Episode 466 | Answering Listener Questions With Craig Hewitt

Rob: In this episode of Startups for the Rest of Us, Craig Hewitt returns to the show to answer listener questions about productized services, podcasting, and more. This is Startups for the Rest of Us Episode 466.

Welcome to Startups for the Rest of Us, the podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing startups. Whether you’ve built your fifth start up or you’re thinking about your first. I’m Rob and today with Craig Hewitt, we’re here to share our experiences to help you avoid the mistakes we’ve made.

Welcome back to the show. As you know on this show, we value building real businesses with real customers who pay us real money. We value the freedom to work on projects that are interesting to us. We value the purpose that it brings us to start our own endeavors and to have equity and ownership, and we value relationships, whether that’s relationships with our family or our friends. We don’t decimate our personal life for the gain of our company. We are ambitious founders, but we are not willing to sacrifice our life or our health to get to where we want to go. We know that starting a company is hard. More than half of being a startup founder is managing your own psychology.

Joining me again today is our guest, Craig Hewitt. He’s the founder of Castos. I did an interview with him a few episodes ago, and I did a call out for questions that folks have for him about his experience about his interview. I wanted to bring him back on the show and it’s something I want to start doing, assuming there is enough demand for it. If you didn’t hear that interview, Craig has grown Castos to six team members, including himself. They are a member of the inaugural TinySeed batch and Craig is really crushing it with Castos, his podcast hosting platform.

Before we dive into that, I want to give some special thanks to Kenneth Khaw for his epic enterprise sales tip. He sent an email to me after David Heller’s hot seat episode, where we dug into David’s enterprise sales issues with things taking too long. Kenneth Khaw obviously has tons of credentials around being in enterprise enterprise sales for 12 years and he had some tips for David, including screenshots, a long write up, and talking about summarizing a quote in one page, providing variations of a quote, figuring out what the get over the line number is for negotiating. He really dug into it.

That was super cool, super appreciated, and David just wants to tell us, “Wow, he really spent a lot of time on this,” so it’s much appreciated that the community can give back to someone like David who is pushing forward and trying to solve problems. That was great when we can share our expertise with one another.

Lastly, another reminder that TinySeed applications for our second batch open on November 1st. Those who don’t know, I run TinySeed, the first startup accelerator designed for bootstrappers and we fund companies in batches for a year-long remote accelerator. If you’re interested, head over to tinyseed.com, enter your email there, and we will notify you when the applications’ available.

With that, let’s dig into some questions with Craig Hewitt. Craig, thanks so much for coming back on the show.

Craig: My pleasure. Thanks for having me, Rob.

Rob: I am excited to dig into some questions today. We got a few questions that were asked directly to you and then there’s a few more general mail bag questions. The first question came from Matt Stainer and he said, “Why TinySeed? Going into it, what were you hoping to get out of it? Now that you’ve been in a while, how’s it going? I ask because as I understand it, TinySeed is focused on helping founders and ‘move from nights and weekends to full-time focus.’ Essentially quit their day job and go all in on your startup. And yet, it sounds like you are already full-time on Castos with six employees. So I’m curious what drew you to TinySeed. Thanks, Matt.”

Craig: That’s a really good question. This was a question I asked myself a lot and had a lot of real heart-to-heart with my wife, and even with other people coming in the space that I know, trust, and respect. Really now, what it came down to is the terms for TinySeed are really, really favorable for founders who want to run a business for a long time just as a high-growth lifestyle business. Not on the VC track but want to accelerate the growth of their business, past what they can do by pure bootstrapping.

If it’s like you mentioned, some of the copy on the website might be let you quit your nights and weekends and focus on this full-time, that would obviously accelerate the growth of business. For us, we had a pretty solid beginning of product market fit when we applied and I thought that joining TinySeed, both for the mentorship and for the funding, would allow us to accelerate that. Rob, we’ve for five months into it now. I think it definitely has. We’re growing faster the we were before and the business is absolutely a better business now than it was six months ago.

