Cheeky Pint Stripe’s 2025 annual letter
274 snips
Feb 24, 2026 A rapid readthrough of Stripe’s 2025 annual letter covering big shifts in the internet economy. Topics include how market sorting is creating runaway winners and a faster, higher-performing startup cohort. Discussion of global-by-default businesses, stablecoins entering real-world payments, a payments-focused blockchain called Tempo, and five levels of agentic commerce.
AI Snips
Chapters
Transcript
Episode notes
Stripe's 2025 Scale And Strategic Acquisitions
- Stripe powered $1.9 trillion in volume in 2025, up 34%, serving 5M+ businesses including top AI firms and 90% of the Dow constituents.
- LINK reached 200M users and Metronome acquisition turbocharged usage-based billing for firms like OpenAI and NVIDIA.
The Sorting Machine Is Accelerating Profits
- Collison describes markets as a faster 'sorting machine' concentrating profits in a tightening cohort of winners across sectors.
- Examples: e-commerce grew 30% vs 5% for brick-and-mortar; top S&P decile now accounts for ~59% of profits.
A Faster, More Global Startup Cohort
- Startup formation accelerated: 57% of new Stripe companies were outside the US and 2025 cohort grew ~50% faster than 2024.
- Atlas startups now monetize sooner: 20% found customers within 30 days versus 8% in 2020.