Tag Archives: stripe

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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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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Open USD – Stablecoin’s New Gold Standard for Trust, Compliance, Governance and Economics

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July 1, 2026

Executive Summary

  • 140+ institutions — Visa, Mastercard, Stripe, BlackRock, Google, Coinbase, and major global banks form the largest stablecoin consortium ever assembled

  • Shares reserve economics — Partners receive yield from underlying reserves, not the issuer; flips the Circle/Tether model

  • Zero-fee minting at scale — No volume limits, no enterprise penalties

  • Pre-transaction compliance — Transfer hooks block sanctioned transactions before settlement, not after

  • Burn and clawback authority — Architectural ability to freeze/burn for OFAC compliance built into Token-2022 implementation

  • Confidential transfers with regulatory visibility — ZK-encrypted balances for corporate privacy; viewing keys for auditors

  • Neutral governance — Independent board of ecosystem partners; no single corporate controller

  • Stripe default — “The default stablecoin for businesses running on Stripe”

Yesterday, we witnessed the launch of what may become the most consequential stablecoin ever: Open USD (OUSD). With over 140 financial, technology, and crypto institutions signing on—from Visa and Mastercard to Stripe, BlackRock, and Google. This isn’t merely another stablecoin entering a crowded market. This is the emergence of a new trust network architecture that I’ve been writing about for years.

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Explaining the Death of OpenAI’s Instant Checkout

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Short Blog

To my regular readers, you know the flow of data within a network is complex (see Data Games). The news that OpenAI is effectively shelving its “Instant Checkout” initiative in favor of a referral-based “conversational commerce” model shouldn’t come as a surprise. While the tech press might frame this as a strategic pivot, those of us in the eCommerce trenches know it for what it is: a collision with merchant’s role in risk, costs, CX, control and their own AI dreams.

OpenAI attempted to solve its monetization problem by trying to seize control of the top of the funnel, betting that the sheer volume of consumer demand would force merchants to bow to their interface. They were wrong. They fundamentally miscalculated the power dynamics of the transaction and the complexity of the global conversion funnel, a funnel that Google understands intimately because they serve both ends of it globally (ie merchant partners).

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MPP Test – Demonstrating Significance: Phase 1 is Live

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For over 60 years we have been focused on human-centric communication in our networks. While we still have payment problems in this interaction, a whole world is evolving where machines interact with other machines. The scale of this interaction is limited by value exchange — after all, who wants to spend resources answering a bot’s question if they are just stealing your data and delivering no new customers (see this blog covering Cloudflare CEO Matthew Prince’s comments).

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MPP (and X402) – Solving the Internet’s “Original Sin”

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Yes another agentic payment acronym. This one is important enough to remember. Where AP2 and ACP address agents acting on behalf of humans, X402 and MPP are about agents paying agents. My friend Simon Taylor just put together one of his all-time best posts on MPP and The Intention Layer. Today’s blog is a follow-up with a bit more of a comparison, and why this is a big deal from a payment and economic perspective. My key takeaways from Simon’s post

  • The “Skinny Master Account”: Taylor suggests that humans will grant “intent” (a budget and a goal) to an agent. MPP’s Session model perfectly mirrors this: a human “locks” $50 into a session (the intention), and the agent autonomously spends it in sub-cent increments (the execution).

  • The Substrate of AI: Taylor points out that AI thrives on Structured Text (Markdown). Ironically, legacy finance (ISO 8583, NACHA files) is essentially structured text. MPP acts as the “translator” between the agent’s markdown-based intentions and the rigid requirements of the global banking system.

  • The Outcome: The winner won’t be the protocol that is “most decentralized,” but the one that most effectively manages Trust and Permissioning. Stripe and Visa, as the incumbent trust-layers of the internet, are better positioned to solve the “Agentic Spend” problem than a pure-crypto protocol.

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Stablecoins Are Not Free — Why They Are A RAIL in Consumer Payments

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There’s a narrative running through payments circles right now that goes something like this: stablecoins will replace card rails because they’re cheaper, faster, and programmable. Stripe makes acceptance easy. Card networks are too slow to innovate. Machine-Machine payments need programmability. GENIUS Act passed. The future is obvious.

I’ve been writing about stablecoins for over two years, from the case for stablecoin as a trust platform to the ECB’s monetary sovereignty alarm. And I keep coming back to the same conclusion: stablecoins are not a replacement for cards, but rather another rail with cards retaining their role as the layer of abstraction for multiple networks (as they do today). They will do well where cards don’t play (micropayments, B2B and uncarded markets).

Here’s why (and why that matters more than you might think).

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Agentic Recap – Last Week’s Big Announcements. 

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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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AP2 as Merchant Signals – 4 Scenarios 

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Today I’m outlining three near-term scenarios (24 months) for how AP2 signals will work in agentic commerce. Per my blog last week, AP2 is the agentic payment scheme with the most momentum (160+ partners), but in the immediate term (2026–2027), it will operate primarily in a “signals” metaphor for 3 main reasons:

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