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  1. Cheeky Pint
  2. Stripe’s 2025 annual letter
Stripe’s 2025 annual letter

Stripe’s 2025 annual letter

Cheeky Pint · Feb 24, 2026

Stripe's 2025 letter reveals an accelerated economy driven by AI, global-first businesses, stablecoins, and the rise of agentic commerce.

Stablecoin B2B Payment Volume Doubled to $400B in 2025, Decoupling From Speculative Crypto Prices

Despite a 50% drop in Bitcoin's price, stablecoin payment volume doubled in 2025, with 60% of it representing B2B payments. This divergence signals that stablecoins are maturing into a utility for real-world commerce, independent of the volatile crypto asset markets.

Stripe’s 2025 annual letter thumbnail

Stripe’s 2025 annual letter

Cheeky Pint·13 hours ago

Stripe Argues Innovation Is Stifled by a 'Republic of Permissions,' Not a Lack of Technology

The primary barrier to realizing the benefits of new technologies like AI isn't the tech itself, but a societal structure Stripe calls the "Republic of Permissions." Non-market forces like regulators, committees, and courts create synthetic impediments that prevent economically superior solutions from being adopted.

Stripe’s 2025 annual letter thumbnail

Stripe’s 2025 annual letter

Cheeky Pint·13 hours ago

AI Startups Have Made the 'Global by Default' Model the New Norm, Unlike Previous Tech Giants

The traditional model of sequential, country-by-country expansion used by Coca-Cola and even early Google has been replaced. Today’s AI-native companies launch globally from day one, treating the entire internet as their domestic market, enabled by modern financial infrastructure.

Stripe’s 2025 annual letter thumbnail

Stripe’s 2025 annual letter

Cheeky Pint·13 hours ago

Most Businesses Operate in 'Low-Revenue Mode,' Leaking Money via Unoptimized Payments

Stripe frames unoptimized payment infrastructure not just as a missed opportunity but as an active state of "low-revenue mode." This leakage from poor conversion, authorization, and fraud prevention rates represents one of the highest ROI growth levers a company can pull, often overlooked for splashy ad campaigns.

Stripe’s 2025 annual letter thumbnail

Stripe’s 2025 annual letter

Cheeky Pint·13 hours ago

Stripe's 'Sorting Machine' Framework Explains Why Market Winners Are Pulling Away Faster Than Ever

Competitive markets act as a "sorting machine," concentrating capital and talent faster than ever. This winner-take-all dynamic is intensifying, with the top 10% of the S&P 500 now capturing 59% of total profits, a historical high. This bifurcation is happening within industries, not just between them.

Stripe’s 2025 annual letter thumbnail

Stripe’s 2025 annual letter

Cheeky Pint·13 hours ago

Stripe's 5-Level Framework Maps AI's Evolution From Form-Filling to Anticipatory Commerce

Stripe breaks down the hyped concept of "agentic commerce" into a practical, five-level framework: 1) Eliminating web forms, 2) Descriptive search, 3) Persistence & memory, 4) Delegation of purchasing, and 5) Anticipation of needs. This provides a clear roadmap for how AI will transform online buying.

Stripe’s 2025 annual letter thumbnail

Stripe’s 2025 annual letter

Cheeky Pint·13 hours ago