The Stablecoin Future, Milei's Memecoin, DOGE for the DoD, Grok 3, Why Stripe Stays Private

**Jason Calacanis** (0:00)
All right, everybody. Welcome back to the number one podcast in the world. I am your host, Jason Calacanis, and with me again, a couple of my besties, David Friedberg. You know him as our Sultan of Science. Lots to get into today, Sultan. How are you doing?

**David Friedberg** (0:18)
I'm keeping busy. Thank you.

**Jason Calacanis** (0:19)
Keeping busy. Chamath and I on Valentine's Day. We had a little trio. We were on MK Ultra's podcast, and it hit number four, All-In podcast, of course, number one. Chamath, reflections on our Meg and Kelly, our triumphant Meg and Kelly Valentine's spectacular.

**Chamath Palihapitiya** (0:38)
It was fine. It was good.

**Jason Calacanis** (0:40)
Okay. Wow, thanks. You're such a great performer, giving me so much to work with, Chamath, as always. But it was a great, great pod. Shout out to our friend and friend of the pod, Meg and Kelly, and awesome. We've got an incredible duo. For the first time, we've invited a duo to join us in the Red Throne. David Sacks is busy saving the country, but we're really excited. The Collison brothers are with us.

**John Collison** (1:06)
Thank you for having us.

**Chamath Palihapitiya** (1:07)
You guys want to hear a great loss porn story? John has one for you.

**John Collison** (1:10)
The last time we met, Chamath, was 18 years ago, when we were working on our prior startup, Octomatic, with Harj and Kool Tagar. You were how old?

**Chamath Palihapitiya** (1:22)
They were 17, 18, 19

**John Collison** (1:23)
It was one of these San Francisco setups where it was like a two-bedroom apartment. There was a few of us living there, I think maybe six people working out of there. A normal number. Exactly. Normal number is to load up a two-bedroom apartment with, and then Chamath, you came and visited.

**Chamath Palihapitiya** (1:37)
This is what's so brutal about this. I could have invested a dollar.

**Jason Calacanis** (1:44)
One single dollar.

**Chamath Palihapitiya** (1:45)
I would have made a billion dollars. I remember meeting these guys, and I was with Alan Morgan, who was my boss at the time. I was a junior principal at Mayfield.

**Jason Calacanis** (1:54)
Shout out, Alan.

**Chamath Palihapitiya** (1:56)
I think we tried to, guys, I don't know if you remember Patrick or John, I think we tried to invest in the business, or it didn't happen, or then you ended up shutting it down, but right away you spun back up and started Stripe.
I just watched from the sidelines the whole way. It is such a, first of all, it's an amazing place for Silicon Valley where you can see these people just keep pushing the boundaries up and up and up, number one. Number two, the thing that is such a learning for me is like, why didn't I just pick up the phone and call them at any point in the last 17 years?

**David Friedberg** (2:28)
What am I thinking?

**Chamath Palihapitiya** (2:29)
It's so brutal.

**John Collison** (2:50)
Two things. One, first, you probably don't remember this, but I remember that meeting that we offered you, do you want something to drink? We did not have a broad selection. I think we had water or milk in the fridge, and you asked for a glass of water. And so I went over to the sink and I realized that we hadn't really been on top of the washing up. So I had to gingerly wash a glass for you to get your glass of water, which I can't remember if you touched it over the course of that meeting. But then secondly, when we started out with Stripe, like the FinTech sector basically didn't exist. I mean, the word hardly existed.
It didn't exist, yeah. Yeah, people just didn't think that, I mean, teenagers weren't actually teenagers at the time, but people in the early 20s, college kids, taking on PayPal or the incumbents or regulated financial services or whatever, people just didn't think it was a good idea. So I don't know, you certainly were like, the vast majority of investors we spoke with in the first year or two of Stripe turned us down. So you were not anomalous.

**Jason Calacanis** (3:53)
John, tell us what that meeting was like, and to just take you back to the moment.

**Chamath Palihapitiya** (3:57)
Here's a picture. Stop.

**Jason Calacanis** (3:59)
Here's a picture. No striking. Here's a picture of pre-9-figure Chamath.

**Chamath Palihapitiya** (4:07)
Oh my God.

**Jason Calacanis** (4:09)
This is when he shopped at Macy's. Maybe that jogs some memories, John. When that guy walked in with his khakis and that light pink Brooks Brothers shirt, what did you think? I don't know.