My eighth year as a bootstrapped founder

Take my advice with a big grain of salt because I'm by no means an expert at finding customers. I can just say what's worked for me.

The thing that's been successful for me is to figure out who my customers are and find ways to show them I have something valuable to offer.

My most successful example was TinyPilot, where I wrote about how I built the first prototype,[0] and that post had an extremely positive reception on HN[1] and reddit[2]. I continued writing about my homelab because readers who were interested in learning about homelab were also people who had a use for TinyPilot.

I did the same thing when making my blogging course a few years ago. I joined a community for developer bloggers and gave people constructive feedback when they'd ask for notes on their drafts. Then, I approached the community manager and asked to pilot the course in the community for free (she actually insisted on paying me because she didn't believe in asking for free work). But the community liked it, the manager liked it, and it was great for me because it gave me feedback and testimonials for my course.

I've used ads but never as a first step. I think the first step has to be highly personalized where I'm out there meeting customers where they are and showing I can offer something useful.

[0] https://mtlynch.io/tinypilot/

[1] https://news.ycombinator.com/item?id=23927380

[2] https://www.reddit.com/r/homelab/comments/hwimys/tinypilot_b...

Thanks for reading!

> Q for OP: looking back at your 8 posts, I don't see you ever reflecting on loneliness (or lack thereof) as part of your founder journey. Yet both founder friends and anecdotes always emphasize this as a big weight.

Honestly, it hasn't been a problem for me.

I'm atypical in that I enjoy solitude more than the average person. I had a mild illness once when I was living in NYC so I stayed home from work and had groceries delivered, and when I went outside again, I realized it had been a week since I'd seen another person, and I hadn't noticed until then.

I do like working with a dev team, but I don't necessarily need to be in person to do that. I enjoyed working with other remote devs for TinyPilot and getting to teach and learn from them.

I host an indie founders meetup in my area every other month. That's been a fun way to meet other founders and swap ideas.

I'm obviously biased as a small business owner, but I think that logic assumes that the market is perfectly efficient, when it obviously isn't. Large companies have massive advantages in so many dimensions.

As a simple example, imagine that I built a site for buying ebooks that's better in every way than Amazon. I pay authors more, readers pay less, the ebooks are compatible with every device, and it's easier for both authors and readers to use my site than Amazon. I still probably couldn't survive against Amazon because they'd tell their authors that if they sell with me, they can't sell on Amazon.[0] They have such a market dominance that authors would lose money by using my platform, even if it's a demonstrably better product in every way with better pricing.

But it goes beyond that. Big businesses have all these other huge advantages so that they can succeed not because they're offering the most value but because they have a pre-existing advantageous market position:

- It's a small percentage of their costs to hire attorneys to look for tax loopholes

- They can manage the overhead of abusing the H1B visa system to hire workers at below-market rates

- They can sue people and get sued and still have 98% of their employees not paying attention to any lawsuits

- They can afford to sell things at a loss just to choke out smaller competitors

Look at trillion dollar industries where 95% of money goes to just 2-3 companies. The iOS/Android duopoly, the Visa/Mastercard duopoly. Do they control the market because they're just so great at offering value? Or does their market position and terrible government policy prevent anyone from competing with them effectively and offering consumers better choices?

[0] https://www.reuters.com/legal/transactional/amazon-must-face...

> Going from zero to one employee is hard.

Story of my life the last 5-10 years haha. Hard to take such a big risk without having a very solid position.

I'm taking an AI-first approach with a project I wouldn't have accepted otherwise, to get a better understanding of how much I can delegate and how quickly I can get it done. Could open up a lot of doors if successful. There are many more projects I'd be willing to pitch/accept if I didn't have to do all the grunt work. Quality still needs to be there though.

when your annual revenue is < $25K this is not typically a concern. Also that's true from the corporation's perspective but not always true because of the double taxation from the individual's side. I always find the timing flexibility (which effective tax year) far more valuable than the employment vs. investment income differentiation.