The Stripe-Advent deal to buy PayPal will happen — the board's rejection is a negotiated dance from a 28% premium to mid-30s, and the fiduciary duty math makes it very hard for the board to say no.
Jason argues the PayPal board's rejection is procedurally required — no investment bank allows a first offer to be the best offer. The spread from 28% to ~35% premium is pre-scripted. The board faces a tough fiduciary question: can they prove on a standalone basis they can outperform this offer? With a revolving door of failed CEOs and no evidence of turnaround, the bird-in-hand logic prevails. The deal lands at 35% premium and closes. ✦ AI generated
Jason · 20VC · 2026-07-23 · original ↗
starts at this moment · 58:30
“Will this happen?”
I think it happens. 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 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. They're go by rejecting it. It means they're going to accept it.
verbatim transcript · starts at 58:30
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