I think what drew me to it was the people behind it and the opportunities that will allow me professionally and personally to develop but also to put Castos on the map and give us access to resources both financially and mentors and network that I don’t have access to myself, and really at a pretty reasonable cost. I won’t say it’s a cheap cost because it’s not. Giving up a piece of your company is always a big decision and a really super personal one, but I think that the trade-off is really reasonable in this respect.

Rob: I remember you felt a lot about it. You and I had a number of conversations as I did with most of the founders that wound up making into the batch. There were conversations about us feeling people out and there was them feeling us out and saying, “What is this going to be like.” We had an interesting almost conundrum of we were startup, too, and this was our first batch. I think it will be much, much easier. I expected to be much easier with the second batch because it’s just more proven. We have more products market fit now. There are a lot of conversations then.

The other interesting thing is we did start out with a thesis of “I think we’ll fund a lot of founders who will move from nights and weekends to full-time” and if I recall correctly, we funded 10 companies and I think two of them and maybe three went from had a day job to went full-time. Everyone else was already working on it.

Even that hypothesis we had is not entirely accurate. Now, one of them has a small software product that essentially provides him with the full-time income, so he didn’t need to have a day job. Another founding team moved to a cheaper place. They did geo-arbitrage. They moved from the US to a much cheaper and that allowed them to live full-time even though they didn’t have a US full-time income coming in.

There were exception-ish things, but overall, if we haven’t already updated on the website, I think we need to in terms of you figure out really who your best prospects, the people who can use this the most, and message to them.

You said Castos is growing and it’s absolutely in a better position today than it was when it joined TinySeed. Honestly, I haven’t talked a lot about TinySeed on the podcast because I never want the podcast to feel like a sales pitch for anything I’m doing. I would talk about my journey building HitTail, or journey doing MicroConf, or journey of Drip, but I try really hard to keep that balance of I’m not just sitting here pitching what I’m doing.

Actually, I have a couple of people ask me to bring someone on to interview me about what’s going on, not necessarily talk about TinySeed but what’s going on with me, my founder’s journey. I think that can be interesting.

All that said, I haven’t talked to […] about it, but I’m curious. You’ve now been in for almost four months at this point; it’s a third of the accelerator. Without putting you on the spot, is it what you expected in terms of the benefits?

Obviously, there is money, and then there’s the mentorship—our list of mentors is pretty solid—then there’s the office hours themselves of hang-out or kind of the mastermind, the community of it, of being in Slack and being on the weekly calls, then the in-person event, and even the network. Even beyond the mentors if you say, “Hey, I need an intro to somebody.” My network and a lot of the mentor’s network are at your disposal. Has it been what you expected and do you feel like it’s contributed to your success over the past four or five months?

Craig: The money is really nice. I think that a lot of people that take money that have a bootstrapper mindset—Josh from Baremetrics talk about this a lot—they haven’t spent a lot of the money they took, and we haven’t either. We used it as a cushion—it’s a big cushion for me—but we’re not burning hardly any money right now. We’ve hired a lot of full-time person-and-a-half since joining TinySeed. That’s been really nice. It makes me feel good to have a lot of reserves and the business is really sound at this point.

It’s cool that comes through in everything we do because we’re able to take a longer-term approach to building the business, features, marketing approaches and things like that, that we don’t have to worry about making payroll next month or next week because we have money in the bank. Where if things went sideways, we’ll be good for a while. That’s how we are using the money.

The best part really is the network and the community, the difference being the network is with the mentors and the mentor’s networks because we definitely have gone second and third layer with some of the mentors that I’ve talked to and they said, “Hey, if you want to talk to this person, we can intro you over here.” I probably have two or three calls a week with either you and Einar, or a mentor, or a mentor’s friend, or a connection that I’ve made somewhere like that. Then we all, the 10 companies, are in Slack all the time sharing stories. We have a fail whale channel, so sharing our successes and learning opportunities. That’s really great because a lot of us are solo founders.

