S1E29 — Stripe and Advent have made a joint offer to acquire PayPal – sources

July 16, 2026 · 4 min

Show notes

A muddled forty-two-billion-dollar guess turns into a real argument: is "we'll break the monopoly up later" a legitimate plan or just the sound a regulatory window makes right before it slams shut on Stripe and Advent's PayPal grab?

Sources

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Transcript

GARY: —and look, if the number's right, we're talking a forty-two billion dollar joint offer, which, forty-two, that's the kind of number where you go "okay somebody's compensating for something," and I don't say that as a criticism, I say that as a founder, I say that as someone who once needed forty-two billion dollars and got thirty-eight million and a strongly worded email—

GARY: Wait. It's not forty-two. Fuck. It's not — is it in the twenties? Is it in the twenties. Somebody said twenty-something to me in the hallway forty minutes ago and I built an entire personality around forty-two.

MAEVE: It's not confirmed. There's no number. It's "sources say."

GARY: Right, but if there WAS a number—

MAEVE: There isn't.

GARY: —if there was, I'm saying I already have opinions about a number that does not exist, which, historically, is my entire skill set, so. Are we — is this thing on? Is the mic—

GARY: Oh. Oh it's on. Great. Great, great, great. Cool. We're doing this now I guess.

MAEVE: Maeve. General partner. I do deal flow, and unfortunately, apparently, I also do this.

OBI: Obi. I keep servers up so founders can go on podcasts and get the number wrong before the show starts.

GRUNER: Gruner.

GRUNER: Field researcher. I watch you people. Is going fine so far.

GARY: Great, love that, love the confidence. Okay. Headline. Headline's the headline. "Stripe and — " — Advent. Ad-vent. Advent. Like the calendar. "Stripe and Advent have made a joint offer to acquire PayPal, sources say." That's it. That's the thing. Sources. Say.

OBI: You said "Advent" like it had four syllables.

GARY: I did not.

OBI: Ad. Vent. Cal. En. Dar. That was five, actually, you gave it an extra one out of nerves.

GARY: I have a lot going on, Obi, I already told you the number was wrong once tonight, we don't need a second inventory.

MAEVE: For the record. It's Advent Capital. Private equity. Buying into payments infrastructure alongside Stripe. That's the thesis. That's the whole shape of it before anybody's said a real sentence.

GRUNER: Private equity buying rails. This I have written down before. Different company. Same note.

GARY: Okay, thread's up. One-ninety-eight comments. Top of the stack, guy named digitaltrees, and he says it plain, no bullshit, he just says—

GARY: "Trying to create a monopoly before the lack of antitrust enforcement window closes."

MAEVE: That's the thesis.

GARY: That's — I just read it, you can't just take his sentence and call it "the thesis," that's plagiarism with a Patagonia vest on—

MAEVE: No, I mean structurally. It's the thesis of the whole thread. Everything under it is either agreeing with that timing argument or getting mad that someone said it out loud in public where regulators could theoretically read Hacker News, which, they don't, but the anxiety's the same shape.

OBI: We agreeing with the guy in under ninety seconds now? That's a new record even for us.

GRUNER: "Window." Is good word. Valley people say it like weather. Window opening, window closing. Nobody ever says who built the window.

OBI: Window's the enforcement environment, Gruner, it's a metaphor—

GRUNER: I know what metaphor is. I am saying nobody built the fucking window. It is regulatory posture. You are speaking about it like it is tide.

MAEVE: Because to them it is tide. That's kind of the point.

OBI: It's not a tide, it's a policy choice made by specific human beings who could theoretically be voted out, which nobody mentions because it's easier to talk about it like weather.

GARY: Can we — can we keep going, there's a reply—

GARY: Guy named toomuchtodo replies to digitaltrees directly. Says — quote — "No reason it can't be broken apart in the future. States will likely file suit, as twelve already have regarding the Paramount Warner deal."

MAEVE: Break it apart later.

GARY: Right, and — okay, look, can I just say something, as a founder—

OBI: Here we go.

GARY: —no, seriously, hear me out, because I have BEEN the guy who says "we'll fix the structural problem after we close," I said a version of that sentence to my own Series C investors—

MAEVE: You did not have a Series C.

GARY: I said it to the investors who WOULD have been my Series C, in a meeting, that counts, and my point is, sometimes "we'll deal with it later" is a real plan. It's not always a lie. Sometimes you genuinely mean to fix it later.

OBI: You didn't fix it later.

GARY: No, I did not, Bauxlite is dead, thank you, but that doesn't mean the logic was bad, it means I specifically executed it badly—

OBI: The logic is the thing that's bad, Gary. "Break it up later" is not a plan, it is a sentence