Tip
Ben Horowitz talks about hesitation killing companies: “The worst thing you do as a leader is you hesitate. The thing that causes you to hesitate is both decisions are horrible.” His example: going public with $2M trailing revenue (bad) versus going bankrupt (worse). He chose the less-bad option while competitors hesitated and died.
Turns out AI adoption decisions work the same way.
You’re staring at two terrible options. Implement AI aggressively: disrupt workflows that currently work, expensive pilot failures, team resistance, uncertain ROI. Don’t implement AI: watch competitors move faster, lose talent to companies doing interesting work, wake up in 18 months fundamentally behind.
Both options feel bad. So you hesitate. Commission another study. Wait for the tech to mature. See what others do first. That hesitation? It’s the worst choice.
Younger managers hesitate because both paths look terrible and they haven’t developed the psychological muscle to act anyway. You’ve watched this play out. You saw colleagues hesitate on mobile (“let’s wait until it’s clearer”), on cloud (“too risky to move production”), on remote work (“our culture requires in-person”). You know how those stories ended.
The ones who hesitated didn’t make the wrong choice—they made no choice. The ones who picked the less-bad option and committed? Some failed, but at least they were in the game. Most of the hesitators aren’t around anymore.
That pattern recognition—knowing that hesitation is worse than either bad option—comes from watching technology transitions repeatedly. You’ve seen which fear to run toward.
Context
Ben Horowitz co-founded Andreessen Horowitz and built multiple companies through technology transitions. The framework about not hesitating when facing two bad choices comes from watching March 2001 when many CEOs hesitated on going public and went bankrupt instead.
For experienced leaders navigating AI adoption, this isn’t theory—you’ve lived through enough technology shifts to know the cost of waiting for clarity that never comes. That judgment about when to commit despite fear only develops from watching both paths play out multiple times.