Financial Wizard Rudy Cline-Thomas Shares The Secrets Behind His Winning Streak

Phebe Wahl | April 30, 2020 | People National


Allbirds, Uber, GOAT, Thrive Global, Zoom, Casper—Rudy Cline-Thomas knows how to pick a winner. As the founder and managing partner of Mastry Inc. (mastryinc.‌com), the financial baller specializes in scouting technology, retail, media and investment opportunities for his partners, which range from startups and Fortune 500 companies to professional athletes. Cline-Thomas began his career as a sports agent, but quickly pivoted to working with players as a financial adviser. We checked in for his rules of the game.

What sparked your interest in finance? I was a finance and business major in college. I had always been interested in investing since the seventh grade when I won a stock-picking contest my math teacher held in class.

You seem to have a magic touch for choosing amazing companies. What are your tricks for picking winners? I wouldn’t call it a trick. I’ve picked a lot of losers as well. I think the trick is being able to learn from the losers. The losers, I say, are a ‘paid education.’

What do you find attractive when you’re looking for new companies in which to invest? Most important is market size. How big is the market the companies are trying to go after? That’s No. 1. No. 2 is: What competitive advantage does the company have versus companies that are eventually going to the market and/or companies already in the market? Warren Buffett likes to call it a moat. So are there any moats that this company has versus the competition? And No. 3 is the founders. Who are they as people? Do they have any experience executing an idea, or do they have any experience scaling an operation and/or business? This is very, very important. It’s one thing to have an idea; it’s another to execute.

How did you get involved in sports? My first job out of school was as a sports agent. I worked at an agency in D.C., and I interned in the NBA before my senior year of college—so I got a head start to the whole sports community.

What excites you about where tech is headed? Everyone is big on data and analytics and how important it is for so many different businesses and industries. What excites me is how it’s being used and what companies are going to utilize it—breaking down walls or white space we never thought of. That’s very interesting and exciting to me. A lot of people are afraid of it—as it attributes to artificial intelligence—and the possible determinants of that. Hopefully we don’t use it the wrong way. But how it can be used to better our lives and make things easier is extremely exciting. The companies leading the charge are well-oiled machines and are going to push us into the next phase.

What’s next? I’m going to get more of my guys and more of my network involved in tech. My network now is not just athletes. I am very close to many of the top CEOs in the world, a lot of whom have run some of the biggest companies that aren’t in tech. So a lot of them lean on me to get them up to speed, mostly in investing and sharing my deal flow with them. That’s really exciting, and I’m looking forward to doing more of that in 2020. I am also very interested in educating—not only athletes, but my culture—on the opportunities that are out there that are not currently available to them and being a beacon of information. We are trying to figure out ways to extend the network to not only being advisers to these professional athletes who make all this money. I’m looking for different ways to bridge that gap and for those who don’t have access, seeing if there’s a way we can give them access as well. That’s extremely important to me—more important than anything else.

What advice do you give to young people who find what you do fascinating? Let your curiosity lead you. There’s no game plan; there’s no template. If you asked me four months ago if I knew what was going to be ahead of me or if I am now where I thought I would be, the answer is no—good, bad or indifferent. Again, if you asked me two years ago, three years ago, I’d tell you no way. Make the most out of every single day, be as curious as possible and understand how important relationships are. Relationships are more important than what you read and/or write.

What are four things you do, or try to do, every day? I always wake up before the sun. I speak to my mother every single day. I read The Wall Street Journal. I always read the Financial Times every single day. I make sure I live every day in the moment, and I live every day like it’s my last.

Tags: finance

Photography by: Robyn Twomey


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