Episode 614 | Deciding When to Quit Your Day Job, Founder Anxiety, and More Listener Questions

and he recently stepped back from that after doing it for five or six years. He and I kick off our conversation by talking about that thought process. Then, we dive into listener questions, deciding when to quit your day job, anxiety from a second-time founder, and some really good questions on the show today. 

But before we dive into that, I wanted to ask—if you have Spotify—if you could go to the search, type in Startups For the Rest of Us, and leave us a thumbs up or a five-star. I don’t even know what the rating system is. We’ve been getting traction in Spotify, more listeners, starts and listens, engaged listeners, and all the metrics. If you’ve gotten some value from the show over the last months or years, it would take you 30 seconds to do that. I would really appreciate it. With that, let’s dive into my conversation with Derrick Reimer.

You’re back on the show. Derrick Reimer, thanks for joining me.

Derrick: Thanks for having me back.

Rob: This has got to be your sixth or seventh appearance, and you are quite the podcasting veteran now. You have done something that not many people do. You started a successful podcast, ran it for several years, and then made a graceful exit.

Derrick: Retired.

Rob: Yeah, you retired from your own podcast. You had The Art of Product co-hosted with Ben Orenstein. I just want to hear a little more about that before we answer these awesome listener questions we have in the queue. 

Was it a hard decision? You guys had several hundred episodes and five-ish, six-ish years of doing it mostly weekly. I know you don’t shoot every week, but I’m sure that was tough because you had a streak going and you have that feedback and comments of listeners saying, this is great. 

I know the value, rush, dopamine, or whatever that I get from having a podcast. At times when I was at my lowest with it, I definitely considered shutting it down, leaving it, selling it, lighting it on fire, or whatever I was going to do, and I never did. At this point, I don’t regret it because I still enjoy the podcast, but I’m curious what that thought process was for you.

Derrick: I guess I should say I’m technically on a podcast sabbatical, not a retirement because the agreement we made at this point is that I’m taking a break and we’re going to let this be the time away to see if this is something I want to add back in. We’re going to reevaluate in the fall.

It was a tough decision, I would say, but it was one that built up gradually, so it wasn’t a snap decision. As I reflect on what the podcasting journey has been, we started in either late 2016 or early 2017. Ben convinced me to start doing some podcasting with him. At the time, we were at Drip post-acquisition, so I had a little bit more headspace. I wasn’t in the fight-or-flight startup founder mode anymore. We landed the plane, I had a little bit more headspace to do some talking, and I felt like I had some things to say from an aspiring bootstrapper phase to the phase that I had gotten to that point. I felt like this is the right time to try this. 

I always loved podcasts like Bootstrapped Web. I liked the Startups For the Rest of Us intros where you and Mike would give us just a few minutes of updates about what’s going on in your businesses. That was often my favorite part. If it was a tactical episode about something that I didn’t particularly need, I would always show up for at least the updates to see if there’s going to be anything from your journey. 

I was like, what if we just do a podcast of all of that, just try that, and see how that feels? It was good for a long time. I really enjoyed it. It was not always easy going through the level journey where it was a low point in the journey for me but still felt fulfilling to let that be a case study out in public, but at this point, I find myself growing SavvyCal. We’re out of the earliest stages where I feel like you have a lot of good radio whether it’s a lot of vision casting and early stage figuring stuff out. You can pretty much talk about everything because it’s so early. You’re not worried about competition or keeping things secret. You just want to be out there as much as possible. 

Now, I’m in a little bit of a different stage where some of the things that I would want to talk about that’s the best radio, I’m wanting to keep off-air because there’s not much value to sharing it. It’s really mostly valuable to other people in the calendar space. Why would I want to potentially give a shortcut or some learning to potential competitors? I’m not super concerned about that, but it doesn’t feel like there’s much to gain and there’s potentially a little bit to lose from doing that. 

I felt a little bit more constrained in the things I can say on the podcasts and that has definitely made it a little bit less fulfilling for me. I just feel like I’ve stagnated with it. I didn’t get to the place of feeling total burnout, I don’t think, but I felt like I was heading in that direction, so this to me felt like the healthy way to handle it. I’m just saying I’ve been doing this for a long time. Part of me, of course, wants to stay in the seat because I helped start this thing and I don’t want someone else to take the seat, but at the same time, I just have to recognize that I got to look after my own well-being and make sure I don’t start to do something that feels like a treadmill and get burned out on it.

