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

2026-07-15 · 74 min · episode 2312 · 28 entities

episode page audio

Asserted relationships

→ references Some Areas Weve Been Investing In website

0.77

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://jamesin.substack.com/p/some-areas-weve-been-investing-in
→ hosted by Jason Calacanis person

0.55

evidence rules-v5
Feed author/publisher: Jason Calacanis
→ discusses Technology company

0.40

evidence rules-v5
Feed category: Technology
→ references Twist website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://rippling.ai/twist
→ references mongodb.com website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://mongodb.com/ai
→ references webflow.com website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://webflow.com/
→ references agree.com website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://agree.com/
→ references hustlefund.vc website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://hustlefund.vc/
→ references Salesforce Signs Definitive Agreement To Acquire Fin website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://salesforce.com/news/press-releases/2026/06/15/salesforce-signs-definitive-agreement-to-acquire-fin
→ references chapterone.com website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://chapterone.com/
→ references flex.one website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://flex.one/
→ references oak.id website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://oak.id/
→ references erebor.bank company

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://erebor.bank/
→ references Peter Thiel Competition Is For Losers website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://wsj.com/articles/peter-thiel-competition-is-for-losers-1410535536

Entities found in this episode

websites 22

mentioned Some Areas Weve Been Investing In website

0.90

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://jamesin.substack.com/p/some-areas-weve-been-investing-in
references Some Areas Weve Been Investing In website

0.77

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://jamesin.substack.com/p/some-areas-weve-been-investing-in
mentioned Twist website

0.45

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://rippling.ai/twist
mentioned mongodb.com website

0.45

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://mongodb.com/ai
mentioned webflow.com website

0.45

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://webflow.com/
mentioned agree.com website

0.45

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://agree.com/
mentioned hustlefund.vc website

0.45

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://hustlefund.vc/
mentioned Salesforce Signs Definitive Agreement To Acquire Fin website

0.45

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://salesforce.com/news/press-releases/2026/06/15/salesforce-signs-definitive-agreement-to-acquire-fin
mentioned chapterone.com website

0.45

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://chapterone.com/
mentioned flex.one website

0.45

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://flex.one/
mentioned oak.id website

0.45

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://oak.id/
mentioned Peter Thiel Competition Is For Losers website

0.45

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://wsj.com/articles/peter-thiel-competition-is-for-losers-1410535536
references Twist website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://rippling.ai/twist
references mongodb.com website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://mongodb.com/ai
references webflow.com website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://webflow.com/
references agree.com website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://agree.com/
references hustlefund.vc website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://hustlefund.vc/
references Salesforce Signs Definitive Agreement To Acquire Fin website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://salesforce.com/news/press-releases/2026/06/15/salesforce-signs-definitive-agreement-to-acquire-fin
references chapterone.com website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://chapterone.com/
references flex.one website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://flex.one/
references oak.id website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://oak.id/
references Peter Thiel Competition Is For Losers website

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://wsj.com/articles/peter-thiel-competition-is-for-losers-1410535536

companys 4

mentioned Technology company

0.50

evidence rules-v5
Feed category: Technology
mentioned erebor.bank company

0.45

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://erebor.bank/
discusses Technology company

0.40

evidence rules-v5
Feed category: Technology
references erebor.bank company

0.38

evidence rules-v5
Link in episode "A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312": https://erebor.bank/

persons 2

mentioned Jason Calacanis person

0.70

evidence rules-v5
Feed author/publisher: Jason Calacanis
hosted by Jason Calacanis person

0.55

evidence rules-v5
Feed author/publisher: Jason Calacanis

Episode description as stored

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