There’s two founding teams in the cohort, but it gets lonely sometimes out here, especially to have people that are doing exactly the same thing that you’re doing. We’re all building SaaS apps that are less than whatever $50,000 a month. We were all in the same boat pretty much. So, it’s a really homogeneous group. That’s what makes a lot of the discussions really interesting among the founding teams. I think that’s the biggest surprise, though, is that the value of the network of mentors, the support of the other companies, and the founders has been awesome.

I know that we numbered the TinySeed 2019 Slack channel that’s just for us. I know there’ll be a TinySeed 2020 and 2021 stuff that I still will definitely be active in our little part in our channel within the group, just with us and the other 11 people because these are really valuable relationships.

Rob: Awesome. That’s what I would hope to hear from anyone who does become part of the batch. Thanks for the question, Matt. Appreciate that. I hope context was helpful.

Our next question is from Meryl Johnston. She is the founder of Bean Ninjas, which is a pretty well-known productized accounting service. I believe they focus on Xero, but they’re pretty well-known. They’ve sponsored a lot of conferences and Meryl is actually one of the TinySeed mentors. She says, “Hi, Rob. I think it’s a great idea to get Craig back on for another episode to answer questions from the listeners.” Meryl sent a voicemail, so let’s dive into that now.

Meryl: Hi, Rob and Craig. It’s Meryl Johnston here from Bean Ninjas. I’ve got a question for you both. Cool content, by the way. I like the idea of having an interview and then giving listeners the opportunity to ask follow-up questions, which you then answer on a podcast. Going back, understanding is that you started with consulting before you transitioned to products and then software, and that Craig used a productized service business model to then leverage your network and skills, and maybe branding as well, to then going to software.

My transition was also from I went from consulting. I did that for nine months, then created a productized service, and then you see it with been moving into digital products. Based on my own experience, I think there is that when you, in building a skillset, as an entrepreneur while running a service business and in my experience it was a faster way to leave a job and transition to working full-time in their business than if I had created products from day one.

So, my question to you both is, if you were starting from scratch again and is transitioning from a job to running a business, and you didn’t yet have much business, you didn’t have much of the network, and didn’t have a lot of capital behind you, what kind of business would you start? Rob, would it be consulting? And Craig, would it be a productized service?

Rob: That’s a good question. Thanks for that, Meryl. What do you think, Craig? Have you thought about this?

Craig: Yeah, I have pretty strong feelings about this. I think a productized service model or even consulting is a fantastic way to transition out of a day job into running your own business. The reason is, as opposed to software where there’s a ton of time and financial overhead that you need before you can start making any money, you can put up a WordPress site with WooCommerce or Gravity Forms or whatever and start making money literally today.

Justin McGill launched the first version of LeadFuze and this 24-hour challenge to himself. We launched Podcast Motor in maybe a week, and that was because it was my third time ever putting up a WordPress site. We were doing $10,000 a month within a couple of months. You compare that to what a SaaS founder has to do to get that $10,000 a month. It’s like moving planets to get to that kind of MRR for SaaS, especially the first time.

I think that if someone has a skill set or a passion and you can create a productized service around it, you absolutely should do that if you goal is to get out of a day job and into this world. But I think Meryl really nailed it on the head when she said leverage because that’s how I view what we’re doing now.

Rob, you probably see it from consulting to your first software product to what you’re doing now is another form of leverage. I just see that a unit of work I do now in Castos is worth a lot more to the value of the entity than a unit of work that I do into Podcast Motor which is our productized service. I think it’s just because creating a piece of software and a team that supports that is more scalable, probably has better margins, and in some ways is easier to run at a higher level.

I think it’s a fantastic way to start and I think that like Meryl is getting into, getting into a digital or software product is really great because they’re more complicated and if you’ve learned some of the things like marketing, project management, and customer service through a productized service, then you have a really good chance at being successful on software.

