Keith Rabois

Who they are

Keith Rabois is Managing Director at Khosla Ventures — co-founded Opendoor in 2014 and OpenStore in 2021, and spent the early 2000s as EVP at PayPal before COO stints at LinkedIn and Square.

Person

Rabois started at Stanford (B.A. Political Science, 1991), then Harvard Law (J.D., 1994), and briefly litigated at Sullivan & Cromwell before pivoting hard into tech — a pattern of using the credential and then abandoning the obvious path. He ran business development and public affairs at PayPal from 2000 to 2002, VP of corporate development at LinkedIn from 2005 to 2007, then COO at Square from 2010 to 2013, building operating muscle at each stop of what became the PayPal Mafia's canonical tour. He co-founded Opendoor in 2014 — the home-buying marketplace — and later co-founded OpenStore in 2021, a Miami-based platform that acquires and consolidates small Shopify brands, alongside co-founder Jack Abraham. He returned to Khosla Ventures as Managing Director in January 2024, rejoining the firm where he had been a Founding Partner from 2013 to 2019, with a stop at Founders Fund from 2019 to 2024 in between. He posts actively on LinkedIn on AI investing, startup hiring, negotiation, and company culture, and appeared on Lenny's Podcast in 2025 ('Hard Truths About Building in the AI Era') and a 2025 CNBC interview. The through-line is operator-to-investor, with company creation woven throughout — he's never just been one thing.

Company

Khosla Ventures is moving fast on AI bets in 2026 — most recently leading a $310 million Series B for mining startup Mariana Minerals in August 2026 and a $120 million Series C for legal-AI startup Norm Ai at a $1.2 billion valuation in July 2026. In April 2026 it led a $150 million Series C in AI coding startup Factory at a $1.5 billion valuation, and in January 2026 co-led a $70 million Series B in Indian AI platform Emergent alongside SoftBank Vision Fund 2, tripling Emergent's valuation to $300 million. The firm is also reportedly in talks to raise $5.5 billion across new funds — the largest fundraise in its history — with $3 billion targeted at early-stage AI startups, reflecting the concentration of its current conviction.

Market

Khosla Ventures competes directly with Andreessen Horowitz, General Catalyst, Sequoia Capital, Founders Fund, Lightspeed, NEA, and Accel — particularly in deep tech, AI, and climate sectors. The firm differentiates on a contrarian, founder-first thesis and multi-decade domain depth in climate tech since 2004, with a portfolio that includes 59+ unicorns, 32 IPOs, and notable exits including DoorDash, Affirm, and Instacart. The broader VC landscape in 2026 is demanding proof of sustainable revenue from AI-native startups, and geopolitical dynamics — particularly around AI and national security — are actively shaping where the firm deploys capital.

Network

Rabois's closest professional gravity pulls toward the original PayPal Mafia — Peter Thiel (co-investor, Founders Fund) and Reid Hoffman (PayPal/LinkedIn) are figures he references frequently as formative. Max Levchin and Elon Musk are also part of that circle. Inside Khosla Ventures today, his peers include Vinod Khosla (Founder and Chairman), David Weiden, and Samir Kaul; he sits on the boards of Ramp, Faire, Pietra, Found, and Trade Republic as a firm representative.

Peter Thiel· Co-investor; PayPal Mafia; Founders Fund
Reid Hoffman· PayPal and LinkedIn colleague
Vinod Khosla· Founder and Chairman, Khosla Ventures
Jack Abraham· Co-founder, OpenStore
Max Levchin· PayPal Mafia colleague
Elon Musk· PayPal Mafia peer

How they likely show up

Hybrid role pattern (operator → founder → investor, repeatedly) → he's most comfortable when he can influence execution, not just write a check — expect him to engage at the company-building level, not just the thesis level.
Co-founded Opendoor and OpenStore while holding senior VC roles → high agency, low patience for passive participation; he builds alongside investing.
Active LinkedIn poster on startup hiring, negotiation, and AI → comfortable being publicly opinionated and direct; he doesn't hedge for the sake of being liked.
Returned to Khosla Ventures in January 2024 after five years at Founders Fund → willing to reverse a decision when the context changes; not rigid about past commitments.
PayPal → LinkedIn → Square operating arc, each role broader than the last → likely evaluates founders on whether they can systematically scale, not just ship an early product.
Barry's Bootcamp fitness instructor as a side hustle → suggests someone who pursues competence outside their domain for its own sake, and is comfortable being a beginner in public.

Conversation tips

→ Reference a specific LinkedIn post or the 2025 Lenny's Podcast episode ('Hard Truths About Building in the AI Era') — he'll know immediately whether you've done the work.
→ Ask about the operator-to-investor translation — he's made the loop multiple times and has strong, specific views on what most VCs get wrong about company-building.
→ Don't pitch a category-following idea; his public thesis is explicitly contrarian and he'll disengage fast if the concept smells like a copycat.
→ OpenStore and Opendoor are both live companies — be current on where they are today before you bring them up, or skip them.
→ He cites Peter Thiel and Max Levchin frequently as formative — if you've engaged seriously with Thiel's writing or Levchin's work, that's a genuine point of connection, not just name-dropping.

Toolbox

Openers

Open on the January 2024 return to Khosla Ventures — he left for Founders Fund in 2019, spent five years there, then came back. That's a rare move and he's spoken about it publicly; asking what changed is a genuine opener, not a soft question.
Reference the Delphi AI 'Library of Minds' project — he was the inaugural participant in an AI-powered knowledge platform designed to make his thinking queryable. It's a specific, slightly unusual bet worth probing.
Bring up OpenStore's Shopify-brand acquisition model — he co-founded a Miami-based platform to roll up small Shopify businesses, which is a distinct structural bet about e-commerce consolidation that sits outside his VC work.

Discovery questions

You've been an operator at PayPal, LinkedIn, and Square, and a founder at Opendoor and OpenStore — when you're evaluating an early-stage team now, what do most VCs miss that you're specifically looking for?
Khosla Ventures led the Factory AI Series C at a $1.5 billion valuation in April 2026 — how do you think about valuation discipline in AI coding infrastructure right now, given how fast the category is moving?
You moved from Founders Fund back to Khosla in January 2024 — what was different about the opportunity or the moment that made that the right call?

Avoid

Don't open with generic AI enthusiasm or broad claims about the AI wave — he's on record with specific, hard-edged views on what AI actually changes about company-building, and vague optimism will read as unprepared.

Make it yours