Long Strange Trip: CEO to CEO with Brian Halligan Harvey CEO Winston Weinberg: Why You Should Reinvent Yourself Every 4 Months
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Jan 15, 2026 
Winston Weinberg, Co-founder and CEO of Harvey, dives into the intense world of hypergrowth as his AI legal-software company skyrockets to a $190M run rate. He shares the audacious strategy of targeting the toughest law firms for initial sales and the chaos of rapidly evolving structures every few months. With insights on hiring leaders based on action bias, and the importance of clear ownership in decision-making, Winston’s drive for overcoming challenges reflects his unique journey from outsider to tech CEO, offering raw honesty and practical advice for founders.
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Bias For Action Trumps Perfection
- Hire people with a strong bias for action and penalize inaction, not honest mistakes.
- Prefer fast decisions followed by quick iteration over months of indecision that let the market move on.
Re‑Earning Position Every Six Months
- Rapid hypergrowth creates constant internal chaos because operating machinery lags.
- You must re-earn market and company position roughly every six months or you break.
Reinvent Yourself Every Four Months
- Reinvent yourself as a founder roughly every four months to address the next set of broken things.
- Hire different leaders, change structure, or cut initiatives to relieve pressure and unlock scale.
