“Fifteen of 21 medals were our athletes”: These private investors are bankrolling Team Canada’s Olympic champions

Another Olympics has come and gone. Between all the meme-able moments, heated rivalries and surges of national pride, Team Canada pulled 21 medals at Milano Cortina 2026. Compared with our 29 medals at Pyeongchang in 2018, it was a mild result—and somewhat disappointing for a country blanketed in snow half the year. The Canadian Olympic Committee has blamed the paltry podium count on funding shortfalls, and there’s been no shortage of talk about athletes struggling to finance their training and competitions.

Nevertheless, many of the medals coming home with Canadian athletes are evidence of a distinctly Toronto success story. Business leaders by day, Moez Kassam and Adrian Rocca have been moonlighting as Olympic fundraisers through their organization Great to Gold, which backed 55 of Canada’s Olympians this year—including Piper Gilles, Paul Poirier and Megan Oldham—all of whom were hand-picked for their medal-winning potential.

Kassam and Rocca raised around $650,000 for this year’s Olympics, mostly from private-sector backers willing to shell out to help Canada win big. Their strategy paid off: 15 of our 21 medals were won by Great to Gold athletes. The program’s success even caught the eye of Shopify founder Tobias Lütke and his wife, Fiona McKean, who announced a $1-million donation on the last day of the Games. Hopefully the funds will help Canada put up a better showing in 2028.

We caught up with the founders in Milan. Here, they break down their approach to championing athletes and explain why Canada needs this kind of program in the first place.

Let’s start with the origin story: what motivated you to found Great to Gold?

Moez Kassam: I joined the Canadian Olympic Foundation board five years ago, and I got Adrian to join a year or two later. The foundation is the fundraising arm of the Canadian Olympic Committee, so we’re responsible for funding athletes and securing them sponsorships. We do well at sponsorships, but there isn’t a lot of funding. The average athlete going to the games only gets about $26,000 a year from the government, and they’re responsible for raising the rest themselves.

Former Olympic rower Marnie McBean, one of our great Canadian athletes, was on the board with me, and she told me about some of the challenges young athletes were facing. I couldn’t believe it. These rowers were doing unbelievably well in competitions while working second jobs, worrying about car payments and such. I started wondering, If they’re doing that well with a headwind, what could they achieve if we got them some funding and turned it into a tailwind? Of course, Canada originally had Own the Podium, with the objective of helping Team Canada athletes win medals, starting with the Whistler Olympics in 2010. But the program’s goals have shifted since then from individual athlete sponsorships to funding sports bodies. So Adrian and I came together and developed a program to give last-mile funding to great athletes to help them get to the next level.

Do you two have any special connection to the Olympics?

Adrian Rocca: We’re Olympic junkies! I have very nostalgic memories of watching the Calgary Olympics in ’88. I was glued to the TV for two weeks. I would cheer for every Canadian. I’ve never felt more patriotic than over the past 12 months, so doubling down on a program like Great to Gold, for us, is really fitting.

Kassam: This is the time when the whole country comes together. With the precarious nature of what’s going on in the world, it’s so important now to have unity.

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I’m sure you’ve been keeping a tally of how many medals you’ve had a hand in. What’s your success rate?

Rocca: Our hit rate has been really great. In Paris, Canada won 27 medals, 17 of which were Great to Gold athletes. Going into Milano Cortina, we gave funding to 55 athletes and three teams, and 15 of the 21 medals were our athletes. The Olympics are the ultimate test of preparation under pressure. At that level, the gap between fourth and first is razor thin. We built Great to Gold to help bridge that final gap with smart, data-driven support. Seeing so many of Canada’s medals connected to the program is huge. But, honestly, medals aren’t just metrics. They represent families, coaches and years of sacrifice. The credit belongs to the athletes—we are so proud of all of them. If we helped tilt the odds even slightly in their favour, then we’ve done our job. Credit is also due to our donors and to the Canadian Olympic Foundation team.

Clearly, funding has a big impact on performance. Why is that? Is it all about clean eating and new equipment?

Rocca: One of the things that I was very naïve to is the stress that our athletes are under. They’re working two, three jobs; they’re stressed about how they’re going to put gas in the car next week, not to mention getting the right nutrition. And that should never happen on our watch. That should never happen on Canadian soil. Really, the program is about giving athletes some additional financial support, whether it’s putting food on the table or freeing them up for an extra training session—anything we can do to alleviate some of the stress of an Olympics run.

There’s been a lot of talk about funding as Canada struggled to reach the podium at Milano Cortina more than in years past. Why is Canada’s funding so meagre?

Kassam: It’s tricky. Athletes are financed in all sorts of ways, individually and through their sports, provincially, federally, so some are falling through the cracks. Plus, the government is trying to keep the country intact, so funding sports isn’t that high on their ranking list.

Rocca: And the situation is still much better than, say, 30 years ago. It wasn’t that long ago that we wouldn’t win medals at all, which was the case at the Calgary Olympics. There’s obviously a lot of different funding needs in Canada, and we’re dealing with an austerity budget right now. We’ve definitely come a long way, but it’s really part and parcel to how you prioritize.

What’s the dollar amount that the athletes are getting? And what are they allowed to spend it on?

