Shaikin: Hey, young athletes: Would you trust this former Dodgers pitcher to manage your money?

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For Ross Stripling, baseball was something of an accidental career.

He joined the Texas A&M team as a walk-on and studied business finance, hoping to get a master’s degree. After his third year of college, he turned down a substantial bonus from the Colorado Rockies. After graduating, he signed with the Dodgers for a significant bonus, but unfortunately, an elbow injury after just one season in the minor leagues ended his baseball career.

He was 24. He was at peace. He called home.

“I believe the best course of action is to admit I pursued baseball and now move forward with my life,” he explained to his father.

Dodgers

Los Angeles Dodgers pitcher Blake Snell will not start on Friday against the Angels. This comes shortly after he returned to the team following time on the injured list and a period of rehabilitation.

Dodgers fans will remember Ross Stripling’s career well. He almost threw a no-hitter in his very first major league game, but manager Dave Roberts took him out with just five outs remaining. Over nine seasons, including five with the Dodgers, Stripling achieved significant milestones, pitching in both the All-Star Game and the World Series. He even had a game where his jersey playfully read “Chicken Strip” instead of his name.

His father wisely advised him to stay positive. When a Tommy John surgery threatened his baseball career, his father suggested he use the recovery time to consider other possibilities. His grandfather then helped him secure an internship at an investment firm, allowing him to explore a career outside of sports.

Five years ago, Stripling and his former mentor started their own financial company, Skyward Financial. Now, almost two years after his last professional baseball game, Stripling is launching a new initiative: helping young athletes manage their finances. He plans to use his own experience to show them how to safeguard their money and create lasting wealth for their families.

Look, I’m not looking to live a life like Jordan Belfort from ‘The Wolf of Wall Street,’ that’s for sure. This is really about wanting to make a real difference for kids and their families. Honestly, the world I’m working in has changed so quickly, and it feels like it’s gotten totally out of control, so I want to help bring some balance back.

I was so impressed to hear how Matthew Houston described Stripling’s internship interview – apparently, he completely wowed the brokers! Houston said Stripling really blew them away.

According to Houston, the man arrived with a small, two-inch folder packed with stock reports he’d written while traveling on buses with minor league teams. He shared a couple of these reports with them, and they were surprisingly accurate, professional-level analyses of stocks, which really shocked everyone.

Stripling quickly became a licensed broker. Houston believes that over the last ten years, he and Stripling exchanged texts about the market and their clients roughly 25 to 50 times each day. One evening, Houston was watching Stripling pitch in a baseball game on TV. Soon after the game finished, he received a text message notification.

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I had just watched him on television when someone asked me about Celgene and Gilead, two companies in the biotech industry,” Houston explained. “It completely surprised me.

It’s well known that professional athletes earn a lot of money, and financial companies are eager to manage it. Some firms even hire retired athletes to help them attract current players as clients.

Marc Isenberg, who used to lead financial education for athletes at Morgan Stanley and wrote the book “Money Players,” offered Stripling his best wishes but cautioned that he’ll be up against tough competition from larger, more established financial firms.

The market is too crowded,” Isenberg explained. “Nearly all Wall Street companies now have a dedicated team focused on working with athletes and entertainers, all competing for the same clients.”

It’s not just the biggest stars either. Stripling spoke with a basketball agent who revealed that he works with 24 college players, and each of them uses a different financial advisor.

Stripling’s advice isn’t groundbreaking: prioritize saving and investing wisely today, rather than spending extravagantly, to build wealth throughout your career and beyond.

Stripling thinks he can succeed by focusing on young athletes who are now receiving large sums of money – from things like professional draft bonuses, college revenue sharing, and endorsements.

I’ve watched some players drafted in the first round quickly waste their money on things like cars, houses, and gambling. But I’ve also seen players like Corey Seager, who were drafted high and seem to have saved every penny of their signing bonus.

When speaking to young athletes – and the professional and college teams who might hire him – Stripling’s company shares a story about a baseball player who received a $900,000 signing bonus. After taxes, the player spent $500,000 on a red Lamborghini. However, if he had invested that same $500,000 in a fund mirroring the S&P 500 for 30 years, it would have grown to $8.6 million.

“That was the dumbest decision I’ve ever seen anyone make,” Stripling said.

I’ve learned a lot from my time in the locker room, and I believe my experiences as a player will connect with people more genuinely than someone from a financial firm simply talking about investments.

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Stripling is eager to address the Dodgers players during their spring training morning meetings, which cover a wide range of topics like safety, security, and social media guidelines.

I’m interested in finding out more, but I’d also be willing to let him work with the team. I have a lot of confidence in him.

Stripling, like all financial professionals, has a record on file with federal regulators. As part of the application process, brokers must detail their employment history for the past decade. What sets Stripling apart from other wealth managers and advisors is that his record begins with, “LA Dodgers, Pitcher,” revealing his previous career as a baseball player.

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2026-05-17 14:31