A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312

July 15, 2026

AI Summary

5 min read

The Stripe-PayPal Deal That Signals a Shift in Silicon Valley

When news broke that Stripe—a private company—was attempting to acquire PayPal for more than $50 billion, even seasoned VCs were caught off guard. "You picture PayPal and you hear the name, you just think they're not acquirable," said Jeff Morris Jr. of Chapter One. The deal, which would take a public company private at roughly $16.50 per share (down from a peak above $300), represents more than just a headline. It crystallizes several converging trends in technology: the advantages of staying private, the natural lifecycle of iconic tech brands, and the increasing blur between public and private markets.

Why PayPal Became a Target and What It Says About Tech Companies

Eric Bond of Hustle Fund framed PayPal's decline through a cultural lens. "My suspicion is that PayPal kind of calcified in its own within itself," he said. "They were start-upy, they did cool things, they innovated, they broke things, and then they professionalized. A bunch of MBAs start to join, and then it's start to become about the employees trying... Innovation kind of stops."

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What you'll learn

1 (00:00) **Episode Intro & Guest Introductions** - Host Alex welcomes Eric Bond (Hustle Fund) and Jeff Morris Jr. (Chapter One) to discuss Stripe-PayPal, AI bottlenecks, and startup defensibility.
2 (01:37) **Stripe to Buy PayPal: Deal Reaction** - The hosts react to the news that private company Stripe may acquire public company PayPal for over $50 billion.
3 (03:56) **PayPal’s Decline & The Public vs. Private Debate** - Eric notes PayPal's peak share price above $300, now possibly going private at ~$16.50, and discusses the cultural ossification of large tech companies.
4 (10:06) **Why Companies Might Still Go Public** - The panel discusses catalysts that could make public listings attractive again.
5 (13:57) **Fintech M&A & The Flex Case Study** - Jeff and Eric discuss Flex's $1.2B valuation and whether Stripe-PayPal will spur more fintech consolidation.
6 (15:20) **Burning the Boats: Webflow & The AI Pivot** - Using Finn/Salesforce and Webflow as examples, the panel discusses when startups must pivot or restructure for the AI era.
7 (17:40) **Human Inefficiency & The Rise of the Individual Contributor** - Alex argues humans cause cultural ossification and asks if the future is high-revenue-per-employee companies.

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Show Notes

This Week In Startups is made possible by:

MongoDB - MongoDB.com/ai

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Agree.com - agree.com

Today's show:

Hustle Fund's Eric Bahn and Chapter One's Jeff Morris Jr. join our venture capital roundtable directly following the news breaking that Stripe wants to buy PayPal. The possible transaction highlights how little interest today's leading startups have in going public any time soon. With host Alex Wilhelm, Bahn and Morris dug into when startups should burn the boats à la Fin, physical AI as the next frontier, the power of Silicon Valley groupthink, and how startups are approaching the first days of widespread, company-specific AI evals!

Guest links:

Eric Bahn https://x.com/ericbahn

Hustle Fund https://www.hustlefund.vc

Jeff Morris Jr. https://x.com/jmj

Chapter One https://chapterone.com

Show links:

Stripe wants to buy PayPal https://www.reuters.com/business/finance/stripe-advent-offer-buy-paypal-more-than-53-billion-sources-say-2026-07-15/

Flex https://www.flex.one/

Webflow https://webflow.com/

Oak https://www.oak.id/

Fin selling to Salesforce https://www.salesforce.com/news/press-releases/2026/06/15/salesforce-signs-definitive-agreement-to-acquire-fin/

Erebor https://erebor.bank/