Rob: It’s good to go out while you’re still on top, so to speak, or still liking it, and not go into that burnout phase because I definitely did. I hear you on that. The transparency is cool and helpful to a point, and then pretty much without exception, there’s just a very, very few doing a lot of money—seven or eight figures—who are actually transparent with the real stuff. Some folks give the appearance of transparency, oh, here’s my revenue or whatever, but really what’s going on? You’ll hear someone talk with an employee who left and it’s like, oh, no, it’s so much different than they presented. They’re not actually transparent. They’re kind of market-y transparent. 

I think at a certain point, that can feel disingenuous. I know I felt the same way. I used to talk a lot about Drip and what we were doing inside, do talks, and then some folks stole stuff that I would say from the stage, used it against us, and competed with us. I remember being like, that’s really […], man. That was when I started changing and started talking less about that. There’s that danger.

Also, I hear you on just getting tired. It is hard to have something truly interesting to say week to week because sometimes, in some weeks, interesting stuff doesn’t happen, and then you’re constrained to be like, oh, I guess I’ll talk about some random thing with my espresso machine, or I got this new monitor. That’s fine too, but definitely, I think the truly incredible material that is really engaging is at the start of a lot of these stories and then at that pivot point of, oh, I just sold, we merged, or some big event happens. But that’s the thing about business, there is just a lot of boring stuff in the middle and having something to talk about all the time can be a stretch.

Derrick: Yeah. Especially being a founder who’s like, I’m deep in the trenches right now, so I spend so much of my time just either building products or working on business things. It’s almost like I’ve narrowed my focus to the point where I don’t necessarily have a lot of interesting industry insights. I’m not spending a ton of time on Twitter just thinking about cryptocurrency or the latest trends where I can just opine about that stuff. It’s just not in my nature to be someone who can just flap my lips and talk about whatever for a long time. I don’t think it necessarily makes great radio anyway, so I felt like it would be a stretch for me to try to just fill in the gaps with other things and still be interesting. I don’t think that’s me, so I had to recognize that.

Rob: That’s cool. So it is a sabbatical. I didn’t realize that. That’s a nice test. To be honest, I remember when Ben approached you about starting The Art of Product. You guys had already been co-hosting his prior podcast before then. I thought it was a great idea—it was outside your comfort zone—but it was something you and I talked about. As we were talking about selling Drip, you said, okay, so we work there for a year or two, and then what do I do? Because I’m going to do another one. 

I said, well, we need to work on making you have a more public brand. You need a personal brand to launch something from because you have the chops, experience, and blah, blah, blah. That to me was just right in that plan. It happened to just sink right in with, oh, Derrick’s going to have some more time. 

I loved the idea. I remember that it was a test. It was a trial period where I think he said, well, let’s do it for two months or three months. This is the reverse of that. Let’s try this for two or three months. I’m not going to replace you for now until you decide it’s more permanent.

Derrick: Yeah, exactly. It was super worth it. Definitely the biggest main launching pad for SavvyCal outside of Product Hunt and Twitter was the podcast audience, so it was definitely worth it. At the time, I think I was also toying around with regular blogging. That would have been just way harder to keep up than getting on the mic and talking about whatever we’re doing. I think it was a great, great thing for the time.

Rob: Great. Thanks for diving into that. Now, let’s dive into some listener questions. Our first question is from Vance Lucas, and it is a video question about how to know when you should go full-time on your startup.

We are starting to run low on questions, so if you want to appear on the show as well, head to startupsfortherestofus.com. There’s an Ask a Question link in the top nav. You can ask through audio or video which go to the top of the stack, or you can just send a text question in to questions@startupsfortherestofus.com. Now, Vance.

Vance: Hey, Rob. This is Vance, a longtime listener from Oklahoma City. My question is how do you know when it’s time to go full-time on your business or side project? I’m in a situation where I have a full-time job. I’m the sole provider for my family and kids, and I’ve finally managed to launch a side project which has been pretty successful. 

