In Episode 588, Rob Walling chats with Courtland Allen about a wide range of bootstrapper and indie hacker topics including the struggles with motivation/depression, bootstrapping today, fighting the urge to quit, and frameworks for getting your first dollar.
The topics we cover
[3:43] Hiring a podcast producer
[6:21] Letting go in business
[7:09] Invite-only experiment on Indie Hackers
[16:03] Thinking about the future
[20:47] Financial freedom and starting a business
[25:05] Depression as a founder and rediscovering purpose
[37:10] Fighting the urge to quit
[41:10] Getting your first dollar
[52:35] The bootstrapper scene in 2010 and the relevance of bootstrapping
Links from the show
- Rob Walling on Twitter
- The Time Paradox: The New Psychology of Time That Will Change Your Life
- Courtland Allen (@csallen) | Twitter
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
Also, if you haven’t seen, applications are open for TinySeed’s Spring 2022 programs. TinySeed is a year-long remote accelerator program is designed to help founders with a revenue-generating SaaS optimize product-market fit and grow faster. Read about the program and how to apply here.
Rob: You’ve tuned in to Startups for the Rest of Us. We are approaching episode 600 here in another 12 episodes or so, and today’s episode is really good. I really enjoyed this conversation with Courtland Allen. He and I basically wander through topics that are relevant to bootstrappers, indie hackers, non-bootstrappers, and mostly bootstrappers. We talk about things ranging from inside baseball and podcast production, to talking about struggles with motivation and depression, to whether it’s easier to bootstrap today, what it looked like 10 years ago. At the end, we talk about Basecamp. We just covered a lot of things.
I did a little ask on Twitter of what topics we should cover, and of course, we got 30 topics or something, so we couldn’t possibly cover all of them. But I am bookmarking that tweet for future episodes because I think some of the topics and questions were really interesting.
Before we dive into our conversation, I wanted to let you know that there are just a few more days in the TinySeed application process. If you are a bootstrapped or mostly bootstrapped SaaS founder, you’re doing at least $500 a month, and you’re interested in a yearlong mentorship advice community program, as well as a little bit of funding, just enough funding, the right amount of funding for a bootstrapper, you should head to tinyseed.com/apply and find out more.
The application process is pretty seamless. It’s 15, 20 minutes. Most people, if you know your numbers, it’s not that arduous. You’d be following in the footsteps of some pretty great SaaS companies that have been coming through our ranks. We are running batches both in the Americas time zones—North and South America, as well as the European time zones—so Europe, Middle East, and Africa. Tinyseed.com/apply if you’re interested. And with that, let’s dive into our conversation
I’m Rob Walling, your Courtland Allen. We’re putting this on both of our feeds.
Courtland: We are.
Rob: I can’t just do the Startups for the Rest of Us intro because people will be like, wait a minute, this is on the Indie Hacker’s feed. So I think we’re coming out a day apart, but I’m excited to sit down with you, man.
Courtland: Me too. You’re always one of my favorite people to chat with in podcast form and in real life too. You asked a question on Twitter, what should we talk about, and we got like a million different answers plus we had a list of stuff we want to talk about and so maybe we’ll go long this time.
Rob: I think we can. I’m excited about it. Likewise too. I appreciate the compliment. I certainly feel the same way. I really look forward to you and I sitting down because I feel like we have enough shared views and enough shared worldviews of bootstrapping and indie hacking that it makes sense, but the overlap is not a complete circle like a Venn diagram that’s just a circle. I feel like I learn from you and I expand my thinking when we talk.
Courtland: It’s funny you say that. I listened to your episode on My First Million, and I think near the end of the episode, you were giving startup ideas and Sam Parr I think was the one hosting that particular one. He’s a funny guy because he’s so disagreeable. No matter what you say he’ll just come out and be like, I think this is absolutely untrue to say the exact opposite, and he’s not afraid of looking dumb and being wrong or whatever. That is really entertaining. I think you and I agree on a lot, so we probably won’t have that kind of talk, but agreement is also cool.
Rob: Oh yes, we will because I’m going to disagree. Now I’m going to make me disagree with everything you say just to do it. Well, the first thing I’m going to say is I just made an offer to a producer who’s going to really be heading up all the back office stuff for Startups for the Rest of Us, the MicroConf podcast, and MicroConf YouTube. Total inside baseball from one podcast to another, but do you still do a lot of the work? I don’t imagine you do audio editing, but are you scheduling guests, putting stuff into WordPress, writing show notes, or have you been able to like get that stuff off your plate?
Courtland: Off my plate. The best hire I’ve ever made was—I call her my podcast boss. Arie was a producer for Mixergy. She still is a producer for Mixergy, but she does the Indie Hackers podcast now. I just have her do literally everything that she possibly can that I don’t feel like I need to be involved in.
I like being involved in the guest selection—who’s going to come on, who do I want to talk to. Because if someone else is choosing who I talk to, I don’t know. Maybe I could outsource that, but right now, I like choosing who I want to talk to and I like helping prepare. But what’s cool about Arie is I have her come on and even these things that I want to do, we’ll be on a Zoom call where she’s sitting there watching me work and offering suggestions. I’m not even like doing that alone. She’s kind of my podcast boss. She holds my feet to the fire. She makes sure I work on it a few hours a week, and she gives me helpful feedback while I’m working on it.
Then I sit down, press record, talk to my guest, press stop at the end of the conversation, we chat a little bit, and then I do nothing else. I don’t title the episode, I don’t describe the episode, I don’t tweet about it, I don’t release it. I’m on to the next thing. It’s such a breath of fresh air because I think a lot of podcasts, people churn. Most podcasts don’t last for much longer than a few episodes, and I think it’s because people get bogged down by all this extra work that they don’t really enjoy as much as they enjoy the conversations themselves.
Rob: All right. That’s awesome, man. I’m happy for you and I’m happy for me that next week, I’ll be in a similar situation. I mean, to be fair, I’m probably 75% or 80% of the way to where you are, but I’ve just piecemealed it together with a part-time freelancer who does the show notes, an editor who does this and that, then there are some gaps there as well, and I am the fallback. With MicroConf stuff, Producer Xander is a fallback. We’re bringing someone in to really backstop that, finally. I mean, it should have been done last year or years ago, to be honest, but it’s just one of those things that you do the same thing for too long and you don’t think about how it should change.
Courtland: Right. You get used to it. Like you said, there are these gaps. It’s stressful having to be the glue that glues all these things together to fill the gaps because then it’s almost in a way as if everything is a gap. You still have to worry about every single thing, every single part of the process, and it’s also stressful to hire somebody and just trust them to do everything. Because they’re not going to be as good at you as you at some things. They’re not going to have your particular eye for certain things.
But the cool thing is that there’ll be good stuff that you weren’t good at if you make a good hire, and they’ll improve your show in ways that you didn’t really anticipate. I think a lot of it is just learning to let go, have someone else do those things for you, see what comes out, and go with it.
Rob: Yeah, and I’ve always been able to let go when building SaaS companies, it’s like I can let go of customer support. I was able to let go of software development. I can let go of customer success, sales, and on and on and on. Letting go of creative stuff for me like writing and podcasting, that stuff’s a lot harder for me because there’s so much subtlety to it. It’s less of a here’s a job description. It’s more like, you kind of just got to do it and make it good and that’s hard, right?
Courtland: There is a popular indie hacker—I won’t say who it is—he has more than 40,000 followers on Twitter. His Twitter account is entirely automated. He never tweets. He doesn’t even know what he’s tweeting. There’s a team of people who tweet for him, and his Twitter account’s fire. It’s awesome. He tweets several times a day, people engage, and some of the tweets are really personal. But he’s like the ultimate in being comfortable, I guess, letting go of the creative element. I can’t imagine doing that.
Rob: Wow. Me either. That’s awesome, though. Yeah, I wanted to ask you, so Indie Hackers went invite-only, is that right about five, six months ago?
