Will Gaybrick joined Stripe as CFO after investing in the company at Thrive Capital. Over the past 9 years, now as President, he’s helped grow Stripe’s into one of the world’s largest private startups. In this episode, we explore his impressive career journey—from Harvard Math to software engineering, Yale Law, venture capital, and now his leadership role at Stripe. Will shares key insights on capital allocation, crypto, AI, investing, leadership, and more. Some takeaways:
(00:00) Intro
(01:09) From Academia to Venture Capital
(02:01) Joining Stripe: The Unexpected Journey
(02:09) Career Philosophy and Decision Making
(05:23) Building Hack Yale and Teaching
(08:15) The Role of a Polymath at Stripe
(09:31) Learning Techniques and AI Insights
(16:15) Operational Shifts and Growth Strategies
(20:36) Hiring and Leadership at Stripe
(28:08) Organizational Systems and Processes
(31:40) Migrating Users to New API Versions
(32:07) Challenges in API Refactoring
(33:57) The Rise of Stablecoins
(34:07) Stripe’s History with Crypto
(35:51) Stablecoins: Use Cases and Adoption
(41:30) AI and Machine Learning at Stripe
(47:59) Risk Management and Compliance
(53:21) Empowering Innovation with AI
(57:14) Decision-Making Frameworks at Stripe
(01:04:07) Stripe’s Product Evolution
(01:09:31) Exploring the Fun and Challenges of Product Space
(01:10:20) Stripe’s Organizational Structure and Strategy
(01:12:12) The Importance of Technical Unification
(01:13:13) User Demands and Capital Allocation
(01:14:18) The Role of ROI in Early Projects
(01:15:53) Stripe’s Unique Approach to Titles and Levels
(01:18:36) Insights on Organizational Design
(01:21:36) Effective Leadership and Decision-Making
(01:24:18) Reflections on Influential Leaders
(01:33:25) The Value of Venture Capital
(01:38:29) Future Prospects and Motivation at Stripe
Executive Producer: Rashad Assir
Producer: Leah Clapper
Mixing and editing: Justin Hrabovsky
Check out Unsupervised Learning, Redpoint’s AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA
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About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures – a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you’re interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.
