‘Focus on what you’ve got to do’: Donovan Bailey shares his tips for success ahead of Entrepreneurship Week

In 9.84 seconds, Donovan Bailey ran 100 metres – about the length of a standard football field – to win gold at the 1996 Olympic Games in Atlanta and set a new world record.

Twenty-six years later, one of the greatest sprinters of all time (Bailey also won a gold medal in relay in Atlanta and still holds the 50-metre record with a time of 5.56 seconds) has traded athletics for business. The company he established during his professional running career – Bailey Inc. – manages real estate and brand partnerships with organizations such as Adidas, Coca-Cola and Big Brothers and Sisters of Canada.

At the same time, Bailey supports youth mentorship, cancer research and Alzheimer’s research through the Bailey Foundation. 

On March 9, Bailey will share his insights on the similarities between athletics and business, and how success on the track translates to success in the boardroom during the U of T Entrepreneurship Speakers Series, one of many Entrepreneurship Week events. He will take questions from the audience in a session moderated by Globe and Mail business writer, Rita Trichur. 

Bailey recently spoke with U of T News writer Geoffrey Vendeville ahead of his keynote talk. 

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Can you tell me about your early experience in business?

My parents have always been entrepreneurs, so I kind of got the bug from that. My father was an entrepreneur. My family in Jamaica were farmers and large landowners. When I was a kid in college, playing basketball, the goal I had while at Sheridan College was to own my home. I was taught by my dad about how important relationships with financial institutions are, and how valuable credit ratings were. 

There’s always been some fiscal responsibility taught to me since I was quite young. When I was 12, my dad took me to the bank and we had that conversation. 

I bought my first house [in Oakville in the mid 1980s] when I was 19 while I was going to school. I was working part-time and saving money. The place that I lived in while I was going to Sheridan – I actually owned it. I had a roommate who is still one of my very good friends today. 

When I finished college, I was able to save money from the work I was doing in Toronto, sell my property and buy my father’s real estate holdings. I was as a 21-, 22-year-old crazy kid. 

What are the parallels between success in athletics and success in business?

When I wasn’t successful in track and field, it was because I had the passion, but I had zero commitment. In business, it was the exact same thing.

A lot of the time, you find people in business who have the desire to own a property, have a nice car or live in a penthouse somewhere – but it really is just a dream. They spend a whole lot of time being mesmerized at the results and not focusing on bootstrapping or on the individual efforts that you [need to] make every single day to get to that place.

I remember thinking I wanted to own a house. What happened for me was, basically, in my mind I wanted to own a house, but you have to dial back to where you are in the present day and what you’re doing to achieve that goal. The number one thing was: I had great credit. Number two: Great relationship with the bank. Number three: Whatever job I was doing, I was banking – because the goal was to buy a house by a certain time.

When I look at that [I can] make the parallel to the Olympic Games, or the world championships. We [Bailey and his coach Dan Pfaff] would have a conversation about the date when I would need to be at my greatest – and then you dial back to the day you’re there, and you put all those things together. And [you] think about all the ingredients: “OK, I have to eat properly, I have to sleep properly, I have to get therapy every day and I have to train and finish my workouts every day.” All of those things. 

Essentially you dial back to the present day and you work toward the goal by adding fuel. Every single thing, every single day. 

What’s your secret for avoiding distractions and getting into the zone? 

In order for you to be successful, you should gravitate towards people who will support you no matter what. I always knew that, whether I failed or not, my mom was always going to love me. I was always going to be a mama’s boy and my dad was always going to be my best friend. That’s just a basic thing. 

If you’re a kid, maybe your coach supports you. Or your best friend. You’ll always gravitate towards those people. If you’re going to do the work and be disciplined – whatever you learned from practice in sports or business – you should always have the ability to be completely free in the field of play or in the boardroom. 

You were part of the famous Canadian relay team that clinched gold in the 4×100 in Atlanta a week after your individual gold. What makes for good teamwork? 

In our case, the number one thing was individual preparation. You must do your work individually. If you have a bunch of teammates doing their work individually, when you get together you understand the value in what you’re doing and the teamwork becomes easier.

