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

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

Author: Jason Calacanis July 16, 2026 Duration: 1:14:03
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

Every week, Jason Calacanis dives headfirst into the swirling vortex of Silicon Valley and global tech with This Week in Startups. It’s a direct line to the conversations shaping our digital future, moving far beyond surface-level news. You’ll hear Jason’s unfiltered analysis on everything from market shifts and media trends to the underlying mechanics of building a business, all delivered with a blend of enthusiasm and seasoned skepticism. The core of this podcast, however, lies in the guests. Jason sits down with the very people driving change-founders who have scaled impossible heights, operators managing daily chaos, and investors who spot trends before they become obvious. These conversations are less like formal interviews and more like insider debriefs, pulling back the curtain on real strategies, painful failures, and unexpected successes. For anyone curious about how technology is built, funded, and ultimately changes the world, this series offers a front-row seat. It’s the context behind the headlines, providing a deeper understanding of the forces at play in startups and technology. Tune in for a consistently engaging and insightful look at the ecosystem, straight from someone who lives and breathes it.
Author: Language: en-us Episodes: 50

This Week in Startups
Podcast Episodes
Bill Gates foresees massive AI job loss: these VCs disagree | E2330 [not-audio_url] [/not-audio_url]

Duration: 1:31:27
This Week In Startups is made possible by: Lightfield https://lightfield.app Northwest Registered Agent https://www.northwestregisteredagent.com/twistdomain Rippling https://Rippling.ai/twist Today's show: *Bill Gates dr…
China wants you to cheer for the robots taking your job | E2329 [not-audio_url] [/not-audio_url]

Duration: 1:20:21
This Week In Startups is made possible by: Odoo https://Odoo.com/twist Quo https://quo.com/TWiST Conservation Fund https://conservationfund.org how old a movie has to be for me to be able to show a part of it on youtube…
Open source is going to win it all: Harvey proves it | E2328 [not-audio_url] [/not-audio_url]

Duration: 1:09:13
This Week In Startups is made possible by: Superhuman https://Superhuman.com Sentry https://sentry.io/twist Lightfield https://lightfield.app Today's show: Jason's been saying it for years now (and we've got an All In cl…
Neurosymbolic AI outperforms chatbots and product search | E2327 [not-audio_url] [/not-audio_url]

Duration: 54:18
This Week In Startups is made possible by: Vanta https://www.vanta.com/twist Agree https://agree.com YSecurity https://YSecurity.io/TWIST Today's show: Frontier AI models can ace PhD-level exams, but it's still bad at tr…
What we'll learn from Anthropic's $2-$3T IPO | E2325 [not-audio_url] [/not-audio_url]

Duration: 1:20:15
This Week In Startups is made possible by: PayPal Open https://paypal.launch.co CLA https://claconnect.com/withyou Odoo https://Odoo.com/twist Today's show: *Anthropic is likely headed for the largest IPO in history. A r…
These robots could cut delivery costs by 80% | Next Unicorns [not-audio_url] [/not-audio_url]

Duration: 1:03:43
These robots could cut delivery costs by 80% | Next Unicorns This Week In Startups is made possible by: Squarespace https://squarespace.com/twist Northwest Registered Agent https://northwestregisteredagent.com/twist Agre…
Zuck's AI manifesto is a data center PR masterclass | E2323 [not-audio_url] [/not-audio_url]

Duration: 1:20:17
This Week In Startups is made possible by: Every.io https://every.io NetSuite https://NetSuite.ai/TWIST YSecurity https://YSecurity.io/TWIST Today's show: *Meta chief Mark Zuckerberg published a 6,500 word essay about th…