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Vince Hankes: Why We Put $300M into OpenAI; Sam Altman's Pitch; Lessons from Josh Kushner | E1009

Vince Hankes is a Partner @ Thrive Capital where he has led the firm’s investments in OpenAI, Melio, and Airplane.dev. He currently sits on the board of Airtable, Benchling, Lattice, and Melio. Prior to joining Thrive, Vince was an investor at Tiger Global where he learned the craft of venture from the legend that is Lee Fixel. -------------------------------------- Timestamps: 0:00 Who is Vince Hankes? 10:22 AI: Hype or Generational Defining Transformation 14:11 How Thrive Capital Invested in OpenAI 22:23 How Will OpenAI Commoditize? 33:17 AI Regulation 45:40 Biggest Investment Mistakes and Wins 50:18 Quick-Fire Round -------------------------------------- In Today’s Episode with Vince Hankes We Discuss: 1. From Tiger Global to Partner @ Thrive Capital: How Vince made his way into the world of investing with Tiger Global? What are 1-2 of his biggest takeaways from working alongside the legendary Lee Fixel? Why did Vince make the move from Tiger to Thrive? How do the two firms differ? 2. The OpenAI Investment: The Memo: How did the OpenAI deal come to be? What were the round dynamics? Market Evaluation: How did Vince and the team analyze the market top down? Competition: Who did Vince identify as the core competitors to OpenAI? Defensibility: How did Vince think through the long term defensibility of OpenAI’s model? Does Vince believe these models will become commoditised? Price: How did Vince and the team get comfortable with the $29BN price? 3. AI: Hype or Generational Defining Transformation: Trend or Transformation: Why does Vince believe AI will be the defining technology of our generation? Startup vs Incumbent: Does Vince think the value will accrue to the incumbent or the startup? Open or Closed: Does Vince think we will operate in a closed (one model rules them all) environment or an open-source environment with many models? AI Talent: Where does Vince think the majority of the best AI talent will concentrate? Speed: Why would Vince be scared if he were a startup today looking at the incumbents? 4. The Changing Investor: Lessons from Good and Bad: How has Vince changed most significantly as an investor over time? What has been his single biggest investing mistake? How did he learn from it? What has been his biggest investing success? How did that change his mindset? What has Thrive done in their org structure to allow them to make bets very few other firms can do? -------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Vince Hankes on Twitter: https://twitter.com/vhankes Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact -------------------------------------- @VinceHankes @ThriveCapital @HarryStebbings

Vince HankesguestHarry Stebbingshost
May 2, 202356mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Why Thrive Backed OpenAI: Inside Vince Hankes’ High-Conviction AI Bet

  1. Vince Hankes, partner at Thrive Capital, explains his evolution from financial rigor at Tiger Global to founder- and product-centric investing at Thrive. He walks through Thrive’s decision to invest roughly $300M in OpenAI at a $29B valuation, emphasizing instinct, technological discontinuity, and potential to rival search-scale opportunities over precise TAM modeling. Hankes discusses how he evaluates AI’s hype versus reality, why he expects most value to accrue at the application layer, and how OpenAI’s ecosystem and infrastructure orientation can defend against commoditization. He also reflects on trust-building with founders, internal culture at Thrive under Josh Kushner, lessons from missing Canva, and how great investing blends empathy for customers with quantitative discipline.

IDEAS WORTH REMEMBERING

5 ideas

Anchor on two core questions: who is the customer and what is the product?

Hankes stresses that clarity on the end user and the exact product/job-to-be-done underpins everything—from go-to-market to financials—yet many founders and investors can’t answer these simply and precisely.

Balance financial rigor with imaginative upside, especially in new technology paradigms.

For OpenAI, traditional TAM models looked “insane” on paper; Thrive deliberately reduced reliance on spreadsheets and emphasized historical analogs (iPhone, AWS, Google) and the potential to disrupt search- and workflow-scale markets.

In fast-moving AI markets, back exceptional founders in rich sandboxes rather than over-optimizing on short-term market structure.

Given daily shifts in AI tooling and infrastructure, Hankes prefers to partner early with adaptable, high-learning-rate founders who can pivot into emergent opportunities rather than wait for perfect clarity.

OpenAI’s defensibility will come as much from ecosystem and infrastructure as from raw model quality.

He expects differentiation to center on reliability, scalability, tooling (e.g., plug-ins), and multi-modal capabilities, making it easier for developers to build on OpenAI than to self-manage open-source models.

Most AI value is likely to accrue at the application layer, not infrastructure.

Hankes compares AI to cloud: infrastructure providers operate lucrative toll roads, but the aggregate value of software and applications built on top is likely an order of magnitude larger.

WORDS WORTH SAVING

5 quotes

There’s only two questions that matter for a company: Who is the customer? And what is the product?

Vince Hankes (citing a mentor)

Things are never as good as they seemed and they’re never as bad as they appeared.

Vince Hankes

We’re not talking about building the next unicorn or decacorn. We’re talking about disrupting search… that’s a trillion dollar opportunity.

Vince Hankes

A financial model is a tool to help you make a decision. You need many tools to make a decision.

Vince Hankes

When you get too pattern matchy on why companies should be the way they are, I think it leads to a lot of mistakes.

Vince Hankes

Vince Hankes’ career path from Goldman and Tiger Global to Thrive CapitalCultural and methodological differences between Tiger Global and ThriveThrive’s investment in OpenAI: rationale, process, price, and upside framingAI hype cycle, value accrual (infrastructure vs applications; incumbents vs startups)OpenAI vs open-source / multi-model world and concerns about model commoditizationTrust, psychological safety, and decision-making culture inside ThriveInvesting mindset evolution, including lessons from mistakes like passing on Canva

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