Rob: For me, I honestly don’t know. I have an inclination of what I would do, but I think if someone came to me for a blanket advice, I would say, “Look, I had a day job and I want to work for myself. I would say there’s the Robert Kiyosaki levels. I’m not a Poor Dad Rich Dad fan, but I do like this one paradigm he has where it’s like, you’re employed for someone else, then you’re self-employed, which typically is consulting where it’s dollars for hours, then you’re an entrepreneur which is where other people work for you, and as you said, it’s that moment of leverage when you have a whole team, and then it’s investor where you’re no longer running the day-to-day and you’re putting money into other businesses.

So, I would first decide do you just want to recur self in this terms of self-employed or do you want to go as far as to be the entrepreneur and let’s just say to have a product business in this context and then go from there? For me, if I could go back, I wished that I could have kept the day job and had it not just drive me up the wall. I hated my day job. I really, really despised working in a cubicle. I liked some of my co-workers and I didn’t like others. I didn’t like that I couldn’t choose who to work with and I didn’t like that a bunch of the policies seemed just dumb. I didn’t like that we’re forced to write really crappy code a lot of the time.

Our CEO is a sales guy and he would go out and sell something. It would be like, “Hey, we have to ship this in six weeks,” and we’re like, “Yeah, that’s four months of effort.” He’s like, I don’t care. Get it done.” So, then we go get it done and then […] would break because we wrote […] code. Then he’d come down and I was like, “This is dumb. Why isn’t someone smarter here?” That seemed to just be an ongoing thing.

Had I been a little more chill or been able to deal a little better with it or just found jobs that weren’t like that because there are certainly jobs that exist and there are people that are calmer and I would like to say I’m unemployable. I am just not going to be a good employee. But if some is like, “Look. I’m at my day job. I’m making $125,000 or $150,000 as a salesperson or as a developer. I work 40 hours a week, I don’t think about it when I get home, and it doesn’t suck the life out of me,” I would say keep doing that and launch something on the side.

Maybe your first step is consulting. Maybe it is productized consulting like you did, Craig, and like Meryl has done, but maybe it’s a stair step approach. Maybe it’s that WordPress plugin, or you write an ebook, or maybe it’s a Shopify add-on, or any one-time sale product. I definitely went to the consulting route because I wanted to be out of a day job in a hurry and I thought that consulting, to be honest, was the end goal for me originally. I thought that would fix all my woes and as I got out, bill $100–$125 an hour. It’s like, “Oh my gosh, this is great, I’m making more money that I ever had.”

I didn’t dislike it as much as I dislike salaried employment for sure, but it definitely got old after a couple of years. For me, it was about I wasn’t building anything that would last. There is no permanence to it. I didn’t build anything that I owned, I had no equity, and my consulting “firm” was never sellable. I thought to myself, “Am I going to do this for 20 years?” and that didn’t appeal to me.

It’s hard when you’re doing consulting and you’re addicted to the incoming cash. It’s really hard to justify. I could work another hour. I used to be booked 60 hours a week, I would say. I didn’t work that much, but I could have worked that much. So, I would look at it like, “All right. It is Saturday afternoon and I could put in three hours and I could make $375 or I could work on this beach towel website that is doing $200 a month.” It was a very hard transition.

So, for me, going from consulting to products was actually harder than if I had just kept the day job because at the day job, I wouldn’t have had that extra motivation to work more on it. Does that make sense?

Craig: Yeah and I think that’s where consulting and productized services differ. Brian Casel talk about this with Audience Ops. You’re able to take a productized service that has a team that supports it, and systems, and processes, and documentation to—I don’t know—say, run itself, because nothing runs itself. But I spend an hour a day on Podcast Motor right now, maybe two on a bad day or whatever, a good day, and it’s a solid mid six-figure business. You could never do that with consulting because you’re directly trading dollars for hours or hours for dollars. I think that’s the difference.

I agree with all you said, Rob, that most high-leveraged thing you might be able to do is keep your day job because you can just save a bunch of money, maybe, and go buy your way into freedom, you can buy an app. Or you can get experience and something that will then allow you to be successful when you do go out on your own.

