Stripe x PayPal, Codex Micro, Saagar Enjeti Joins | George Kailas, Mukund Jha, Russ Tedrake, Glenn Youngkin

**Jordi Hays** (0:00)
You're watching TBPN.

**John Coogan** (0:02)
Today is Wednesday, July 15th, 2026 We are live from the TBPN UltraDome Temple Technology, the fortress of finance, the capital of capital. Let me tell you about ramp.com. Time is money, save both, easy to use corporate cards, bill pay, accounting, and a whole lot more. All in one place.
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 sort of 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, was it a couple months ago, Sheil 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** (1:37)
Sorry, I'm still working through these two.

**John Coogan** (1:43)
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. So 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. And they have bank info attached. That's difficult. You can't get that from many other consumer applications. That's sort of 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. So 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 complement to Apple Pay for e-commerce penetration. They never got social payments going. Could get Apple back in buy now pay later. Remember, PayPal bought, did they buy after pay? No, that was Block bought after pay. Does PayPal have a buy now pay later?

**Jordi Hays** (3:19)
No, they were just building this out themselves.

**John Coogan** (3:20)
Oh, they built that up themselves, okay.

**Jordi Hays** (3:22)
And not very well.

**John Coogan** (3:22)
Got it. So Shield says those are the two logical options from a business value creation perspective, but he identifies the problem. He says in both cases, Apple and Stripe, the culture fit makes them a non-starter.

**Jordi Hays** (3:37)
I take it back. They actually did buy a BNPL platform.

**John Coogan** (3:39)
Which one?

**Jordi Hays** (3:40)
That I've never heard of called Paydee.

**John Coogan** (3:42)
Okay.

**Jordi Hays** (3:43)
For 2.7 billion.

**John Coogan** (3:44)
Okay. So they do have an asset there that they are hopefully trying to grow.

**Jordi Hays** (3:48)
But prior to that, they had already built their own.

**John Coogan** (3:51)
Got it. So 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.
Maybe less of a problem. 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.