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.
I've found it tough to talk about being a solo bootstrapper though. People don't seem all that interested in it until you catch them in the right light or perspective. Mostly they just care to know how much money you make (which to me ends up being rather shallow), or they can't relate to the process since it's so divorced from the traditional path. I mostly just keep my head down and keep working, since that's what I enjoy the most.
> 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.
I've witnessed many firms run the gauntlet with varying levels of success, and would suggest the following:
1. sell what the customer already wants, as people with loss aversion stick with what they already know.
2. sell what makes customers feel good buying, and reward them with actual functional utility in their life
3. Never compete, focus on service with a novel niche product. Stupid people by their nature destroy everything around them regardless of long term benefit.
4. Never hire people unless absolutely necessary, and contract with tax responsibility clauses when possible.
5. Never buy equipment unless absolutely necessary, or lease when possible
6. Never enter legal or subscription agreements even with your own legal specialists feedback
7. Never become a poser burning $170k/month on labor in a vestigial office
8. Position your firm to leverage tax and grant programs
9. Stay quiet (especially online in a sea of cons), and only talk about the distant past when people try to goad you into telling them how you make revenue
10. Avoid bums in suits as many are dangerous well practiced thieves. Never let technical staff talk with the customers, or vendors. Some people go crazy when they see a bit of money, and do not behave rationally.
11. There must only be 1 president, and all agreements must be in contract form.
12. Never risk more than 15% of annual revenue on ANY deal. Customers lie and disappear on rare occasion... Large firms can grab your firm like a dog with a rag doll, and may still stiff you on the contract knowing the legal and fiscal power asymmetry
13. Chasing customers means your business model still needs work. If people are happy with what you are providing, than growth should naturally happen every year
14. Go to trade shows to see what other people are selling, and ask yourself what else does the customer need
15. Cash is king, as long as the money flows most other problems are irrelevant
Best of luck, =3
> 2. sell what makes customers feel good buying
What did you have in mind? What would make a purchase feel good or bad for a customer?
> 3. Never compete, focus on service with a novel niche product. Stupid people by their nature destroy everything around them regardless of long term benefit.
I'm not sure how the second sentence connects to the first - could you clarify what you mean there?
> 9. Stay quiet (especially online in a sea of cons), and only talk about the distant past when people try to goad you into telling them how you make revenue
You mean staying quiet about the specifics of your current products and strategy, as opposed to sharing general advice like here, right?
> Never let technical staff talk with the customers, or vendors.
Could you elaborate on the reasoning behind this?
Thanks again.
Ooops, now you have multiple bosses (each client).
Almost all growth was done via word of mouth. There are business models whose network effects lean in this direction. In order to use my product, you must bring along peers so it's inherently 'viral'. I fell into this by accident rather than by some grand design, but it became obvious to me after I saw it happen. Design a business in which the flywheel can spin without you, if you don't want to spend your time marketing.
My next business that I'm working on is B2B, so I'll have to have a much stronger handle on marketing and sales. But I'm more ready for that now, after a decade of running a B2C business.
Don't bother spamming with FAANG, as the conversion rates are still hypothetical for many. Go to trade shows, and note how sales people operate with the public... hint, the big deals are never done on the floor area.
The sales conversion rates and tax postures will determine if this type of business is viable in your area. =3
I think you've hit the nail on the head (solo bootstrapper here): People are not interested because A) it's not about them, it's about you, B) it sounds somewhat scary, C) it sounds completely detached from their reality of corporate jobs, and finally D) it's scary because your life might be "better" than theirs.
I don't tell people about my work anymore, and almost nobody ever asks, except for other entrepreneurs/bootstrappers.
Most people can't relate when they talk about a terrible boss or some ridiculous drama at work..and you don't have any of that.
I don't even talk about work anymore with family.
"Real job", yes and no. Writing a book is an enormous amount of work, and people probably understand that. But, in most cases, it doesn't bring any real money, and that's what's confusing to strangers. "How do you make a living then?" is what they mean, I think.
This isn't just the relatively small segment of "solo founder" almost all single-person and small amily businesses don't pay salaries like a corporate employee would recognize.
