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?
> 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.
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.
>Looking back, how do you feel about your slate of past projects?
I feel like I learned something valuable from all of them.
The ones I'm most proud of are TinyPilot, my book, and my blogging course (in that order). Those are, uncoincidentally, the ones where I found product-market fit, whereas the rest never really achieved that.
TinyPilot was business-oriented by mistake. When I initially made it, I thought the market was entirely hobbyists who would rather make a DIY KVM than buy a $600 enterprise-y device. As I continued working on it, I found that my customers were much more interested in paying a higher price for a pre-made device than saving money with a DIY solution.
But yeah, I think the fact that it appealed to businesses made it more viable than my other business attempts that were consumer-focused.
>> I found that my customers were much more interested in paying a higher price for a pre-made device than saving money with a DIY solution
This could have been a 50-yr-old comment about the Apple I computer! Lol
>> Wozniak intended to share schematics of the machine for free; however, Jobs advised him to start a business together and sell bare printed circuit boards (PCBs) for the computer, without any components soldered on.
...
Terrell told Jobs that he would order 50 units of the Apple I and pay $500 each on delivery, but only if they came fully assembled – he was not interested in buying bare printed circuit boards with no components.
$200k really isn’t that much in this context. Less than a year’s income for a good developer in the US. Even if you haven’t worked for a FAANG, in the software industry in the US it’s not that difficult to find yourself with that amount, or more, available for investment after working in the industry for a while. Similarly, an amount like that isn’t necessarily going to take you very far.
out of curiosity, which one is the bigger part of your "financial cushion" nowadays? is it still mostly the ex-Google income/savings or has the TinyPilot exit taken that place?
I recommend having an initial talk with a broker if you're thinking about it at all.
The brokers I've met are happy to talk if you have a profitable business, even if you don't plan on selling anytime soon, and you don't have to sign anything to commit to them. They can talk to you about what you can do to prepare for an exit even if you don't expect that to happen for several years (and it might take you several years to manage yourself out of the business).
I personally liked the broker I worked with and recommend him.[0]
This is a really good idea, similar to raising money when you don't need it. It could help prevent you from making a mistake or getting into a unattractive position for when you are thinking of selling. I've seen this with one & few person companies, everything from messy ownership & cap tables, to tax obligations, to the structure of multi-year sales or contracts. This is why even big PE portfolio companies start planning for a sale years in advance; the difference (making it harder for you IMO) is that they have a pretty good idea when the sale will happen.
> Thanks for being so transparent. As a fellow solo bootstrapper, I think the thing people most often misunderstand is the relative inconsistency (income, "wins", the camaraderie, etc.) so it's nice for you to bare all.
> That being said, you do get the consistency of independence and autonomy. As I watch my peers deal with crappy work environments, losing their jobs, and other bullshit, I just keep chugging along: self-directed and happy to not have to answer to anyone.
Yes, I completely agree.
Bootstrapping, you realize that employment smooths out a lot of issues for you. Like if you're sick for two weeks as an employee, maybe it hurts your OKRs, but you'll be fine. If you're sick for two weeks as a solo founder, that can be catastrophic. And if you need to do something like take parental leave for six months, the company can't just continue on without you like it could if you worked for a large company.
But as you said, you get the consistency of being your own boss and directing your own time, which more than makes up for it for me.
Yup, I always say – the hardest part of my job is that if I don't do it, nothing gets done. That copy error on the website. That minor bug. We take for granted the velocity we get by having colleagues. If I get lazy, everything grinds to a halt. And those little nits add up. But I strongly agree it's all worth it.
Can I ask you if you consider that AI changes anything about that? Since I'm embarking on the same boat, my dream is a team of AI which supports and ensures business continuity while Im on vacation or "OOO" otherwise.
If we get to the point that AI can run a complete business unencumbered then the world looks very different. At this time, I have very little confidence that AI today can operate my business untouched while OOO. Nor would I want it to. I enjoy my work and I don't trust AI to run amuck with the valuable asset that is my business.
But it certainly has helped me gain velocity working alone. My business is very hands off after ten years of automating most things and cleaning up the hot paths. Things break, but usually due to external factors that have nothing to do with me. A few support emails and hands-off monitoring is hardly a deal-breaker for me on vacation. I'm not entirely sure why zero-effort is a goal, when you can genuinely attain a 5-hour work week today.
