EXITS $20m ★ 10 upvotes 2010

I sold my startup and have $20m in the bank. What would you do with it?

Retrospective Overview & Key Insights

Distilled analysis of the business dynamics, operational challenges, and strategic takeaways:

In this 2010 acquisition retrospective, @mikeyur reflects on the journey of bootstrapping and successfully selling their business. The deal highlights significant financial milestones ($20m).

Core Principles for Independent Builders:
1
Unsolicited buyer inquiries versus running a deliberate auction process require very different negotiation leverage.
2
Bootstrapping for years without external capital provides extreme freedom, but exits are often triggered by energy depletion as much as financial gain.
3
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.

Community Discussions & Critical Reviews

High-signal perspectives, counter-arguments, and peer founder insights debated on Hacker News (3 total discussions):

KI @Kilimanjaro Peer Contributor

Diversify.

Retire for one year to a buddhist temple in china/india and find inner peace and nirvana.

Come back (you may not, I warn you) and do what you really want to do with your life, nothing else.

Right now I am coding just to get some money to do what I really like to do with my life: coding.

MA @mark_l_watson Peer Contributor

I would diversify my investments internationally, pack my laptop and reading material and book a long cruise. Seriously: no matter how long the trip, my wife and I never get bored on a cruise ship. Also, on board a ship is a good place to think and do some creative work.

PC @pclark Peer Contributor

Serious congrats to him. Wonder if he is a Hacker News user.

If I had $20M I'd do another startup and angel invest a bit. Video Game Studio or Printer Manufacturer. Go all in for IPO.

YA @yason Peer Contributor

Doesn't that depend entirely on how you see life and what you want in yours?

HISTORICAL ERA Web 2.0 Genesis (2007–2013)
COMMUNITY SCORE ★ 10 points
TOTAL DISCUSSIONS 3 comments
TOPICS & TECH STACK: