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

This Week In Startups is made possible by: MongoDB - MongoDB.com/ai Rippling - Rippling.ai/twist 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/ "Competition is for losers" https://www.wsj.com/articles/peter-thiel-competition-is-for-losers-1410535536 Chapter One piece on the value of software https://jamesin.substack.com/p/some-areas-weve-been-investing-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 https://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 https://MongoDB.com/ai 21:16 Does VC need an AI revolution? 30:50 Rippling - Thanks to our partners at Rippling! Head to https://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: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp   Follow Lon: X: https://x.com/lons   Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm   Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis