Trust, Data, AI and Specialized Agents

Trust and Governance could turn AI into a powerful force for decentralization, community, and value creation.

This is a big picture blog: my hypothesis on the forces shaping how AI and commerce will evolve. It builds on two posts I return to often. The New Economy: Small Wins (2016) argued for an economy where millions of small businesses thrive. Part 3: Internet 2.5, The Next Wave is Here (2022) argued that trust is the core of networks and commerce, how it changes is the key shaping force in the “next wave”. AI is now testing both ideas at once.

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PayPal – Stripe/Advent: Whose Deal Is This?

As a reminder, I’m not a financial analyst, more of a payment historian, operator and P&L exec. This is my third pass at the Stripe/Advent bid for PayPal. The first was reporting on the Reuters story. The second was opinion, built around three concerns: merchant pricing, enterprise access, and consumer engagement. Something changed since then, and it did not come from the deal. It came from Stripe.

This week Stripe confirmed its acquisition of OpenRouter for more than $7 billion, and the Collisons published a letter to investors talking about “the singularity” and the economics of AI token flow. OpenRouter has nothing to do with PayPal. That is precisely why it matters. Read the letter alongside Stripe’s annual letter from February and you get an unusually clear statement of where this company thinks its growth comes from. PayPal is not in that statement. Not adjacent to it. Not implied by it. Absent.

Thus this blog represents my internal dialog as I ask myself: whose deal is this? My answer: this is Advent’s deal. Stripe is in the room for one or two assets, and the structure of the bid is starting to show it.

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Apple – Klarna: Equipment Financing

Last week, Apple launched Apple Upgrade, a device leasing program for iPhone, Apple Watch, Mac, and iPad in the United States, provided by Klarna. Apple simultaneously retired the iPhone Upgrade Program (financed by Citizens Bank) and iPhone Payments.

This is a very big deal, and it is the culmination of a strategy I first outlined over a decade ago. Equipment financing has always been the prize. Everything else Apple has done in consumer finance (Apple Card, Apple Pay Later, Apple Card Monthly Installments, the savings account) was either a stepping stone, a learning exercise, or a partner accommodation. Apple Upgrade is the main event.

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Stripe/Advent – PayPal: My Thoughts

Two weeks ago I wrote up the Reuters report that Stripe and Advent had offered $53B for PayPal. That post was mostly reporting, plus some structural background on operating models and processing volumes. This one is opinion. You have been warned.

Let me start with the disclaimer that matters. I am not a financial analyst. I have no idea whether paying roughly 7x PayPal’s ~$8B in EBIT is a bargain or bizare. Kenneth Suchoski at Autonomous Research put the implied multiple at about 11x 2027 NOPAT and called the financing “a lot of debt to put on this asset,” which sounds about right to me, but he does this for a living and I do not.

What I do know something about is payment networks, merchant behavior, and consumer adoption. On those three dimensions I have 3 concerns:

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Stripe/Advent offer $53B to buy PayPal

Sometimes the biggest signal is not the price, it is who is showing up with the money. This morning, Reuters reported that Stripe and Advent International have jointly offered to acquire PayPal for more than $53 billion. Stripe, the largest privately held payments company on the planet, has walked into the room and said, in effect, we would like to own the incumbent. That framing alone reorganizes how you should read the last five years of PayPal’s decline and the next five years of network competition.

I have been writing about PayPal’s structural problems for a long time. Most recently in PayPal, Alex is Gone, Enrique is In. Recommended Focus, where I argued that Enrique Lores was inheriting a “dumpster fire” of acquisitions and shifting consumer focus, and that the only path forward was decisive surgery on the operating model. A $53B “take private” from Stripe and Advent is one very specific answer to that question. Today’s blog is a quick overview of the Reuters report together with my own read, and questions any investor should be asking before they get out over their skis on this.

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Can Processors Win a Role in Agentic?

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Adyen’s stock is down over 40% this year. Investors aren’t just punishing one company; they’re repricing the entire processor category as agentic commerce threatens to restructure who controls economics and merchant relationships. The market sees what I’ve been writing about for 18 months: processors are at risk of becoming dumb pipes.