Rob: I don’t know if you’ve talked about that publicly, but I’m just wondering, what was around that decision? Does that just come with the growth of a community?
Courtland: I mean, it was very simple, spam was out of control. I have been fighting spammers from like day two of the forum for like five years, and they’re so good. They’re not just like people making little bots. They are actual human beings, sitting in offices somewhere on the other side of the world getting paid to spam websites and not caring at all. If you put up obstacles, they will figure out what the obstacle is and try to get around it.
At some point last summer, I think we had 6000 or 7000 people join Indie Hackers and 2000 of them were spammers. I was like, this is a battle that I’m losing. I just want to go back to basics. I’m not obsessed with growth at all costs. We don’t need to have thousands of people joining every week. We can just go invite-only mode, completely cut out the spammers, and have the community return to some level of normalcy.
I like the idea of an invite tree where you can see every single person, who they were invited by, who that person was invited by, who that person was invited by because then you start to build a clear picture of, okay, this guy’s a spammer. How did they get invited? All these other accounts of spammers too, and so we left it on invite-only mode for the better half of last year. I’m pretty sure we’ve rooted out literally 100% of the spammers.
Six months ago, when people complained about spam on Indie Hackers, they were complaining about people posting escort ads and Viagra pills ads. Today, when people complain about spam on Indie Hackers, they’re saying, oh, this person made a post that I didn’t like, which is a huge improvement.
Rob: Right. They’re marketing their startup. That’s a trip. I mean, I’m on Indie Hackers relatively frequently and I never saw the spam. Was it just getting rooted out before I saw it or what was the deal?
Courtland: Yeah, I mean. What time zone are you in, you’re in the United States?
Rob: Central time.
Courtland: Okay. So if you were in Europe, you saw a lot of spam. So what happens is we would go to sleep, the community manager would go to sleep, the forum would be overrun with spam, or depending on your browsing habits, if you go to indiehackers.com/newest and you just see a firehose of posts. A lot of that was just spam, and most people don’t go there. But the people who do go there are the people who want to curate the community and have some sort of control over what makes it to the front page by uploading stuff. They were just deluged with spam.
That sucks because if they can’t go there and get a good experience, they’re not going to go there, which means no one is giving us the signals we need in uploading posts to figure out what should go to the homepage.
Rob: That’s a problem, a big problem. One of the things I was most frustrated with running Drip was the spammers/people who would hack—not hacking, but they’d sign up for an account and they do phishing attacks out of Drip. They would send shady emails and get us on a blacklist. It was such a headache, and we had all these checks in. We had this code that would validate. It was a credit card versus some actions in the app. These days, if we were raising funding, we would call it an AI thing, but it was just code that measured. We could detect patterns and behaviors.
I hated it. It was a smaller factor, but I remember being, I could see selling this company purely being on the worst days of those when Derek and I went to sleep. It was just Monday morning at 2:00 AM, and then Russian spammers created a bunch of accounts and sent a bunch of phishing stuff. I thought I could sell this company. That was early on. We’re like $20,000 MRR. Did it do that for you? Did it ever feel like, you know what, I could rage quit this thing up in the air because of this?
Courtland: Yeah, I never got quite to the point of I would quit because of this, but it’s super demoralizing. The number one thing I think about every day is how do I improve the community? How do I promote the people who are doing a genuine and authentic job of contributing great content and stories? And then you have these other people who just cause you to lose your faith in humanity. They’re just total […] like sociopaths. They just don’t care. You’re trying to build a good thing. They are just trying to ruin it. Not even trying to ruin it but just trying to promote their own thing. They don’t care that it’s going to ruin your thing.
I talked to so many people who dealt with this problem. Famously at PayPal, they’re sending money over the internet, and a huge percentage of what they needed to do to make that business work was getting really smart at fighting fraudsters. That was super hard for them to do and they had a super talented team to do it. I talked to Amjad Masad at Replit. It’s an online code editing tool and code education tool, and it’s like, what do people use Replit for? Buildings crypto bots to mine crypto using his server’s bandwidth and costing the company a whole bunch of money. They just don’t care if they’re going to ruin Replit’s business if they can make a few thousand dollars.
Time and time again, I talk to people who have this issue where you just deal with the worst people. The internet’s cool because you can reach everybody. You can reach all the good people, but you also end up on the radar and straight in the crosshairs of the bad people who don’t care.
Rob: Yeah. When you get any modicum of success, I mean, we have TinySeed companies who by the time they hit $20,000 MRR, $25,000—so it’s still relatively small—facing any type of email, if there’s any type of email sending capability, people start targeting them. In terms of I’m going to do a phishing attack, I’m going to do a spam attack, I’m going to send unsolicited email based on your good IPs.
Courtland: This doesn’t happen in real life as much. If you have an events business or a store, you don’t get people who come into your store and just start yelling loudly to advertise their product. You just don’t deal with that many. I guess you’re going to yell at shoplifters and stuff. There are not as many […] when you can see people face-to-face. You can look the owner in the eyes and see that it’s human. You’re like, I don’t want to ruin this person’s business. But online, people are just kind of […]. They default to everything is a faceless corporation. If I can take advantage of them, I’ll do it.
Rob: That’s right. Anonymity is a real problem, that they can remain anonymous. I mean, we’ve seen that with online forums, right? Facebook, I know people get out of control too, but at least, usually, real names attached to it versus YouTube comments, even Reddit to a certain degree. I think there’s a big, big case to be made there.
Courtland: Yup. But Indie Hackers is no longer invite-only as of three weeks ago. Anybody can join and now we have a whole process. A lot of it is manual where we’ll look at your contributions.
So when you join, you can’t make a post, but you can make comments. You can help other people out in the community, contribute, discuss, and upvote comments. Essentially, if you earn your way out of that second-class citizenship (shall we call it), you’ll get a little email from me and we’ll promote you. You can now be a fully-fledged member of the community. Every now and then we’ll just promote somebody. If you do an AMA with somebody, we’ll just kick them right up to a full-fledged member because that’s somebody that we know and trust, but everybody else has to go through this process.
It’s really good at weeding out who wants to be an authentic member of the community and who wants to just do a drive-by, hey, I’m launching my product today. Can you give me access so I could launch today and then disappear and go somewhere else? It’s really funny to me how people will literally ask to do that.
I get emails every day like, hey, I’m launching today. I haven’t put any work or effort into the community. Can you just whitelist me so I can do my drive-by post? Even when we got rid of the spam with the invite codes, I got DMs on Twitter from spammers. They’re like, hey, I’m trying to post my Viagra pills thing and I can’t get it in. Can I get an invite code? I’m like, are you kidding me? Why would you ask me this?
Rob: Yeah, it’s crazy. It’s like they think you’re a customer service rep who just doesn’t know any better and who’s going to send that. That’s such a trip, man. Similarly, it’s odd that forum spammers, community spammers, and email spammers are similar because we built up a thing, we architected it out, and we never got to build it, but it was a trust score. It was when you first signed up for Drip, your trust score was zero. And then depending on what you did, your open rates, your click rates, and what your credit card is, if it was prepaid or not. There were all these factors. There were 10 factors.
Over time, that score would go up or it would go down. If you got a bunch of spam complaints or you got low open rates, we would start to knock that down. When you get below a certain threshold, we block sending on your account. You built it up over time, I think, if you had a bunch of sends that went great, you get up to 10, 20, 30, or whatever. It sounds like you figured out perhaps an easier way to kind of hack that.
Courtland: Same thing with Indie Hackers. You basically get a little score. You don’t see your score, but okay, below a certain score I don’t even look at your comments and stuff. Above a certain score, admins can—we have some moderators and stuff—see, okay, here are the people this week who’ve reached the score, here are their comments. Who should we promote into a fully-fledged member?
