Chris Paik: How I Raised $400M; Substack's Broken Business Model; Music on TikTok vs IG | E1011

... you're surfing a wave. Half the battle is making sure you're in the water when the wave comes, right? That is really important because, like, if you see the wave coming, you're still on the beach, there's, there's no way that you're gonna get out there in time to be able to surf it. I think that goes into the importance of timing. The other thing is, no surfer really can make waves. You don't have the power to change the actual tide. And so, I think that great founders are incredible at putting themselves in the position to surf waves, but I don't think anybody can make waves themselves. You can just surf them.

Chris, I am so excited for this. I love the frameworks that you wrote. I heard so many great things from Josh, from Jared, from many others. So thank you so much for joining me today, Chris.

Thank you for having me. It's, uh, uh, it's a pleasure to be here.

Now, we're gonna have a great discussion today. I always love a little bit of background, a little bit of context setting. So how did you make your way into the world of venture first? And let's start there.

Yeah. Uh, I wish I could say it was, uh, in- intentional and not accidental, but (laughs) it was more accidental. Um, truth be told, I didn't even know that venture capital was a thing when I was, uh, growing up or in college. Um, I actually maybe thought it was... I, I probably as a kind of bleeding heart liberal college student lumped it in and maligned it with all the finance of like, oh, the like, this isn't that actually interesting. Um, it wasn't until I graduated, um... I graduated, I didn't have a job, I wasn't sure what I wanted to do. Um, I stumbled basically backwards into, like, the tech meetup scene in New York. I remember going to a meetup at Shake Shack back when there was just one Shake Shack, and it was like a couple dozen people, it's this meetup called Hackers and Founders. And I just became enamored by the idea of, uh, a tech ecosystem in, uh, in the non-, in that's not Silicon Valley. I, I grew up in Burlingame, uh, which is like halfway in between San Francisco and Palo Alto on the peninsula.

(laughs) Yeah, you've got-

So I grew up in kind of-

... Alana's there. It's one of my favorite brunch spots. (laughs)

(laughs) It's, it's an amazing, amazing place to grow up. I feel like the, the cops in Burlingame have pretty easy jobs. Um, for me-

Right.

... for better or for worse, I'm a hipster with all, like, the insufferable qualities associated with it. And the idea of a tech pla- like, a tech epicenter that wasn't too on the nose was really interesting. And I think in retrospect, in hindsight, I just got very lucky that rising tide lifts all boats, and, you know, New York and other cities, um, anywhere that wasn't Silicon Valley also benefited greatly from globalization, internet, and Zoom, and inter- you know, digital communication. Um, but to answer your question succinctly, um, I knew Josh Kushner from college. Um, we were classmates. He was a year above me. And, uh, uh, ver- you know, as I was getting my feet wet in the trying to figure out what was up from down in tech, I was reaching out to all my friends who were in, in tech, tech adjacent, and they're like, "Hey, have you caught up with Josh recently? He's, um, he's like starting a venture capital firm and angel investing." "No." So he and I caught up and I obviously had lo- very low switching cost at the time not doing anything. And I asked him if he wanted help. And, and very graciously started working together. And that was my introduction to venture. I... Thrive Capital at the time, it was a $10 million fund. Um, I'd like to think that I got a startup experience, but it just happened to be a venture capital firm, um, because we really went from zero to, you know, you name it, uh, in a ve- very rich, very short period of time.