Jason, Rory, and Harry analyze the Stripe/Advent bid for PayPal, concluding the rejection is standard process, the deal will land at around a 35% premium, and the only thing that could stop it is if PayPal's internal metrics are already improving under the new CEO. ✦ AI generated
Jason · 20VC · 2026-07-23 · original ↗
starts at this moment · 58:10
“was it inevitable Stripe would acquire PayPal?”
The board rejected it, right? And the fact that the board rejected it means to me that they're going to accept it. You reject it because no no investment bank will tell you you're allowed to make your highest offer up front. It's like not a it's like you probably breach your fiduciary duty if you make your you have to offer like uh whatever. You have to have another five or 10% to put into the deal. So it's a dance. They they they're going to accept it. They're just uh it's a bunch of mercenaries in a brand new CEO who's probably going to make nine figures for uh 10 or 12 months of work.
verbatim transcript · starts at 58:10
58:04to consummate this deal and just be done as a public company but obviously Stripe has chosen not to go public. So, um, at least yet. And so, but it may well be that even though that makes it less easy to do, it may also have pushed into this kind of contained strategy with Advent, right? >> Yeah. >> Will this happen? >> I will actually getting done. >> I think it happens.
58:30>> I think I think it does, too. >> Let me just step back. Rory's got even more experience, the two of us, but it's just a dance. The board rejected it, right? And the fact that the board rejected it means to me that they're going to accept it. You reject it because no no investment bank will tell you you're allowed to make your highest offer up front. It's like not a it's
58:48like you probably breach your fiduciary duty if you make your you have to offer like uh whatever. You have to have another five or 10% to put into the deal. So it's a dance. They they they're going to accept it. They're just uh it's a bunch of mercenaries in a brand new CEO who's probably going to make nine figures for uh 10 or 12 months of work.
59:07They're go by rejecting it. It means they're going to accept it. You know, I think Jason is could well be right. I think it I hinted at this when you're a private company, you going remember we talked about the sale king, Harry. You when you're a private company, you can decide not to sell for any reason. When you're a public company, you know what the bankers are telling them right now
59:26is you're right. First thing you do is instantly reject cuz you got to look strong. And then you've just hired the bankers and they're going to say to you, you can only and the lawyers in particular are going to come in the room and they're going to say to you, Delaware law, you can only turn this down if you have good business judgment belief that on a standalone basis, you
59:45can do better than this offer in a reasonable period of time. So, even as we speak, the PayPal team are building a three-year model, a five-year model, trying to prove that, you know, they're going to be amazing and um therefore this is a this bid is too low and they can they have the they are comfortable in the risk of turning it down. But what's going to happen is this the and
60:07they'll be able to make a model because they have smart people and the banks are smart people and and the MPV will be wonderful because the banks will make it that way. But the push back will be, "Well, guys, if you were so [ __ ] smart, why didn't you fix it in the last 5 years?" Right? And then you're sitting there as a board member going, "Am I
60:25really sure that this guy can turn it around?" You know, do I believe if I got an extra 10 or 15%, would I say risk adjusted, I should take it? And as Jason pointed out, I don't know the CEO from Adam, but he's sitting there going bird in the hand versus slogging at PayPal being the third CEO in a row trying to turn this thing around. At some point, if this if Stripe wants