It’s funny because there’s a whole Black Mirror episode on this. It’s very dystopian. Everyone in society has a little score and people can constantly score you. She just has the worst day ever and gets a negative score. Now she’s an outcast and she can’t get an apartment and can’t get invited to parties. But I think, in reality, it’s not so bleak. It’s usually pretty useful, and it makes the community better for everybody for there to be the score that’s invisible, so long as it’s responsible and it can’t be gamed to ruin a perfectly good person’s time, it works.
Rob: Yup, I agree. So I sent a tweet out. I found some pictures from MicroConf 2011. It was the very first MicroConf, and so this is like 11 years ago. I posted a picture of Andrew Warner taking the stage for the first-ever talk at the first-ever MicroConf, and we all look super young because it’s 11 years ago. So Andrew Warner, then there’s me and Mike Taber, Ramit, Hiten Shah, and the […] guys or Sean Ellis. There’s just a handful of pics.
It got me thinking though as I look back, I was like, man, we were really young and we didn’t know what we were doing and here I am still doing. I was doing the podcast then.
Courtland: Same thing.
Rob: Yeah. I was talking about startups, I was running events, and I’m still doing those things. It got me thinking. Often we’ll try to look out 5, 10, or 15 years because it’s just so far in the future, but I’m wondering if you have. Do you ever think, what am I going to be doing in a decade? Am I still going to be doing something similar, related to this, or do I think I’ll have a time doing this and maybe switch it up?
Courtland: I live in the future, man.
Rob: Me too.
Courtland: I think way too much about the future. There’s a good book, it’s called The Time Paradox where they talk about how a lot of our decision-making in life comes down to the default time frame that we live in, and some people default to the past, some people default to the present in certain situations. I think probably most tech founders and entrepreneurs are very future-focused people, which I think correlates highly with success because we’re often thinking, what can I do now to get to this desired state 5 or 10 years from now? That turns out to be a really good way to plan and strategize, but it’s also not the best way to enjoy life in the present.
I remember being in school and going to MIT and thinking, at the end of our four years in our fraternity, everybody could get up and you could just talk, you can give a speech. You can say whatever you want. It was an awesome tradition because you just got four years to think about what you’re going to say and then you get up and you talk. One of the cool things about it was everybody felt so lucky to go to that school, people would default assume that you were smart and give you the benefit of the doubt.
But I thought a lot about it and it’s like, none of us are here because of who we are now. We’re here because of decisions we made when we were 12 years old, when we were 13 years old. We’re going to take school seriously and I’m going to study for the SAT, and now, 10 years later, that’s paying off. It’s a lesson that never really left me. The decisions you make now will change your life dramatically 5, 10 years in the future.
I hope that 10 years from now I’m still working at Indie Hackers. If I’m working at Indie Hackers 10 years from now, that means Indie Hackers is an amazing place that I’m probably super jazzed about or it’s way bigger and more impactful than it is now. If I’m not working at Indie Hackers 10 years from now, that doesn’t necessarily mean it’s a failure, but it definitely means I moved on to something else that was more exciting, and it’s not really my plan right now.
My plan right now is to try to build Indie Hackers into an institution, something that really touches a ton of lives in a really positive way. I think it already does, but I think if you build a good thing, bringing it to more people is an even better thing. If you build a really cool tool or a really cool sandwich shop and you could franchise it, and now more people in the world can eat that sandwich, that’s a good thing. If you invent penicillin, it’s 100 times better if you bring it to 100 times more people.
I’ve been trying to make Indie Hackers a good thing and I want to bring it to thousands of times more people, and that might take 5 or 10 years.
Rob: It’s interesting you say that because obviously, you and I have both been doing this now for years. Talking to and trying to help aspiring and actual founders, I guess we’re all actual founders but founders who have actually shipped and who are just working on it and want to do it. It wasn’t until the last couple of years really as like, I have this podcast, I have MicroConf, and now we’re going to launch TinySeed out of it.
I started thinking, I think we’re grown up enough that I need a mission, you know what I mean? What is the mission? I’ve been honing it, refining it, and I still struggle with the exact wording. I tossed it to Producers Xander, I showed it to Einar and Tracy. What’s interesting is the mission of all three of those properties is the same thing—the mission of TinySeed, MicroConf, and Startups for the Rest of Us, it’s all the same. It’s to dramatically multiply the number of self-sustaining independent startups in the world.
Whether the word wording exactly is a SaaS startup, I just want there to be more and I want them to be self-sustaining. So look, maybe they took funding, maybe they didn’t, I don’t give a […]. In fact, I never have. I just don’t want the dogma.
What’s interesting is once I said that mission, I was like, wait a minute, I’ve been doing that for 16 years, more than that. 2005 is when I started blogging about this, and it’s like, I didn’t have that mission in mind, but that is what I want to do now for the rest of my life. That’s it, for the rest of my professional career. I think I’ll be working until I basically keel over dead.
That was an interesting umbrella term for me to realize, you know what, I enjoy podcasting and I’m going to keep doing it, but I don’t need to podcast if I’m still doing something that follows the mission, right? I don’t need to have an online community. I don’t need to have a fund, but I think I will be doing something under that umbrella forever.
Courtland: I think that’s a great vision. One of my heroes is Charlie Munger. He has a lot of writing and business advice that influenced me, just life advice and ways to think that influenced me when I was younger. The dude is 98 years old. We did last year a podcast where he’s distilling investment advice and talking about how he’s running Berkshire Hathaway with Warren Buffett. He’s 98. He’s found what he loves. It’s kept him healthy even mentally, he’s super sharp, just as engaged as ever. I think that’s a great goal.
I think your mission for MicroConf, not just MicroConf but everything, even TinySeed as well, is kind of the same as mine. I want more people to become financially independent and free to live the lives that they want to live. I think that starting online businesses is one of the best ways to do it. It’s increasingly becoming accessible and a good way for people to do it, and […] it’s encouraging to see everyone doing it. That’s my mission too.
I was reading some research. My buddy Julian turned me on to this researcher. Her name is Erin Westgate, and she published this paper about the different types of lives that people can live that are good. There’s kind of this idea of a happy life. A happy life is characterized by some of the most obvious life that people want, like a life full of comfort, joy, security, free time, money, and satisfaction. But then there’s also this other type of life that people can optimize for, which is a meaningful life. That’s a life full of significance, purpose, coherence, and societal contribution.
I think the older one gets, the more we think about living a meaningful life like, what’s the purpose of it all? Because more and more of life is behind us and less and less is ahead of us. So we think, okay, what’s the lasting impact that I’m having? That starts to become much more valuable to us than it was when we were 25 just thinking about how to be happy in the short term.
I think it’s the same with the business and a career. It makes a lot of sense as we get older to think about what’s the impact of what I’m doing? How do I tie all the things I’m doing together into some sort of mission and impact, and there’s a lot of personal satisfaction that comes from having a meaningful life.
Rob: Yeah. I always say, entrepreneurs most should seek freedom, purpose, and relationships kind of in that order, although relationships probably before purpose, I think, or in tandem with it. But I think that’s one of the reasons I sought entrepreneurship was the freedom from a day job and the freedom from being told what to build and when. I remember working, working, working towards it because I live in the future you do and just thinking to that day when I quit the job.
Then I got it and I was like, this is amazing. It was amazing for three months and then I was like, I’m kind of bored. What do I need to do next? Because I had freedom but I really didn’t have a purpose. I had a bunch of small apps that kind of all had this autopilot traffic from SEO, ads, and this and that, but nothing was that interesting to me. It was just a paycheck. It was a nice paycheck. It was $120,00–$150,000, this is in 2007 so it went a long way. Yeah, it was great. I was like, yeah, I’m free. But then I was like, uh-oh. I need to find a purpose.
That was where I really started doubling down on talking about this in writing, doing the book, and the podcast, and all of that came out in about an 18-month period because I was like, I want there to be more, and here’s the other thing—relationships. There was kind of no one else doing it. Joel Spolsky was blogging in the early 2000s, he started a software company, and then Patrick McKenzie started blogging a couple of years after I did and he and I ran across each other.