I had a sales background before and it’s hugely beneficial to me in the biz world to know how to sell stuff. If you have the opportunity, get into a sales or marketing role where you can learn that side of the business and of the world. I think that might set you up for success. I won’t say more, but it will definitely give you a leg-up versus just going on flailing around and figuring out on your own if you’re able to hold down that day job.

Rob: Yup. I think that if you can learn skill sets either at the day job or as you’re consulting or productized consulting, if you can learn skill sets there that add to your product tool belt—your product marketing, your product sales, your product development, whatever—that’s a big win. That’s something that I found.

Again when I was solo consulting, I had 1–3 clients at any one time, my marketing was my blog, I invoiced using Excel spreadsheets, it was very stripped down, and I didn’t have direct copy, I didn’t learn marketing, I didn’t learn AdWords, I didn’t learn any of that from consulting.

When I look back on my experience, if I had any regrets, is that my salary job. I learned to code for sure, got better at it. So I was already coding before that. That obviously helped me with products. Eventually, you top out and you’re working on different problems than you work if you had a little SaaS website or whatever.

When I transitioned to consulting, I don’t feel like I really learned much that later helped me to translate it into supporting and building a product. Whereas productized services, it sounds like to me from what you’ve said and what I’ve observed that there’s a lot more parallels between that and, say, SaaS. Would you agree with that?

Craig: Everything about it is the same except for the software. It’s marketing, it’s customer service, it’s processes and deliverables, and then SaaS adds on project management of development teams, testing of technology and stuff like that.

Rob: Yup, it really is a nice proxy for that. It’s not just a revenue stream. I already mentioned it in the intro, but if you haven’t already heard Craig’s story, if you go back to episode 459, he tells a story of how he had a day job, launched Podcast Motor which is his productized service, left the day job, and then leveraged that into essentially a WordPress plugin and doing Castos. Not only did it provide revenue, but it provided that whole skill set and the learning curve that you didn’t have to do while you’re communicating with developers and designers, building and supporting a product, and doing all that stuff.

Thanks again for the question, Meryl. I hope that was helpful. Our next question is from Cain about how to run a beta. He references an episode from 2012 where Mike and I talked about running a beta, and he said he’d love to hear a little more on how to select the beta users and figure out beta phases. Any references, similar discussion happen on Matt Wensing’s podcast which is called Out of Beta, not coincidentally I hope, which made me think to look and see what you guys had on this subject.

Craig, I know that you had beta periods with Castos. Talk about that.

Craig: We don’t. No, we don’t have any beta testers or beta functionality in the app.

Rob: Really? Have you never? Were you in beta early on? Or did you just never have a beta?

Craig: No. We just launched.

Rob: I guess to define it so people know, typically I don’t call it beta. I typically call it early access. Beta implies that it is a buggy product and it’s pre-launch. It’s a preview you can use, but beware of the bugs. Typically, we might nuke the data. There’s different agreements and such. Google is famous for having Gmail in beta for five years or something. But betas are, (a) not required, and (b) these days, I would like not to have a buggy product.

When we did Drip, we did early access and we tried to make sure there’s minimal bugs. It wasn’t about testing, it was more about customer development. User experience or fun rather than, “Oh, they clicked on a link and something crashed.”

With that said, I had assumed wrongly, obviously, that you had run a beta with Castos in the early days. So, you just launched straight away.

Craig: Yeah. We just dove head first. I also think there’s two parts to beta. One is before you launch and then the other is beta testing or beta releasing features after you’ve launched. You develop a new feature, you release it to a small cohort of your total user base to let them test it before you go throw it out to the whole world.

We very much would like to do the latter now because we have thousands of users and we don’t want to release something to everybody that could be buggy or whatever. We have extensive unit test and staging environments, and we have testers that run through everything before it goes out the door. But I would still like to take the time to develop feature flags or beta flags for certain users.

