How I sold my app for +$100k via email (and why I regret it)
In this 2021 acquisition retrospective, @shadowysupercdr reflects on the journey of bootstrapping and successfully selling their business. The deal highlights significant financial milestones ($100k).
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 Pandemic Bubble (2020–2022)
COMMUNITY SCORE ★ 14 points
TOTAL DISCUSSIONS 20 comments
This seems like a huge humble brag. Guy graduates, makes a successful startup with his friend, lives on exotic beaches coding all day, sells the app for 6 figures, and in the end this is the second biggest regret of his life? Are you kidding me? Would really love to hear what his #1 regret is...
edit: the more I think about it the more I'm not buying this story.
By the time they left the accelerator (of course they were the #1 startup of the batch), they had a startup with an app that had traction, they had paying customers, they had thousands of downloads a day, and were pulling in at least $55k per year, revenue the author describes as "stable". The author claims at that point he was demotivated (why??) and decided to backpack across the world (which was funded by the app income, I would assume).
Then he gets a mysterious offer out of the blue from a faceless, nameless buyer, who the author never saw or even talked to personally even after the eventual sale. The buyer stays engaged for an entire year despite being ghosted in an attempt to buy this thing (because it's just that amazing?), and somehow the founders manage to talk him up to 2x the original offer! Afterwards, the app goes on to be a great success, and the author attributes that all to himself, and not anything the buyer did with the app ("The buyer is doing minimal updates, just enough to keep the app alive.")
I'm sorry but this whole story just seems fantastical. At every stage, the author paints himself in the best light possible, and everything good happens to him, despite this being a cautionary tale of woe and regret. Nothing bad happened in this whole story. Add to it the author offers no personal details in order to corroborate the story, and his entire online presence seems to be one of self-promotion, and I'm just not buying it. I mean, his pseudonym is "shadowy", which is pretty on the nose here.
Interesting story. I chuckled when I got to
Making money takes work, and often the things that bring in the most revenue aren't the most exciting tasks to do. Like bug fixes, customer service and other such drudgery. So many I work with in tech want to be able to chase the latest tooling, change the world with a killer app and other pie in the sky fantasies - and nothing wrong with those, they serve a purpose. But the vast majority of revenue out there is in the boring stuff. The details. Or not being a sportsball kid growing up but constantly hearing sports casters rant about "the fundamentals". Yeah, now I get that the fundamentals permeate every aspect of life and are key to success - no matter the subject area.
If this guy would have treated his app as a long term commitment and been prepared to really work it and not be mentally checked out looking for the "big sell", he'd probably still be growing it. Chasing the unicorn of striking it rich is like planning to play the lottery as your full time job. Yeah you could get lucky but more than likely you are not going to.
Some context about this post from their Twitter:
https://twitter.com/shadowysupercdr/status/1427226334158282752
This is a pretty common story. You can make a lot of money just buying things that are slowly going up and to the right at good prices. This guy might be the warren buffet of SAAS/apps.
These things must come out of a generator somewhere, they're all written in the same style, but people upvote for the clickbait headline.