Then I’d heard of Basecamp and they had a SaaS that I didn’t use. But I’m getting to 2008, 2009 and I’m like, is anyone else thinking about or doing this whole kind of indie hacker, bootstrap startup path? Is it a thing or am I the only one that’s done it or will do it? Because I genuinely didn’t know, and that was part of building the audience that then turned into the community was like, I want to be able to hang out with other people who talk about this stuff because this is really interesting to me. No one else in my town gives a […] about this. Can I find 100 people that I can get into a room with that care about it? That was a big thing.
Courtland: I mean, it’s that purpose thing you’re talking about like freedom. When I talk to Indie Hackers, the vast majority of Indie Hackers are looking for some type of freedom. That’s why they’re starting their business because they feel they don’t want to work for somebody else. They want more time. They want to work with people. They want creative freedom. They want financial independence and no ceiling on their income. I think that that is the purpose, right? That can be your purpose to have this epic adventure that you’re going on in order to earn your freedom.
You and I both have been on that adventure for some part of our life, but then you get your freedom, you get there, and suddenly, you lose your purpose. It’s like you had this epic journey, you completed it, you succeeded, and now it’s like, now what? It’s like Frodo at the end of the Lord of the Rings. The movie ends there. He casts the ring to the fire—I don’t know, there are 10 different ending scenes—but then it’s over and the credits roll. It’s like, well, what did Frodo do after that? Sit around in the Shire telling stories about how he had this epic adventure at some point. It’s kind of hard to figure out what you do after you’ve accomplished your mission. How do you find a new purpose?
Rob: Right. We can’t just get on the boat to the Undying Lands like he did.
Courtland: Right. He just sailed west. Not a thing.
Rob: I want to piggyback on that topic because you just talked about losing your purpose or you find it. It’s the arrival fallacy is what it is. You arrive and then you’re like, I will arrive once I do this, and you do for about a month or three months and you decide, oh, I need to do something new.
I tweeted out and you retweeted (thanks), what should you and I talk about on this episode. There are too many topics for us to cover. One that I think’s interesting as Arvid Kahl said, “Please give them mental health topics some time. Building anything is hard, building in the middle of a pandemic is even harder. Some people need permission to let themselves feel this, and you both can help there.” And this, obviously, is a topic that my wife talks.
My wife’s a clinical psychologist, you should check out the ZenFounder podcast if you want. Every week, she’s releasing an episode on this topic as a founder married to a founder, consults with founders, and as a psychologist. But aside from that, you and I have shared our own struggles with building businesses and mental health during that. Why don’t you start and then I’ll go because I think we both have more stories, you know.
Courtland: Mental health is super important. I’ve struggled with various mental health issues sometimes. I’ve been very depressed, I think. three times in my life. One of them was this past year. I had a good six months where I was just like, what’s the point of anything? Why do anything? It was a hard time because the pandemic is very isolating. I have this road trip that I’ve talked about where I was just not really seeing anyone. I moved to Seattle and it was kind of isolating as well.
I think for me, it really tied into this topic of purpose because from probably age 8 to age 34, I’ve always had this vision of what do I do with my life? It’s like I’m on this epic adventure. I’m trying to build some very big ambitious project, and it’s usually creative. It usually involves building a website, designing it, and putting code together, which is this awesome feedback loop of reward and work and then reward and then work. I think for the first time since I was eight, I kind of got off it last year and was like, well, what else is there to life? I sort of found myself spinning, and I wasn’t sure what the reason was. It was all these other proximate reasons like, is my relationship with my girlfriend going okay, or is it my living situation?
It’s really easy to blame the wrong thing. But I think at the core, I just lost the drive that I had that filled up my days and made every day feel like I was excited to wake up and do something. I think everybody has their own loop, their own natural process where left to their own devices they’ll do something. For a lot of people, it’s like, I’m going to look at social media. I’m going to come home and look at TikTok on my phone. For a lot of people, it’s like, I’m going to come home and spend time with my family.
I dated someone once, she would just impulsively just go out and just meet strangers, and she loved to do that. That was her happy resting place. For me, it’s always like, I’m going to sit down on my computer, I’m going to code something really cool, and try to work on it. I think without that and without replacing that with anything, it was very easy for me to sit around and be like, well, now what?
Now I’m dependent on other people to come in and hang out with me to do something entertaining or stimulating. It was very easy to just start questioning my purpose in life. I think this happens to a lot of founders. It’s kind of a cliché. People reach some level of financial success or they achieve some goal, and then they’re just aimless. Embarrassingly enough for me, it took me six months to figure out why. Then another few months, I go, okay, well, what can I do that has meaning and purpose that’ll be interesting and fulfill me? Then the answer is like, oh, I should just work on Indie Hackers.
Oh, yeah. I’m working on Indie Hackers for more than just these earlier reasons. I’m working on it because it actually is fun for me. It actually is entertaining. It actually is meaningful. I love the people that I work with, the people that I talk to, the problems that we’re trying to solve. All the challenges in front of me with Indie Hackers and the way that I want to grow the site are really interesting for their own sake.
I had to have this period of rediscovering why and not even rediscovering. It’s sort of changing the reasons why I’m working on the site and diving into those. I’m hoping that my entire life—I hope for everybody that this is the case—is full of these epic adventures and there’s never really an endpoint. There’s never really a midlife crisis point where I’m done, I’ve accomplished the goal, and that’s it. I hope that I’m always struggling towards something that is really meaningful and really enjoyable in the meantime, and that even if I never reached the end of that tunnel, it’s fun the whole way through.
Rob: Yeah. I don’t know if you’ve known people who retire, who work a day job for 20, 30 years and then they retire. They totally lose that meaning. Folks who sell a company and don’t have anything else to do, it can wreak havoc on their motivation, their mental health, and you can go downhill.
Courtland: Yeah. I mean, it’s kind of a cliché at this point, don’t do that. You don’t realize what you have until you lose it. I’d never had a second of my life where I didn’t have something like that, and without it, I’m like, what’s going on? It’s sort of hard to diagnose.
Rob: I have 100% gone through exactly that. I don’t even know how many times in my life from the time I was a teenager. I’ve talked on this podcast about burning out essentially while growing Drip and just how hard some of that piece was. I don’t know what I had. If I had clinical depression for part of that or if it was just burnout because it was just hard. I was stressed all the time. It was a rough go.
But what’s interesting is more recently, during COVID, 2020 I think a lot of people had a tough year that year for a lot of reasons, so did I. In fact, Sherry and I had just some—we’ve been married 22 years now. You’re going to go through ups and downs. We had a pretty tough stretch there in the middle of COVID. There were a few days where I kind of didn’t get out of bed, and I’ve never been that messed up before emotionally.
I remember being like, I really want to keep doing life and I really wanted to hang out with my family, but I just didn’t have the motivation to get up. I couldn’t look at my Trello board and say, I want to do these things. I didn’t want to do anything. It’s tough. I don’t have depression. That’s not a thing that plagues my life.
In fact, I’m on the other side of the spectrum where I’m a stress anxiety person. My whole family tree is all alcoholics, drug addicts who were self-treating themselves for these anxieties. My dad, I’ve talked about this before, has OCD. He had OCD so bad he didn’t leave his bedroom for seven months when I was a senior in high school. OCD is an anxiety disorder, so it definitely runs in my family, and it’s something I’ve learned to cope with as an adult.
I guess all that to say, this topic of founder mental health, in general, has always resonated with me. People never used to talk about it 10 years ago, and I think a lot more of us talk about it these days. I think that’s probably helpful to normalize it.
Courtland: One of my favorite things about living on the West Coast is that everybody on the West Coast compared to the East Coast, in my experience, is so woo woo and froufrou. Everyone on the West Coast that I know has a therapist. On the East Coast, it’s like a dirty word. You have a therapist, what’s wrong with you? I would never tell anybody about that.
