevin. He’s asking about the best city for bootstrappers. He says, “What do you think are the top cities for bootstrappers? I’ve heard San Francisco and New York City are too expensive. I’ve heard cities like Raleigh, North Carolina, Denver, Austin, Salt Lake City, Minneapolis, and Atlanta are good choices. Do you have any thoughts on this and how much does it matter? Thanks in advance. Kevin.”

Courtland, you’re actually currently moving about the country. What do you think about this?

Courtland: I did the SF thing for 10 years. I bootstrapped a business in SF and I can say you’re 100% spot on. It is too expensive. My burn rate was absolutely insane trying to bootstrap a business from SF, which was fine for me because I probably needed a little bit of pressure, something to light a fire under my ass and get me coding. But I then embarked on a six-week road trip earlier this summer. Now, I’m in Seattle, which is also expensive but much less expensive than SF.

My take on this entire question is that it does matter where you live. But in terms of business, it matters less and less, especially as the world becomes more remote, which we’ve seen happen in a drastic fashion with the pandemic. There’s more to life than just business and the city that you’re living in decreasingly matters to your business and increasingly matters to your life outside of your business. These two things are related actually because it’s easier to continue with your bootstrap business if your life outside of your business is happy. There’s a lot here to paying attention to the universal things that we know contribute to happiness and not trying to innovate too much here.

Health. Do you live in a place where it’s easy for you to exercise, it’s easy for you to eat well? For me, like in Seattle, I picked a place where I’m about half a mile from the nearest Whole Foods, which is one of my favorite grocery stores. I pretty much walk there, walk a mile every day to get groceries and cook. Just having that habit in my life is super easy. If I had to drive to go to the grocery store, I would just be less healthy.

Relationships. If you live near friends and family, that’s huge. In Seattle, I have four of my closest friends in the world who live here and they all know each other. We’ve been going on lots of hikes and doing lots of stuff together. It’s just been so great just for me personally. I’m just having more fun in life living next to them than I would if I moved somewhere where I didn’t have friends or family. That’s a big thing to take into account.

Obviously, financial security. Living places where you can afford, especially if you’re bootstrapping. You want to keep that burn rate low. Maybe the one caveat here is, I will say, that there are places where the people there can give you energy and actually be motivating. It does help to be near people who are actually getting stuff done because they will inspire you. A lot of the cities that you listed—Raleigh, Denver, Atlanta—there are burgeoning tech scenes and it’s not impossible to find somebody who’s doing something that you’re doing. People aren’t going to look at you like you have two heads when you tell them you’re bootstrapping a tech business.

If you can get all of those, I would try to check all those boxes. But if you don’t check a few, I would check the ones that align with your personal happiness and health over trying to be somewhere where there’s some weird business advantage because that just matters less and less.

Rob: Those are great insights. What he asked, what you echoed, and what I will also echo is that if you’re bootstrapping, stay away from expensive cities unless you have a lot of money. One of the advantages of bootstrapping Drip in Fresno, California is that we could hire developers for about a third of the price as the Bay area. It was about a three-hour drive to the Bay area. We could live in California, but not deal with the high rents and high salaries. You have to weigh those to a certain extent.

What you touched on, which is what city resonates with you, there is a Paul Graham essay called Cities and Ambition. Basically, what he says is certain cities that he’s lived in, they have an ambition. The people around you have an ambition. He had lived in Boston, and Paris, and New York, and a couple of other places. He said, in Boston, the ambition is to be more intelligent. There are more universities per capita than any other city in the country. In Paris, it was something about art. It was either to enjoy beauty or enjoy art. In New York, it was about money. The Bay Area was about power. Seattle is outdoors. That doesn’t mean you have to be that.

In LA, I lived there, it was about looking good. There’s a lot of physical attractiveness and some people are shallow, but some people are also just really into being fit and that’s okay. But if you really don’t want to have to be cool, LA can grind on you. If you don’t want to own the new sunglasses and you don’t want to dress in the new fashion and you don’t want to be really in shape, it can wear on you. The same thing, if you’re not into outdoorsy stuff and the rain bothers you, maybe Seattle is not a fit.

Trying to find a city, trying to live in a lot of different cities, and figure out which one’s ambition fits you is what you’re saying and it lines up. Cities and Ambition—I highly recommend. Folks, check that out. For me, if I were to just pick some cities and it’s based on travel and a lot based on listening to the Tropical MBA podcast because they talk a lot about location. If you think about ‎Startups For the Rest of Us, it’s about SaaS, and startups and software versus TMBA is about all different business types. But the unifying factor there, it started as digital nomadism, the ability to travel while you start companies.

In the US, if I were to just pick cities, for me personally, it would be Seattle, Portland, or Austin, and Minneapolis is one, too. Although the winters here are tough but man, the quality of life here is amazing. If you can get over the winters, those are some great cities. If I was in Europe, I’d probably live in Barcelona, there’s an entrepreneur community there, it’s a beautiful city. South America, Medellin is a big hotbed of TMBA folks. In Asia, it’s Chiang Mai and Saigon, those are places that I hear there being entrepreneurial activity.

