Serial Founder Q&A with Greg Isenberg

Can you please introduce yourself with recent updates as if you were catching up with an old friend?

I just got married. I actually proposed and got married all within 45 days or something. So it’s been really quick. I know some people might be thinking that she's pregnant. No, that's not the case. We just wanted to have a very very small wedding and we had a fall wedding. And we were in Japan for a month. And I just got back and Japan is a special place.

I met my wife at a friend’s dinner party in Miami in 2019. She was sitting next to me. So just through common friends and got to know each other. And when you know, you know, that's amazing.

Who has impacted you the most in your life? How and why?

Other than my grandfather, my late grandfather was an entrepreneur and he used to take me around. Earlier on, he struggled in the different real estate projects that he was involved in, and just like seeing it first hand, it's really, really made me see opportunities and entrepreneurship and how he treated people with kindness and how you can build a business of kindness. And always thinking about the community too. So he impacted me the most, and I guess the why is this because a light bulb went off and I could do something similar.

You started a business and dropped out of college. Could you please tell me more about your origin story? What inspired this idea and when did you decide to pursue this full-time?

When I was growing up, other kids’ heroes were Wayne Gretzky and Michael Jordan at the time. My heroes were people like Bill Gates and Steve Jobs. People like that. Nerds. So in the early 2000s, when the internet was starting to mature, I just started creating a bunch of essentially blogs and a bunch of different niche communities. So I'd create like, a video game blog or focus on Nintendo, for example, and then I would add forums to it. 

So it’s the combination of niche plus social was always something that I’ve been doing, and still do it basically for the day. And I spent my teenage years building these things. When I went to McGill University in Canada, I started doing this for other people like I did. 

I just started doing their design, designing these extreme product people. And it started getting big. So I partnered with some brands and we built an agency together. Before I knew it, I was helping work with TechCrunch and AOL and all these big companies and I was just actually studying computer science. That’s when I realized that I'm learning more doing the side stuff than I am in school. 

I remember the iPhone had just come out in 2008. And there were no courses on iPhone development. It’s like the biggest thing in the world like GPT store came out today. 

To summarize, I started working with big, big names and realized that my informal education surpassed my formal education so I dropped out.

What are your hobbies?

I love playing tennis. I love playing music and listening to music and getting to know musicians.

What are some things people normally don’t know about you?

Maybe I live really beneath my means.

For example, I just picked someone up from the airport this morning. And it's someone I work with, and he was just expecting (you know, I live in Miami) maybe I pick him up in like a Porsche 911 or something, But it’s a 10 year old Volvo and he said “I didn’t expect that”. 

So I’m quite simple in that in that sense, like I just really like my hobbies and spending time with friends and family.

How did you become an Advisor for TikTok and Reddit? What’s the backstory?

It’s a long story, but basically I had built a video discovery app back in the day. We had worked at YouTube and for whatever reason, I don't know how but we got connected when I was running Islands, which was a discord for college campuses. At that time, TikTok was trying to age up and change for better safety perception. There was the talk to sell our company but then maybe we slipped out the pipe. We ended up not selling to TikTok but I really got behind TikTok’s mission and had so much respect for how they were thinking about things. Then the CMO invited me to come onboard as an advisor and helped them think about growth. And it was such a great experience, and I really loved the team there. With reddit similar things happened. I was talking to Reddit team about an acquisition and I got to know the team through that.

So I guess the lesson is through acquisition, you can make a lot of friends even if they don't end up buying your company. Because we ended up selling to WeWork and that was that was my experience there. When you think about selling a company, you usually think of either they’re gonna do a deal or not, but you don’t realize that there are actually a lot more ways that you could end up working with these people or even just becoming their friend.