Jason Calacanis and Brad Gerstner: Skift Global Forum 2023

05.10.2023 - 22:39 / skift.com / Justin Dawes / Brad Gerstner / Jason Calacanis / Generative Ai

Jason Calacanis and Brad Gerstner are looking forward to the days that generative AI becomes reliable and has a real effect on how the world operates. And they believe that could be the case in some areas in as soon as a year.

Jason Calacanis, a tech entrepreneur and investor, is the author of the book “Angel” and hosts two podcasts: This Week in Startups and All-In. Brad Gerstner, is the founder and CEO of Altimeter, a tech investment firm based in Silicon Valley. He says he has participated in more than 100 IPOs. They spoke with Skift CEO Rafat Ali onstage last week at the 2023 Skift Global Forum in New York City.

Watch the full video of the discussion below.

Ali: You are in for a treat because nobody’s left in this room and we’re just going to shoot the breeze. We’re going to talk about all kinds of stuff.

Calacanis: Let’s do it.

Ali: The reason I was so excited for both of them, I emailed them, I don’t know, four months ago together and my email was, “It would be my dream for both of you to come to the Global Forum.” And literally within five minutes he said yes. And he said, “Jason, what are you going to do? You want to come or not come?” And he said, “Jason, of course I’m going to come.” The back history is that I’ve known Jason for 25 years now. I was one of his employees.

Gerstner: I’m sorry.

Calacanis: Yeah, very sorry about that.

Calacanis: We had a good time.

Ali: In the Jason 1.0 phase.

Calacanis: Silicon Valley reporter.

Ali: Silicon Valley reporter phase.

Calacanis: You were how old? 23?

Ali: 24, 25, yeah.

Calacanis: And I was maybe two or three years older than you. I was probably 27 or 28.

Ali: And this a story for another time. But Jason literally saved my life, which is a story that at some point I will tell the world.

Calacanis: Maybe for your autobiography in 20 or 30 years.

Ali: I’m sitting here alive because of him. So it’s actually a true story. But Jason is also an investor in Skift, which has nothing to do with why he’s here, but he just happens to be a huge supporter of Skift as well.

Calacanis: It’s amazing to see what you’ve built, by the way. I mean, I read it and it’s just amazing.

Ali: Appreciate it. And also, he’s at this point, probably one of the most famous podcasters in the world. How many of you know the All-In podcast?

Calacanis: Holy cow. Wow, that’s incredible.

Ali: So most of the people here are in the room for Gerstner, and there’s groupies that really want to meet Jason.

Gerstner: That makes sense.

Calacanis: But we’re also best, we’re besties. We do a lot of business together and travel together. So we have a lot of adventures that we can talk about.

Ali: Literally, I got so many emails, “Can you please introduce me to Jason?” And so there’s going to be a