I have a therapist. He’s awesome. He’s this 75-year-old Canadian dude. I want to go a million miles a minute. I talk so fast. The second I got into the therapy thing, I got 15 things I want to talk about. He’s like, let’s slow down, Courtland. Let’s take our time, find your center, and be one with yourself. I get so frustrated the first 5 or 10 minutes, and then I slow down. I’m like, okay, I want to smoke what this guy is smoking because it feels good. I know that I need it. I need to chill out a little bit.
I think it’s worth taking the time, whether you’re a founder or not. I think everybody should take the time to check in with themselves and work on your mental health because if your mental health is in a good place, I don’t think it’s wise to take that for granted. If your mental health is in a tough place, obviously, you got to prioritize that because that is the engine that powers everything else in your life.
I think about it a lot when I think about success and people struggling to do things. Everybody’s going through different […]. I had a ridiculously good Leave It to Beaver childhood. I have zero trauma. Zero real true lasting hardships that I really had to push through that left a scar on me, and so I was free in my 20s to just go tackle challenges without any mental health issues and stuff like that.
Other people were struggling to get out of bed. They’re struggling to deal with terrible things that have happened to them, and they’re trying to take on these big challenges. I think that it’s really easy to underestimate that. If you’re going through that kind of stuff, if you’re just ignoring it, I think you’re doing yourself a disservice.
Rob: At times in my life, I have ignored it for too long. The other thing I ignored was physical issues. I know we’re talking about mental health, but I had a really bad shoulder, back pain, and neck pain because we all hunched over our desks. I had it for years and it was kind of debilitating. It was to the point where I was under constant pain, and why the […] didn’t I do something about it?
I remember saying I don’t have the time, and then I went to a chiropractor and massage therapist and it didn’t fix it quick enough. I was like, I just don’t have time to carve out two hours a week to do this so I didn’t do it. It wasn’t until we moved to Minneapolis, I had sold the company, I went to three different massage folks, and I found a dude who’s really good. He integrates all these different things. It hurts like crazy, but I went to him twice a week for months. I just said, I’m carving out this time.
It also helped that I didn’t still run the company so I could just take a couple of hours a week. It took him months and months to work it out. I mean there were all these toxins and crap in your muscles when they’re like that. I would almost get sick after because I had just let it go for too long. This chronic mental, you shouldn’t live like that. I say that as much for anyone listening as I do for myself in the future. I refuse to live that again, you know?
Courtland: Yeah, it’s hard. I met a person and she was telling me about this phase of her life where she was super grumpy. She was just kind of a […]. I asked her, why are you such an […]? Why are you being this way?. She’s like, chronic pain. She literally had chronic back pain and it would fire up. You know what doesn’t make you a happy, agreeable person? Being in physical pain all the time. That makes me really short-tempered. I think lots of people have different things that affect us at a lower level and that bubble up to how we actually behave.
I think for founders, in particular, we can be so single-mindedly focused on what we’re working on, so ambitious, so driven. I got to work on this business. It’s got to take up every hour of every day. Nothing else is a higher priority. It’s easy to get into a mode where like, oh, let’s put working out on the backburner. Let’s put mental health on the backburner. Let’s put physical, all this stuff on the back burner. That can come later. I think that that is a recipe for disaster.
All these things are really basic advice. Get eight hours of sleep, take care of your body, blah blah blah, but it’s not about whether you know that advice, it’s about whether or not you’re doing it. I think 99% of people are not doing it. They’re repeating it, I’m repeating it, but not always doing it.
Rob: Yeah. And it wasn’t until I retired from Drip. Do you know TinySeed’s my retirement project, right? That’s what I told Einar.
Courtland: You’ve been put out to pasture.
Rob: Yeah, okay. I could do this thing just in my spare time. So I want to switch it up. We have so many topics on this thing, but Liam Symonds says, “If you had to fight one horse sized duck or 100 duck sized horses, which would you choose?”
Courtland: A hundred duck-sized horses easily. Can you imagine how terrifying a horse-sized duck would be?
Rob: It would be insane. I mean, that beak alone. Those things are hard. I don’t know if you’ve ever been pecked or nibbled at by a duck or a goose, that stuff is scary.
Courtland: I have.
Rob: And their tongues are terrifying.
Courtland? Have you ever looked a duck in the eyes, any bird? If you look in their eyes, they’re terrifying. They’re these deeply inhuman eyes. I can’t imagine a horse-sized duck. I would rather do almost anything.
Rob: Not with a 10-foot pole.
Courtland: Easy answer for me.
Rob: Me too as well.
Courtland: I like that one to start though. Let’s talk about mental health and depression. Okay, let’s talk about horse-sized ducks.
Rob: I had to switch it off, man. It’s too close to home. Oh, this is a good one. Greg Digneo says, “At what point in Drip for Rob and Indie Hackers for Courtland did you guys want to quit? And why didn’t you?”
I wanted to quit. I wanted to quit when Russian spammers were hacking us. I wanted to quit when I thought I couldn’t make payroll because I had overhired and I got a big personal tax bill. I wanted to quit when competitors would rip off my stuff. When we would spend months building, thinking, and marketing things and someone would just rip it off shamelessly. The worst part was they would claim that it was their idea. I take business a little too personally, I’m going to be honest, and that kind of stuff really bothered me.
When I left Drip 2018, I took a few months and I evaluated, do I want to walk away from startups altogether? Do I want to sell the podcasts and MicroConf? There were times where I was like, I don’t know if I want to keep doing this. I mean, the reason I didn’t is because, we talked about it earlier. I realize, oh, my mission in life is this thing, to promote entrepreneurship and to get more people finding freedom, purpose, and relationships through it. When I realized that it was like, well, I already have these platforms. Why don’t I build on them and just do more and double down?
In terms of Drip, the reason I didn’t quit when those were happening was momentum. To your point earlier momentum, I just had momentum going and I had a team I was working with. I couldn’t just walk away. If I was an indie founder, I may have trashed some stuff at a certain point, just table flip and say, this is too hard. I could do an idea that’s more lucrative for less work, but I had this team of 3, then 5, then 10. It’s like, everybody’s on board and they kept me accountable unintentionally. They didn’t come and say you need to be accountable, but I felt the burden of like, no, I had the vision, we all got on board with this thing, and I can’t walk away from this.
Courtland: Yeah, I see this a lot with founders. I think it’s kind of a miracle. If you look out into the world, there are billions and billions of people who wake up every day at 9:00 AM and go to a job they don’t even that much and work that job and come up. They’re consistent. They’ll do that day after day for years, right?
I talk to a lot of founders and it’s really hard for founders, podcasters, or whatever it is to last for more than a few months where they’re like, I give up. It’s too much work. I think one of the biggest difference-makers there is, besides the obvious, I got to get the bills paid, is that accountability. It’s the fact that I actually have teammates, a boss, and people who are depending on me. I think we’re just tribal creatures. We’re wired to not want to let down the people around us. If we commit to something, we agree to something, and we have work that’s waiting for us, it feels […] to just quit and not do that.
I think one of the best things you can do as a founder, if you really want to stick with what you’re doing, which is sort of necessary for succeeding, is to surround yourself with people who you feel accountable to. Even if you’re their boss, you still feel accountable to your employees, partners, cofounders, or team. I love feeling that way. I like Arie in my podcast because I don’t want to let her down. Part of her work is dependent on me getting the podcast out. We have a calendar event twice a week, I got to meet with Arie. Sometimes I cancel, but I’ll feel bad if I just abandon it.
For me, I’ve also sort of written off momentum. I never really wanted to quit Indie Hackers at all when things are going up into the right. And then in the early days, I had this email list where I would send out my progress every single week. Here’s what I did, here’s what I did, and people would respond. I feel super bad if I just didn’t do anything for a week. It would be embarrassing, quite frankly. What am I going to tell these people? I did nothing.