I’m at about $1600 MRR now, and it’s growing consistently. I’m still not quite at the point where I can go full-time on this. I think that’s a little ways away given tech salaries right now that I’m depending on for my family, so I’m wondering how you would go about making the decision to go full-time, what that would look like for you, and how you guide other people to do that. Appreciate your thoughts. Thanks.

Rob: It’s a good question. It’s a question every one of us who builds on the side has to face eventually. Derrick, what’s your take on this?

Derrick: I’m assuming he’s not asking about whether he should go full-time right now because $1600 MRR is probably not enough for sole income for a family. I’m assuming he’s looking out a little way if (say) this continues to grow a bit, when’s the right time to pull the trigger? I think the answer to that question is really about risk tolerance and your resources.

Rob: Startups For the Rest of Us drinking game in effect. What’s your risk tolerance?

Derrick: Is that one of them? Nice.

Rob: It depends, risk tolerance, or both.

Derrick: There’s going to be a lot of drinks, I think. 

Assuming that he has some amount of runway, whether it’s just money in a personal savings account, an investment account, or whatever, the main question to answer is can you reasonably expect to cross into default alive without depleting that resource too far? 

I’ve been a big fan of Summit, my friend, Matt Wensing. He’s a TinySeed fellow batchmate as well. He’s building a tool that helps you do financial modeling and really any kind of modeling in a way that’s less grueling than an Excel spreadsheet. He has some templates for SaaS in particular. You can just gauge I have this much money in the bank, I have MRR, here’s my churn, and here’s my growth rate. You can visualize your plateaus in there, which is pretty cool.

I would play around in Summit, honestly, and basically do napkin math on different scenarios on how long do you think you can make this savings account last? Is that within your risk tolerance? Is it going to dip low enough where you’re like, okay, if in the worst-case scenario we get below this certain threshold where I’m not comfortable, then you can wait it out a little longer. 

I think putting modeling around it will alleviate a lot of concerns as opposed to saying, well, maybe you’ve got $100,000 in a bank account and that feels like a lot of money, so you’re just going to take the leap. If you do that without doing the napkin math, then you’re always going to have that anxiety in the back of your mind like are we going to make it? Are we going to catch up? That’s probably what I would do.

I can say this because I’m not directly affiliated, but I would consider something like a TinySeed when you have a little bit more traction to also help alleviate the financial concerns in the early stage.

Rob: What’s funny is I should have thought of that myself, but I wasn’t going to say it. It occurred to me, but of course, yeah, if you get to even $1000 MMR, we funded companies that small. Vance, if that’s something of interest, one of the original hypotheses of TinySeed was we see these people in the $2000–$5000 or $2000–$10,000 MRR and they can’t quite get the job, but they can have enough money to where they have more runway and don’t have to worry about it. What we found is that’s actually a minority. Maybe 20%–25% of folks who come in to sign a seat aren’t already working full-time on the company but still, it’s not nothing given that we’ve funded 80-something companies today. That is one option. 

I love your idea. I was going to say model it out too just in a simple spreadsheet, but I always think of Summit as a forecasting SaaS, and in this case, that’s what it would be. It would be a really solid tool to be able to give you an idea of your comfort level. 

If you don’t have any money in the bank—you said if you have $100,000 in the bank, you could map that out—or if you only have $5000 in the bank, then you have to pretty much match your burn right now and match your expenses. You don’t have to make as much as you make from your day job. You just have to make as much as you burn in a month and feel okay that it’s predictable. 

It gets more complicated when you have a spouse or a significant other involved for sure, but I think that’s got to be a conversation of what is her comfort level and what is your comfort level with looking out three months and saying I project growth will be this versus looking out a year. There’s more uncertainty. In a year, I’ll be at $15,000 versus in three months, I’ll be at $5000. It’s just more likely the nearer it is. That’s how I’d be thinking about it.

The other thing I say all the time—I still think this is good advice—is if you go full-time on it and it doesn’t work out, what is the backup plan? What is the worst case? The worst case is you go back and get a job. Under normal circumstances when the economy is booming, that’s a fruit for you as a developer with entrepreneurial experience. That’s a two-week process. You’re going to have your pick of anybody.

Now, I will say there’s a bit of a slowdown, there are layoffs happening, and it’s not terrible yet, but if it gets there, the worst case right now could be worse than it was a year ago. You could be out of work for a bit. I still don’t think the worst case is that bad. That’s how I’d be thinking about it. 

