I Spent 100+ Hours with 4 Billionaires (here’s what I learned)
28 Jan 2026 · 8 min
Dan Martell spent 100+ hours with Mark Cuban, Richard Branson, Travis Kalanick, and Tobi Lütke. Cuban stresses network plus knowledge plus grit. Kalanick obsesses over single-minded focus and management leverage. Lütke treats people development like software systems to scale.
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Welcome to the Growth Stacking Podcast. This is Dan Martell. I spent over a hundred hours with four billionaires and here's what I learned. The first one is Mark Cuban. I first met Mark, long story, but I decided to cold email a bunch of billionaires when I was in my 20s. And I was asking these questions like, you know, should you focus on your network, what you know, or your grit? Obviously most of them didn't reply, but Mark actually replied back then and he said, doing all three while everybody's trying to pick one. And I remember just how, like that's crazy. A billionaire replied to me. And it wasn't until a decade later I was building a company called Clarity and we were on a site called Angelist and Naval. The founder pushed it to all of the members and Mark was obviously on there. We started an email exchange. He asked questions about the product and the vision and the roadmap and the team and all these things. And after about 13 or 14 email replies, he said, I'm in for a quarter million bucks. So. So a few things I wanna share. Number one, he loves the art of the deal. If you've seen him on Shark Tank, you can tell that he loves the entrepreneurial journey, the spirit. He also absolutely loves the entrepreneurial game, the strategy, the tactics, the different ways you can enter a market. How can you position the product a hundred percent of the time? When I sent an investor update email, he always replied. And then finally, you have to have the drive. You gotta want to grow, you have to have a desire. You have to be engaged in the game of business and have that level of drive. That's what Mark taught me. The second billionaire is Richard Branson. This is such a crazy story. I want you to understand. I grew up in a small town in eastern Canada. The fact that I got an opportunity to spend a week with him at his home in Switzerland still blows my mind. A few years prior, I helped this guy out who had a startup and he appreciated so much that he ended up raising from Richard. And Richard was going on vacation to his place in Switzerland and asked him to invite people that he thought Richard might find interesting. And I got the email and honestly I was like looking at this like, is this an April Fool's joke? Like, is this real? And it wasn't until I was sitting in the living room and Richard walked out that my brain allowed me to believe. Oh my gosh, this is happening. Tim Ferriss was there. Brian Johnson from the Biohacker Blueprint, the co founder of Stripe. So many incredible Entrepreneurs and then me, Dan Martell. I was like, okay, I better show up, ask great questions, and just be generally helpful to everybody. There. Three core things. One was watching him interact with his executive assistant, Helen. I've talked about this several times. I wrote about him in my book Buyback youk Time. But there was just something magical to watch him work through her to move all of the businesses forward. And then once that meeting in the morning was done, he had the rest of his day to pursue his passions. The other thing that was interesting about Richard is watching how curious he was to learn from other people. In many ways, that's kind of how he lives his life. If you've seen Necker island and many of his other properties, they're all boutique hotels. And that's probably because he likes to have people around that he can learn from. The most powerful thing he ever said to me, we were having dinner one night, and I asked him, I said, hey, when it comes to business, what's the skill? What's the strategy? What's the one thing people should focus on? And he replied, brand. And I'll be honest with you, at the time, I didn't really understand it. You know, I build companies and exit them. Like, why would I invest in a brand? What's crazy is I wish I would have really f to figure it out. And I learned it from Richard. The third is a guy named Travis Kalanick, and he was the founder and CEO of Uber. Now, the way I met Travis is kind of interesting because Travis had just sold his company, Red Swoosh, to akamai, this old CDN company. And there was an event called the TechCrunch 50. My friend Steve Poland was coming to San Francisco for the event. And I guess Travis posted on Twitter back in the day, if anybody needed a place to sleep, let me know. You can crash on my jam pad. And Steve was one of those people. And it wasn't until I was raising money for Flowtown that I reached back out to him. Cause he was an investor, and he invited us to the jam pad. And it was in that moment that I realized who Travis was. There are some serious lessons that I learned by spending a lot of time with Travis that I want to share with you that I know is the reason why Uber became what it became. One is when you decide, decide to build the business, go laser focus. I mean, it was pretty much like a light switch. The moment that Travis took over CEOing of Uber, every relationship, every conversation, any other extracurricular activity, it all went to zero. I mean, he was an advisor to our company, but it went from almost daily weekly communication to we can't get a hold of Travis. He dealt with the New York City mafia, he dealt with the politicians. I mean, whether you know or agree with some of the tactics they use, the thing that I learned from Travis, Travis is that if you want to change the world, you have to be so friggin focused on one singular outcome that you have to be willing to sacrifice everything else. And some people are just not willing to do that. Remember I ran into him at an event at that point, probably four years after the start date of Uber. They had hired over 5,000 people. And I remember going like, dude, how do you even do that? And he gave me some great advice. He said, well, the truth is I only have five direct reports and I work through those five direct reports to execute that. I just have to ask myself, do I have management bandwidth? And then my job is to make sure I have the right people. If I don't, I got to coach them up. And to the degree that I learned to work through them, I can do things like hire 5,000 people in four years. And I'm just like, whoa, what an interesting mental model and a concept. At one point he was facing 50 years in jail. He was essentially violating all the taxi laws or whatever, transportation laws. But he kept putting, pushing. You asked about it, he said, I'm going to raise so much money that by the time I have to go to court, I'll just hire the best lawyers to get me out of it and even change the laws to make sure that he doesn't go to jail. That's how creative and intense he was. The fourth billionaire is Toby Luca. He's the founder of Shopify. An incredible story of growth and determination competing against one of the biggest companies in the world, Amazon. I met Toby online because he had built a product called Active Merchant. We all use that. We kind of ran into each other through different circles and at one point he actually invited me up to Ottawa to speak at one of their fresh founders events. I got to see Shopify go from small 25, 35 people to, you know, thousands of employees in their HQ today. This is the one thing that I got from Toby that every entrepreneur needs to hear that can transform their whole business. He applied software development principles to people development within a company in big companies. On the tech side, they have a thing called DevOps, a department that's dedicated to improving the efficiency of the engineering team, the developers. And what he did is he created engines of growth in not only the engineering side, which is world class, but also in the HR side and the marketing side and the customer success side and all these different departments within the business. I mean, they were one of the first companies to hire executive coaches for their leadership team because he just felt like if everybody's hiring the same people, the company that has the ability to support and unlock the creative and execution of their team is going to win. That was such a huge idea that I've applied in every one of my companies. Why I keep telling people, we build the people, the people build the business. And if you apply that to your business, you're going to unlock your talent. That is my favorite thing that when I look back on my time talking with Toby, that he, he's done that nobody else has figured out how to do at that level. That's what I learned from a hundred hours with four billionaires. Now, if you want to learn how CEOs schedule their day, click the video and I'll see you on the other side. If you like this week's episode, be sure to visit itunes, leave a review that'll help us get in front of other founders just like you. And if you're looking for more resources and video trainings, be sure to check out dan martell2lsmartel.com to subscribe. Keep up the hustle, keep stacking your growth, and I'll see you in next Monday's episode. Peace. Grow Peace. Bye Bye.