A Startup Is Trying to Buy PayPal… Craziest Deal of 2026! | E2312
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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!
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20VC: Investing Lessons From Observing Doug Leone and Bill Gurley, Why It Is Easier To Be Contrarian As A VC Than As An Angel & What It Takes To Run Tinder's Product and Revenue Alongside A Seed Fund with Jeff Morris Jr, Founder @ Chapter One
Jeff Morris Jr is the Founder of Chapter One, an early stage seed fund investing in blockchain assets, mobile and subscription businesses. Chapter One's Portfolio includes the likes of Lyft, Brandable, Crypto Kitties and many more incredible companies. However, Jeff is unique as Chapter One is only one of his hats, Jeff is also the Director of Product & Revenue @ Tinder and when asked to lead the revenue team they were ranked #17 in the app store. Within a year, under Jeff's leadership, Tinder became the #1 top grossing app in the world.
In Today's Episode You Will Learn:
1.) How Jeff made his way into the world of startups and angel investing, how that lead to his role as Director of Product and Revenue @ Tinder and a leading early-stage investor with Chapter One?
2.) Jeff has previously said, "apply an investor mindset to every product decision I make". What are the foundational questions involved? What are the inherent challenges of being so deep in product and investing simultaneously? What does Jeff think of VCs giving product advice to founders? What should the founders look for? What advice does Jeff give to the common question of "how do I get into investing and VC"?
3.) Why does Jeff disagree with the platform shift and the downturn in consumer mobile? What core innovations will drive the next wave of consumer mobile? Valuations in the space are often lofty, how does Jeff think about price and evaluate his own price sensitivity? How does Jeff think about scalable customer acquisition today in a world where incumbents dominate and price up the traditional channels?
4.) Jeff has said before that "investors treat crypto teams as if they are superhuman", what makes Jeff think this? How do their interactions differ than towards non-crypto teams? Why are lofty expectations dangerous for valuations? How does that put undue pressure on employees? Why are lofty expectations dangerous for product development? How do they affect the product roadmap negatively?
5.) How does Jeff approach the diligence aspect when it comes to investing? What have been some of his major lessons from making over 35 investments on the right diligence framework? How do shortened fundraising cycles negatively affect investor diligence processes? What can founders and investors do under these constrained time frames?
6.) Having worked with some of the greats from Doug Leone to Bill Gurley, what are some of the common traits in how the very best investors engage with founders? What were Jeff's personal learnings from seeing these greats in action? How did it change the way Jeff thinks about founder interaction and engagement?
Items Mentioned In Today's Show:
Jeff's Fave Book: The Catcher In The Rye, Googled
Jeff's Most Recent Investment: Radar Relay
As always you can follow Harry, The Twenty Minute VC and Jeff on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
“Tinder babies” and the power of connecting people online and offline
In this episode of Product Hunt Radio, I'm in Los Angeles talking to Brian Norgard and Jeff Morris Jr., both of whom may be indirectly responsible for a generation of “Tinder babies”.
Brian Norgard is an entrepreneur, investor, and Chief Product Officer at Tinder. He has worked on a number of other products and was Tinder's first acquisition. He collaborated with Sean Rad on an earlier app called Chill, which we discuss on the podcast. Brian is also an investor in Lyft, SpaceX and AngelList.
Jeff Morris Jr. is the Director of Product for Tinder's revenue initiatives. He previously worked at Zaarly and has created a number of products, including one stretch over three months where he built and launched three products, reaching the top of Product Hunt. He is also an investor in Lyft, CryptoKitties, Particle, Brat and others.
In this episode:
The joy of turning online connections into real-world connections. Jeff is great at this. He once went biking with Lance Armstrong in Hawaii after reaching out to Armstrong on Twitter.
How seemingly minor design decisions, like adding a subtle animation to a play button, can “nudge” users into a new pattern of behavior and make products more enjoyable to use.
Brian and Jeff discuss the design of Tinder Places, including the thoughtfulness that went into the privacy features of the product, and how they took inspiration from Foursquare.
We get nostalgic and discuss some of our favorite products from the past, like Chill and Highlight. They leveraged location on mobile in an attempt to merge the online and offline world.
Jeff tells the story of the time he reached out on Twitter about a job opportunity and less than 48 hours later had moved from San Francisco to Kansas City.
Why Product Hunt has gained a reputation as a positive, fun, and upbeat community and how subtle, very intentional design decisions — like our ridiculous Google Glass-sporting cat — contribute to the community and brand.
Of course, we also chat about some of their favorite products, including messaging apps, trivia games as well as a couple of now-obsolete apps that were onto something at the time but didn't end up taking off.
We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Also, big thanks to our sponsors, Airtable, GE Ventures, Intercom and Stripe for their support. 😸
Quotes from This Episode
“I like to respond to people who I shouldn't be taking to. I'll email people I shouldn't email. I don't care if they email me back. One in one hundred responses could change your life.” — Jeff
“Tinder's really a serendipity engine... It's one of the few experiences where you're actually leaning forward to meet someone you don't know.” — Brian
“[After he hired me via Twitter and a Skype interview] he said 'I'm in Kansas City, will you move here?' I packed my bags, got on a plane, moved to Kansas City and didn't go back to San Francisco for nine months. That was all from Twitter, within 48 hours.” — Jeff
“[When building products and communities ] follow the traffic anywhere. Things happen, a bunch of people aggregate, you find ways to give them unique value, and you reduce the friction because people are already there.” — Brian
“No one wants another copycat product in any category.” — Brian
Companies and Products Mentioned in This Episode
Chill (RIP) — A fast and fun way to communicate.
Discord — Free voice and text chat for gamers.
Highlight (RIP) — Find friends and new people nearby.
HQ Trivia — Live trivia game show by the founder of Vine.
Slack — Be less busy. Real-time messaging, archiving & search.
Telegram — Fast, encrypted messaging app.
Tinder Boost — Skip the line for 30 minutes to get more matches.
Tinder Places — Discover new people who hang where you hang.