Skip to content
Uncapped with Jack AltmanUncapped with Jack Altman

Comparative Advantages | Keith Rabois, Managing Director at Khosla Ventures | Ep. 2

This week I enjoyed speaking quickly with Keith Rabois, a Managing Director at Khosla Ventures and the CEO of OpenStore. At Khosla, Keith led the first institutional investments in DoorDash, Affirm, and Faire, invested early in Stripe, and co-founded Opendoor. While a General Partner at Founders Fund, he led investments in Ramp, Trade Republic, and Aven, and before that made early personal investments in YouTube, Airbnb, Palantir, Lyft, Udemy, and Eventbrite. Keith started his career in leadership roles at PayPal and LinkedIn before becoming COO of Square. We covered: (0:00) Competing where there isn’t competition (2:29) Traits of top decile founders (7:16) Picking people (9:57) Being a consigliere (13:54) Decision making (21:51) Acting when confident (26:43) Advantages of a large fund (31:06) Raising in a frothy market (35:47) Tech and the government (43:21) Being vocal on politics (46:47) Valuing board members (52:24) Former operators vs career investors Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

Jack AltmanhostKeith Raboisguest
Mar 20, 202556mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
March 20, 2025
Duration
56m
Channel
Uncapped with Jack Altman
Watch on YouTube
▶ Open ↗

EPISODE DESCRIPTION

This week I enjoyed speaking quickly with Keith Rabois, a Managing Director at Khosla Ventures and the CEO of OpenStore. At Khosla, Keith led the first institutional investments in DoorDash, Affirm, and Faire, invested early in Stripe, and co-founded Opendoor. While a General Partner at Founders Fund, he led investments in Ramp, Trade Republic, and Aven, and before that made early personal investments in YouTube, Airbnb, Palantir, Lyft, Udemy, and Eventbrite. Keith started his career in leadership roles at PayPal and LinkedIn before becoming COO of Square. We covered: (0:00) Competing where there isn’t competition (2:29) Traits of top decile founders (7:16) Picking people (9:57) Being a consigliere (13:54) Decision making (21:51) Acting when confident (26:43) Advantages of a large fund (31:06) Raising in a frothy market (35:47) Tech and the government (43:21) Being vocal on politics (46:47) Valuing board members (52:24) Former operators vs career investors Linktree: https://linktr.ee/uncappedpod Twitter: https://x.com/jaltma Email: friends@uncappedpod.com

SPEAKERS

  • Jack Altman

    host
  • Keith Rabois

    guest

EPISODE SUMMARY

In this episode of Uncapped with Jack Altman, featuring Jack Altman and Keith Rabois, Comparative Advantages | Keith Rabois, Managing Director at Khosla Ventures | Ep. 2 explores keith Rabois on outlier founders, conviction, and VC decision-making frameworks Rabois argues that venture returns are driven by identifying rare outlier founders early—often when they have only a deck—because that’s where competition is lowest and alpha is highest.

RELATED EPISODES

Mike Volpi on Why AI Breaks Traditional Venture Capital | Ep. 52

Mike Volpi on Why AI Breaks Traditional Venture Capital | Ep. 52

Joe Lonsdale on AI, Defense, and American Optimism | Ep. 51

Joe Lonsdale on AI, Defense, and American Optimism | Ep. 51

Tobi Lütke – Building Shopify and the Future of AI | Ep. 50

Tobi Lütke – Building Shopify and the Future of AI | Ep. 50

How AI Is Rewriting Seed Stage Investing with Kevin Hartz & Bennett Siegel | Ep. 49

How AI Is Rewriting Seed Stage Investing with Kevin Hartz & Bennett Siegel | Ep. 49

Kalshi CEO Tarek Mansour on The Case for Prediction Markets | Ep. 48

Kalshi CEO Tarek Mansour on The Case for Prediction Markets | Ep. 48

Instacart Co-founder Max Mullen on Building a $10B Consumer Marketplace | Ep. 47

Instacart Co-founder Max Mullen on Building a $10B Consumer Marketplace | Ep. 47

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.