**Jason Calacanis** (0:00)
I got to wrap, guys. I got to catch a flight to Miami. Let me do a closing here if you want to keep going. You're welcome. Two, three, two.
**Chamath Palihapitiya** (0:05)
The plane just waits. Just text the pilot and just tell them you're... All right.
**Jason Calacanis** (0:08)
Listen, I'm not burning all the All-In credits, so to speak, and all of our tokens.
**Chamath Palihapitiya** (0:14)
I'm kidding. I'm kidding. I'm not like Friedberg.
**Jason Calacanis** (0:17)
You're worried about missing a flight? He's flying private to everything and then putting it on the All-In budget, and the rest of us are flying southwest for your Caremen dictator, Chamath Palihapitiya.
**David Sacks** (0:27)
Did I miss a flight? It's a strange concept.
**Chamath Palihapitiya** (0:29)
Yeah.
**Jason Calacanis** (0:29)
David Sacks, what does that mean? David, when was the last time you flew commercial? Clinton.
**David Sacks** (0:33)
I haven't missed a flight in about 15 years.
**Jason Calacanis** (0:54)
All right, everybody. Welcome back to the number one podcast in the world. We're back, we're back. And what an amazing panel we have today with us. Ryan Petersen, friend of the pod is back on the show. He's the CEO of Flexport. How are you doing, Ryan? Did you get any skiing in this year? I know you like to ski in the deep powder like me.
**Ryan Petersen** (1:13)
I tried, man, but it was a busy year for work and I got two little kids. I did a few days.
**Jason Calacanis** (1:19)
OK, so you're out. Yes, we all forgot you gave control of your company to somebody. It got a little shaky, got a little contentious, and then you took the reins back. How has it been being back in the pilot seat?
**Ryan Petersen** (1:33)
Well, that was a year and a half ago, so it's a distant memory. In Flexport time, that's like a decade. We've really had an amazing run, although these tariffs, I mean, I guess that's why you guys invited me on. These tariffs have kind of made a lot of created a lot of new uncertainty in the Flexport world.
**Jason Calacanis** (1:48)
Okay, so we'll definitely get into that. And of course, fan favorite, back for his fourth appearance on the pod.
**Aaron Levie** (1:55)
So first of all, I saw the comments last time I was on. I'm officially not a fan favorite, but glad to be back on. And I will be representing free markets in this version of the US.
**David Sacks** (2:08)
What do the comments say about you?
**Aaron Levie** (2:10)
It was like, you know, like, loves Biden, totally beta, you know, all the, all the things.
**Chamath Palihapitiya** (2:20)
Soy boy.
**David Sacks** (2:21)
Was that when you were filling in for me, though?
**Aaron Levie** (2:24)
I think so. Yes. I was trying to represent, I was trying to represent libertarian values at the time, but I loved that the leftists are embracing Milton Friedman.
**Ryan Petersen** (2:32)
I think it's all worth it if that's what comes out of all these characters.
**Aaron Levie** (2:36)
AOC is going to be a complete free market person soon.
**Jason Calacanis** (2:40)
Free market months are coming soon.
**David Sacks** (2:41)
Embracing free market values in the stock market, right?
**Aaron Levie** (2:44)
Yes, exactly.
**David Sacks** (2:45)
Because any decline in the stock market is Trump's fault, so now they're embracing the stock market.
**Aaron Levie** (2:49)
Well, unfortunately, the one day that he said it's Biden's market, it was a green day, so that didn't help the case.
**Jason Calacanis** (2:55)
I mean, gosh. Well, listen, it's started already.
**David Sacks** (2:58)
Looks like another massive green day already.
**Jason Calacanis** (3:02)
All that matters to me is that Uber is the anti-tariff stock. It just does great. It's not impacted by tariffs. So here we go. Chamath, it's started already. We have TDS on both sides. We've got Trump Derangement Syndrome from Aaron.
**Aaron Levie** (3:14)
Wait, no, no, no, no, no. I want to be, oh, I want to be.
**Jason Calacanis** (3:16)
Defender Syndrome from Sacks. We've got both. Defender and Derangement. Here we go.
**David Sacks** (3:21)
TDS. How about Trump Bias Syndrome on your part?
**Jason Calacanis** (3:24)
Who? Me? Me? I call balls and strikes. What are you talking about? Let's get started. It's starting already, folks. It's going to be a great episode. Lots of excitement with us again.
**Chamath Palihapitiya** (3:35)
Jason has the self-sabotage, find every way to not get rich syndrome.
**Jason Calacanis** (3:41)
I do? What are you talking about? You guys said you'd buy me out of this thing and I could get the hell out of here.
91 more minutes of transcript below
Try it now — copy, paste, done:
curl -H "x-api-key: pt_demo" \
https://spoken.md/transcripts/1000651996090
Works with Claude, ChatGPT, Cursor, and any agent that makes HTTP calls.
From $0.10 per transcript. No subscription. Credits never expire.
Using your own key:
curl -H "x-api-key: YOUR_KEY" \
https://spoken.md/transcripts/1000705909034