Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)

Keith Rabois was an early executive at PayPal (part of the famous PayPal Mafia), COO at Square, VP of Corporate Development at LinkedIn, and an early investor in Stripe, DoorDash, Airbnb, YouTube, Ramp, and Palantir. Currently he’s managing director at Khosla Ventures. Also, he hasn’t touched a computer since September 2010 (he does everything from an iPad).

Listen on YouTube, Spotify, and Apple Podcasts

In our in-depth conversation, Keith shares:

1. The barrels vs. ammunition hiring framework (and how to spot barrels)

2. Why talking to customers is actively harmful for consumer products

3. How to identify undiscovered talent

4. Why the PM role is dying

5. The three traits of the best-performing companies right now

6. The specific interview question he asks every senior candidate

7. Why CMOs (not engineers) are becoming the #1 consumer of tokens

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Where to find Keith Rabois:

• X: https://x.com/rabois

• LinkedIn: linkedin.com/in/keith

• Website: https://www.khoslaventures.com

Referenced:

• Square: https://squareup.com

• Jack Dorsey on X: https://x.com/jack

• Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens

• Simon Willison’s Weblog: https://simonwillison.net

• Vinod Khosla on X: https://x.com/vkhosla

• Peter Thiel on X: https://x.com/peterthiel

• Max Levchin on X: https://x.com/mlevchin

• David Sacks on LinkedIn: https://www.linkedin.com/in/davidoliversacks

• Tony Xu on X: https://x.com/t_xu

• David Sze on X: https://x.com/davidsze

• Faire: https://www.faire.com

• Max Rhodes on X: https://x.com/MaxRhodesOK

• Jeffrey Kolovson on LinkedIn: https://www.linkedin.com/in/jeffreykolovson

• Uncapped | Comparative Advantages w/ Keith Rabois: https://www.khoslaventures.com/posts/uncapped-comparative-advantages-w-keith-rabois

• Lattice: https://lattice.com

• Taylor Francis on LinkedIn: https://www.linkedin.com/in/taylor-francis-4ba49640

• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

• The art of hiring: insights from Khosla Ventures, Airbnb, Ramp and Traba: https://ramp.com/velocity/the-art-of-hiring-insights

• Eric Glyman: Seek out super individual contributors (ICs): https://ramp.com/velocity/the-art-of-hiring-insights#Eric-Glyman:-Seek-out-super-individual-contributors-(ICs)

• Eric Glyman on X: https://x.com/eglyman

• Mike Moore on LinkedIn: https://www.linkedin.com/in/mike-moore-802223177

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Why you should work much harder RIGHT NOW: https://marginalrevolution.com/marginalrevolution/2026/03/why-you-should-work-much-harder-right-now.html

• Opendoor: https://www.opendoor.com

• The Craft of Early Stage Venture | Peter Fenton, General Partner at Benchmark | Uncapped with Jack Altman: https://www.youtube.com/watch?v=vRiblwiXt-Q

• Lovable: https://lovable.dev

• The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder): https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code

• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

• Jeremy Stoppelman on X: https://x.com/jeremys

• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead

• Andy Warhol: https://en.wikipedia.org/wiki/Andy_Warhol

• Curation and Algorithms: https://stratechery.com/2015/curation-and-algorithms

• Ernest Hemingway: https://en.wikipedia.org/wiki/Ernest_Hemingway

• William Shakespeare: https://en.wikipedia.org/wiki/William_Shakespeare

• Evan Moore on X: https://x.com/evancharles

• Andrew Mason on X: https://x.com/andrewmason

• Read Taylor Swift’s Full Viral Speech After Record-Breaking Awards Sweep: https://www.newsweek.com/entertainment/read-taylor-swift-full-acceptance-speech-record-breaking-awards-sweep-11745941

• The Chainsmokers: Stories Behind the Songs, AI’s Impact on Music, and Venture Investing | Uncapped with Jack Altman: https://www.youtube.com/watch?v=9GMSC-2pYnw&list=PLtpH7YnTL8ihy0nR2BV32n5VkRtqlDAS1&index=16

• How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early

• David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden

• Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred

• Keith’s post about vertical integration on X: https://x.com/rabois/status/870673635375104000

• Jon Chu on X: https://x.com/jonchu

• Kanu Gulati on X: https://x.com/KanuGulati

• Rogo: https://rogo.ai

• Profound: https://www.tryprofound.com

• Basis: https://www.getbasis.ai

• Spellbook: https://www.spellbook.legal

• Roelof Botha on X: https://x.com/roelofbotha

• Delian Asparouhov on LinkedIn: https://www.linkedin.com/in/delian-asparouhov-87447742

• Lessons From Keith Rabois, Essay 1: How to become a Venture Capitalist: https://delian.io/lessons-1

• Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp

• Nuremberg on AppleTV+: https://tv.apple.com/us/movie/nuremberg/umc.cmc.3sg4y0382byupy76bfy7307k4

• Eight Sleep: https://www.eightsleep.com

• “NO DAYS OFF”—Bill Belichick on X: https://x.com/SNFonNBC/status/829036279069364224

Recommended books:

• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012

• The Jordan Rules: The Inside Story of One Turbulent Season with Michael Jordan and the Chicago Bulls: https://www.amazon.com/Jordan-Rules-Sam-Smith/dp/0671796666

• The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It: https://www.amazon.com/Upside-Stress-Why-Good-You/dp/1101982934

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.

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My biggest takeaways from this conversation: