EXITS $5m ★ 142 upvotes 2010

Ask HN: I sold my company last month for $5m. What do I do with the money?

The Founder's Submission

Direct narrative and submission text authored by @radicaltype on Hacker News:

I'm a 20 year old guy who sold his company last month for $5m in cash. I really don't know what to do with the money or how to manage it. I never gave it a thought and now suddenly I have $5m. Hacker News, please help me out. Should I deposit the money? Buy stock? Or what the heck am I supposed to do with it? I am just a regular guy who spends around $3000 a month. I don't buy fancy stuff and now suddenly I have more money than I can ever spend.

Retrospective Overview & Key Insights

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

In this 2010 acquisition retrospective, @radicaltype reflects on the journey of bootstrapping and successfully selling their business. The deal highlights significant financial milestones ($5m).

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 (168 total discussions):

ST @stevenbrianhall Peer Contributor
VE @vessenes Peer Contributor
BR @brk Peer Contributor
FI @figurethistuo Peer Contributor
HO @howradical Peer Contributor
HISTORICAL ERA Web 2.0 Genesis (2007–2013)
COMMUNITY SCORE ★ 142 points
TOTAL DISCUSSIONS 168 comments
TOPICS & TECH STACK: