Inside Stripe: Stablecoins, AI, and (not) Going Public | Will Gaybrick, President of Technology and Business at Stripe
Will Gaybrick is the President of Technology and Business at Stripe.
Stripe builds financial infrastructure for the internet, and if you’ve ever purchased a product online, you’ve probably used Stripe.
We talk about what Stripe’s doing in crypto and stablecoins, how AI is changing commerce and payments, how they’re thinking about going public, how they build products internally, and interesting data they’re seeing around AI-native companies, like how they’re growing 3.5x faster than SaaS companies.
Thank you to Claire Hughes Johnson, Josh Kushner, and Cosmin Nicolaescu for help brainstorming topics for the conversation.
Thank you to Numeral and Amplitude for sponsoring this episode.Numeral: The end-to-end platform for sales tax and compliance. Try it here: https://www.numeral.com
Amplitude: Listen to users at scale with AI https://www.amplitude.com/AI-Feedback
Timestamps:
2:42 Will’s promotion
5:29 Build vs Buy in AI
6:39 Inside the Bridge acquisition
8:54 Stripe’s stablecoin strategy
11:20 Why building Stripe is so complicated
13:22 How Stripe builds new products
18:29 AI companies growing 3.5x faster than SaaS
22:58 New fraud vectors in AI businesses
25:19 Agentic commerce in ChatGPT
29:34 Building modular products
34:05 How Stripe uses AI internally
42:12 Building the first payments foundation model
48:23 Link, Stripe’s 200M user consumer product
56:52 Will Stripe ever IPO?
59:14 Blurring of private and public companies
1:03:39 Starting Hack Yale
1:08:23 Joining Thrive’s $5 million Fund 1
1:12:30 Low margin businesses are underrated
1:16:30 Joining Stripe as CFO
1:21:59 How Stripe’s go-to-market has evolved
1:25:56 Stripe’s margins
1:29:52 Why financial services are so hard to use
1:33:04 Lessons from Alan Mulally
Referenced
Stripe: https://stripe.com/
Careers at Stripe: https://stripe.com/jobs/search
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EP 118: Will Gaybrick (President of Product and Business, Stripe) on Capital Allocation, Org Design, AI, and Global Growth
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
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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 of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.
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