I think that if you have an established product, it’s super valuable because you can pick the people that have been around for a long time and you know they really care about you and your product and are going to be there even if you ship something that isn’t the best experience the first time. Those are the perfect beta testers. They’re the people that love what you do no matter what but will give you a lot of latitude if you ship a feature that’s in beta that might be a little rough around the edges.

That’s how I would select those people. You probably know who they are. They’ve been around for a long time, your exchanges with them and support are really positive, they refer other people over to you. Those are the characteristics of what I would consider a good beta user to be and they’re inquisitive, natural, learning people, still go poke around and give you constructive feedback without being overly critical in a non-productive way.

When it comes to beta, that’s the only place I really see a good use for beta. We launched Castos and just launched it. It was not pretty, but it worked. I think we only did it because we tested the hell out of it in staging and had confidence that the product and the market had good alignment because there are other people doing similar things. It’s not like we’re creating a whole new product segment or something like that. That’s why we just launched it.

Rob: And how did that go? How were the results? Because you referenced it was not pretty.

Craig: We had some technical issues with deployment. I think that just happens sometimes. We learn and do things smarter and better now, but that would have happened even if we would have released it as a beta, I think. We would have these issues.

I think people might get hung up on this a little bit and there’s a lot of discussion around this, like when is a launch really a launch, when do you come out of beta, and what does that mean? I think it’s fuzzy, to be honest with you and maybe not super important, like how and where do you draw those lines?

You get the thing out there, have some people use it, make sure it’s not going to break the world, then release it and start getting real, new, fresh customers or trial users so you can see unbiased people using your app. I think that’s the real thing that you want to get to, is how does this person I don’t know and won’t give me that extra leeway, how are they interacting with what I build? Because that’s the real acid test.

How did you guys do both beta period when you were launching Drip and then did you beta release features to certain users?

Rob: Yeah, we did. This is what I would do today. The fact that I’m referring back to Drip doesn’t change […]. This is still […]. The first, let’s say, 10 or 15 customers we let in that weren’t paying yet, they were just on an unlimited free trial and I said, “Look. Once you start really using this and get value out of it, then you pay and I’m just going to monitor it.” So, I would just boomerang emails back to them every 2–3 weeks, checking on their account, touch base with them. It was a very manual process.

Those people knew we were building something new and we said, “Look. We don’t expect it to be buggy and we test the crap out of this stuff. There is a possibility of bugs, but we don’t expect any.” The people were early adopters, obviously, and the way we hand-picked those people was that I looked at people, a lot of them actually either had a dire need for it or they were folks who ran other SaaS apps.

The reason I did that because I knew that they would give helpful, constructive feedback from a product-minded perspective. I had the luxury of folks on the launch list who, when they gave their email, I could tell that they ran another SaaS app. Again, when you have a lay person, they can know a problem that they have, but they’ll often try to propose a solution and that’s not a good solution for you to build into your product.

Having folks like Ruben Gamez from Bidsketch, Jeff Epstein from Ambassador, Brennan Dunn from then Planscope but now with RightMessage, it’s folks who have a pretty good knowledge of that, and then there were some folks that were from ecommerce and there was a couple of bloggers, but they were all folks who I think had good ideas and, as you said, didn’t have a bunch of noise.

That’s the struggle you run into is if you get 15 or 20 people in there and they’re all have diverse goals—you get a blogger, then you get a photographer, then you get someone who runs ecomm, and you SaaS—they’ll have just wildly different request for you and that starts getting complicated. It starts making it hard to figure out what to do next.

And then really, our beta, I say, truly ran—again it’s called early access—from about July to November. It’s five months long. The reason we did that is we have this big launch list and we were still doing customer development. We hadn’t even proven that we build something people were going to pay for. Podcast hosting existed and you knew that if you build a platform, customers will pay you for it. You just needed a channel. That’s how I would see Castos.

With Drip, we were trying to build something new and I didn’t know if we sent an email to the 3500 person launch list, if everyone would just show up and leave. So, we were pretty cautious about who we let in. Then, we just did 300 people at a time every couple of weeks, let them in, build some features.

