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Keith Rabois: Lessons from PayPal Mafia, $OPEN, & Investing

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Manage episode 507301479 series 3681251
Content provided by Sourcery with Molly O'Shea. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Sourcery with Molly O'Shea or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

Keith Rabois, Opendoor ($OPEN) co-founder & newly appointed Board Chair, Managing Director at Khosla Ventures, & a core member of the PayPal Mafia, joins Sourcery for a masterclass on talent, culture, and contrarian thinking.

You don't want to be the best in the world at what you do. You want to be the only one who does what you do.” Paraphrasing Jerry Garcia, The Grateful Dead

He shares how he scouts extraordinary individuals, why every successful startup begins as a cult, and the frameworks he’s developed to simplify complex problems into actionable advice. From the Barrels & Ammunition metaphor to building Olympian-level work cultures, Keith reflects on lessons from PayPal, Square, Opendoor, and Khosla.

We also dive into his takes on stress, sleep, and performance, his potential book, and why he believes venture capital is the best job for the intellectually curious.

Book Recommendations:

Upside of Stress

High Output Management

The Score Takes Care of Itself

1. Keith Rabois: https://x.com/rabois

2. Molly O’Shea: ⁠https://x.com/MollySOShea⁠

3. Sourcery: ⁠https://x.com/sourceryvc⁠

Brought to you by:

Brex—The modern finance platform, combining the world’s smartest corporate card with integrated expense management, banking, bill pay, & travel.

As a Sourcery Listener you get: 75,000 points after spending $3,000 on Brex card(s), white-glove onboarding, $5,000 in AWS credits, $2,500 in OpenAI credits, & access to $180k+ in SaaS discounts. On top of $500 toward Brex travel, $300 in cashback, plus exclusive perks (like billboards..) visit → https://brex.com/sourcery

Turing—Turing delivers top-tier talent, data, and tools to help AI labs improve model performance—and enables enterprises to turn those models into powerful, production-ready systems. Visit: https://turing.com/sourcery

Kalshi—The largest prediction market and the only legal platform in the US where people can trade directly on the outcomes of future events: https://kalshi.com/sourcery

Follow Sourcery for the latest updates!

https://www.sourcery.vc/

  continue reading

95 episodes

Artwork
iconShare
 
Manage episode 507301479 series 3681251
Content provided by Sourcery with Molly O'Shea. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Sourcery with Molly O'Shea or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://podcastplayer.com/legal.

Keith Rabois, Opendoor ($OPEN) co-founder & newly appointed Board Chair, Managing Director at Khosla Ventures, & a core member of the PayPal Mafia, joins Sourcery for a masterclass on talent, culture, and contrarian thinking.

You don't want to be the best in the world at what you do. You want to be the only one who does what you do.” Paraphrasing Jerry Garcia, The Grateful Dead

He shares how he scouts extraordinary individuals, why every successful startup begins as a cult, and the frameworks he’s developed to simplify complex problems into actionable advice. From the Barrels & Ammunition metaphor to building Olympian-level work cultures, Keith reflects on lessons from PayPal, Square, Opendoor, and Khosla.

We also dive into his takes on stress, sleep, and performance, his potential book, and why he believes venture capital is the best job for the intellectually curious.

Book Recommendations:

Upside of Stress

High Output Management

The Score Takes Care of Itself

1. Keith Rabois: https://x.com/rabois

2. Molly O’Shea: ⁠https://x.com/MollySOShea⁠

3. Sourcery: ⁠https://x.com/sourceryvc⁠

Brought to you by:

Brex—The modern finance platform, combining the world’s smartest corporate card with integrated expense management, banking, bill pay, & travel.

As a Sourcery Listener you get: 75,000 points after spending $3,000 on Brex card(s), white-glove onboarding, $5,000 in AWS credits, $2,500 in OpenAI credits, & access to $180k+ in SaaS discounts. On top of $500 toward Brex travel, $300 in cashback, plus exclusive perks (like billboards..) visit → https://brex.com/sourcery

Turing—Turing delivers top-tier talent, data, and tools to help AI labs improve model performance—and enables enterprises to turn those models into powerful, production-ready systems. Visit: https://turing.com/sourcery

Kalshi—The largest prediction market and the only legal platform in the US where people can trade directly on the outcomes of future events: https://kalshi.com/sourcery

Follow Sourcery for the latest updates!

https://www.sourcery.vc/

  continue reading

95 episodes

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