I definitely took a huge pay cut, so to speak, when I left my full-time consulting job because I was making a ton of money, but I didn’t enjoy it. I think I took a 50%+ pay cut when I just said, oh, no, I’m just going to do products. I had some cushion in the bank of $20,000 or $30,000. It wasn’t a huge amount, but I was making enough from recurring revenue that it covered all of our expenses and it was growing each month. 

That’s the other thing that I actually left. It was $8000 a month, the number I needed to hit. When I was at $6500 but I was growing at $500 a month, I was like, that’s three months. I’m out of here. I think I can do it. I think I hit $8000 the next month or something because there was some fortuitous serendipity going on.

It’s a good question, Vance. Risk tolerance and it depends are part of that, but I think as an engineer, if you can map it out somehow and feel some confidence in it, that’ll probably help with the decision. Thanks for that. Hope it’s helpful.

The next question is from Patrick. He says, I’ve spent 15 years consulting in the healthcare software space as a nontechnical implementation manager. As a SaaS founder, I will be able to lead development efforts and can prioritize features if partnered with the right dev firm. 

My question is before shopping for firms, should I know the best front-end and back-end architecture for my SaaS MVP? Meaning should I be shopping for firms who specialize in X, whether that be Python, React, Java, or what have you? 

What do you think about that, Reimer?

Derrick: I would probably think of it this way. When evaluating tech stacks, I would narrow the choices down a bit to a handful of the most popular ones with the most energy behind them. I wouldn’t necessarily pick one especially if you’re not an engineer. You’re not going to be participating in the writing code part of things. I wouldn’t necessarily be super concerned about picking the one best. I don’t think there necessarily is a best one, but I would be looking for a stack that has that momentum, a really thriving ecosystem, and engineers that are working in the stack so you can just find and hire them and not have to train them on something bespoke or something really niche.

Right now in the backend, it’s Ruby on Rails and Laravel. I think there’s still a lot of Python Django out there. I’ll throw Elixir Phoenix out there just because I will say Elixir was voted the number four most loved language on last year’s Stack Overflow Developer Survey. It’s gaining some steam especially from former Rubyists like me. Probably the big three are Rails, Laravel, and Django. There are a ton of shops out there doing any of those, so I would be comparing those against each other.

On the frontend, you’ve got React and Vue as the two dominant front-end frameworks.

Rob: What if I don’t want a front-end framework, Derrick? So many TinySeed companies come to me and say, well, we have a bunch of bugs. I’m always like, well, where is it? It’s this untestable, single-page front-end app. I’m like, why did you do that? Tell me to get off my lawn. Tell me, okay boomer. Go ahead and send an email to questions@startupsfortherestofus.com.

When we built Drip, this was all a big thing. People were doing React and they were doing all the noun.js. I specifically said, all right, do you want to use one of these front-end frameworks? You’re like, it’s going to be Ruby to HTML. What are even the libraries now that we used?

Derrick: We had jQuery in there for sure. We were an app of a certain age, so we had jQuery. There were other lightweight front-end things that we added in that weren’t fully taking over the page. Honestly, this is the structure that I advocate and this is what I use for SavvyCal actually. I have React in the places where I need a lot of reactivity, and then on pages where there’s not a lot, it’s just server-rendered HTML.

I see this pattern actually emerging more and more. Trends are swinging back towards the monolith as what I’m seeing. There are some new libraries and frameworks out there. There’s Hotwire in the Rails world. Phoenix has a thing called Live View. That’s basically replacing a lot of what you would use a heavy JavaScript frontend for and moving it back to the backend, so you’re just sending HTML down over the wire to the frontend, but it’s still super snappy and feels like a single-page app.

One of my big recommendations for anyone starting something new is to stick to a monolithic architecture. I probably wouldn’t start by architecting a fully separated frontend from a backend even though there are a lot of shiny frontend-only frameworks. 

Next.js is a very nice thing, but I have experience in trying to marry it up with a separate backend and putting everything over an API to communicate between the two. That architecture can be good for large teams where you have a whole entire separate dedicated team working on the frontend and the backend and then you have the API layer that’s the contract between the two, but when you’re just starting out trying to build an MVP and iterate fast, that’s a lot to take on, a lot of maintenance. I don’t recommend that. You can always move to that if you need to, but to start out, monoliths are really the way to go.

