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.
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 FAAG, 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'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 suites 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
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.
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]
To legitimately be a founder/entrepreneur you have to found a successful business ... and even the most minimal definition of that includes being able to pay at least one employee (yourself) a living wage after eight years of effort!
Happy to answer any questions or take feedback about this post.
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...
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]
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.
Edit: just skimmed your prior post (https://mtlynch.io/i-sold-tinypilot/). Great stuff, love the transparency!
Mostly the sale. The deal closed in April, but Jan-March was an especially profitable quarter.[0]
[0] https://softwaremisadventures.com/p/michael-lynch-on-quittin... (2022, two years into the business)
[1] https://softwaremisadventures.com/p/michael-lynch-indie-hack... (2024, just after I sold)
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.
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 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).
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.