That was quite stable during that time. I think we only had one bug that missent email, like double send it to a group or something, which is a big deal. That sucks when you are running an ASP to oversend or to miss a schedule. If someone wants it to send at 11:00 AM and it sends three hours later, that’s a problem. More so than some apps, you have the leeway of it not being mission-critical but any ASP can be that.

It could have been more compressed, for sure. I think that also comes back to Derick and I work 40-hour weeks. If we had worked 70-hour weeks, we probably could have gotten it then in two months, but that was a lifestyle choice. That wasn’t the time when I was going to work long hours. That’s not totally on-topic with beta, but that is how we ran it.

To your other point, you said you beta test features. The answer is yes, we have feature flags from the start where we could just ship something and I’m trying to think about split testing or even automation and such, and it was just a checkbox. In the admin panel we would open it up for three four early access folks, send them an email, “Hey, you have this. Check it out. You want to test it.” Get feedback, iterate quickly, and then slowly either release it to a few more people if you are still in doubt or at that point, then we’d actually launch the feature to the whole audience.

Do you guys do that as well? Are you able to feature gate to specific users?

Craig: Yeah. We’re able to do that to really just the admins. It’s myself and our lead developer. Basically, both who have podcasts, so we’re able to run stuff on our podcasts. I guess we definitely have beta versions of the plugin. We manage a WordPress plugin called Seriously Simple Podcasting that integrates with Castos and we absolutely run beta versions of that on our live and test sites all the time. I think that’s more important because not like a SaaS app where you can ship it and then if it’s not exactly right just fix it, push new code, and everyone is happy.

With a WordPress plugin, people’s sites can break or their podcasting go down or whatever, so we are ultraconservative with what we ship there. We test beta versions of the plugin for weeks sometimes, just on our live site to make sure everything is cool. That’s another thing to consider. So, if you have a Shopify app or a WordPress plugin or something like that, running a proper beta program there is very important for different reasons than a SaaS app where you push it, if it’s nice […] right, just fix it and push it again. That’s what we do a lot of times and it works.

Rob: So, thanks for the question, Cain, I hope that was helpful. We will answer one more question and this one is about podcast sponsorships. He asked it for Startups for the Rest of Us but it’s cool that you’re on the show because you have your own podcast. He says, “I’m a long-time listener on your podcast and I’ve followed your startup journey over the years. I, myself have worked for several VC-backed startups until about 10 years ago when I got interested in bootstrapped companies and decided to be a marketing consultant for non VC-backed companies.

I was recently looking at podcast sponsorship opportunities and I read your FAQ that you’re not interested in sponsors. I thought to reach out more out of curiosity. Why did you decide to not have ads? I assume doing a podcast is a time-consuming effort and while not all endeavors need to be money-making, I’m curious what the motivation is for why you do the podcast. I figure you want to help other entrepreneurs, but is that it?” and that’s from […].

So, Craig, you run a podcast and you don’t sponsors. Why is that?

Craig: We coach a lot of our clients, particularly on the Podcast Motor side of things on the why you do a podcast. I think around monetizing a podcast, there are two distinct routes you can take. One is directly monetizing your podcast which is ads or now becoming more popular is selling premium subscription so you can charge $5 or $10 a month for access to limited content or something like that. That’s directly monetizing your podcast.

The other way that I would argue and the vast majority of situations is more lucrative and maybe easier is to indirectly monetize your podcast with products, or services, or conferences, or membership sites, which is what you guys do. Most or all of our customers at Podcast Motor, which are a lot of startups and successful entrepreneurs that everyone that listens to this podcast has heard of, that’s what they do. We have very, very few people who monetize their podcasts just through advertising or through this premium subscription memberships that are becoming popular now.

I think the reason is you have to have enormous download volume to make good money through sponsorships. I know you guys have a really successful podcast, Rob, but you wouldn’t make nearly the money that you might through other things that you can do with having a whole bunch of people that are interested in what you’re doing. Then you have a conference or a membership site that people can become a part of if they like what they hear on the podcast.

