How I Built a $10M HoldCo of 6 Internet Businesses (100% Bootstrapped) | Greg Isenberg Interview

PrivatEquityGuy (0:00)

My guest today is Greg Isenberg. He's the founder of Holding Company of Internet Businesses, which does eight figures in revenue. And to be even more specific, Holding Company of Community-Based Internet Businesses. Thanks a lot, Greg, for coming to the HoldCo Builders show.

Greg Isenberg (0:16)

Stoked to talk all things holding companies with you.

PrivatEquityGuy (0:20)

Perfect. Let's start with you sharing your background, starting all the way from graduating from university.

Greg Isenberg (0:29)

Well, the first thing is I went to university but I never graduated. So I went to, I'm Canadian, I went to a school called McGill University. It's one of the best schools in the country. I was studying computer science, but I was building startups while I was doing it. And I remember it was in 2008, 2009, App Store had just come out, and I was designing and building mobile apps. And I remember going to one of my programming classes and asking my teacher why we weren't learning Objective C. Objective C was the programming language of the time that helped build mobile apps. And he was like, oh, you know, that's not going to make it into the course curriculum for five or 10 years. And I just remember thinking, well, that doesn't make sense. Here we're on the cusp of one of the greatest paradigm shifts ever, the mobile phone app store. And we're learning to develop for desktop software. Like desktop is about to die. And that along with one of my businesses starting to take off was when I realized, you know what? I can learn more outside of school than I can inside of school. And I dropped out. So since then, it's been a journey of venture-backed startups. I've started three venture-backed startups, sold all three.

My last exit was to WeWork, which was famous for raising, I think, $20-plus billion and spending all of it. Their market cap today is $280 million. So that's a big change. And that has led me to my HoldCo, or what I call multi-preneurship journey, owning a portfolio of internet-based businesses where we're bootstrap or self-funded.

PrivatEquityGuy (2:41)

Maybe talking a little bit about VC, back to the startups you founded, because as you said, you've started, you've sold three businesses. Obviously, you know something which many people don't because they try and keep starting those different businesses, different ideas, different niches, and they pretty much fail, like 100%. What did you learn from the first one, which helped you to fund and start the second one and the third one?

Greg Isenberg (3:13)

I mean, the game of entrepreneurship is like, people think it's like maybe a linear graph, but it's really more in terms of learnings, but it's really more of like a step function. So I feel like every startup that you do, you have just this massive firehose of learnings that come to you. So the massive firehose of learnings I had from Startup One and the big step I made was, honestly was selling too early. So I started the business and I sold it 11 months after I started it to a company called StumbleUpon, which at the time was one of the largest social networks at the time. It was actually started by Garrett Camp, the co-founder of Uber. It was a great experience. I raised a little bit of venture for it. I sold it. But from that, I actually moved to San Francisco.

Our board of directors at StumbleUpon, who I worked very closely with, were these legends. These guys like Ram Sharam, who's on the board of Google, David Hornick, Samir Gandhi from Excel, these legends. I got to really learn, and I had another step function, where I realized I wasn't thinking big enough for startup number one. So then I started another one and started another one. But yeah, I think the biggest learning was just that a startup isn't one big learning, it's really just a fire hose of learnings.

And it's something that isn't like a book where there's an end to a book, it just continues and continues and continues. And for example, I just came out of Love Him or Hate Him, but there's a motivational speaker called Tony Robbins that I was just at an event with him. And the guy's worth almost a billion dollars, and he's actually a HoldCo entrepreneur or multi-preneur. He's got a hundred plus companies that he co-owns. And it's like, why does a guy like that still like, he's still doing these seminars? Like, why is he still working so hard flying around? He was in Europe last week. Why is he working so hard? It's because he loves the step function. He's addicted to the step function, and I'm sure he also loves providing value. But yeah, I'm obviously not comparing myself to Tony Robbins, but I am comparing the journey that I have had has been a step function each way.