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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PayPal – Alex is Gone, Enrique is In.. Recommended Focus

Don’t say I didn’t tell you. As I related in June 2025 The Shakeup PayPal Needs, Dan created a dumpster fire that the BOD just added to in their AWOL engagement. 

Yesterday PayPal delivered FXN Branded growth of 1%, and announced that PayPal CEO Aex Chriss is out and HP’s CEO Enrique Lores is in (March 1st).  This event serves as the final, public admission of a decade-long strategic failure. Lores replacement of Chriss hopefully marks the end of an era of “spectator leadership” and the beginning of a desperate attempt to reintegrate a fragmented “mash” of acquisitions into a cohesive operating model. To understand the depth of the “dumpster fire” that Lores inherits, let’s look back across the last eight years, beginning with the BOD’s decision to renew Dan Schulman’s contract, a move that effectively decapitated PayPal’s operational core and set the stage for its current state of institutional irrelevance among top merchants

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PayPal Advertising?

Yesterday PayPal announced PayPal Ads Manager

“PayPal Ads Manager gives tens of millions of small businesses access to high-margin ad revenue while creating valuable new inventory for advertisers of all sizes.”

“Retail media networks have become a multi-billion-dollar industry that generates high-margin revenue by enabling businesses to sell advertising on small business websites and apps”

As the Founder/CEO of Commerce Signals we brought card data to market primarily for measurement (now part of TU). It gave us a view of how advertisers performed and what data was valuable. I went into great detail on the challenges of  JPM’s Retail Media network in my June 2025 blog  Understanding How Payments Data Plays in Advertising (2025), and more generically in my 2021 blog Data Games

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The Shakeup PayPal Needs

Rumors are that a substantial organizational change at PayPal is in progress. Frankly, it’s overdue. For any global payments company to succeed, its leaders must possess a deep, almost intuitive, understanding of the global payments ecosystem. This is where PayPal is currently failing.

We have a CEO, Alex Chriss, known as a product specialist. While he may be excellent at getting products out the door, this is not the problem PayPal faces. Unfortunately, the team can’t see the forest fire given their conspicuously poor payment background. For example, look at Diego Scotti as EVP and GM of the consumer group. His experience comes from Verizon, and his chief credential is that he is the husband of Janey Whiteside, one of Alex’s closest payment advisors. When growth doesn’t happen and targets get missed, investors begin to look for the reasons and the resumes of those running the ship.

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eCommerce 2025 – Wallets, Share Shift, Conversion Rates and Key Segments

© Starpoint LLP, 2025. No part of this site, blog.starpointllp.com, may be reproduced or retransmitted, in whole or in part, in any manner without the permission of the copyright owner. Also, see our Legal/Disclaimer (this is a highly opinionated and partially informed blog).

My estimates for how US eCom market share will shift in next 3 yrs are at the end of this blog.

eCommerce is not a single monolithic market. There are many “segments” to optimize that vary by geography, retailer type, consumer device, customer type (guest vs loyal), transaction type (recurring vs new), ad type, payment type,…etc. A great source of this information is Monetate (highly recommend). For example, let’s look at conversion rates by industry, device and region.

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eCom 2025 

18 months of Revolutionary Change in How we Buy Online

Short Blog

Follow up to my June 2024 blogs – eCom Politics and Scenarios and Fastlane + FIDO Enabled Checkout. Today, we focus on the changes, what merchants are asking for, and what consumers will adopt (and when). 

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eCom – Politics and Scenarios

Frank Young – Contributor

What are banks talking about this week? How did Apple’s announcement impact them? While 15bps on 2% of eCom GDV is a nuisance, 15bps on 15% of eComm GDV is an earthquake. 

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