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710: (Solo) I Asked 10 Billionaires The Same Question - Here's What They Said artwork

710: (Solo) I Asked 10 Billionaires The Same Question - Here's What They Said

The Foundr Podcast with Nathan Chan

September 28, 2026

Over 12 years of interviewing more than 100 billionaires, I started asking every one of them the same question: if you lost everything tomorrow, the money, the brand, the team, and you had to start completely from scratch, what would you do first?

Speakers Nathan Chan

TopicsEntrepreneurshipBusinessMarketing

Nathan Chan (0:01)

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Welcome back to another episode of the Foundr Solo to Solo Podcast. I share my lessons building Foundr for the past 10 years. I get so many questions. This is the number one thing that people ask me, like what are the pearls of wisdom that you've learnt from interviewing so many successful people? I've interviewed over 100 billionaires and I've been doing this for 12 years. People like Richard Branson, Mark Cuban, Drew Houston, Kendra Scott, people who've built billion dollar companies from absolutely nothing. At some point during one of these conversations, I start asking the same question. If you'd lost everything tomorrow, the money, the brand, the team and you had to start completely from scratch, what would you do first? I'm going to share with you 10 billionaires, 10 different industries, 10 different personalities and their exact answers. Wildly different on the surface but underneath, every single one of them was the exact same theme. It's probably not what you think, so this is what they told me.

SPEAKER_2 (1:57)

Hear the stories, learn the proven methods and accelerate your growth and future through entrepreneurship. Welcome to The Foundr Podcast with Nathan Chan.

Nathan Chan (2:11)

All right, so let's kick it off. Number one, Richard Branson, the first person I asked this question to. I'll never forget, this was one of our most earliest cover stories at Foundr. I was literally working at my parents' house in their basement in Melbourne, no credibility, no connections, no audience. I somehow got Richard Branson. So his answer was instant, didn't even think about it. He said, I'd find the right people. That's it. Just got to give people a go. Let them go, have fun with it. No talk about strategy, no talk about a business plan, no market research. He's always starting with people and he's an incredible leader. He runs like a 100 different companies, right? And he's got one assistant, you see, he lives on his island and he leaves other people to run this stuff.

It's incredible how he thinks about people management, people leadership. And when you think about it, that's how Virgin was built. Every time Branson entered a new industry, airlines, music space, the first thing he did was find someone brilliant and back them. He didn't try to become an expert in every field. He found the experts and got out of their way. And to be honest, this is something that I need to do a better job at. In my history and my career, I could do a better job at stop trying to micromanage, let go.

And this is something I need to keep reminding myself because I've got an amazing team. And sometimes I just get two hands on because I've got a passion. And it's something that I'm still working through as a leader. All right, number two, Drew Houston, the founder and CEO of Dropbox.

He built Dropbox into a company worth billions and billions of dollars listed on the Nasdaq. It's one of the most visited and used tools on the Internet. And he gave me a completely different answer. He said, the first thing you do is learn. He used this phrase that stuck with me. Founders have to be learning machines. The moment you stop learning, the business starts dying. And he didn't mean take a course or read a book. He meant develop the habits of relentless curiosity, study what's working, study what's not, talk to customers, reverse-engineer the competition, make learning your operating system. And what I took from that is the gap between where you are and where you want to be almost always is a knowledge gap, a knowledge and a wisdom gap. And the fastest founders close that gap faster than anyone else. All right, number three, John Paul DeGioria, JP. He's built two separate billion dollar brands, Paul Mitchell Hair Products and Patron Tequila. And this guy was a guy who was homeless.

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