AI is really just a tool and there's a lot of incremental room between "helpful" and "totally autonomous". This calculus could all change one day, but it's not a personal desire of mine.
Even Anthropic consistently says their own AI can't help with meaningful work in their own corporation. Any person that tells you it can is overhyping it. Probably to sell you something.
I’ve been reading your blogs for the past 8-years.
Question: do you not have income concerns / pressures?
Please take this question from a positive place but it seems like you’ve been able to sustain years of relatively low pay (especially since you’re a father now) without concern.
I’m not sure most people can endure as long as you have and it makes me wonder if you have supplemental income not accounted for.
Not asking you to share anything you don’t feel comfortable with … and your transparency over the years has hugely influenced my thinking on should I start my own business.
> Question: do you not have income concerns / pressures?
Yes, definitely. I am a bit worried about not being able to get back to $100k+/yr in income, and I'm less confident that the safety net of "just go back to FAANG" is still available.
> I’m not sure most people can endure as long as you have and it makes me wonder if you have supplemental income not accounted for.
I do. We have investments that provide additional income. We also live in Western Massachusetts, in an area where living costs are fairly low, so we fortunately don't need to draw down much from our investments to get by.
I'd love to learn more about your process of the sale. And in your graphs, is that attributed to profit/revenue in 2024?
I'm on a super similar journey. Started in 2022, did about 400k in revenue in 2025 at 79% margin, we'll se how this year goes. Theres a world where i'd love to add a lot of scale, but that'll rely on some experiments (underway) panning out. It's 'failure' in most peoples books but 2x'ing would be great too?!
How did you find a buyer? How did you come to a sale price? Why didn't you keep going?
> I'm on a super similar journey. Started in 2022, did about 400k in revenue in 2025 at 79% margin, we'll se how this year goes. Theres a world where i'd love to add a lot of scale, but that'll rely on some experiments (underway) panning out. It's 'failure' in most peoples books but 2x'ing would be great too?!
Nice, congrats!
Yeah, I think depending on what bubble you're in, bootstrapping to 400k and 2x'ing every few years is either failure or amazing. The VC/hypergrowth path doesn't appeal to me, so I think something that gives you $100k+/yr in profit is a huge success.
> I'd love to learn more about your process of the sale.
Sure, I wrote a couple of posts with the details.[0, 1]
Thanks for the reply. Just to clarify the picture for me, was the 2024 jump in profit attributing the sale or was that just a solid year?
Agreed on the 2x every year or two being a weird failure state. I've done both, and I'm at a junction point right now, but I really think a huge part of going all in on the VC route is finding the right money to work with. I've been mostly technical, hidden in dark places all my life. I love having the chance to be customer facing, i love the business side of my work, but doing that with the wrong backers is so unappealing i'd rather not have their money.
I'm curious about your book journey. Sounds like having a big audience and pre-existing list really helps! How did you go about building that audience and list, and what helped the most to doing that? Which lists / audience converted the most for your book offer, and how did you promote or otherwise let folks know about your book? What was the compelling ask to pre-order a book? And, how do you plan to publish the book? Lots of book questions
> Sounds like having a big audience and pre-existing list really helps!
I didn't have a particularly big audience. I had about 2k mailing list subscribers on my main blog, but a pretty small percentage of them purchased. And I had something like 600 subscribers for the book because I've been saying I'd write it since 2021, but all I had was a mailing list.
> How did you go about building that audience and list, and what helped the most to doing that?
I haven't been focused on growing the list that much.
My main goal right now is to get feedback from readers and use it to improve the book. Once the book is done and I can't think of ways to improve it, I'll probably switch to focusing more on finding more places to find paying readers.
> Which lists / audience converted the most for your book offer
I find the most paying readers from HN, actually. I don't think it's the most in terms of conversion percentage, but it's the most in absolute terms because HN is so big. And then there are secondary effects of something doing well on HN because people share the link on other, smaller sites and social media.
> how did you promote or otherwise let folks know about your book?
The thing that's always worked best for me is writing blog posts that I hope my target audience will find interesting. So the thing that's worked for the book is adapting parts of the book to standalone blog posts and sharing those online.[0] A few of those posts did well on HN because I tried to make them interesting to developers interested in writing/blogging.[1]
> What was the compelling ask to pre-order a book?
Haha, maybe I should craft that more. It's mainly that they get to read more of whatever samples they've already hopefully found useful.
My pitch for early access is that early readers get to read it and ask me questions and help shape the book.