My two overarching recommendations are stick with popular frameworks on the backend and the front end if you’re going to need any and stick to the monolithic architecture.

Rob: Wise advice. I was going to say Django or Rails because I’m pretty simple and old-school that way. Laravel, I think, is a perfectly viable option as well. We can name 10 other service-add languages, but in startups, we know that those are sellable assets. If it’s written in one of those, we know that those are maintainable. We know you can find developers that are not ridiculously expensive. We know that there are amazing ecosystems around them. 

There are the Ruby gems and the Django packages or whatever they’re called, and there are things like Bullet Trains. It’s starting a SaaS app infrastructure scaffolding. It’s just all this stuff that you get. I’m assuming it’s user auth, billing, login, password reset, and just all that crap you don’t want to write over and over. 

People have done that now in these starter packages. You pay a trivial amount of money, frankly, for them based on how much it would cost you to write them or have someone write them. You start with Rails, you buy a bullet train, and you find an agency who’s willing to work with that, or you start with Django. I forget what it’s called, but there’s something similar like that. That might even be open source. It is a SaaS foundation and some scaffolding. 

I think what both of us would do, Patrick, in your shoes is pick one of those three, or just say, hey, these are the three options so find an agency that does one of those. Thanks for the question, Patrick. I hope that was helpful.

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Our next question is actually one that came through MicroConf Connect which is MicroConf’s online community and Slack channel. This came through probably a month or two ago. I think I was doing a live stream Q&A, and I either didn’t have a chance to answer this question or I remember not having as much time as I wanted to, so I wanted to address it here on the show.

It’s from Carlos in MicroConf Connect. By the way, microconfconnect.com is free. If you want to join, we have more than 3000 mostly bootstrap founders in that channel. It’s a thriving community.

Carlos’ question is, “I’m starting a new SaaS business and despite a successful previous experience, I can’t stop feeling extremely anxious about it. Is this something you’re familiar with? How did you deal with it?”

Derrick, have you ever found yourself exactly in Carlos’ shoes?

Derrick: Never.

Rob: Why don’t you enlighten us with your experience?

Derrick: One, I think it just comes with the territory. There are resources out there. Dr. Sherry Walling’s book, The Entrepreneur’s Guide to Keeping Your Sh*t Together, has a lot of tools in there that you can use to try to balance the mental health aspect because it is quite grueling. I can attest to the fact that even having success under your belt doesn’t make the next rounds really any easier. Things do get easier once you gain that little bit of traction and once you start to feel product-market fit. The anxiety does ease up a bit, generally speaking, but those early days can be really, really tough. I would try to identify the primary sources of that anxiety, name them, and then work towards resolving them.

If you’re concerned, for example, if anyone will buy this, there are things you can do to feel less worried. You can go out there, start trying to drum up conversations with people who are in the market you’ve identified, and have conversations with them. Read The Mom Test so you can learn how to have conversations that are hopefully free of most biases. Test your hypotheses, see whether you are on the right track or not, start to get a picture of what the ideal customer looks like, and keep doing that until you feel reasonably confident that, okay, there are some people who want this thing. I’m not totally on an island here thinking that there’s a problem when there’s really not one.

To the question of building the right features, you can definitely mock things up and show early mock-ups to those people who have expressed interest and get a sense of is this on the right track or not?

A lot of these anxieties you can combat by getting outside of the cave and interfacing with customers or potential customers. That’s not often our first inclination as engineers, I know that for sure, but that stuff can go a really, really long way towards making you feel confident that you’re on the right track.

The other piece is just a mindset. I would try to look at the early phase as truly an experimental phase and try to stay as loosely committed to your existing assumptions as possible so that it becomes less about like, oh, no, am I completely off-base and going to fail, and instead as more like, let me learn as much as possible and try to form the proper assumptions from this. If I’m wrong about something, I’m going to take that as a win because I’ve just learned how to adjust my assumptions. I think that can also help if you break out of the rigid mindset of this is what I think I want to do, this is what I want to build, and if I’m not right out of the gate, then I failed. You’re probably setting yourself up to be really anxious.