That’s a really natural way to use content marketing and podcasting is a form of content marketing. That’s what we really like to see and is more successful and easier for people to do. I think that’s why you don’t see a lot of ads in podcasts, especially in our space.

Rob: I would second that. I think that’s a good way to think about it. Mike and I toyed around with sponsorships. Some listeners might recall us making an announcement nine months or a year ago and saying, “Hey, were thinking about this. If you want to sponsor, email in,” and we just never made it that far.

We got a few emails and, to be honest, managing a sponsorship program is quite a lot of work. It’s enterprise sales in a way and you’re going to many conversations, there’s going to be lead times. Then you’re going to need to follow-up on invoice and get paid. Then you need to work on ad copy because most people do not know how to advertise on podcast. Typically, the first ad copy you get is not very good, so then you’re rewriting that.

It’s not as if you’re cashing a check for free. It is an amount of effort, it is another side job for two software entrepreneurs who also run multiple conferences, also have a podcast, and also write books. It’s just one more thing to tack on and it’s always been like how much value will this actually provide? So that’s it. I would never say never. Might we have sponsorships someday? Maybe. I’m not opposed to them. I just want them to be a fit and I want them to be the right choice both for us and for the audience.

To you point about monetizing indirectly, when we started the podcast, I remember we had the Micropreneur Academy already and I remember I viewed it as a way to not only build more credibility but also have a more personal connection to the audience that I was already building on the blog.

To be honest, I really did want to build a community of folks like us because I knew five people who are doing what we’re doing in 2009 when I started writing my book. I could list them in one hand of like, “These are the solo software entrepreneurs,” Every time I would hear about one of them, it’s like, “What? This is just crazy. There are that many people.”

As the blog started going and after I published my book, more people started coming out of the woodwork. The podcast I really view it as an avenue to just get more of us together. Of course, in 2011 it was finally like, “I think we might actually get together in a room,” and our delusions of grandeur of 200 people in a room quickly turned into, “Uh-oh. How are we going to sell enough tickets to fill 105 seats?”

I think the first MicroConf […] be 105 and I had to discount tickets late there, but all of that became more important than making a couple of grand a month. I don’t know how much we’d make if we monetize the podcast, but I just think that other stuff is more important than the platform. I don’t do it to directly monetize. I just never thought of it that way.

I do it for all of these other things and it’s to continue to be a voice in the community, but also to continue making sure that this community of bootstrappers, independent startups, and indie funded startups that this thing keeps moving forward. I’m playing long ball and I believe we have decades and decades of growth, and this is the new frontier. 99% of companies don’t need venture funding and that’s us. So, let’s band together.

I don’t know. I don’t want to get grandiose and act like that I hate it. That’s what I thought from day one because it wasn’t that deliberate, but that’s where I see it now and that’s why I’m spending my focus, instead of doing enterprise sales, asking for invoices, and rewriting ad copy, I’m focusing on the MicroConfs, the TinySeed, the blogging, and all the other stuff to try to push that forward.

Craig: Yeah, the leverage we talked about from Meryl’s question, right? That the podcast is your probably biggest form of reach and you’re able to do a lot of things now with it that you could never do just by making some ad money.

Rob: Yeah, it’s a good point. That’s a good question. Thanks for sending it in, […]. Craig, thanks again. That was super fun. As your first Q&A episode, how did that feel?

Craig: It was great, a lot of fun, really interesting questions, and thanks for having me on. It was a blast.

Rob: Absolutely. So, if folks want to know what you’re up to, they can head to castos.com for your podcast hosting services and @TheCraigHewitt on Twitter, is that right?

Craig: That’s it, yup.

Rob: Awesome. Talk to you again soon.

Craig: Thanks, Rob.

Rob: And if you have a question for the show, whether it’s myself or a guest, leave us a voice mail at (888) 801-9690 or email us an MP3, or an Ogg-Vorbis, or attach a Dropbox link, or even just write your question out in text, old school style, questions@startupsfortherestofus.com.

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