I had a lot of late nights on Wednesdays where I would just try to do something to report because I was accountable. The only time I ever got to feeling you know, maybe this is what I shouldn’t do, was last year when I started feeling a little depressed, a little bit down. Some of the things I was trying to do to grow the site weren’t working out. That feedback loop I’ve talked about before of positive things happening and encouraging you to try more things in the future, being optimistic was sort of slowing down.
I was like, I’m trying these things and the site’s not growing like I want. Maybe this is it. Maybe I’m out of ideas. Maybe I should rest on my laurels, I’ve done a good thing. I wasn’t working as much. Rosie Sherry, our Community Manager, quit and so our team was sort of winding down a little bit and we didn’t replace her. I had fewer of those mechanisms in place that keep you motivated. It’s the closest I’ve ever gotten to wanting to quit and exploring different things.
Rob: Wow. John Howard asks, “I always love the conversation of the scrappy early days for Indie Hackers and bootstrappers,” and then throws out a bunch of questions. “What does it take to get to an MVP? What does it take to get to dollar 1? What does it take to define your audience? I’ve been through it a bunch but a framework is always fun!”
Courtland: My favorite framework, if I was an indie hacker right now starting from nothing, is to literally just solve someone’s problem, like any problem. Put as little […] as possible between you solving somebody’s problem and getting paid for that as you can.
Nathan Barry has this excellent blog post called, The ladders of wealth creation—I recommend it. The way he puts it is there’s a reliable progression that you can take to earn, build more wealth. At the bottom ladder, you’ve got trading your time for money, working for an employer, having a job, and then on top of the ladder is you’re selling products, right? You’ve got a social network, marketplace, a subscription software business, or something. You work your way there gradually.
I think what I would do is I would just start at the bottom, okay, I’m selling time for money. Well, how do I do that, but instead of working for somebody else, working for myself, right? You can go to, for example, Indie Hackers is a website where people have tons of problems. You can go to Indie Hackers, click monthly, see the top posts for every month. I think the top post for January is, share your projects and I’ll try to find you users.
There are 330 comments of people who were like, I’m working on this project and I have a problem. I can’t find any users. There’s just this one guy who is going through replying to everyone and just trying to figure out what their problem is and try to help them solve it. I bet you 10%, 20% of the people he talks to could get on a phone call and be like, hey, $200 I’ll do a consulting call with you. We’ll see where it goes. He can make thousands of dollars tomorrow with five or six consulting calls just because he’s solving somebody’s problem.
He doesn’t have to build a fancy website. He doesn’t have to hire a team and build an app. He doesn’t have to do anything. Just literally, what’s your problem? I will try as hard as I can to solve it for people who are motivated to solve these problems because I think they’ll make money.
If I were starting out I would do that and just follow that path and see where it takes me. Because when you solve somebody’s problem, they pay you for it. That’s a pretty good indicator that you’re onto the right thing. You can maybe tweak your idea, try to change your customer or the problem that you solve, but it doesn’t require you to be particularly brilliant. It just requires you going to a source of problems, which is really easy to find on the internet, and then rolling up your sleeves and doing something today, like right now.
Rob: I’m glad you brought up the solve a problem because I always forget to mention it because it is so ingrained. It is such a fundamental precept that I don’t even bring that up because I expect everyone already knows that, but they don’t. I’m glad that you did.
Courtland: Right, the curse of knowledge.
Rob: Yup, it totally is. I forget. Well of course you should solve a problem, but it’s well, not of course. For some people listening to this podcast it’s of course because I’ve been talking about this stuff for 17 years. I think it’s fascinating. We have the MicroConf State of Independent SaaS Survey. We do a survey and then put out a report. We talk about how people found their startup idea, their SaaS ideas specifically.
I just pulled the report up and 45% of respondents said they came up with their idea for their product or company, 45% it was a specific problem that they were experiencing, and then it’s another 22% a problem my customers or clients were experiencing. So you’re at 2/3 now. Another 13% was a problem or experience at my day job. So now we’re at 80%. Another 11% a problem a friend or relative was experiencing. We’re at 91% of hundreds and hundreds of respondents.
We’re at 91%. The last three are 8% said research, 1.5% said other, and 0.2% said I purchased the business. It’s just a problem that me or someone around me is experiencing.
Courtland: But it’s a problem.
Rob: It is and I think it’s super important because if you’re not solving a problem, this is where I get a little prescriptive with the B2B versus B2C thing. You and I have talked about this in the past. I just am so bullish on B2B and really bearish on B2C. Not only because I’ve owned I think two or three products or companies, one was an ecomm site that served consumers, but because every B2C company, specifically a subscription company that I see, bootstrappers the churn is too high. They can’t find customers’ lifetime values. It’s the same problem over and over.
I never say never do this, but I say, you probably don’t want to do this because the problems you solve for consumers, there’s not as much value as if you solve it for businesses.
Courtland: It’s super true. At the end of the day, businesses have way more money than consumers. They are more motivated to fix it most of the time. They have a gigantic list. They need to hire, they need to find office space, they need to market, they need to do sales, they need to solve their own customers’ problems. They need an email solution, they need hosting, they need accounting. Businesses have so many problems that need to be solved, it’s just generally a better bet to go that way.
That being said, I do think if you’re judicious about it and you want to do something that targets consumers, you can, you just have to really think about the problem. Again, you can’t think about, oh, I want to build the solution. I want to build this app or this service. You have to think about, what’s the problem I’m solving and what is the nature of this problem? Specifically, is this a problem that is lucrative to solve? Because if it’s not, you might solve it, you might get happy customers who say thank you, and you’re not making any money because they’re churning or they’re expecting it for free.
If you look at where consumers spend money or even where businesses spend money, I think the same formula applies. We want to find a problem that’s lucrative just what people are paying to do, right? Every time somebody spends money, it’s because we’re trying to solve a problem. People spend a ton of money on housing. People spend a ton of money on transportation. People spend so much money on education, it’s crazy. I think that’s what people are most business-like where they think, okay, if I get this education, if I go to school or I take this course, I will then be able to use those skills I developed to go make more money in the future.
People are willing to go into hundreds of thousands of dollars of debt to get an education because they see how it will make them money in the future. I think it’s not a coincidence that most of the people I know who have consumer businesses that are successful are educating consumers in some way and helping those consumers become better versions of themselves. Whereas people who are trying to sell these little tools, apps, and productivity software find it much harder because the problems they’re solving for consumers are not that valuable.
The average consumer doesn’t need a to-do list to organize their life, whereas a business might need that because they have a bunch of employees to coordinate, et cetera, and it’s valuable for them.
Rob: Yeah. And then there’s a bunch of different ways to do that, right? I’m working on this book and I have seven different thoughts of finding a problem, looking around you, translating an existing idea to a new niche where it’s like, oh, CRM software. Well, you know who doesn’t have CRM software are home improvement contractors. You know who built a home improvement contractor CRM is Jonathan with Builder Prime. He built it to good revenue and then applied to TinySeed and he was in batch 2.
Just taking a simple idea of like, we’re all familiar with CRM, but there are all these spaces that don’t have it. Another one is looking at a large space, a competitive space. This is if you’re probably further along on the stair-step approach, but have a hated competitor. For Drip, it was Infusionsoft, Marketo, and Pardot. I think for Xero, the accounting software, it was QuickBooks. They were then not QuickBooks. For Derrick Reimer and SavvyCal, a very competitive space. I wouldn’t say Calendly is a hated competitor, but there are definitely some improvements and some stagnation in that space.
The problem is the paradox of choice where there’s infinite—it’s like, well, I could look anywhere for a problem and it’s like, well, maybe focus on something you have, at a day job, or a friend or relative. Look at each of these things in turn and keep a notebook around for a month, and then look at what your expertise is in. If you’ve been a software developer at a credit card company for 10 years, you probably know more about credit card companies, finance, and banking than others, so maybe you should lean into that a bit. If you worked at Shopify for 5 or 10 years, you probably know ecommerce better than most people. There’s opportunity there.
