Greg Isenberg is unbundling internet communities

Aimee Pearcy (0:00)

You've got a really interesting background. So you're a Canadian Internet entrepreneur and venture capitalist. You previously founded interests based communication app, Islands. WeWork and video discovery platform 5B. Is that how you pronounce it?

Greg Isenberg (0:16)

5B, yeah.

Aimee Pearcy (0:17)

5B, okay, close enough. Which you sold to StumbleUpon. Right now you're a growth advisor at TikTok and a venture partner at Indicator Ventures, a tech venture fund. And you are heavily involved in building internet communities. And you recently launched a site called Late Checkout, which sounds really interesting. I definitely want to go more into that. And that's a company that creates and acquires internet communities.

Greg Isenberg (0:45)

That's me.

Aimee Pearcy (0:46)

So first of all, I kind of want to go all the way back because I did some research on you. And it turns out that you started your first internet company when you were 13

Greg Isenberg (0:58)

Yeah, I mean, I've been, as long as I could remember, really been tinkering with the internet.

I read a book when I was 13 It just was on a shelf in the library. It was a book by Bill Gates. It was called The Road Ahead. And basically Bill Gates, this is like a book from probably like the early 90s. And he basically like outlined exactly how the internet was going to be like, that there was going to be social networks, that there were going to be like, kind of like Zoom and video conferencing. There was just, he just, he saw the future and he basically predicted it. And I was like, whoa, I'm living in Montreal, Canada. And you know, it's a big city, but it's not New York or Tokyo or London. And it allow, I was like, this internet thing is going to be, is going to allow us to sort of transport, you know, everyone's going to be using it and all the time. So I just started tinkering at 13 and I've been tinkering since.

Aimee Pearcy (2:08)

Okay. So what was your first project when you were 13?

Greg Isenberg (2:12)

First project was really like these e-commerce, you know, websites and apps. This was like, you know, kind of in the eBay heyday when you could, you know, I'd go to like this store called Future Shop and Future Shop was like a kind of Best Buy competitor. Actually Best Buy ended up buying it and they would have these deals on DVD box sets. So you'd have like Family Guy DVD box set season one and they'd be lost leaders for the company. And I realized that, you know, you can buy them for 20 and then sell them for 20 Canadian and then sell them for 50 US. And so just starting creating, you know, content websites around that, e-commerce sites around that. And you could also make money on shipping. And then so how do you bring traffic to it? So just like all the pieces around, you know, building a brand, creating a destination, understanding go to market, building marketing funnels.

You know, that's how I got started.

Aimee Pearcy (3:30)

Did it work?

Greg Isenberg (3:32)

I mean, some of it, you know, I think, yeah, I mean, it worked in the sense like, you know, I remember this is like I'm 31 now. So this is like 2002 or 2003, 2004 So a long time ago, but you know, there's a magical feeling you get when you create something and people use it. There's a double magical feeling when you create something, someone uses it and someone buys it.

So, you know, for me, it was just like mind-blowing that anyone would buy anything that I would created. And like in the background, like I'd be talking to customers and like they didn't know I was like a 13-year-old kid, 14-year-old kid. And I bought like I needed to have Wi-Fi during class. So I bought these like this is like pre-smartphone. I bought this, you know, these pocket, they were called pocket PC's. They're like these phones that ran on windows. And I'd be like in class, like checking orders and like, yeah, good time.

Aimee Pearcy (4:43)

That's great.

So after that, you went to McGill University. Is that right? So in Canada, yeah.

Greg Isenberg (4:53)

Yeah, exactly. So tinkered from, you know, 13 to 18 or so. Went to McGill, studied, did double bachelors in computer science and international development. And but never stopped tinkering basically, and ended up, you know, creating an agency with a couple of friends.

Where we designed just really cool apps and websites. And then we also built our own. So we did, you know, we designed techgrunch.com. We designed a lot of like really interesting, above our weight kind of, you know, apps and websites. And then we took those learnings and we built our own startups. So we built stuff like startcooking.com, which was one of the biggest video cooking sites on the internet. Or we built a network of, you know, financial education websites that ended up getting acquired or just like we would basically find ideas and we would build them ourselves. And I dropped out of McGill at that time.