Rocca: It depends on the sport, but it’s typically a $12,000 cheque for each athlete, and there are no strings attached—they can spend it on whatever they need to spend it on. We also do special one-off projects, like with Cynthia Appiah. Cynthia is a tremendous bobsledder—she was ranked top five in the world. She had the best start in the world, but she would lose time throughout the race because she was running with a five-year-old sled. The Germans, on the other hand, have a partnership with BMW, which gives them a tech advantage. And so we wondered, If we do a special one-off project with Cynthia and buy her a brand new sled, can we pick up the time to actually allow her to medal? Unfortunately, it wasn’t her day, and she didn’t have a great run at Milano Cortina, but we’re super proud of her and plan to keep doing those one-offs.

I’d love to hear your elevator pitch to backers.

Kassam: For some background, I run a hedge fund, and Adrian runs a real estate rental business, and we’ve sort of developed a reputation for growing excellent companies. Now, we’ve applied that secret sauce to Great to Gold. We just went to people within our own network and said, “Hey, why don’t you back this?” We put in the time and the effort. We’re not charging anything to do the coordination, and it’s all to develop better results for our country. Plus, it’s a lot of fun along the way.

We also hold fundraisers where the backers can meet some of the candidates for funding. The athletes come and just tell their stories and show their entrepreneurial spirit. When a leading business person hears that, they can relate to it. Piper Gilles and Paul Poirier came to a recent fundraiser and told their story, about Piper’s cancer and their struggles with funding—they were on the verge of not being able to make it work. We were able to get them funding, and when they won bronze, they texted to tell us how ecstatic they were.

Actually, Piper and Paul ended up getting a cease-and-desist letter from a music company over a copyright issue with the music they danced to, basically telling them to pay $50,000 that they don’t have. And I went, “You know what? I actually know the CEO of the music company.” I called him and said, “Listen, these guys are working night and day for our country. Is there any way we could get around this?" With a little bit of work, they were able to negate that payment. So the idea is that we’re not only providing funding but we’re offering our network.

Can you share who your mysterious backers are?

Kassam: Some very fancy people. I can’t reveal everyone, but one of our most vocal supporters has been Jay Klein, the founder of Pür gum (and the new guest dragon on Dragons’ Den). Another has been Richard Pilosof, the head of the big hedge fund RPIA. And a lot of people have been inbounding as they hear about the impact we’re having, looking to support in the future. Tobias Lütke and Fiona McKean just committed $1 million. It’s our largest donation to date, and it gives us great momentum to really start showing the effects. If we want Canadian athletes standing on podiums, we need a system that backs them properly.

How do you choose which athletes to back? Is it all intuition, or are there some fancy AI models involved?

Kassam: Well, at the hedge fund, we’re working with data and models all day long, so we take all the data from the Canadian Olympic Committee and other organizations and go through it on a quantitative basis. The athletes have to be in the top 15 in the world in their sport. Then we ask them questions about what they’re dealing with and what they would do with the funding.

Rocca: The idea is to find athletes who don’t have sponsors. Mikaël Kingsbury is a two-time medallist; he’s sponsored by Oakley; he doesn’t really need our money. We want to find the next Kingsbury and help them level up—then, when they get a medal, they’ll get sponsors and won’t need us either, and we can start looking for new athletes all over again.

Kassam: Everyone around us is startled that we can get over 70 per cent of the country’s medals when we support only 20 per cent of its Olympic athletes, but we’re not surprised. We know that it’s working because we’re putting in enough effort, given our backgrounds, to get them that last-mile funding, and then the athletes are putting everything into it, taking them to that next level.

It seems like a bit of a Moneyball approach, which obviously changed the face of baseball. Are other countries doing this too?

Kassam: Oh, for sure they are. I mean, in the US there are boosters for every sport—they’re doing this kind of analysis on an individual sport level. Right now, we’re doing it only on a country level, but we would love to get a lot more specific. That’s how you get excellence.

You were both in Milan—what were the vibes watching the games, knowing that you had a hand in getting some of the athletes to where they are?

Rocca: It’s amazing to have our fingerprints on some of these athletes’ medals and to speak with some of the athletes we’ve backed here, to see their gratitude. They’re so thankful that the private sector was able to step up and help them and believe in their pursuit of their dreams. My favourite moment so far has been Megan Oldham winning the big air competition, seeing her celebrate with her brother and dad—he was just incredibly proud of his daughter. My wife and some friends were there as well. With the snow coming down, it was just a very special moment, especially since it was an athlete we funded.

Were you at either the men’s or women’s hockey finals?

Rocca: I was at both finals. The buildings were electric. You could feel how much it meant to Canadians, especially this year. Everyone was dressed in Canada gear. When Canada controlled long stretches of the men’s final, the belief in the arena was palpable. Overtime hurt, no way around that, but the reaction wasn’t anger—it was immense pride. They played incredibly. The women showed that same resilience. We’ll get there next time.

Looking toward LA, what’s next for Great to Gold?

Kassam: I think the Olympics are only getting more popular, especially when the time zones are closer to Canada’s, like with Milano Cortina. The LA games are going to be huge because they’re right next door. There’s going to be so much enthusiasm and patriotism, and we hope that, by showing the efficacy of what we’re doing, we’re going to be able to get more money, support more athletes and really take Canada to a new level for medals.

This interview has been edited for length and clarity.