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
Jason turned $11 and one tweet into 1.1M views | E2311 [not-audio_url] [/not-audio_url]

Duration: 1:29:50
This Week In Startups is made possible by: Quo https://quo.com/TWiST PayPal Open https://paypalopen.com Northwest Registered Agent https://northwestregisteredagent.com/twist Today's show: *Jason spent $11 building out Po…
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Duration: 1:00:53
This Week In Startups is made possible by: NetSuite https://NetSuite.ai/TWIST Squarespace https://squarespace.com/twist YSecurity https://YSecurity.io/TWIST Today's show: *America posted 400,000 farm jobs last year, and…
Why Data Is the Next $1 Trillion Market [not-audio_url] [/not-audio_url]

Duration: 1:06:00
This Week In Startups is made possible by: Digital Ocean - do.co/twist Agree.com - agree.com Every.io - every.io. Today's show: How many startups matter in tech? Fewer than you think. That's why venture capitalists are t…
$100T is managed by "human duct tape" | E2308 [not-audio_url] [/not-audio_url]

Duration: 58:01
This Week In Startups is made possible by: Northwest Registered Agent https://northwestregisteredagent.com/twist Vanta https://www.vanta.com/twist Sentry https://sentry.io/twist Today's show: *There are $100 trillion in…
Why the VC Hype Cycle Always Gets It Wrong | VC Roundtable | E2307 [not-audio_url] [/not-audio_url]

Duration: 1:14:10
This Week In Startups is made possible by: CLA - www.claconnect.com/withyou Northwest Registered Agent - www.northwestregisteredagent.com/twist Agree.com - www.agree.com Today's show: Forget the triple-triple-double-doub…
Chamath on why young people need more agency, risk, and adventure [not-audio_url] [/not-audio_url]

Duration: 1:12:05
This Week In Startups is made possible by: Plaud https://Plaud.ai/twist Shopify https://shopify.com/twist LinkedIn Jobs https://LinkedIn.com/twist Northwest Registered Agent https://northwestregisteredagent.com/twist Tod…
Why F1 Teams are Replacing Wind Tunnels with Smart Tape | E2305 [not-audio_url] [/not-audio_url]

Duration: 1:30:26
This Week In Startups is made possible by: Plaud - https://Plaud.ai/twistSentry - https://sentry.io/twistNorthwest Registered Agent-https://northwestregisteredagent.com/twistDigitalOcean - https://do.co/twist Today's sho…
Why the Future of Video Games is Moving Back to the Dinner Table [not-audio_url] [/not-audio_url]

Duration: 1:08:51
This Week In Startups is made possible by: Deel - deel.com/twist Northwest Registered Agent - northwestregisteredagent.com/twist LinkedIn - linkedIn.com/twist Today's show: Jason sits down with Brynn Putnam, CEO and foun…
The hottest running app has nothing to do with speed | E2303 [not-audio_url] [/not-audio_url]

Duration: 1:03:04
This Week In Startups is made possible by:Agree - https://agree.comQuo - https://quo.com/TWiSTSuperhuman - https://superhuman.comToday's show:In this double-header, Jason and Lon chat with Louis Phillips, founder of the…
Why SpaceX Buying Cursor Changes Everything [not-audio_url] [/not-audio_url]

Duration: 1:41:05
This Week In Startups is made possible by: Deel - deel.com/twist LinkedIn - linkedIn.com/twist Northwest Registered Agent - northwestregisteredagent.com/twistPlaud - https://Plaud.ai/twist Today's show: Anthropic stabbed…