Stripe’s 2025 annual letter is out, and it’s a masterclass in Silicon Valley surrealism. Patrick and John Collison are back with their signature blend of high-brow economic theory and relentless product placement. But if you look past the $1.9T volume flex, the narrative starts to feel a bit like a choose-your-own-adventure book where every path leads back to a Stripe fee.

Let’s look at the 2025 Letter and debunk the four biggest stretches in this year’s sermon from our Irish lads.

Stripe claims eCommerce grew 30% over three years, while brick-and-mortar grew only 5%.

Not so fast. This 30% figure is for whom exactly? The baseline for most seems to be about 12%; Amazon is about half of eCommerce in North America. While Walmart is at 30% growth, is that what most mature brands are seeing? What year is this?

Stripe is leaning hard into stablecoins, calling it a “stablecoin summer” following the crypto winter. They cite $400B in payment volume, claiming 60% is B2B.

The Reality Check: Most stablecoin volume is still crypto companies paying other crypto companies. The average small business isn't accepting USDC yet. Stripe’s acquisition of Bridge and the launch of Tempo are bold bets, but let’s be real: they are building a solution for a problem the general public doesn't even know exists yet.

Apparently, hope is a strategy now.

In a wild bit of advice, Stripe is telling CEOs to stop wasting money on advertising and optimize their payment flows instead.

Self-serving much? I mean, it's fine advice, really. Lower-funnel optimizations tend to lead to ROI. No qualms there. Tongue firmly in the cheeky pint, they even suggest throwing an awards ceremony for payment improvements instead of winning Lions Awards at Cannes for the best ad.

Eh. Your CFO might appreciate it, but your CMO would likely be crying in the corner.

Stripe’s report describes Five Levels of Agentic Commerce, which moves from eliminating web forms (Level 1) to Anticipation (Level 5), where things just show up at your door without a prompt.

The Ground Truth: John Collison admits that we are currently fighting for our lives somewhere between Level 1 and Level 2. The idea that an AI agent will soon autonomously spend $400 on back-to-school gear (Level 4) assumes a level of trust and interoperability that simply doesn't exist.

Stripe’s Agentic Commerce Protocol is a play to own the toll booth for these future robot-shoppers, but until an AI can distinguish between itchy clothes and cool clothes for a third-grader, Level 5 is just a fancy way to describe a predictive subscription you'll eventually forget to cancel.

No, thank you.

Whether it's stablecoin summers or agentic shopping sprees, the goal remains the same: ensuring that when the "sorting machine" finally stops whirring, Stripe is the only one holding the keys to the vault.

In the ever-shuffling deck of AI alliances, the news that Amazon is dropping $50 billion into OpenAI’s lap ($15B at first, with $35B that has strings attached to it)—while scaling their AWS infrastructure deal to a cool $100B—is the ultimate “it’s complicated relationship" status update.

For years, Microsoft was the exclusive prom date. But as of February 2026, Sam Altman is clearly playing the field. Follow the computation to understand the partnerships and who actually benefits from these multi-year agreements. By diversifying away from Azure and leaning into Amazon’s custom Trainium chips, OpenAI isn’t just looking for cash; it's seeking redundancy and a way to lower the cost of intelligence at scale. NVIDIA continues to see hyperscalers move across the aisle to AWS and Amazon chips.

Amazon gets OpenAI’s Frontier capabilities to supercharge its own customer-facing agents, potentially protecting its retail dominance against a rising tide of specialized AI competitors.

For OpenAI, it’s a masterclass in platform leverage—locking in the two biggest cloud providers on earth, all the while maintaining a $730B valuation.

What’s not in the deal, you ask? There is still no Amazon inventory in the OpenAI global catalog for its shopping service.

TBD.

Is the era of the single-vendor AI stack dead? Grab your popcorn; the infrastructure wars just got a lot more expensive. You do not negotiate with Amazon; they simply allow you to participate.

Tuesday, March 3

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