Jay trader: Toronto pitcher is a stocks whiz

TORONTO -- Ross Stripling has been monitoring the market this offseason, where timely investments and trades set up long-term success. We’re not talking about baseball, though.

Many know Stripling as the Blue Jays right-hander, and that’s how he’d like to be known. Baseball is his craft and the mound is his stage, which is where he focuses his energy. Ballplayers have downtime, though, and how Stripling spends his makes him one of the game’s most unique personalities.

Stripling is a financial advisor with B. Riley Wealth Management, with $10 million in assets under his management. This all began as a fallback plan for Stripling, who graduated from Texas A&M University with a bachelor’s degree in finance, back in 2014 when he underwent Tommy John surgery.

“I’m staring 14 months of rehab in the face in Arizona,” Stripling said. “I have my college degree. I’m a busybody by nature, I’m always doing something. I wanted to be productive. I didn’t just want to sit around and drink beers by the pool and play video games for 14 months, even though I still did plenty of that. I wanted to make something of that time.”

Given his background and own personal interest in finance, Stripling started to take the first steps. His grandfather had invested with B. Riley Wealth Management for 40 years, so Stripling was put in touch with Matthew Houston, their managing director of investments. Houston’s father had managed Stripling’s grandfather’s investments, and while Stripling was just looking to shadow Houston and learn more about the industry, they saw a greater opportunity.

Being a professional athlete, Stripling’s network includes plenty of people who aren’t only making money, but looking to invest it wisely to protect themselves and their families long term. Pro sports are filled with cautionary tales of athletes who have spent too much, too soon, or been given poor advice on how to invest their earnings, and Stripling saw an opportunity to change that for some of the people around him.

Back then, though, Stripling just saw the potential. Since then, it’s boomed.

“Tenfold. It’s more and more every year,” Stripling said. “When I debuted in 2016, it was like, ‘Strip knows a little bit about the market, maybe I’ll ask him something.’ Now, multiple teammates text me every day about stuff. I don’t manage their money, they’re just trying to get knowledge themselves, they’re interested in it, or maybe their money manager bought them a stock or a bond that they’re not familiar with. That’s been the most fun about this whole thing, being a soundboard for people as they try to learn."

Whether it’s baseball or the stock market, Stripling believes that having the right information is just the start. Understanding that information and engaging with it in a way that makes sense for you on an individual level is what makes this whole thing click.

That can be overwhelming for athletes, some of whom come into money rather suddenly. In nearly all of those cases, too, they’re entering that world without any of the finance background that Stripling possesses.

Simply put, it's complicated. Really complicated.

“When you make a lot of money, doors open for opportunities elsewhere, whether it’s private equity, commercial real estate, things like that,” Stripling explained. “When you get into opportunities like that, there’s a lot off random jargon that will come at you like IRR [internal rate of return] and all of these things that people don’t understand. They’ll come to me and ask, ‘Hey, does this look like a good deal? This is what my portfolio looks like right now.’ That’s what is fun, to answer and help guys learn.”

It’s easy to assume from this that Stripling is all data, all the time, with numbers dancing and flashing across his mind like a scene from "A Beautiful Mind." That’s not really the case, though.

Stripling has the data and believes in the data, but on the mound, he also knows there’s a line where pitchers can tiptoe into overanalysis. How about an example using a Yankees hitter who cashed in on the other market this offseason?

“If you want to know what DJ LeMahieu hits against 2-1 sliders, you can find that information. But now, if I’m facing DJ LeMahieu with a man on second in the sixth inning and I’ve got a billion things running through my head, that’s going to bog me down,” Stripling said. “You’ve got to really pick and choose the information you want, and a stock is the same. Yes, you want the big picture, but you’re going to find your avenue that you believe in, whether it’s growth numbers, earning numbers, EPS [earning per share] growth or whatever you’re looking at that fits your investing strategy. It’s the same when you’re scouting a lineup."

This spring, a normal day might see Stripling checking the market from home as it opens before he heads to the facility, where the real work happens. Some nights, he’ll let himself relax. On others, though, he puts on another hat as the co-host of the Big Swing Podcast.

Pitcher. Financial analyst. Podcast host.

Along with his co-host and friend Cooper Surles, the Big Swing Podcast has attracted major guests and generated a real following. Stripling has already started to hear from more Canadian listeners, too, since joining the Blue Jays. He’s recently produced episodes with Toronto teammates Bo Bichette, Ryan Borucki and Robbie Ray.

Like anything else, Stripling wanted it done right.

“I’m not going to do anything half-[baked]. If we’re going to do it, we’re going to do our best,” Stripling said, thinking back to their launch. “We’re going to research, be prepared, find guests with our network that make sense. We’re not going to annoy people, but we’re going to try to have a guest every week. It’s been two years and over 100 episodes and we’re still plugging along. I don’t view it as a job, I view it as a one-hour escape a week where I get to sit down with my buddy and someone really interesting.”

The show has come a long way from when Stripling and Surles started with one microphone sitting in the middle of the table. Their podcast has joined the Jam Street Media network, which Stripling says has helped with the structure and production of the show, too.

Their first episode dropped in early 2019, when Stripling and Surles kicked things off with their picks for Super Bowl LIII, which the Patriots won, 13-3, over the Rams. On Wednesday, their most recent episode dropped and, among other things, they’re breaking down another Tom Brady Super Bowl, this time between the Bucs and Chiefs. With that touchpoint two years in, Stripling dug up Episode 1.

“We went back and listened to that first one and it is so bad,” Stripling laughed.

Stripling will soon be adding another title to this growing list, too. He and his wife, Shelby, are expecting their first child in the coming weeks.

Then it’s off to Spring Training for Stripling, who is entering his sixth season in the big leagues and first full season with the Blue Jays. The right-hander has been building up with bullpens recently and added a long-toss program to his offseason at the suggestion of Matt Buschmann, the club’s bullpen coach.

Stripling fully intends to build up as a starter and win a job in the rotation, which he’ll have an opportunity to do amid a crowded depth group. Just like off the field, though, Stripling can be valuable in a variety of roles.