My sixth year as a bootstrapped founder

Thanks for reading and for the kind words!

>Have you always been so disciplined in life? If not, how did you improve it?

No, I was a lot less disciplined when I was younger. I remember as a teen trying to learn Java several times and always getting bored a day or two in. I was a good student, but I would procrastinate work and distract myself while working.

I probably became more disciplined in my twenties, but I unfortunately don't think it was something I tried to do as much as it just happened.

One thing I think helped was protecting my focus more. I used to hop between different tasks a lot and constantly check social media or email if I had a moment of downtime or boredom, so I became more aggressive at stopping that.[0]

I also found the book Deep Work by Cal Newport to be helpful in staying more focused.[1]

>As you shared here (https://mtlynch.io/solo-developer-year-1/), doubts are natural when you haven't succeeded yet; how did you keep going? Did you ever come close to giving up and going back to corporate America?

I went into it with the expectation that it might take 3-5 years for me to find a successful business, so I think that was helpful. I've spoken to other founders who feel disappointed that nothing they're doing is working because they were expecting success to come quickly.

I definitely did worry that I wasn't cut out for being a founder and that my skills made a lot more sense for a big tech employee. The thing I found comforting was reading stories and listening to podcast interviews with other founders where they talked about how many failures they had before they landed on the right business.

I never came close to going back to a corporate job because I knew I had enough savings to last me, but if my financial situation had been different, I might have given up before I landed on something that worked.

>I believe you have a partner; how did this affect your relationship with your partner?

There are lots of effects in different directions. Me not having a regular job means that my income is less consistent and certain, and she absorbs some of the risks I take. I also feel like I'm not a good partner when I'm stressed a lot about work, and so part of my motivation in de-stressing the business has been to be a better partner in my personal relationship.

>Knowing what you know now, what would you do differently?

I wish I'd done educational products ("info products") earlier. They're like a microcosm of the experience of launching a product because you have to find customers, pitch to them effectively, and then deliver something they'll want. Like you can do that whole cycle in a month, whereas it would probably take 3-10x that long to do it with a SaaS. I made my first course right as TinyPilot was getting traction, and that course made more than anything I'd done in the previous three years.[2]

[0] https://mtlynch.io/eliminate-distractions/

[1] https://mtlynch.io/book-reports/deep-work/

[2] https://mtlynch.io/solo-developer-year-4/#hit-the-front-page...

Just found about your blog. Great job and you are a great inspiration. This is a personal question and I hope you don't mind. Do you have kids? How do you manage risk, especially financial risk of startup?

No, I don't have any kids. I think it would be much harder to follow the path I did if I'd had children to support.

I've been thinking about risk a lot in the past year. I used to feel like I had this safety net of getting a job in big tech again if the founder thing didn't work out. When all the layoffs and hiring freezes began, I realized that my safety net may have disappeared.

It's scary to lose the safety net, but at the same time, I felt grateful that I've had the last six years to practice earning money without an employer. If I had been laid off, I'd be in a terrible position of competing against thousands of other recently laid off employees who are all desperate for work. If TinyPilot were to fold, I don't think I'm guaranteed another successful business, but I feel like I'm more likely to build a profitable business than to get a job as a developer in a poor tech economy.

| The thing I found comforting was reading stories and listening to podcast interviews with other founders where they talked about how many failures they had before they landed on the right business.

Can you recommend some?

The first 50 episodes of the Indie Hackers podcast had a big influence on how I approached bootstrapping. The episodes that stood out in particular are:

- Pieter Levels: https://www.indiehackers.com/podcast/043-pieter-levels-of-no...

- Tracy Osborn: https://www.indiehackers.com/podcast/029-tracy-osborn-of-hel...

Josh Pigford (who sold Baremetrics for $4M) has also documented all of his failed ventures:

https://joshpigford.com/projects

Thank you!

> I wish I'd done educational products ("info products") earlier. They're like a microcosm of the experience of launching a product because you have to find customers, pitch to them effectively, and then deliver something they'll want. Like you can do that whole cycle in a month, whereas it would probably take 3-10x that long to do it with a SaaS.

Something that helps with this fast cycle is that many people have prior experience which they can turn into an info product. For example, Daniel worked for many years at AWS, and then after quitting could write up https://dvassallo.gumroad.com/l/aws-good-parts by leveraging his many years on the job.

If the info product is along the lines Daniel describes,

"This is an opinionated book. We only cover topics we have significant first-hand experience with. You won't find most of the knowledge we share here in the AWS docs."

it's really valuable.

I find it similar to how it's more effective for a fresh university student to ask senior classmates which classes are good and which professors to avoid, rather than asking professors or academic advisors. They'll get more relatable advice from peers.

The same goes for lots of knowledge or skilled work, whether accounting, construction, or something else. First-hand experience that doesn't appear in textbooks can be so valuable to others.