PayPal – Stripe/Advent: Whose Deal Is This?

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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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Agentic Reality: Advertising

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The hype machine behind agentic commerce is at its apex. Every week brings another protocol announcement, another pilot, another prediction that autonomous agents will soon do our shopping for us. For payment executives trying to separate signal from noise, here is the signal: the first real agentic business model is not autonomous checkout. It is advertising.

What Is Actually Working: AI Inside the Retailer

AI is making great strides within the retailer’s own domain. Amazon’s Rufus, Walmart’s Sparky, and Michaels’ “Mike” are conversational agents built by retailers, trained on their own assortment and category expertise, driving basket sizes up over 35% in the best implementations. Amazon told investors that Rufus helped generate nearly $12 billion in incremental annualized sales, with monthly active users up 115% and users 60% more likely to complete a purchase (Bain & Company, “Agentic AI in Retail: How Autonomous Shopping Is Redefining the Customer Journey,” May 2026). Michaels took “Ask Mike” from concept to production in six weeks on Google Cloud, as I covered in Google Pulls Back From “Buy For Me”.

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eIDAS – Top 3 Problems

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Europe is twelve months away from a legal deadline for a wallet no one has asked for. Governments are required to issue digital IDs, banks are not required and will likely hold off given the success of Norway’s Bank ID model (commercial terms there). Under Regulation (EU) 2024/1183, commonly called eIDAS 2.0, every Member State must offer at least one certified European Digital Identity (EUDI) Wallet to all citizens and residents by December 2026. The Commission’s stated ambition is that 80% of European citizens use a digital identity solution by 2030.

The wallet is a container. It holds Person Identification Data (PID), the citizen’s legally recognized core identity issued under national authority. It holds Qualified Electronic Attestations of Attributes (QEAAs), which are verified claims such as a driving license, a professional qualification or a bank account identifier. It also supports Qualified Electronic Signatures (QES), which carry the legal weight of a handwritten signature in all 27 Member States. For payments, the relevant consequence is that a certified wallet credential satisfies Strong Customer Authentication, so a bank cannot arbitrarily reject a wallet based authentication event in a payment flow.

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Processors: Understanding Competitive Dynamics

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Warning – Big Blog 12 Pages

The last three weeks gave us a full sweep of processor earnings, and the results were a mixed bag (a phrase that undersells what actually happened). What we saw was not the processor sector moving together with a common tide. It was a sector splitting apart. Adyen raised guidance and jumped 16% in a day. Toast added a record number of locations and raised its full year outlook. On the “bad side of town”, we have Fiserv, which cut guidance, missed consensus, and is now down roughly 23% for the year with a brand new CEO. FIS is down about 36%. The gap between the best processors and the worst has never been this wide, and I do not think most investors have a working framework for why.

That framework is what I want to lay out here.

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Google Pulls Back From “Buy For Me”

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Summary: Refocusing on a Merchant Message as Merchants control these early days of Agentic

Something quietly changed in Google’s agentic commerce story over the last twelve months, and almost nobody has called it out.

As I related in Google I/O 2025 the headline was “Buy for me.” The pitch was clean and consumer facing: AI finds the product, you set the price you are willing to pay, Google watches the market, you confirm, and Google completes the checkout using Google Pay. Google called it agentic checkout. I wrote at the time that the price of entry for merchants was simply adding the GPay button, and that qualified agentic demand would finally give merchants a reason to do it.

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Tokenization and Trust

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Tokenization is taking hold. That much is settled. It is showing up in financial market clearing and settlement, payments, and in products that did not exist three years ago. What is not settled is what “tokenization” actually means.

My read: the majority of tokenization efforts are best categorized as updating existing flows between existing parties using new DLT technology. Improving flows is not the same thing as remaking a market, and the press releases rarely distinguish between the two. I recommend you parse the hype carefully as it is at or near its apex.

Regular readers will recognize the theme, and I laid out the taxonomy in 101 Update: CBDCs, Stablecoins and Tokenized Deposits, and also argued in Stablecoins: A New Model of Trust enabled by Technology that the defining innovation is the trust architecture rather than the technology, and applied it most recently to SWIFT’s blockchain announcement in Parsing the Hype.

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Apple – Klarna: Equipment Financing

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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

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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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Visa Stablecoin Platform

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Exec Summary

  • Consumers never wanted stablecoins, they wanted 5% yield or a crypto off ramp, BIS data confirms retail use is under 1% of volume
  • Stablecoins are a settlement innovation, networks did not hijack them, incumbents always adopt new tech to compete
  • Visa’s value is governance, operations, and distribution, VSP is just the next network in the network of networks
  • VSP = single Visa managed environment to mint, burn, move, and manage OUSD, with wallet as a service, passkeys, maker/checker controls
  • OUSD first because compliance and trust win, banks trust banks, not Circle, 63% of corporates want stablecoin access via their bank (EY Parthenon)
  • Use cases anchor on ramps and off ramps, treasury funding, global payouts, merchant settlement, stablecoin linked cards ($7B settlement run rate, 160+ programs)
  • VSP is to stablecoin what Visa DPS is to debit, same playbook, different rails and connection points
  • Visa enables Bank Issuers without picking winners, Mastercard bought BVNK and owns a single roadmap, overlap is real but philosophies differ
  • Enablement models win, every member becomes an investor in the network’s growth
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Stripe/Advent offer $53B to buy PayPal

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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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