Courtland: I love constraints for that. What you’re listing are basically constraints and not just any constraints. They’re clever constraints that raise your chances of succeeding. I think the challenge with most people looking for ideas is you get into the scarcity mindset. You’re like, oh, there’s just so few ideas out there. It’s so hard. I can’t constrain myself and limit where I focus on ideas. I need to look at everything, otherwise, I’m never going to find one.
I think the counterintuitive answer to that is actually, you’re way more likely to find a good idea if you have a bunch of constraints and rules that limit where you search because then you’ll dig much deeper. Your constraints could be anything. It could be like what you’re saying like, hey, what do I have‚ skills or experience? What have I done in my job? What problem have I experienced myself?
Your constraints can also be totally arbitrary. You can have a constraint of like, I like to be outside. What can I do that lets me be outside. You can have a constraint that says, I like to have an impact on the world. What would allow me to have an impact on the world? You can have a constraint that says, I like to work with my family. Something I can do with my family members, like food. Any of these constraints will just narrow your focus and help you dig deeper on an idea without having to have this paralysis of choice, where you’re juggling a million different balls.
The cool thing is if there are constraints that make you happy, there are constraints that build relationships with people, there are constraints that allow you to do things you’re going to enjoy doing, not only do they help you sort of come up with an idea, but they help you enjoy working on that idea after you come up with it. For me, I have a gigantic list of just random constraints and things to ask myself if I ever start a new business that I’m going to kind of go through. I could do this all day. We get a thousand questions.
Rob: I know. I am going to come back to these at a minimum in future episodes where I am answering questions or just as topics. I think you and I separately could cover these and it would be interesting. If we’re back together at some point here in the next three to five months, we should—
Courtland: I like this as a podcast format. I think you do this on Startups for the Rest of Us sometimes where it’s just Q&A, ask us questions. I never do it in Indie Hackers, but I should do it more often. I could do a Q&A and always bring on a guest and just do joint Q&As like this. I think it would be always entertaining once every couple of months.
Rob: Yup. So I have gotten a lot of positive feedback about the listener question episodes. I sometimes do them solo because, I mean, I’ve just done a bunch of them. That’s hard to do when you’re first starting out, but I’ve been able to do it and then about half of the ones I do are with guests and I rotate through the guests. It helps if people know who the guests are because if it’s just a relatively unknown person that most of the audience doesn’t know, you have to give a lot of background about why they have the credibility to answer these questions and why people should listen to their answers.
But if they’re someone that most people know or maybe you interviewed them. I mean, what I used to do is I would interview them one week, do a listener question the next week with them to be like, refer back to that episode because you just heard their story. Then I would handpick the questions. This is way inside baseball, but I would handpick because I have 20 questions available for Startups for the Rest of Us. I would think of what is this founder’s experience?
They bootstrapped to half a million and then they sold, so I’m going to do anything about early stage bootstrapping, nothing about raising funding, nothing about being a multimillion-dollar company. I would handpick the questions to make sure that they would have input on it.
Courtland: That’s super smart.
Rob: To curtate.
Courtland: Yeah. It’s such a challenge, I think, podcasts and media in general when you’re doing stuff with guests. It’s like, who in my audience even knows who this person is? Even within an episode, it’s like, okay, I know this person I’m talking to has a lot of good advice, but also, people might not even care about their advice if they don’t know their story or what they’ve accomplished, et cetera. I try to structure episodes. That stuff comes first. Doing Q&A episodes is the same. Maybe I do it the way that you do it. Have a story first, an episode like that, and then do Q&A. But then my worry is, okay, what if people didn’t listen to that episode and are like, who is this person?
Rob: What I would do is I would say if they were on the last episode. If for some reason you didn’t have it, here’s 60 seconds. I would basically have bullets of like, they started this, they got it to this size, they sold it. I would try to build their credibility really quickly.
Courtland: Here’s why you should care.
Rob: Here’s why you should care because this person knows a lot about XYZ, you know. All right. Pieter Levels asked, “How was the bootstrap scene in 2010 or earlier, and how did it change with indie makers, et cetera?” Were you around bootstrappers that long ago?
Courtland: Yeah. I was reading a bunch of Basecamp stuff back then. I was reading much of Patio11 stuff. I was reading Peldy in Balsalmiq back then.
Rob: What about me, bro? What am I, chopped liver? I have been writing all kinds of stuff. You’re like, this guy’s so […]. I hate this guy.
Courtland: I just skipped. I just click, mark read.
Rob: Nope. Spam. His emails go to spam. But you’ve named everybody. That was it. I mean, in 2010, I say everybody. I’m being a little facetious, but there was Joel Spolsky. The only two people I knew talking about entrepreneurship in any way that resonated with me that wasn’t just […] Silicon Valley, everybody raise, raise, raise dot-com was Joel Spolsky, who started blogging in 2000, 2001, and Paul Graham. Well, you could say he started Y Combinator venture capital, but I was like, no, no, no. But he actually built a startup. He actually sold it to Yahoo in the ’90s. And then he thinks so pragmatically compared to a bunch of the VC crap I was reading in Inc. Magazine, Red Herring, and all that stuff.
That was just the two of them in the early 2000s. Then Basecamp came around, it was 2005, 2006. It was called 37signals. First, it was a blog, then they were a consulting firm, then they launched a SaaS, and then it was me, Peldy, and Patio11. Those were the only people that I knew until 2008, 2009? That was kind of it.
Courtland: Super niche. It was super niche. I mean, I did Y Combinator in January 2011. I remember going into it and talking about Graham. I was like, I really like the Basecamp guys. I like what they’re saying. I remember Kevin Hale from Wufoo came in and gave a talk. He’s like, yeah, we never raised any money. We’re making $5 million revenue. We moved to Florida. It’s pretty cool.
Paul Graham went, he was super pragmatic. He’s like, don’t raise more money than you need to. It kills a lot of companies that could have had a $20, $30, $40 million exit. They just swing for the fences, try to become unicorns, and they weren’t destined. Their company can’t do that. So don’t raise that money and go for the gold if you can’t, and so he was even pragmatic about it.
There wasn’t a lot out there that was inspirational. Nowadays, it’s like a deluge. You could read and read and read all day, listen to 15 different podcasts, then discover another 200 podcasts, and never get to the bottom of it. It’s just the secret’s out, right? You can make money online in a self-funded, self-sustainable way from the comfort of your own home. I think that’s the biggest difference.
Rob: And bootstrapping, I mean, it was kind of a thing. Now you say bootstrapping and people know that’s a movement. There are tens of thousands of us that want to do that and it just wasn’t. There were a handful of people. There was no community, there was no central hub. In fact, that’s why when we started this podcast and I wrote my book, it was Startups for the Rest of Us.
If you look back, this podcast should probably be called bootstrapping blah blah blah. While the term existed, it just didn’t have the resonance with this idea. It was more like, well, I want to do startups because they sound fun, but I’m going to do it in a different way was really the angle there.
Courtland: In my opinion, I think it’s a less relevant term than it was in the past. I wonder what your thoughts are on the future of bootstrapping and how it is today.
Rob: I feel the same way. I think you put out a post about this a year ago where you’re just like, is this really important? Is the funding mechanism the most important part of this business, or is the problem that you solve, how you go about solving it, how you grow, isn’t that all really important? I’ve struggled with that whole thing technically, like ScrapingBee post, they’re a TinySeed company, but they’re very public about their revenue, they’re doing north of a million dollars. They got to the top of Hacker News with a post. It’s like, how we bootstrapped to north of a million.
The biggest conversation in there was just arguing over the term bootstrapping and whether they really bootstrap because they took TinySeed money. It’s like, if you talk to venture capitalists, if you raise less than a million dollars, most will be like, well, they’re basically bootstrap then. To them, it’s bootstrapping. I’ve built businesses with literally $0, that is technically bootstrapping. But is it at all important to define? What if my dad gave me $10,000, am I still bootstrapping? Yeah.
