Three years ago, I sold my startup because I was an idiot
In this 2010 acquisition retrospective, @briandoll reflects on the journey of bootstrapping and successfully selling their business.
Core Principles for Independent Builders:
Unsolicited buyer inquiries versus running a deliberate auction process require very different negotiation leverage.
Bootstrapping for years without external capital provides extreme freedom, but exits are often triggered by energy depletion as much as financial gain.
Retaining ownership of code and operations creates pride, but transitioning to an acquirer requires letting go of absolute autonomy.
Community Debate Themes:
Hacker News peers debated transaction structures (cash vs earnout), founder tax strategies, and life after liquidating a long-term indie asset.
CATEGORY Startup Exits →
HISTORICAL ERA Web 2.0 Genesis (2007–2013)
COMMUNITY SCORE 204 points
TOTAL DISCUSSIONS 89 comments
Peter, I think it somewhat boils down to your motivation. If you're thinking you want to start a new business similar to the one you sold solely because it can make you more money and "legally, it's ok," then sure, that's probably a bit unethical and rude.
But face it: by your own admission, you didn't really know what you were doing the first go around. You think you can do better this time, and, most importantly, build something that can scale better and be very useful to a wider range of people and enterprises. You'd be building on past experience to create something better that adds value to the world and (possibly) wouldn't exist otherwise.
Try to look beyond your own particular situation and think, "could the world be better if I started working on this stuff again?" And if you think the answer to that is yes, I feel like you should be able to proceed without any feelings of guilt or rudeness. The fact that you can make some money doing it is certainly motivation (we're human, after all), but it's almost besides the point.
You sold your company, and you honored the terms of that sale. If you think you have an opportunity to do something awesome that you'd enjoy and you're passionate about... go for it!
Honestly, calling yourself an idiot is a huge turnoff. You automatically make me want to not cheer you on. It makes me feel like you deserve to fail. Bill gates, Steve Jobs, Paul Grahams and many other famous people have had failures before becoming successful but you have never heard them call themselves idiots (as far as I'm aware). If nothing else they would call those failures "early attempts at success". And the worst thing is that what you did cannot really be called a failure so what is wrong with you? Even if you think that you are no longer an idiot the title and article gives waves of no confidence. My advise, please never call yourself an idiot; your subconscious will start to believe you're an idiot and so will other people. Is difficult to describe but just remembering your article I feel repulsion. I wonder whether other people feel like this. Anybody else or do I just have issues?
I'm going to take the contrary view here and I'll say that you did fine.
Starting a business, operating it for a while and a successful exit are the whole meal, if you had continued to run it you might have crashed it or you might have been in debt now.
There is no way to know what would have happened in an alternative universe, and it's a pretty good thing on your resume to say that you ran a startup that made you and your investors money. That puts you in the < 5% bracket of the entrepreneurs.
Now you simply need to do that all again, with the lessons learned and your newfound energy, capital and the success story behind you.
You'll do very well indeed if you play your cards right.
Don't be so hard on yourself, don't compare with the 'could have been' from the perspective of it could have been more, it could have been a whole lot less too!
interesting... so what are the rules here? I mean, you sold a company, now you are thinking about starting another company that essentially competes with it... is that legally questionable? is it rude? is there usually a time-limited non-compete written into the sale contract?
I mean, I've turned down a few offers for my own business in the same price range. If I could turn around and build another, competing business, it would likely make sense for me to sell. but if I have to find some other line of work? well, unlike you, I value the few grand a month I make over the couple hundred grand I'd get from selling it. I really, really like doing this.
But if I could sell out, then turn around and start over, competing with the company I sold, keeping my knowledge and experience uh, I probably would.
'it would be an understatement to say I was naïve about the concerns of "running a business."'
He missed the forest for the trees in terms of his industry. As he says at the end of the article, it is only now - 3 years later - that he has enough perspective to see some of what he did wrong.
His story reminds me a lot of Gerber's master technician who is good at his craft but not the business thereof. Fortunately for him, that industry is still quite small but has massive potential, and he could jump in again (assuming the terms of sale allow it).