To your point, Courtland, it’s not that my business should be based there. It doesn’t matter where my business is based. I named those cities because there are enough other entrepreneurs around to keep you motivated and that you can meet up. I have a friend who’s extremely successful now and lives in a city where he has entrepreneur friends and stuff, but he lived in Miami for years, or somewhere in Florida. He said just no one here is starting companies. And he’s like, I have to get out of this place, even though he had a business and it was successful. He’s like, I can’t stand to be here because nobody thinks as I do, and everyone’s retired, or they’re partying. This is not fun for me.

You have to know yourself. Are you cool with just not having anyone with anything really in common with you? Well then, maybe go live on the beach in Florida because I’m sure that’s an amazing life from a climate perspective and from enjoyment and a partying perspective to nightlife. But if you want to have some type of face-to-face community, then you need to think about there are a lot of cities in the country that just won’t have that.

For you to try to determine this, I would look at Tropical MBA. I would look at the locations of Indie Hackers meetups, I know they’re not happening right now because of COVID, but they’ll come back. I would look at places that we hold MicroConfs because we are probably going to have seven, eight, nine MicroConfs in 2021. We’re picking cities that have a lot of entrepreneurial activity. And, you can go to meetup.com and search for a startup founder, entrepreneur stuff.

As I was moving around, because Sherry and I, we moved 10 times in 10 years when we got married and she was in grad school. When we were going to go to that next city, I would always go on bait up and try to figure out is this going to be a place where I basically have no entrepreneurial friends or do I think I can meet some people?

Courtland: I think that’s such a great point. Paul Graham asked a point that basically, we’re very tribal creatures and every city has its own tribe. People value different things, have different cultural norms, and different tribes. I lived in Boston as well, and I met at least 5 or 10 people in Boston who imitated John Nash from that movie A Beautiful Mind, they just wanted to be the crazy genius because that’s what Boston elevated—academic excellence and genius. I’ve lived in SF for 10 years and I met at least 5 or 10 people who emulated Steve Jobs. They wanted to be like the crazy, super successful startup founder. Even if you are a contrarian person, a lot of your energy comes internally, yeah, but a lot of your energy as a human being comes from your tribe and your surroundings.

If you’re in Miami and everybody’s partying all the time, you’re just going to feel bad about staying in to do any work. If you’re in Seattle, everyone’s hiking, you’re going to feel bad if you don’t go on a hike every now and then. I want to second that idea of understanding what tribe are you gonna be moving into and make sure it’s one where the things that people value or going to push you the direction that you want to go

Rob: To close us out on this question, there’s an interesting point around venture-funded versus bootstrapped and mostly bootstrapped companies. Venture funded companies have traditionally been very densely packed in a handful of cities. I don’t remember what the exact number was, but as of 5 or 10 years ago, 80% of entrepreneur companies were in two or three cities. It was really, really low. Maybe even been 90%, it was incredible. Well, when we did the state of independent SaaS survey and then the report last year, we had 340 different cities of bootstrappers and bootstrap and mostly bootstrap founders.

The interesting thing is the number one city—at least according to this report, which had just under 1600 responses from around the world—the number one city is London with 4% of the respondents. The second city is remote with 3%, meaning they just had no headquarters. And then the third city, which may be skewed because I’m here, it was Minneapolis. I’m actually surprised that it’s that high, but it’s 2.5%. From there, 2% is Austin, New York, San Francisco, Toronto. We have 1.7% in Denver, Portland, Boston, Chicago. It’s just all these cities and then it goes to Australia. It is all over, it really is. You can live anywhere. It’s just a matter of balancing all of these things—balancing the ambition, then the desire of the place itself, of the community. And then, are there entrepreneurs around to kind of have camaraderie with.

Courtland: A lot of the cities you just listed were at the top of the list of Indie Hackers’ meetups cities, where you could go to those cities. They have great meetups in Toronto, London, Dublin, and Denver. One continent that we missed was Africa. I’ve been to Cape Town twice and just met a ton of bootstrap founders living the life. That’s one of the most beautiful cities in the world. It’s extremely cheap, extremely affordable, and people that are very motivated. I love this idea of the fact that these bootstrap companies are spread out. There is no like one base for bootstrappers. It’s all over the world.

Rob: Courtland Allen, thank you so much for joining me today, sir. I had a blast.

Courtland: Same here. Thanks for inviting me on

Rob: Folks who want to keep up with you, you are @csallen on Twitter, as well as @indiehackers. I assume you’re one of the mischief-makers behind that account.

Courtland: Yeah. I occasionally get behind the Twitter account.

Rob: That and then indiehackers.com, of course, if they want to see what you’re working on every day. Thanks again for joining me, man.

Courtland: Thanks for having me, Rob.

Rob: Thank you for joining us this week, I hope you enjoyed that. We have several listener questions left in the coffers. But as always, voicemails go to the top of the stack. If you want to send us a Dropbox link to questions@startupsfortherestofus.com. Google Drive links work, too. You can also send text questions. We don’t have such a huge backlog, we could use some additional questions on any of these topics or any questions you are facing. You can remain anonymous or you can plug your project that you’re working on if you want. Feel free to send your emails to questions@startupsfortherestofus.com.

Thanks again for joining me and I will talk to you again next Tuesday morning.