> And, how do you plan to publish the book?
I'm already publishing it as a PDF/epub that I sell through Stripe.
I might eventually do a print run or sell Amazon, but I hate dealing with Amazon and physical products, so I'd have to be really confident it would have a big impact on sales.
I'm currently a solo bootstrapped founder, have done short stints in the past - 1 year in 2022, then became cofounder of a funded startup for a year. Now doing it again.
Question is how you stay motivated to keep at it - looks like it took about 4 years before you made similar to your Google salary, did family pressure or external pressure ever impact you? Or is it mainly just keep your eyes on the longer term goal?
I'm also quite lucky that I was aiming for lean-FIRE before I left Facebook, so I have the luxury of being able to keep at it, but sometimes it is demotivating seeing peers / others.
> Question is how you stay motivated to keep at it - looks like it took about 4 years before you made similar to your Google salary, did family pressure or external pressure ever impact you? Or is it mainly just keep your eyes on the longer term goal?
I found it helpful to go in with low expectations.
I was listening to a lot of podcasts about bootstrapping while I was still at Google in 2017-2018, and even the big success stories usually had 5+ years of failing or succeeding only marginally. So, I went in with the expectation that I'd probably fail for the first 5 years, and so there wasn't that feeling of disappointment from not earning much the first few years.
I also had a lot of lucky conditions that made it easy to take the risk at the time, including no family to support, lots of savings, low expenses.
> I'm also quite lucky that I was aiming for lean-FIRE before I left Facebook, so I have the luxury of being able to keep at it, but sometimes it is demotivating seeing peers / others.
Yeah, honestly I do sometimes think, "Wow, if I'd stayed at Google and kept getting that comp (which was about 50% equity IIRC), that would be a lot of money." But I also am very pleased with my life now, and I know I wouldn't have enjoyed my job nearly as much for the last 8 years had I stayed an employee. And that's a huge amount of my life to not do what I'd like to do.
> How do you see the solo bootstrapping landscape going forward? In what ways do you see agentic coding changing things?
It's hard to say. I think it could go either way.
My optimistic take is that it has a similar effect to cloud computing on solo bootstrapping. If you tried to start a SaaS company in 2005, you'd have a hard time because in addition to knowing software, you'd also have to know how to provision servers in a data center, so you didn't see a lot of one-person software success stories from that era. But then with cloud computing, it radically lowered the barrier to entry, and there were lots of one-person SaaS businesses making $1M+/yr.
So, the best case for me is if that AI increases the power of solo bootstrappers even more so if you're great at software but terrible at website design / running ads, you don't have to hire people to help you anymore, and you can achieve more by yourself.
The pessimistic outcome is that it becomes less profitable to be a bootstrapped founder because the reduced barrier to entry means you're competing with 10-100x as many people and that companies are more comfortable building in-house tools with AI rather than purchasing B2B SaaS products.[0]
I actually have a hard time imagining B2B SaaS dying because AI makes it easy to roll your own tools. I feel like even if you reduced dev cost to nearly zero, there's still headache of maintaining an app. Like, for my last business, we were paying $200/mo for HelpScout to manage support emails. If one of the devs said they spun up a reimplementation of HelpScout over the weekend that we could run for $2/mo, I'd still say no because the cost of managing it internally is at least $200/mo of people's focus.
> I actually have a hard time imagining B2B SaaS dying because AI makes it easy to roll your own tools
Agreed. I think software engineers are misunderstanding why the SaaSpocalypse is (has?) happening.
It feels like software engineers think the SaaSpocalypse is due to technical commodity: "Oh no! Claude can bang out a fully functioning Slack/Monday.com over a weekend! There goes Slack/Monday.com"
The selloff is being driven by the "Seat Replacement" fear: SaaS charges "per seat" or "per human user" - but if an agent can do the work of X (>1) humans, then "seats" sold shrink, reducing the valuation and profitability of SaaS companies that are driven by seat multiples.
This has no impact on the valuation or stress of bootstrapped businesses like yours where you don't have to answer to either VCs or shareholders. It's more likely bootstrapped businesses will get a revival as people seek to work closer with founders who are focused on building a sustainable, long term value add than an unsustainable, blitzscaling play.
In fact, if I am not mistaken, it will reduce the edge VC funded companies have over bootstrapped businesses like yours (eg: the CAC is set on a more level field when blitzscaling funds reduce or disappear).
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