🤝 Meet Donovan Bailey. An icon of Canadian athletics, you know him as the former record-holder of the fastest 100-metre dash — a record he broke 30 years ago this week on his way to gold at the Olympic Games in Atlanta. He is also an entrepreneur and author of the 2023 memoir Undisputed. We chatted with Donovan about his past life as a stockbroker and the significance golf holds for retired athletes.
It's the 30-year anniversary of your gold-medal-winning performance in Atlanta. What do you remember most about that experience today?
I think in reflection, it was all about setting the standard in sport — a personal accomplishment, but also I think I'm reminded every single day of the fans. All of the incredible Canadian fans and track and field fans around the world, and what it meant to them.
I have a fantastic relationship with the fans, and I get to hear some incredible stories and people that name their kids after me, and their dogs, and their boats, and what it meant to them. So in reflection, I think it's awesome to have such an incredible relationship with Canadians.
You grew up playing other sports like basketball and found track relatively late in your life. Do you think it's important for kids not to specialize in certain sports too early?
Listen, I played every sport possible, man. I tried football, but I just thought, “why are you trying to hit me because I have a ball in my hand?” Maybe as a kid I was probably a little bit too smart for my own good. But basketball is still my passion. I love golf, pickleball, squash, badminton, and volleyball. I think it's crazy to specialize so young. I talk to parents all the time with a five-year-old or a six-year-old and they say, "Hey, how are we gonna get Lil Johnny skating faster?" I'm like, leave him alone.
It's extremely important for every single child to participate in sport, but not only the sport that they like. You certainly don't need to be specializing, especially at a young age — I'm talking four, five, six years old, you don't need that. Just let them play everything. The specialization comes later on. Norway is a great example. Every year you've got really good people in the Summer Olympics, really good people in the Winter Olympics, for a relatively small country. And you see success at the highest level, and for all purposes you see balance, because most of those athletes can do two, three, four things.
What was the hardest part of adjusting to life after competition at that high of a level?
I think I just loved the structure. I loved waking up and understanding what I have to do every day. And I think what retirement did was it allowed structure to be dismantled. So it was very tough — I lived and breathed sports. It was all about the amount of sleep I needed, therapy, physio, hot and cold, when I was eating, all of that. And when you get to just a regular life, you don’t really prepare like that just to go to a board meeting.
So it was tough to adjust to a different kind of busy. And unfortunately, the adrenaline rush that you get from competition and practice — there's really not a whole lot you can get that from in retirement.
What do you do in retirement that comes close to filling the adrenaline rush of being on the line?
It's tough, but I'll tell you this — a lot of the reasons why professional athletes like myself retire and then attempt to tackle golf is because of that chase. The competition is not you versus the guy next door. The guy next door could be five foot one and 400 pounds. So golf, it's you versus you, versus the course.
It’s a sport where you have to dedicate time to. I was training eight hours a day, every day. If you don't make that sort of commitment in golf, and clearly you can't unless you're on the pro tour, you're always gonna have that disappointment. But there are also signs of brilliance over those 18 holes. So I think golf is the one that allows a competitive mind to continue going.
What's the most important piece of advice you would give to anyone that wants to excel in their field, whether it's athletics or something else?
I would say surround yourself with people that are also cheering for you. There's a saying that you can be in a room and people are clapping, but they're not cheering for you. So surround yourself with people who are really cheering for you.
Always go back to your support system — parents, friends, family, whatever. And be patient, man, be patient. I remember when I was very young, I couldn't be patient, but now, I get why it's so important. But have people that are cheering for you, that's so important. The support system is so important. The last thing is to be disciplined. When you make a commitment, be disciplined and get it, because no matter what, you're always gonna get out what you put in.
You used to be a stockbroker in Toronto before you became a professional sprinter. What did that experience, if anything, do to help you on the track?
I think one thing I learned was that I wasn't made to be in the office at that age. I hated being indoors. And that sort of structure, I just wasn't built that way then. I think I loved the structured environment, but I didn't have the patience to deal with business. I recognized back then, when I was on Bay Street, that I wanted to be outside. I wanted the freedom of sport. That’s what made me feel alive. What I do today — sitting on boards, being in the C-suite, raising capital, taking companies public — all of those things I would have never had the patience for back then, no matter how much money you're paying me.
You’ve said athletes need to be the CEOs of their own brand. What does that look like in practice, in 2026, versus when you were competing?
It’s very different today. You have to control everything. The environment and playing field right now is so incredible and so wide that any student, any person, can stay in their basement and build a multi-billion-dollar brand. We didn't have that back in my day. I was called many names, whether it's arrogant or whatever, because I'd run my business as an athlete. A lot of times people would say, "Hey, why are you like this?" I'm like, well, “I'm the CEO of my brand.” Who's the CEO of Tiger Woods? Who's the CEO of Wayne Gretzky? You have to educate yourself, get people around you that can manage and understand you and your brand. It was vital back then. I think it's definitely important now.
You wrote in your book about setting up the business side of the SkyDome 100-metre race against Michael Johnson yourself. What went on behind the scenes to make that happen?
First of all, thank God for Bob Costas. The great Bob Costas from NBC, who said that Michael was faster than me. That made it happen. So the opportunity came, and we negotiated how many races we were going to have, but I wanted the first one in Canada. We were trailblazers in managing your own brand, right, because that was the first foray into the actual business. My job was to find people who could raise the capital so I could get paid and Michael could get paid, and set up an entertainment event, sell tickets, and do all those things.
What was your method for steadying your nerves on the starting line and does it work for other things today?
For me, to get on the line and be completely and totally relaxed and in the zone, a lot of that is done in my preparation to get there. I was very comfortable with the work I put in. So my mind and body are prepared as much as possible, but I'm also trusting the people around me. My responsibility all along is to make sure I'm comfortable — whether standing in front of a stadium of 50,000 people or in a boardroom. Just like running a race, putting one foot in front of the other and understanding what I need to do to get ready. I have to put in the same amount of work and use those same characteristics every day to prepare for what I want to do.
That’s not to say I was never nervous or never panicked. But my preparation, along with not caring about the validation from anybody. So it's the work you do every single day that allows you to get there and be nervous, but be relaxed and embrace the moment.
What's one change you'd like to see in terms of how Canadian athletes are supported here at home?
I think athletes need to make more money so they can live a balanced life. Far too often we don't represent all of our Olympic athletes. Our movement has had some incredible people, and a lot of those incredible people just get lost in the shuffle. Obviously I'm the fastest man, the greatest Canadian sprinter ever, but there are so many athletes who I don't think get recognized enough. Respecting, celebrating, recognizing, and certainly paying the young athletes.
You're literally working your butt off just to be patriotic. Imagine you have a bunch of kids in the military who go away and we all say, “Here's a couple bucks, hope you get some food.” One thing I always tell CEOs is that if you see a retired Olympian, especially someone who hasn't gotten to the top, and you want a killer on your team, hire that person. Because it’s all built in already.
This interview has been lightly edited for length and clarity.
