Taking money off the table

Original Article ↗ Hacker News Discussion ↗

Core Principle: Take Some Money Now

  • Many comments endorse “bird in the hand” logic: guaranteed money today beats a small chance of a much bigger payout later.
  • Greed and overconcentration in a single company (especially your employer) are framed as major risks: you’re already “structurally long” your company via your job.
  • Strong support for taking at least a partial cash-out and diversifying, rather than waiting for a maximal exit.

How Much to Take Off the Table?

  • 10% tender offers are seen as an obvious yes unless already wealthy; selling 10% meaningfully reduces downside while leaving most upside.
  • Some advocate a simple “sell half” rule each time to hedge while staying exposed. Others argue even 50% in one company is still dangerously undiversified.
  • References to Kelly criterion: optimal bet size is smaller when your bankroll is small; this favors selling more, not less.
  • Same logic is applied to public RSUs: if you wouldn’t take cash and immediately buy your company’s stock, you should probably sell and diversify.

Counterpoint: If They’re Buying, It’s Worth More

  • One contrarian view: any buyer must think the business is worth much more than the offer, so selling is irrational.
  • Rebuttals stress risk and portfolio context: buyers can spread risk over many bets; individuals usually have only one.
  • Analogies to insurance (paying to avoid ruin) and examples of turned-down buyouts that later went to zero underline that offers can disappear.

Life Stage, Experiences, and Psychology

  • Several argue that money’s ability to buy meaningful experiences declines with age; using some windfall now (travel, time off, housing stability) can be rational.
  • Others prioritize early retirement and heavy saving, but many see it as a both/and: sell some, invest most, still fund a few “now or never” experiences.
  • Mortgage discussions mirror the theme: mathematically optimal isn’t always psychologically optimal; independence, lower stress, and cash-flow flexibility often justify “suboptimal” choices.

Freedom and Optionality

  • Recurrent theme: the real payoff is “fuck-you money” — owning your home, having reserves, and being able to walk away from bad situations.
  • Making money and keeping it are framed as different skills; taking money off the table is presented as the bridge between the two.