Rob: That was great, the last point. Especially what I want to drive home and what I was going to start with is that your second, third, and fourth are still way harder than you remember. They’re way harder than they should be. I remember coming off of HitTail and starting Drip like, I know this. I was not anxious at all because I’m like, I got this dialed, I have the experience, I have the knowledge, I have the money, and I have whatever else you need to make this, the hard work, the luck, and the scale. It’s just going to work.

My reckoning was we built up the launch list, it’s all working, and we launched. Then, it just plateaued, people are bleeding out, and we don’t have product-market fit. I would shout, I should know how to do this. I’m pretty good at this right by now. Shouldn’t I be? Why am I floundering for months and months? 

For me, it wasn’t apparent anxiety, but it was a memory lapse of forgetting how hard this is every time. I’ve talked to Hiten Shah about this. What is he, on his fourth or fifth? He’s had venture and not venture-backed. He’s had things to throw off tens of million a year in profit. He’s one of the most accomplished SaaS founders I know with his most recent effort. We met at a Starbucks when I was in town and we were chatting. He’s like, it’s still so much work. You forget that even when you know what you’re doing and you have “infinity money”—I’m putting words in his mouth at this point—it’s still just a grind to figure it out.

David Cancel, same. I’m not trying to name-drop here. These are (again) some of the most accomplished founders. I believe he’s out there on his fifth or his sixth startup. He’s exited all of them, and they’ve been real exits, not acquirers and stuff. The dude was set for five startups ago. He and I were speaking at an event, and I was talking to him. I was like, David, you raised $10 million out of the gate with no product. He said, yeah. I said, did it make it easier? He said, nope, not at all. He was 1 ½ years or 2 years into Drift, and they were still just grinding and trying to figure out how to make it work.

With David, Hiten, and folks like yourself, we know you’re going to make it work eventually. We know that. But you tend to underestimate how long it’s going to take because if it’s your second, third, or fourth, it’s like, well, certainly, it will be shorter this time. Of course, you have a better network, you have a better audience, you have better people giving you advice to sanity check stuff, you have a better founder gut, you have more resources, and you have all this stuff. I would say it’s definitely not starting over, but it doesn’t put you as far ahead as I think one might think given all those factors.

Carlos, you’re feeling anxiety. I hope Derrick made you feel better, and then I hope I didn’t make you feel worse by basically saying it’s still going to be hard, but I love what you called out, which is to figure out and truly write down the sentences and the reasons that you are feeling worried about, and then figure out how can I address each of them head on? It’s a great question. Thanks for that, Carlos.

The next question is super tactical from Andres. It’s about TLD or top-level domain name choice. 

He says, “Hello, Rob, love the podcast. So many stories, words of advice, Q&As, guests, and founders with the most diverse experience. I’m currently in the pre-launch phase of a SaaS product, and one thing that’s been on my mind a lot is the choice of the product name and the domain name. The latter is much more of a challenge since most of the best .com domains are taken. Many founders go for .io, which is perfectly fine. As the company grows and makes enough revenue, they can afford to purchase .com but have to pay a lot of money, sometimes even in six figures. The URL of my company is very important to me, so I would like to avoid that expense beforehand by choosing a .com domain. What would you suggest: go with a meaningful and expressive name but a less serious tld.io—”his words, not mine”—or with a somewhat fictional name combined with the best tld.com?”

Derrick Reimer, what’s your take?

Derrick: I have split opinions on this because on the one hand, I’m of the mind that the domain does not make or break the business in most cases. Unless you’re being hey.com and you want those three letters, then maybe it’s a big deal. But in most cases, it doesn’t make or break. 

We had getdrip.com. We were called Get Drip forever and it was super annoying, but we made it. 

That being said, I am personally committed to .com for life. I think that’s all to do in the future and that’s definitely what I chose for SavvyCal. 

There’s just a ton of evidence out there—a lot of it anecdotal, some of it more scientific—that suggests that .coms perform better in organic search. It’s just simply the cold standard of TLDs. It’s what people expect. People kind of expect you to be on a .com, especially if you’re interfacing with customers outside of the tech space. That’s where alternative TLDs are still somewhat confusing and hard to remember. I’m a big proponent of just going .com.

Laura Roeder has a really good article about this and it’s effectively how I chose the SavvyCal domain name, although I don’t think I had read this article at that time and then came across it later. It’s called How I Nabbed The .Com for My Bootstrapped Startup, talking about how she got paperbell.com. 

The gist of that article is to set your budget and figure out how much you’re willing to spend in probably hundreds to thousands of dollars. We’re not talking huge amounts of money especially if it’s an available domain name. It may be billed as a premium domain or something, but you shouldn’t have to pay exorbitant amounts of money. 

Then, brainstorm branded words that you would want to include in the name and then run it through a domain name generator. 

I’m a big fan of Lean Domain Search. That’s what I used for SavvyCal. I knew that adding the Cal modifier on the end is something that’s been done before. It’s an established pattern for calendar-based tools, so I just put a search through there and said, give me domains that end with Cal. Then, it gave me hundreds and hundreds and hundreds.

Rob: I remember going through those lists. We’re texting back and forth. I was like, there are some really bad domain names in here.

Derrick: Yeah. Really, really bad ones and then a couple of good ones so you can weed through. I’m a big fan of tools like that because I have the domain or app on my phone. Anytime I think of a domain while I’m out at dinner, I can just pop that open and check to see if it’s available. I used to just try to come up with ideas out of thin air, type them in, and then I always get sad when they’re taken because they probably are.

Use these services that surface domains. I think Lean Domain Search is for only ones that are completely unregistered, but there are other services—I think Laura lists some of them in her article—that are maybe taken but not used, so you can potentially buy it for some negotiated fee from the owner. That’s where the budget comes into play. 

A lot of times, these domains that are just squatted on that are not a single word whatever. You can grab them for $1000–$2000. They’re usually not exorbitant.

I think at this stage in your company, it’s a great opportunity to reverse engineer a name for your brand where you can get the .com, go that route, and just not have to worry about trying to acquire it later or adding on get, use, or whatever on the front if you don’t have to. Again, that’s not the worst case and not the worst thing in the world. Plenty of successful companies have made it with that, but if you can avoid it at all possible, I would recommend it.

Rob: Yeah. I don’t mind the .io, the .co, and the .apps. It used to be .ly although that’s been phased out. I do wonder if .io and .app will eventually be that way or if they’ll stick around, but when I see a startup today with a cool domain name .io, .co, or .app, I think, yeah, I just know that there aren’t that many domain names. There are not that many .coms left. 

Is it as prestigious as .com? No, but if I had the choice of trying to get a crappier .com versus mycompanyname.io or .co, these days, I think I would do my company name. 

You brought up the Get Drip and how people would say yeah, Get Drip is this crazy product. I was like, that’s not what our product is called. 

In fact, one of the big mistakes I made—I have probably told you this—is as we were negotiating the sale, it was after the letter of intent and there was 60-day due diligence or whatever it is we were closing. Clay Collins, the CEO of the acquirer, told me, I want to let you know that I’ve bought drip.co and drip.io, and I paid $2500 for one of them and $3000 for the other. It’s a very low amount. It was a low single-digit thousand.

He says, if the sale doesn’t go through, I will sell them to you for what I paid. I’m not trying to squat your domains, but I want to get them now because I don’t like Get Drip.

I smacked myself in the forehead. I was like, why the […] did I not do that a year or two years ago? It was a few thousand dollars. It wasn’t a costly thing. It hadn’t occurred to me. I remember seeing that drip.com was super expensive. It was six figures. I was like, well, I’m never going to get that. I just didn’t think creatively about getting an almost domain.

Now, what I would say is with that said, I don’t like seeing getyourappname.io or .co because then it’s too many. The .co is not quite the .com, and then you have a get, a let’s, or whatever other prefix or suffix of that. If you’re going to go with a slightly less prestigious TLD, then I would only do it for the exact thing like Paperbell when she got the .com. But if she was paperbell.io, to me, that’s still a domain name. It’s really solid.

Think about it, man, customer.io and close.io now have the .com, but they didn’t need it. Certainly, Customer has been public, and they’re doing tens of millions in ARR. Close, I think, haven’t been public. Let’s just assume it’s tens of millions in ARR. There’s no chance it’s not given their team size and how long they’ve been around in this space they’re in. I do not think the .com would have made that much of a difference to them in their trajectory.

