Book Excerpt: David Grutman’s Prince Play Is Bigger Than Tennis

In his new book, Grutman breaks down his hands-on investment strategy and role in reviving Prince as a lifestyle brand, using tennis, cultural influence, and strategic collaborations.

The following is an excerpt from ‘Take It Personal: How to Succeed by Building Relationships and Playing the Long Game’ by David Grutman, available now.

The key for me when I’m considering working with a brand is this: It has to make sense in my ecosystem. I don’t just invest in things because they might blow up. I want to know I can help them blow up. I want to be able to put something in my venues, wear it, taste it, use it, show it to my audience. That’s what makes me valuable to these companies. I’m not a silent investor. I’m not the guy who wires money and disappears. I’m involved. Over the years I’ve made a lot of friends, and a lot of those friends have millions of followers on social media. If I’m investing in a company, I want the product to be something my friends are genuinely excited to use and post about.

A few years ago, my team and I sat down and came up with a plan: “Let’s pick a brand. Let’s push it together. Let’s own it together.” I was looking for a lifestyle brand, but it was important to me to pick something that felt authentically me, and I landed on Prince, the tennis brand. It had that Americana vibe—you’d see it at country clubs, and it reminded me of the ’80s and ’90s when Andre Agassi was the biggest tennis player in the world and also a total rock star. When the opportunity came up to become part of Prince, I thought, “Why not?” I might not have been a tennis fanatic, but I remembered the brand and its potential. We could make it cool again.

So I partnered with Prince. At first, I focused more on the off-court lifestyle side of things. I wasn’t trying to compete with Nike or Wilson on their turf. That’s not the game I play. I play the cultural relevance game. I’d send gear out to celebrities and influencers. We didn’t sign contracts with dedicated brand ambassadors because, honestly, we couldn’t afford them like the other brands anyway. But I’d send hundreds of boxes, handwritten notes included, and then just wait to see if they posted about it on social media. I knew there was a good chance they’d be rocking Prince merch courtesy of yours truly.

Through this, I developed a relationship with the Bollettieri family — the best tennis coaches in history. That sparked my own interest in playing tennis. Now, I play tennis regularly with some of the top twenty players in the world, and I always make sure Prince gear is on the court with them. It’s wild to me — I’ll hop on Instagram and see Grand Slam winners sharing clips of themselves hitting unreal shots in Prince outfits while I post about being a dedicated player but a regular guy, trying to hit against someone who’s literally won at Wimbledon. Tennis has become an obsession. I play every day now, and I care as much about what happens on the court as off it. The first time I really played, at Amanyara in Turks and Caicos, it was love at first serve. I was just hitting the ball with a trainer, and suddenly I felt that topspin. I’m hooked now. And once you get passionate about something like that, it doesn’t feel like something you have to balance anymore. It just feels right — like an obvious part of your life. Now, every day, I’m so excited to play. I remember going to the French Open to support my friend Stan Wawrinka, a Swiss tennis player. I thought I’d be there for an hour, but it turned into five full hours. The heat was intense; you couldn’t move. But then, fast forward to last summer when I was a total tennis freak. I went to Wimbledon and other tournaments, and it was totally different. I wanted more than just five hours of tennis. The whole experience had changed because I was invested.

Prince itself is doing incredibly well. We’ve done collections with brands like Brooks Brothers, Sporty & Rich, Happy Dad, and other big fashion brands. It’s the same philosophy I honed at Velvet Lounge all those years ago — building collaborations with other brands helps build our brand equity. That’s what I mean when I say I incorporate everything into my lifestyle. If I’m into it, I’ll sell it better than anybody else. This isn’t just about tennis gear; it’s about the whole culture around it.

Reebok made these special sneakers for me as part of a promotional campaign, and I started talking with them. I was like, “Why don’t we do a Prince Reebok?” Back in the day, tennis player Michael Chang, a big Prince guy, also worked with Reebok, and it felt like an organic connection. It turned out to be a really cool collaboration for me. I thought it was next level — another iconic brand excited to work with Prince. That felt really rewarding.

Tennis itself is such a social sport. It really puts you in the perfect position to make connections. I’ve built so many great relationships on the tennis court. People come and train with me for an hour, we play some tennis, and our connections become stronger and more organic. It’s incredible how much business flow I get from the court. Tennis has become a real platform for me, not just for the love of the game but for connecting with people in a fun space.

I’m most excited about keeping that momentum going. We’re not just selling rackets and track suits; we’re selling a true lifestyle brand. I’ve gone from someone who barely followed the sport to someone who lives it, breathes it, and uses it as a platform for cultural relevance and business. Prince has become a major part of my lifestyle and my business, and I’m excited to see where we can take it next.