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

This Week In Startups is made possible by:
MongoDB - MongoDB.com/ai (mongodb.com/ai)
Rippling - Rippling.ai/twist (rippling.ai/twist)
Agree.com (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 x.com/ericbahn
Hustle Fund hustlefund.vc
Jeff Morris Jr. x.com/jmj
Chapter One chapterone.com
Show links:
Stripe wants to buy PayPal reuters.com/business/finance/stripe-advent-off…
Flex flex.one
Webflow webflow.com
Oak oak.id
Fin selling to Salesforce salesforce.com/news/press-releases/2026/06/15/…
Erebor erebor.bank
"Competition is for losers" wsj.com/articles/peter-thiel-competition-is-fo…
Chapter One piece on the value of software jamesin.substack.com/p/some-areas-weve-been-in…

Timestamps:
0:00 Eric Bahn (Hustle Fund) & Jeff Morris Jr. (Chapter One) join the show!
1:35 Stripe's reported $53B offer for PayPal
6:29 Why founders don't want to go public
10:08 Agree.com - Stop chasing invoices and automate your entire contract-to-cash stack. Go to agree.com and tell them Jason sent you to get 50% off for life!
15:16 When is it time to burn the boats?
20:12 MongoDB - AI-assisted and agentic coding is helping you build faster than ever. Start building at MongoDB.com/ai
21:16 Does VC need an AI revolution?
30:50 Rippling - Thanks to our partners at Rippling! Head to Rippling.ai/twist and get the only AI built to give you full visibility across your startup and take complex actions across your entire business.
32:36 Custom evals, open source models, and avoiding vendor lock-in
36:37 Physical AI and robotics as the next frontier
37:42 Oak's $60M seed and startup clusters chasing agent infrastructure
40:43 Escaping the Silicon Valley "think tank"
48:28 Consumer AI's missing wave
1:00:18 AI regulation and how to get it right
1:12:01 Where to find our guests and wrap-up!

Subscribe to the TWiST500 newsletter: ticker.thisweekinstartups.com
Check out the TWIST500: twist500.com
Subscribe to This Week in Startups on Apple: rb.gy/v19fcp

Follow Lon:
X: x.com/lons

Follow Alex:
X: x.com/alex
LinkedIn: ⁠linkedin.com/in/alexwilhelm (linkedin.com/in/alexwilhelm)

Follow Jason:
X: twitter.com/Jason
LinkedIn: linkedin.com/in/jasoncalacanis