Speed, Standards & Building Moats in the AI Era with Keith Rabois

Keith Rabois - one of Silicon Valley’s most contrarian and accomplished operators - shares hard-earned lessons from shaping PayPal, LinkedIn, Square, and Opendoor, and now investing at Khosla Ventures.

Keith unpacks his frameworks for operating at the edge of speed, quality, and conviction - revealing how great founders adapt when the tech frontier shifts every 3–6 months.

What you’ll learn:
Why speed is the ultimate competitive advantage in the AI era
How to design orgs for adaptability and avoid “A/B-test theater”
The hidden cultural signals that separate compounding teams from decaying ones

Whether you’re a founder, operator, or investor, this episode offers a blueprint for building enduring companies in a world where iteration is infinite.

🔗 Talk to Keith’s Digital Mind: https://www.delphi.ai/keith-rabois
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Timestamps:
00:00 - Intro
00:56 - Who is Keith
03:13 - Can you judge a startup by its Office?
04:28 – Litigator to PayPal Mafia, zero business experience
08:52 – Start a company, or work for someone great?
11:15 – All-nighters and culture at PayPal
13:03 – Do vacations mean you hate your life?
16:05 – Square’s zero-defect rule
17:23 – Speed of adaptability vs. speed of execution
21:35 – Is AI sustaining or disruptive?
25:53 – Why stress is good for you
28:14 – Building moats in AI
30:39 – Slack & communication

See who's the next guest at: https://libraryofminds.com/