Stripe’s $53B PayPal Offer, OpenAI’s First Device, TBPN’s New Business Ideas | Diet TBPN

**John Coogan** (0:01)
Big news in the fintech world, not related to Ramp actually, but Stripe, another Founders Fund project, it's Founders Fund Day. Stripe is offered to buy PayPal. This was rumored, and on the timeline, on and off over the past year, as PayPal has been a little beat up, we can pull up the five-year chart. It's down over 80% since the pandemic highs.
If you go back further, the 2020 to 2021 era for PayPal was like an anomaly because of the big shift to e-commerce during the pandemic boom. But things have not been looking good for the last five years. And so just a couple months ago, Shiel Monod posted in February of 2026, he posted a little question for the timeline. He said, so who's buying PayPal? He says, it has the opportunity of being one of the great distressed value opportunities in FinTech history. It's down 85% at the time, still generating $5.5 billion in free cash flow. This is a $50 billion company. We'll go through the PayPal, the Stripe offer, which is at 53 billion. But you're getting a 10% free cash flow yield. I'm unaffected.

**Jordi Hays** (1:18)
I'm still working through these two, Sam.

**John Coogan** (1:23)
We got new ones.
But if you think about it, it's like you have a $50 billion company printing 5.5 billion in free cash flow. You can use a lot to finance debt, obviously, which is what's proposed here. 400 million consumer accounts. Lots of consumers have PayPal accounts, have Venmo accounts. Maybe they're not fully active, but they're ready to be engaged. It's a huge footprint and huge distribution mechanism.
They have bank info attached. That's difficult. You can't get that from many other consumer applications. That's the white whale of consumer. How deep can you go in the KYC flow, in the consumer bank relationship? You really know these customers, which is valuable for a potential buyer like Stripe in this case. Checkout buttons are on millions of merchant sites, although that has been slowing, and that's part of the reason why a change of ownership might make sense at this point. And they also have this peer-to-peer brand with Venmo, which was bought by Brian Johnson, Braintree, and then sold to PayPal. Old lore. So, Shield, the first company he calls out is Stripe. He says they have a lot of desirable assets for Stripe, a consumer-facing checkout, bank account details for hundreds of millions of consumers that you could integrate into Stripe's checkout flow, and they have a consumer brand in Venmo. Apple would also be a potential buyer, says Shield. Good compliment to Apple Pay for e-commerce penetration. They never got social payments going. Shield says those are the two logical options from a business value creation perspective, but he identifies a problem. He says in both cases, Apple and Stripe, the culture fit makes them a non-starter.

**Jordi Hays** (2:57)
I take it back. They actually did buy a BNPL platform.

**John Coogan** (3:00)
Which one?

**Jordi Hays** (3:00)
That I've never heard of called Paydee.

**John Coogan** (3:02)
Okay.

**Jordi Hays** (3:03)
For 2.7 billion.

**John Coogan** (3:04)
Okay. They do have an asset there that they are hopefully trying to grow.

**Jordi Hays** (3:09)
But prior to that, they had already built their own.

**John Coogan** (3:11)
Got it. Shield calls out that culture fit might be a problem with Paypal integrating into Stripe. Paypal is a, quote, sprawling legacy fintech with 25,000 employees. That's a huge company. Decades of technical debt. Neither Stripe nor Apple would want to absorb that. Although technical debt, you can clean it up. Coding agents, not too bad these days. Apple also might face big tech antitrust with this type of thing. That's a good call out. And yeah, you do have to wonder, Stripe incredible on the product side, on the innovation side, on the just building a fantastic, massive $159 billion as of the last tender offer business.
But are they the team to be the ruthless cost cutters if that's what it takes to turn PayPal around? That might be a different challenge culturally. Same thing for Apple. They're not this private equity firm that goes in, buys and legacy assets and turns them around. So a little bit of a culture shift that I think Sheila's correct to call out. He also identifies Visa and MasterCard as potential buyers so they could both afford it and they've been creeping into merchant acquiring and checkout. Also, we talked about that the big banks are now taking a shot across the bow of Visa and MasterCard with their own card network. So there's potential that Visa and MasterCard might want to expand into a different territory, although that's not what's playing out right now. But who knows what other bidders will come out of the woodwork now that Stripe has made this offer to buy PayPal for $53 billion. So PayPal's checkout button placement is enormously valuable real estate for either Visa or MasterCard. The networks have been trying to move beyond interchange into direct merchant relationships, and PayPal could accelerate that by years. I think they may be burned out on antitrust. Either network acquiring the largest independent online checkout provider would and should face brutal regulatory scrutiny, says Scheele. He goes on, he says, what about Elon? Elon co-founded PayPal and always wanted it to be called X, so there's some poetry in it coming back under his fold as X. Of course, he is a Stripe shareholder, I believe. I think he was an angel investor, one of his very rare angel investments with Stripe. So he might be getting a slice of PayPal with this, not too bad. His bandwidth is spread impossibly thin across Tesla, SpaceX, XAI. This is pre-merger X, politics and replying concerning to posts at 3 a.m. Never been a problem for Elon, but he said, but you could have made the case he was spread too thin before he started to acquire the last several companies too. Technical debt at PayPal is a big challenge that he knows. I would never count him out. I just don't see it though.