That’s where I’m like, stop. It’s not binary. I never thought it was binary. It’s a continuum, right? There are people who raise a little, raise a lot, raise half a million and are still acting bootstrappers. They are super capital efficient, they’re super pragmatic, and they’re building a real product for real customers and paying real money. That’s what we all do whether you have $0 in the bank or half a million.
I say bootstrapped and mostly bootstrapped now you’ll hear me. You’ll hear us say independent SaaS or indie SaaS because it implies, well, I’m not beholden to anyone. Even if I raise money, I still have control of my company. I’ve toyed around with all these terms. The thing I struggled with is in the State of Indie SaaS this year—the report’s not out yet. We did the survey, we said, what do you call your type of company, and we had all these options. It was bootstrap SaaS, indie SaaS, independent SaaS, blah blah blah, and it was overwhelmingly bootstrap SaaS. Even people who had raised $100,000, $200,000, or $300,000.
Courtland: Yeah, I think in a way, the focus on bootstrapping even as a thing, it was sort of a reaction. It’s a reaction to the fact that big tech really only cared about people who were fundraising. If you wanted to get any sort of media attention, if you want to have any sort of success, if you want to have any sort of support or resources, you kind of had to go that path, which is not surprising because it was an early nascent day of startups, not that many people were doing startups, and so the people who had all the money—the VCs—sort of control the narratives.
If you wanted to do something outside of that path, you had to be very vocal about the fact that this is different, I am bootstrapping, there’s another way. It’s like a measure of success that’s not as important anymore. The fact that it’s no longer a shocking thing that you didn’t raise a whole ton of money to start your company and it still was successful means that bootstrapping won its place. It’s a valid way to get started, which means it’s not worth glorifying quite as much as it used to.
There are a lot of different paths. Everyone’s well aware of that and pick your poison. Pick your preferred choice. When Indie Hackers started, I felt there was a big fight I was always trying to wage. You don’t have to do it this other way. The VCs, the investors—you don’t have to do that. Now I’m like, it’s obvious you don’t have to do that. I don’t need to toot that horn now. It’s more about, okay, what do you want to do and how do you do it?
Rob: There’s all these paths and funding is a tool. If you want and need that tool, then do it, and if you don’t, then don’t. You could be on Indie Hackers or part of MicroConf, and you can raise money or not. It’s just we’re all in this trying to become independent sustainable companies.
I find it interesting because you brought up that bootstrapping and the real, I think, religious adherence to it was a reaction against the broader narrative of venture funding. I had this exact conversation about two weeks ago with a friend of mine. I think Basecamp was a big part of that, to be honest. Basecamp was so vocal about it and they got a lot of press about it.
I was talking to my friend and I said, I understand why they did it. I like Jason and DHH. They invested in TinySeed’s first fund, they mentor—I get it. I think they may have long term done some damage by making it such a religious thing. They used to say like, well, bootstrap will never take funding. Anyone who takes funding is XYZ. They also would say, like, we don’t split test, we don’t track in our funnel, we would never sell our company. Planning is guessing. We don’t market. It just works.
They said all these things and they were shocking, but I think a lot of people saw that or still hear it and think that that’s the way to grow a business. I actually think it’s not. I think those are anti-patterns. I asked Jason Fried. He’s been at MicroConf. He and I have had breakfast. He was on stage. I did a Q & A with him. I asked him about some of these things, about why was Basecamp successful? He said, we got a lot of things right, but we got a little lucky. He admits that.
They were early, they built a good product, and they did hit something just right at the right time. But I do think that that narrative, the religious nature of it or this black and white nature of it I think is a bit played out. I think it’s an anti-pattern. I think it’s detrimental to new entrepreneurs coming into the scene.
Courtland: Yes, there’s a sense in which it’s like—you got to look at why are people writing and saying the things that they’re doing? The Basecamp guys are just expert marketers. They are really, really good. I mean, they built productivity software. They are trailblazers. I mean, they created Rails. They were doing this way before everybody else. But also, they’ve really got people excited about the fact that they built productivity software. How do they do that?
By having great marketing, great messaging. They always stood for something. They always had an enemy. The point there wasn’t necessarily like, let’s be responsible stewards of how everyone starts companies in the future. It was like, how do we get the word out about our philosophy and our ideals? You don’t do it by making lukewarm statements. You should go by saying, fundraising is evil. You do it by saying like, we’re fighting against the big guys.
That’s the kind of messaging that resonates, that gets people talking, people argue against you. People will take a side. Even on their Rework or It Doesn’t Have To Be Crazy At Work, one of their books. They have a chapter that’s basically like, pick a fight. They’re just telling you their strategies—pick a fight. If you are not the person to think about things deeply, it does create religious zealots who take a side and who don’t give the other side any real thought. I don’t think that’s the best way to be as a founder.
I think the best way to be as a founder is when you’re marketing, pick a side. Be super out there and—
Courtland: Opinionated, exactly. But when you’re making decisions internally, be rational. Do a cost-benefit analysis. Figure out what it is that you want. Don’t close yourself off to any particular path for religious reasons.
Rob: I think that’s good advice, not only for founders but for all humans actually to evaluate both sides of that. I’m glad you said they’re expert marketers and they did this as marketing. The best marketing is when you don’t know you’re being marketed to, right? This is what Steve Jobs and Apple did so well is he would do these things that everyone would want to be like, we’re not going to live stream our product announcements. No other company does that. They want as many people to see it, but they’re like, no, no thanks. It’s this secret thing and Basecamp did well with that.
Courtland: I had DHH on Indie Hackers a couple of years ago and we did a debate. All right, DHH is this firebrand on Twitter. Let’s do a debate on work-life balance. I was trying to set him up with somebody that would be his hated enemy like Keith Rabois or something, he refused. He’s like, no, I’m not going to come on and talk to somebody that I hate. So I had him talk to Natalie Nagele, who runs a very calm company, Wildbit. It’s very bootstrapped. It’s very kind of in his style, but she had kind of a different point of view. I thought that DHH’s point of view was unrealistic.
It was so interesting the difference between him on Twitter starting his crazy fights taking these crazy, hardline, opinionated positions, and when you talk to him and it’s a real-time conversation, he’s utterly reasonable and rational. It’s like, okay, you can see the difference. Marketing is marketing.
Rob: Well, sir, we’ve been chatting for a while. There are a lot of good topics here. I hope that folks in both of our feeds have enjoyed this conversation. I’m @robwalling on Twitter, you are @csallen. And of course, indiehackers.com and microconf.com. We do a lot of things, but thanks for hanging out, man.
Courtland: Yeah, well, I think if you’re an indie hacker listening to this, you’re considering starting a company, and you want to do something a little bit bigger, raise money from TinySeed. I love TinySeed. I think raising money is totally cool. At the end of the day, TinySeed is sort of designed for people who have the bootstrapper mindset. Trying to find investors, I think, a big part of that is finding the right match. I like what you’re doing at TinySeed. I like anyone who’s basically trying to help indie hackers. I’m putting in here an involuntary ad for your funding mechanism. Check out TinySeed if you’re an indie hacker.
Rob: Thanks. This will go live when applications are still open. We do two funding batches a year in the US and the Americas, and then we do one in Europe. If you hear this and you get there quick enough, head to tinyseed.com/apply and apply to our Accelerator. It’s super fun. It’s a year-long remote, and it is focused on bootstrap and mostly bootstrap SaaS.
Rob: All right, man. Thanks for coming out.
Courtland: Yeah, thanks for having me.
Rob: It’s always great to talk to Courtland, and it’s been too long. He and I both agreed that we should do this more often because we could have gone another hour and I think it would still be interesting. I hope you enjoyed that. Thank you as always for tuning in. I will be back again in your ears next Tuesday morning.