Ex-Twitter CEO gave Musk the Bird, 01A AI investments & IPO Landscape

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**Dan Nathan** (1:49)
Welcome to the Risk Reversal Podcast. I am Dan Nathan. This is my friend, Dick Costolo. Welcome to the Podcast.

**Dick Costolo** (1:55)
Happy to be here. I hope you like what I've done with the place.

**Dan Nathan** (1:57)
I love it, man. You got that little hostage video thing going here. But we're going to talk about your relaunched podcast, The Dick & Paul Show, Paul Kudrowski. He is your partner there. And, you know, the relaunch is really interesting to me because you had another partner and you guys started the podcast earlier this year. I love this podcast.
And we're going to get into that because it really is something unique within the tech ecosystem and you guys have an amazing overlap between what's going on in the public markets, too. And so your background as a founder, as an operator, now as an investor, as 1 Advisors, which you started in 2018 We're going to talk about how you guys are expressing views in the markets. AI, you're not new to this thing. You know, we're going to talk about valuations. We're going to talk about exits and then we'll finish off talking about the podcast. So let's do this, because I think a lot of folks know you as the former CEO of Twitter at a very important time.

**Dick Costolo** (2:56)
On my tombstone.

**Dan Nathan** (2:58)
Yeah. Well, it's funny.

**Dick Costolo** (2:59)
I remember CEO of Twitter.

**Dan Nathan** (3:01)
Yeah. And I remember, you know, another good friend of mine, Adam Bain, who is the president of Twitter.
When you guys worked together, you guys took the company public. You guys did not do a ton of media at the time. I remember shortly after you guys left, you were my good friend, Scott Watner's show out from San Francisco. And it was really illuminating because you guys were, you know, on the other side of Twitter and there was a lot of stuff going on. So let's just talk about that journey a little bit because it's pretty fascinating. And then there's some other interesting stuff in there along the way.

**Dick Costolo** (3:30)
Yes, there was a lot of other interesting stuff in there along the way.

**Dan Nathan** (3:34)
Well, let's start then with really your comedic chops, because this is something that you wanted to do out of the gate.

**Dick Costolo** (3:42)
When I graduated from Michigan, I had a computer science degree and had a bunch of offers to go work mostly on the East Coast with the IBMs and at the time, I'm dating myself with the Honeywell and Burroughs and those kinds of companies at the time.
But I decided I wanted to try to get on Center Night Live. So I did what you do when you want to go that route, which is I went to Second City in Chicago. I actually showed up there the same day as Steve Carell. We performed together for a bunch of years. I ended up auditioning for SNL twice. As you may have gathered, I didn't get it.
I didn't even get invited to... You know, they do the first auditions in Chicago, on stage, actually, at Second City. And then they have callbacks to 30 Rock and never made it to 30 Rock. But, you know, in fairness to me, my buddy Steve Carell, I actually haven't seen him in quite some time now, but Steve auditioned a few times and didn't get hired either, but then he got his huge break in 40 Year Old Virgin. Actually, he had a bunch of breaks along the way. He was on The Daily Show as a roving reporter, and then had The Dana Carvey Show, which was one season, and then got the 40 Year Old Virgin. I just abandoned SHIP when I didn't get it the second time and went back to tech.