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Amar Gupta, left, Denis Shapovalov and Josh Barr.Handout

Last month, when Denis Shapovalov lost his cool during a match at the Italian Open and began swearing at the crowd, a pair of Toronto entrepreneurs were watching more closely than mere casual hometown fans. That’s because, shortly before the tournament, Amar Gupta and Josh Barr had signed a deal to bring on the Canadian men’s tennis star as an equity investor in brüst, their four-year-old company, which sells an innovative cold-brew coffee with enough protein for a full meal.

Still, in a recent interview, they insisted Shapovalov’s competitiveness was part of why they had gone into business with him. “We love his intensity, we love his aggressiveness,” Gupta said. “He has an edge to him that we’re aligned with, as a disruptive brand.”

In taking an ownership stake in brüst, and becoming a face of the company – or, in the new industry parlance, a “brand ambassador” – Shapovalov joins a rush of Canadian athletes who are flexing their growing market power, as investors in products and services they believe in, rather than mere paid spokespeople in advertising campaigns.

Not so long ago, athletes would wait until they hung up their skates (or cleats, or running shoes, etc) before going into business, accepting a sinecure in a bank that prized having a former star on staff, or maybe buying a car dealership. (One of the exceptions to the rule, of course, spawned an iconic Canadian company, after NHL defenceman Tim Horton opened a coffee-and-donut shop in Hamilton in 1964, while still playing for the Toronto Maple Leafs.) But for the most part, their business activities were limited to endorsement deals.

No longer. For several years now, a growing number of U.S.- and European-based athletes have caught the entrepreneurship bug. Canadian athletes based in their home country, limited by the smaller scale of Canadian businesses, had been shut out. (On Thursday, Forbes reported that, according to its calculations, LeBron James’s earnings had surpassed US$1-billion, including an estimated US$900-million in endorsement and investments.) But now they are joining with a clutch of Canadian startups to strike long-term agreements that give them real power to affect a company’s fortunes.

“Influential people, whether they be athletes, whether they be celebrities, whether they be musicians, they have become much more educated over the years, and much more aware of their draw and their ability to influence brands and consumers,” said Tom Chapman, the head of commercial for tennis at the agency WME/IMG, who oversees the off-court business dealings of Shapovalov and his fellow Canadian Bianca Andreescu, as well as Serena Williams, Maria Sharapova, and others.

If Shapovalov, “is going to spend time generating buzz and awareness for a brand, and that company is going to grow, he wants to participate in the long-term upside of that, as opposed to making a few hundred thousand dollars a year in a kind of sponsorship format,” said Chapman, who noted the development is a reflection of athletes “betting on themselves.”

The Canadian gold-medal Olympian sprinter, Andre De Grasse, recently became an equity investor in Plantiga, a Vancouver-based company that makes smart insoles that track the amount of force an athlete uses in movement, whether walking, running, jumping, or landing after a jump shot.

Quin Sandler, the CEO of Plantiga, said he had seven athletes among his investors who had each put between $25,000 and $75,000 into the company. But just as important as the cash, he said, was that those athletes leveraged their elite networks to help grow the business, introducing Sandler to their former NCAA programs and the pro teams they play on. Sandler also said that the current Toronto Raptor (and MBA degree holder) Thaddeus Young, who holds equity in such companies as Coinbase, Airbnb, Space X, and the Toronto startup Trufan, connected him to a footwear company he’s invested in.

And Sandler said he expected some of his investor-athletes would do social-media posts about how Plantiga’s technology and data collection help them avoid injury. “That’s actually a critical part of our go-to-market strategy,” Sandler said. “Because that’s what I think is a big gap in the broader society. People just don’t know how they move.” Last year, De Grasse shot a video encouraging people to sign up for Plantiga’s beta test program.

Young was introduced to Plantiga by Randy Osei, a former business manager of pro basketball players (including Anthony Bennett) who now runs the Athlete Tech Group (ATG), a digital marketplace bridging the gap to the future of work for athletes. Osei said investors in ATG include the Lethbridge-born hockey player Kris Versteeg and the Mississauga, Ont.-born former NBAer Andrew Nicholson.

Osei said the athlete-investment revolution is a long time coming, given that the global sports industry is estimated to be worth about US$600-billion, after years of double-digit growth. “The biggest value creator, the athlete, is still seeing the smallest percentage of that growth.”

Some athlete investors are more involved than others. The brüst founders say that, as a big coffee drinker who is often pressed for time to get enough protein into his diet, Shapovalov will be a passionate and authentic ambassador for the product. They plan to include him in meetings with big accounts such as Loblaws, as well as retailers south of the border, when the company begins to move into the U.S. market, possibly later this year.

“We think it’ll be exciting for potential customer managers to see that Denis is truly a fan of the product, that he uses it in his daily life,” Gupta said. The company will also run “tennis with Denis” promotions, in which customers and clients can win the opportunity to play against Shapovalov.

Chapman cautions that not every pro athlete is cut out to be an active investor. “This model is not for everyone. It is very important that you do not forget the day job. The day job is practising, surrounding yourself with the best coaching staff in the world, performing at a high level, getting out on the court, winning tennis matches, and being successful. That is the bread and butter, that is the day job, and nothing whatsoever should detract from that.”

But Brian Levine, the president of Toronto-based Envision Sports and Entertainment, who represents De Grasse and also worked on behalf of brüst to sign Shapovalov, said investments are natural expressions of the athletic mindset. “Some athletes are laser focused on their sport and family and nothing else,” he told The Globe. “However, others find great personal fulfilment in being actively involved in other pursuits, including investments. It also helps keep them balanced. Maybe they have a bad game or get injured, but they can still look to success in an another arena. Athletes are highly competitive individuals, and many are looking to the business work as another field to compete in.”