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]
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.
Is it a significant factor for you, compared to your past life at FAANG? Do you you ever think about spending your time differently to optimize for more social fulfillment (vs. fulfillment from building or becoming profitable)?
> 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.
You have to be first and foremost indie entrepreneur and indie salesman and only then you can afford free hacking if you have time left.
Not to assume your definitions but in my experience I often get the impression that "pure" means one just gets to code and not worry about anything else.
"indie" means one gets to pick what to code, how to code, when to code, why to code, etc.
"solo" means not having to deal with anyone one doesn't want to deal with.
"hacker" means standards, processes, tests, commits to main, etc. are only necessary when and if one wants them to be.
"sustainable" means at an equivalent or more income and less or similar costs as a job where someone else handles the marketing, sales, legal, design, anything one doesn't want/like to do as well as absorbing most of the downside risks of market shifts, loss of customers, competitor moves, etc. Additionally, one can go on vacation whenever they want and the income keeps coming.
All of this for as long as one wants the situation to last.
Sounds great to many I'm sure as it basically describes being a wealthy gentleman inventor/scientist/artist in 1880s England.
Most activities are hobbies until someone other than the participant is paying for it. Most everyone has a status of amateur until they get paid then convert to professional.
There are a lot of nuances in above statements and hobby and amateur are not reflective of lack of quality or expertise. There are I'm sure many hobbyists building wood chairs of finer quality than anyone can buy anywhere. It's up to them if they want to get paid for it.
May sound harsh to the person wanting their hobbies to be paid for unconditionally but if you're the one doing the paying it's reasonable to expect something out of the deal.
> In total, I had $8.2k in profit on $16.3k in revenue. That was my total income for the year, which is obviously not enough to support a family, but my wife also works, and we have savings/investments.
Self bootstrapping is not for the weak. At the height of the "indie grind set", you would get all of these "indie developers" raiding your social media feeds with click bait shit like "I bootstrapped my project and earned 100M pre-revenue11!1!!!1"
In reality, a very small minority even make a living self bootstrapping. It’s quite literally the lottery.
Author in this case clearly has fallback (rich/working partners, savings, and ofc probably still has $ from TinyPilot sale).
Unfortunately, for the lot of us. You end up working for shitty Fortune 500 company, work on useless/mindless shit, grind for 8 hrs, collect paycheck, eat, sleep, and repeat.
No unions to have our backs when incompetent management wants to cater to shareholders. No stability. Maybe get laid off for vague reason. Find another shitty job and hope for less shitty management.
I used to think like this but what if it isn't the case? Maybe the market is making the right decisions after all? Maybe contributing a tiny amount to a successful business really is worth more to society than contributing a huge amount to a project with barely any customers, and that's why we get paid more working for large companies?
(Not suggesting OP's projects have barely any customers, I am more talking about my own forays into small business.)
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...
I'm curious as TinyPilot is your most successful project and it looks like the most business-oriented thing you built: as in, its a product aimed at serious businesses. Whereas Zestful is a niche micro-saas and Is It Keto is a niche website. Perhaps I'm characterizing things wrong, but that's my rough perception.
>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.
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.
On the one hand, it could make it accessible to many more people, who previously couldn't have built a business alone because they lacked coding skills.
On the other hand, it could make it harder to get customers because they can also code their own customized tools, making it less necessary to buy software and some services.
There's probably a third and fourth hand, which haven't yet sprung to mind.
I don't think even the tools are advancing, allowing us to build in a new way, not everyone will be able to develop production ready products. Or good looking ones. So there will be always in need for people know how to orchestrate the new workflows with good taste and years of experience.
Couple of articles I've bookmarked recently:
● What, then, are we paying for? https://quinnkeast.com/writing/software-is-problem-ownership
● Designers as agent orchestrators: what I learnt shipping with AI in 2025 https://uxdesign.cc/designers-as-agent-orchestrators-what-i-...
● The new UX Toolkit: data, context, and evals https://uxdesign.cc/the-new-ux-toolkit-data-context-and-eval...