The other thing is: As the captain, leader and person my team members were looking at, they understood that I was someone who had huge expectations for myself – and so when we got together as a team, I have huge expectations of them.

So, it was very important for these guys to understand what their commitment was – and also understand that, regardless of anything that was said and done, nothing was taken personally, because we got into it a few times.

At the end of the day, my goal was leading by example. Every single time those guys were on the field with me, they were 100,000 times more confident in their own ability because I was actually on the track with them. That allowed our team to be probably the greatest team in Canadian history. We were the number one team on the planet for six years straight.

Can you tell me about Bailey Inc.?

I opened Bailey Inc. in 1995. It’s essentially the business of Donovan Bailey, the branding business. I owned a restaurant franchise, have a real estate portfolio, several investments in real estate development, and manage my brand partnership with many Fortune 500 companies. My focus lately has been more on startups just because I have more time to sink my teeth into it and because I can get more equity. 

Bailey Inc. essentially covers all Donovan Bailey branding global business. 

You’re also engaged in philanthropy through the Bailey Foundation. Can you tell me about the causes you support and why they’re close to your heart?

The Bailey Foundation is a roll off from the Donovan Bailey Fund, which I also started in 1995. We partner with the Oakville Community Foundation and we raise money and give scholarships to the best student athlete. That’s part of the fund. The foundation is a little bit more expanded. I will always commit to doing work and helping children. Leadership and mentorship are things that I think every single kid in this country – anywhere, actually – needs.

We do a lot of work with Big Brothers and Sisters and Boys and Girls Club because we know that, in one-parent households, some of those kids might drift wayward. By having someone else to speak to, those kids could become prime minister or hugely incredibly successful people. So, the foundation is really a spin-off with the Donovan Bailey Excellence Awards.

I support Alzheimer’s [research] because my mother passed away and she was affected by that. My dad passed from cancer, so we raise money for cancer research. And we support all things children. Leadership and mentorship is the number one thing. 

In 1996, you called out racism in Canada in an interview with Sports Illustrated. What led you to speak out at the time?

First of all, let me tell you this: I’m not an activist. I’ve never professed to speak on behalf of a culture. What I always speak of is my journey and the journey of my teammates. I was very blessed to grow up in Oakville. I moved from Jamaica, from a farm, to Oakville, Ont. That’s not exactly a journey through places where you’re dodging bullets or seeing racial profiling and all of that. I didn’t experience that. 

In 1996, when I was asked the question, I thought the honest thing to do was to be as honest as possible about what I have seen and what I’ve heard from my teammates. In Canada a lot of things were done underhandedly, with Black kids here not getting supported. 

What has changed today? Technology. Everyone has voices. The internet. We are talking more about it 26 years later.

I think there’s more happening now, but I don’t think it’s enough and I also believe there’s still a lot of work to do. 

In entrepreneurship, one saying goes: “Fail fast, fail often.” What were some failures that became important life lessons for you? 

One of the things I talk about all the time is the greatest race I ever had. It was when I came fourth in June of 1994 – when I felt that I could compete with all the big athletes in the world at the time. I got out to a great start, looked around for the other guys wondering where they were – and three of them ended up passing me. 

I thought, “Huh, this is probably one of the life lessons that I need to learn.” That is, number one: It might sound cliché, but stay in your own lane and mind your business and focus on what you’ve got to do. You’ve got a good team around. You’ve got to get out there and do what you’ve got to do based on the things you’ve been practising. 

We don’t ever talk about the races that I’ve lost – and I certainly lost a few. But for me, I’ve never used that word [failure]. I’m writing a book and the original title was Win or Learn. That’s something I’ve always said. I’ve never thought I’d lost anything. If I had the ability to participate with my peer group and people who are the very best at what they do, it seems to me that if I didn’t come in first place that doesn’t mean I’ve lost.

In business it’s the exact same. I’m currently partners in several businesses and there’s some of them that are new – some are tech-based others aren’t. I’m learning as I go – and, believe me, sometimes it’s not easy, but it’s all part of the process for me.