E133: Market melt-up, IPO update, AI startups overheat, Reddit revolts & more with Brad Gerstner

**Chamath Palihapitiya** (0:00)
I'm so fucking tired. I've slept six hours in three and a half days.
Six hours, maybe seven hours.

**Jason Calacanis** (0:05)
So, wait, wait, you went to the World Series of Poker with Hellmuth, so you spent?

**Chamath Palihapitiya** (0:10)
No, no, no, first of all, I flew public, took Southwest.

**Jason Calacanis** (0:13)
What?

**Chamath Palihapitiya** (0:14)
Yeah, cost me $49.

**Jason Calacanis** (0:16)
You were on a Southwest flight?

**Chamath Palihapitiya** (0:16)
Yeah, I got a ticket for 49 bucks. It's like so fucking incredible.

**Jason Calacanis** (0:19)
Oh, did you sit in seat A1, also known as J Cal's Reserve seat? It has my name on it.

**Chamath Palihapitiya** (0:24)
Well, I was in the front row.
Great. Yeah, it's great, like Southwest has these numbers.

**Brad Gerstner** (0:29)
Hold on, you were in first class on Southwest?

**Jason Calacanis** (0:32)
No, no, no, no, premium plus.

**Brad Gerstner** (0:34)
He was in the front row.

**Chamath Palihapitiya** (0:35)
No, there's like these signs that like have a number that attaches to your ticket. And then you stand in that line and then you go on in this orderly way.
And so I was, I had like A5 or something. So I was like the fifth person on and then I sat in the front and I put my bags up top.

**Jason Calacanis** (0:51)
Yeah, you carried your bags, yeah.

**Chamath Palihapitiya** (0:52)
An hour later, I was in Vegas. It was so easy, Southwest is phenomenal. And then I flew back. Anyways, and after losing as much money as I did, it felt good to fly for $49. I gotta be honest with you.

**Jason Calacanis** (1:03)
Well, austerity measures have their benefits. You can sleep better at night with austerity measures. And did you go to the All You Can Eat Buffet and take a to go as well?

**Chamath Palihapitiya** (1:11)
No, I'd never do that.

**Jason Calacanis** (1:12)
You never know.

**Chamath Palihapitiya** (1:30)
Why did you fly Southwest? Why did I fly Southwest? Well, the planes in Europe with NAT, that's number one. And then two, I just wanted some flexibility to get in and out depending on when I busted these tournaments. So let me tell you about these tournaments.
The 100K is literally like a murderer's row of like every great poker pro. So it was like 96 of us or something. I got to be honest with you, it was so much fun.
So much fun.

**Jason Calacanis** (1:59)
Why? How so?

**Chamath Palihapitiya** (2:00)
You know, we play 40 minute levels and you have to really get the chips moving, which means that there's only so much like, you know, game theory, optimal poker you can play. And at some point, you just got to gamble it up and you got to take your shots and you have to be willing to bluff. And, you know, you have to bet for thin equity. It's so much fun. And then you see some of these guys that just lose their minds. Anyways, it was really, really a lot of fun. I finished in the middle of the pack, like 40 second or something. So that was brutal. But then the thing that I'm the most proud of is, and I went from that and I hopped in the 3K, six-handed right afterwards. And there was like 1,250 people in that. And I got to 80 first and-
The problem was I just couldn't get anything going. I couldn't get any real card. Like you need some card distribution. Like you have to at some point make some hands. You can't just, you know, I could bluff my way to 80 first, but I needed hands to really, to really, really have a chance to chip up and run it.
Then I played in the Raz, which is seven card stud low.
There's 126 people in that one. I finished in the middle of the pack there. And then this 10K bounty, there was about 600 people and I finished like 150th in that.

**Jason Calacanis** (3:08)
Those are all respectable.

**Chamath Palihapitiya** (3:09)
I mean, I know play tournaments. I have no idea how to play a tournament, to be honest. I know how to play poker. I know how to play cash games, but tournaments are very different. So I feel like I was very ill-prepared, but I had so much fun. And you know, the crazy thing is when you're playing for 12 hours a day, you are focused for 12 hours.
The thing that I forgot is that you end up, I ended up losing like two and a half pounds.

**Jason Calacanis** (3:31)
Oh wow.

**Chamath Palihapitiya** (3:32)
If your brain is going, going, going for eight hours a day, biggest fucking thing. And I was mentally devastated at the end of each night. You're just lying in bed, eyes awake, and then you can't sleep. And so then, you know, you go and you play craps and buck rot, break the casino for a couple hundred dimes a night there, and then go back to bed.