Keith Rabois

Who they are

Keith Rabois is Managing Director at Khosla Ventures — co-founded Opendoor, the home buying and selling marketplace, and was COO of Square during its formative years.

Person

Keith Rabois studied Political Science at Stanford (B.A., 1991) then went to Harvard Law (J.D., 1994) — a path that suggested litigation but turned into one of Silicon Valley's more consequential operator careers. He moved through the PayPal mafia's core: executive roles at PayPal, LinkedIn, and Slide, then COO at Square from August 2010 to February 2013, a stretch that covered Square's critical early scaling years. In 2013 he originated the idea for Opendoor — a home buying and selling marketplace — and co-founded it in April 2014, one of the rare cases of a VC-track operator stepping back out to build. His first stint at Khosla Ventures ran March 2013 to February 2019; he then moved to Founders Fund from March 2019 to January 2024, before rejoining Khosla in January 2024. He posts on LinkedIn on startup hiring, negotiation, AI, legal tech, and the Miami tech scene — practical operator takes, not theory. He's based in Miami and has been a vocal advocate for the city's startup credibility. The through-line: early operator in breakout companies, pattern-matcher who co-founds or backs the category-defining version.

Company

The most recent headline from Khosla Ventures is April 2026: the firm led a $150M Series C in Factory AI at a $1.5B valuation, one of the larger AI-coding bets in the market right now. That same month, Khosla led a $14M round for Shade, a file management platform for creative teams, with Rabois joining that board directly. In January 2026 the firm co-led a $70M Series B in Indian AI startup Emergent alongside SoftBank Vision Fund 2, tripling Emergent's valuation to ~$300M. The firm made 104 investments in 2025 and 22 by April 2026, and in early 2025 raised $3.5 billion across three funds — including a $405M dedicated AI vehicle used to participate in OpenAI's $6.6B round.

Market

Khosla Ventures competes directly with Andreessen Horowitz, General Catalyst, Accel, Lightspeed, NEA, and Founders Fund across AI, climate tech, healthcare, and fintech — the same deep-tech lanes where competition for the best seed and Series A deals has intensified sharply. The firm differentiates on a contrarian 'black swan' thesis and longer-standing climate tech expertise dating to 2004, and its portfolio of 59 unicorns, 32 IPOs, and 157 acquisitions — including DoorDash, Affirm, Instacart, and Square — gives it strong signal credibility with founders. The 2026 VC environment is demanding proof of sustainable revenue models, especially in AI, which aligns with Khosla's historically rigorous early-stage posture.

Network

Rabois works most directly with Vinod Khosla, the firm's founder and managing partner, and with partner Ethan Choi. His board seats at Ramp, Pietra, Found, Trade Republic, and now Shade put him in regular operating contact with the leadership teams of those portfolio companies.

Vinod Khosla· Founder and Managing Partner, Khosla Ventures
Ethan Choi· Partner, Khosla Ventures

How they likely show up

Career arc through PayPal, LinkedIn, Slide, Square as an operator before moving to VC → thinks like a builder first, investor second — expects founders to show real operational clarity, not slide-deck strategy.
Co-founded Opendoor from inside Khosla's orbit → high agency; willing to bet on himself, not just others.
Medium tenure shape across roles (Square ~2.5 years, Khosla first stint ~6 years, Founders Fund ~5 years) → not a job-hopper, but moves when the strategic context shifts rather than staying for inertia.
Active LinkedIn poster on startup hiring, negotiation, and AI → comfortable being publicly opinionated; likely responds well when you come in with a specific view to pressure-test, not a blank question.
Board seats at Ramp, Trade Republic, Pietra, Found, and Shade simultaneously → operates across multiple contexts at once; values concise, prepared interactions over exploratory conversations.
Based in Miami and publicly advocates for its startup scene → has a geographic thesis he's personally invested in, not just professionally.

Conversation tips

→ Come in with a specific operational question or a concrete bet — he's a pattern-matcher from PayPal/Square/Opendoor and engages best when the conversation has a point of view to push back on.
→ If you're building in AI coding, fintech, or real estate tech, name the specific Khosla portfolio company adjacent to your work — he's on boards at Ramp and just led Factory AI; he'll connect dots fast.
→ Ask about the Miami tech scene — he's been a vocal defender of it even as other investors have pulled back, and it's clearly a personal conviction, not just a portfolio talking point.
→ Reference his Opendoor origin story (the idea came in 2013, the company launched in 2014) rather than treating it as a simple 'co-founder' data point — the timing and the operator-to-founder move is the interesting part.
→ Don't come in with a generic pitch on why AI is big — he's been investing in AI since before most people used the word; go specific on the wedge and the revenue model.

Toolbox

Openers

Open on the Factory AI Series C — Khosla just led a $150M round at a $1.5B valuation in April 2026 for an AI coding company; that's a pointed bet on autonomous developer agents, and it's fresh.
Reference the Opendoor origin: he conceived the idea in 2013 while at Khosla and co-founded the company in April 2014 — one of the cleaner examples of an investor stepping back out to build the category himself.
Bring up the Miami advocacy angle — he's publicly argued Miami is still a great place for startups even as a16z pulled back, a contrarian position he's held in his own name.

Discovery questions

You led the Factory AI Series C at $1.5B — how do you think about the difference between AI coding tools that augment developers and ones that actually replace workflows end-to-end?
You originated Opendoor while at Khosla, then co-founded it — how do you decide when a thesis is better executed by the firm writing a check versus you personally getting back on the field?
You've been posting about the Miami tech scene for years — what's the honest read on where it is in 2026, and what would need to change for it to produce a breakout company at the scale of a Square or a DoorDash?

Avoid

Don't open with a broad question about his investing thesis or 'what he looks for' — he posts detailed views on this regularly on LinkedIn and will clock immediately that you haven't done the reading.

Make it yours