Uncapped with Jack Altman Uncapped #40 | Vinod Khosla and Keith Rabois from Khosla Ventures
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Jan 21, 2026 
Vinod Khosla, a tech pioneer and founder of Khosla Ventures, and Keith Rabois, a former PayPal exec and current Khosla partner, dive into the evolving landscape of venture investing. They discuss what defines exceptional founders, the importance of direct communication, and the shift in investor ethos from previous generations. The pair also explore AI’s rapid growth potential, emphasizing the need for innovative team structures and strategies. They share insights on identifying hidden gems like Airbnb and OpenAI, while highlighting the transformative role of AI in startups.
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First Principles And Brutal Honesty
- Vinod and Keith prioritize first-principles thinking and brutal honesty to align quickly on decisions.
- Direct communication prevents guessing and attracts ambitious founders who value clear feedback.
Prioritize Portfolio Over New Deals
- Start every partnership meeting with the current portfolio before discussing new deals.
- Treat investing as a long-term partner role, focusing on changing company trajectories over decades.
Earned Credibility Beats Niceness
- Earning the right to advise founders comes from having built companies, not age or niceness.
- Hypocritical politeness harms founders; strong founders prefer candid, tough feedback.