That’s where I am now. Ten years ago, it was different. There were still more .coms available, but these were taken. 

I do love your idea. I think that’s where I would start. If I had an idea today, here’s what we did. The most recent domain name I purchased for a company was TinySeed. Back in late—I guess it was four years ago now—2018, we were trying to figure out names, and eventually, I was like, TinySeed because it’s small and micro and it’s seed funding. The tinyseed.com was taken and tinyseedfund.com was $9, so I registered tinyseedfund.com. That was our original domain name for two months while I tried to buy tinyseed.com. That worked out and I got it for a very small amount. It was a trivial amount of money.

That’s something along the lines of what I would do today. First, I would try to use Lean Domain Search, try to find just a .com, and arrange the company name around it. Then, if I couldn’t, I’d buy a […], whether it’s .co or .io until I could work on maybe hitting the .com

Derrick: I definitely agree with the rules around if you’re going to have an alternative TLD, then make an exact match on the brand. If you have the .com and an established brand that you’re settled on, you may need to add the modifier. Maybe you use it forever, wait until you can afford the .com, or whatever, but that seems like the right move for sure.

Rob: Yeah. I remember basecamphq.com That’s how they started. Teamwork has teamwork.com now, but it was something like getteamwork.com or teamworkhq.com. They got the .com user list recently because I think they were a .io for a while. They paid a few thousand. They were public about this.

Derrick: Yeah, it’s interesting. This is just one data point, but I think Pieter Levels, the Nomad List guy, remarked that he’s gradually buying the .coms for all of his brands, and he’s probably ponying up a bunch of money for it. He was sharing traffic charts for a lot of those properties. When he flipped them over to .com, there was just a noticeable uptick across the board. He has 10 different sites or something.

For me, if I went with the .io, I would always be pining after that .com probably because it’s just the gold standard. If you have that kind of affliction like I do, you might be better served by just reverse engineering the name to get the .com out the gate, but that’s not always a luxury that we can always afford. Start with stalling your business out over.

Rob: Totally. The thing is I think people get analysis paralysis over this. I’ll admit, I have bought five domains in the past two years aftermarket because I wanted the .com and paid in the thousands for all of them. 

One of them was robwalling.com. I didn’t own that before. Another stylish and distinguished gentleman with an amazing name happened to own it, and he was willing to sell it to me. 

I bought startsmall.com because I changed the name of my LLC to that anyway. I talked to some guy who had retired and paid a decent chunk for it, but that to me was a prestige thing. 

As you’re saying, it’s a gold standard. It’s a personal thing. It makes me feel good every time I go to startsmall.com and I see the book. I had startupbook.net. That was the domain for that, which was fine. It was an SEO play.

I get it. I see it both ways. I’m doing this because I’m not super cash-strapped. It’s a little bit of vanity play, not that I want to brag to people, but it actually makes me feel good. 

That’s like having a T-shirt. We have MicroConf and TinySeed T-shirts. Do I think those drive our bottom line and get us more companies and more conference attendees? No, but I really like having T-shirts for my companies.

Derrick: I don’t know man. When I see you walking down the first avenue here in the North Loop, I think you’re a walking billboard for TinySeed.

Rob: Walking billboard, yeah.

All right. Well, sir, if folks want to follow you on Twitter, you are @derrickreimer. We’ll link that up in the show notes, and of course, savvycal.com if they want to see what you’re working on. It’s the calendaring tool that you, me, and all of our cool friends use.

Derrick: Exactly. You can be in my group.

Rob: If you want to be as cool as us, go to savvycal.com. Sign up today.

Thanks again, man. Thanks for coming to the show.

Derrick: Thanks for having me. It’s fun.

Rob: Thanks for showing up for this show every week. I’m doing some traveling over the next couple of months. We have MicroConfs and MicroConf Locals happening. If you head to microconf.com, you can look at our in-person events. It would be amazing to meet up with you. 

We’re heading to cities like Seattle, Atlanta, Austin, Texas, and a few other spots. It’s likely that we’ll be within driving distance of many of you listening, so it’d be amazing to meet up in person.

With that, I’ll sign off from this week’s episode and look forward to being back in your ears again next Tuesday morning.