● How I Stopped Worrying and Learned to Love the Terminal https://pablostanley.substack.com/p/how-i-stopped-worrying-a...
● The rise of the Model Designer https://uxdesign.cc/the-rise-of-the-model-designer-cef429d9c...
'ish' because I had a partner, but he was non-technical.
AI is a boon. I'm currently finding it works best in apps that have established patterns but aren't enormous. If you lay some groundwork (as I did, because the AI didn't exist when I started), it's quite lovely for migrating heaps of old code and just doing all those annoying little things which were never very high priority but needed fixing.
If you're just starting, AI will do what you ask but it just doesn't know how to structure things in a maintainable way. So I'd argue it's still not particularly great if you "lack coding skills" but it might trick you into thinking so.
My customers (B2B) were generally older folks. They never once asked about AI. I don't see it being a serious threat yet. People are still afraid of spreadsheets and other things I would consider quite basic, the fact that coding is more accessible than ever... I don't think that's really enticing many people. Some, sure, but why would they want to mess around with that if your product is fairly priced, does what they need, and you will maintain it for them?
It's the same as us software engineers when we're deciding whether to pay for a 'managed' platform (SQL, Cloud, k8s) etc or roll our own. Sure, we can do it ourselves and for cheaper, but it just doesn't always make sense due to time and maintenance.
Anyway, I'm excited for the doors this opens up for me. I was looking to hire someone a few years back the guys I brought on briefly were very mediocre and required a lot of ramp up time. And also hiring is really hard. I can get away with not hiring for much longer now because the AIs understand the project and are productive instantly. Going from zero to one employee is hard. After that I imagine it would get easier but I never made it that far.
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.
I know about Entrepreneur First, but that's not for bootstrapping and has a too much of the unicorn vibe for me. The obvious is of course luck through one's social network.
Basically I think it depends on your customers. If they’re just regular people, developers, etc. looking for a productivity tool, you should worry.
But if your clients are actual businesses looking for reliable, secure software, I wouldn’t worry too much. A real business isn’t going to trust hacked together, vibe coded solution. At that level it’s better to just pay $100-1,000 a month than deal with unpredictable problems.
Happy to answer any questions or take feedback about this post.
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'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?
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]
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.
[0] https://refactoringenglish.com/chapters/
[1] https://refactoringenglish.com/tools/hn-popularity/domain/?d...
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.
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.
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 don't think I'd have the stomach to actually go solo after understanding the risk/reward
I had an idea for a hardware business for years and it was nice to dream, but thinking about it more and reading this story makes it pretty clear that it is way way waaay easier to continue my career at big tech, for better or worse (sad cry emoji)!
But, come on ... isn't it just a touch disingenuous to call this a bootstrap situation?
I assume an ex-Google developer jettisoned with a decent safety net. Perhaps I'm wrong. But I have a very different idea of what bootstrapping is.
Anyway, kudos to you ... making your own move is brave and commendable.
> But, come on ... isn't it just a touch disingenuous to call this a bootstrap situation?
> I assume an ex-Google developer jettisoned with a decent safety net. Perhaps I'm wrong. But I have a very different idea of what bootstrapping is.
Yeah, I agree and wish I had a better term. I've heard people talking about "bootstrapping" a business with $200k+, and I roll my eyes.
I used to call these updates "My Xth Year as a Solo Developer" but that stopped making sense when I was working with a team.
Impressive patience by the wife and probably other extended family, as his "carry".
Big credit for his honesty and transparency though. Good he's telling his story.
Do you have advice on finding first clients? Especially in B2C?
Throwing money on ads seems tempting because it’s such an easy way to reach clients but I’m not sure about “quality” off the clients.
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...
These concepts helped me a lot with marketing to consumers and SMBs
Also, follow @mtlynch's content - even though he says he's not an expert, I feel that atleast regarding marketing to devs and builders - he is one of the best out there
The conversation here is centred on how others simply “do not understand how awesome I am for bootstrapping”. All veiled under a very transparent layer of self-aggrandising faux-humility.
What is the deal with that? Compensating for something?
Also appreciated the honesty about the $50K goal vs $8.2K reality. That gap is familiar.