Yesterday, Adyen announced Adyen Agentic a suite of modular APIs encompassing Agentic Feed (product/inventory), Agentic Cart (checkout orchestration), and Agentic Payments (authentication, fraud, tokenization). The positioning is explicit: a “universal translator” that lets merchants integrate once and participate across every agent platform, protocol, and payment method.

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Augustus Protocol & Emerging Settlement Standards: The Crypto Clearing Bank Arrives

In May 2026, Augustus (formerly Ivy) received conditional OCC approval to establish the first “AI-era clearing bank” a federally chartered national bank built on a stablecoin-native core designed for 24/7 programmable clearing. The announcement has drawn attention for its ambition: replacing legacy correspondent banking infrastructure with always-on, machine-initiated settlement. But beneath the compelling narrative lies a more nuanced reality about the structure of U.S. financial settlement and the commercial dynamics that govern it.

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WWDC 2026: Apple Wallet

Apple announced a suite of new Wallet and Apple Pay features this week at WWDC 2026. None of them will make the front page of TechCrunch. But taken together, they reflect something far more interesting: a payments team that has been quietly executing “the best” wallet vision for over a decade, among the most disciplined groups in consumer payments.

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Stablecoin Strategy – Visa and Mastercard Are Taking Very Different Roads

The two dominant card networks are both committed to stablecoins. Both see digital assets as a meaningful component of their long-term growth story. Both have articulated clear strategies to their investors. But the roads they are taking could not be more different and the implications for how value-added services grow, who captures the upside, and how fast innovation moves are significant.

Mastercard is buying the infrastructure. Visa is building a network and enabling shared investment.

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Agentic Recap – Last Week’s Big Announcements. 

Sorry for delay.. Just had a new grandson on Wednesday, and everyone is doing fine. One quick note, if your looking for one of my old posts, or topics like AP2, try my new search. Completely rebuilt to look through my posts and all “trusted” authorities on a topic.

Exec Summary

Last week’s flurry of announcements confirmed our thesis: Agentic commerce is off to a slow start, and the “machine-to-machine” (M2M) revolution is currently a “human-in-the-loop” (HIL) reality. Despite the hype, machines aren’t autonomously settling transactions yet; they are discovery engines landing consumers on retailer checkout pages. While “lab” pilots show machine to machine transactions are technically possible – in a lab. The reality is conversational commerce, more like an enhanced search. 

Key Items covered today

  1. Agentic Hurdles are huge. Changing consumer behavior, shifting risk, economic “Gordian Knot” of value creation and pricing, Trust and Authorization, …etc. The payment piece is the “easy” party.  There will be no wholesale change in the next 2-3 years, merchants and marketplaces want to retain consumer behavior and leverage their own data, the future for most transactions will be a checkout on the merchant’s website. 
  2. Card networks are firmly established as the payment method and will retain their role as the identity infrastructure of the internet. Stablecoin is a settlement  innovation, and cards can sit on top. Visa is at least 2 yrs ahead of MA. MA’s agent pay integration to Google’s AP2 mandates is still a lab experiment that will require both Issuer and merchant approval. For example Banks will want the full intent mandate to take the risk, something neither Google nor Merchants will be keen to share. 
  3. OpenAI’s abandonment of their own wallet is very significant and a realization that merchants hold the keys in the early days of eCom, with many major merchants wanting a PAR to reference COF, not a tokenized credential where they own the risk. 
  4. Visa’s two big announcements are significant. The partnership with Bridge to issue stablecoin linked cards in 100 markets will propel a new market for cards in M2M based UCs.  “INTELLIGENT AUTHORIZATION” a universal acceptance API against different schemes and payment types, thus eliminating the need for costly infrastructure rebuilds. 
  5. When perfect authentication does happen, it will be a watershed moment for payments and every entity that provides risk services. Processors will be particularly hard hit, afterall how will processors differentiate when every payment type has 0 fraud and 100% authorization rate. Shopify and other merchant service providers (MSPs will gain significant leverage and expand their own VAS). This dynamic explains why Stripe is investing so heavily in Stablecoin, its an effort to differentiate and improve speed and a developer community in something unique.

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