Donovan Bailey’s secret to success: investing in himself – and real estate

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Olympic track champion Donovan Bailey’s athletic career as one of the best sprinters ever is well documented. He is a two-time Olympic gold medallist, three-time world champion sprinter and the only person to be twice inducted into Canada’s Sports Hall of Fame. He is also the first man in history to simultaneously be the world champion, Olympic champion and world record holder for the 100-meter dash.

His secret to success? Investing in himself.

Today, as CEO of Bailey Inc., he owns real estate that makes up the foundation of his investment portfolio. He also invests in early stage companies. Among his other entrepreneurial activities, he is a sought-out motivational speaker, podcast host and coach on a reality competition TV show that just premiered. And he has a book scheduled for release in the fall.

Indeed, Bailey has figured out how to successfully balance physical and fiscal health.

Where were you born and where did you grow up?

I was born in Manchester, Jamaica, and moved to Oakville, Ont., at seven. I moved back to Jamaica to attend boarding school from age 7 to 11, and then returned to Oakville where I’ve lived ever since.

Did your parents talk with you about money or success when you were a kid? What did you absorb either implicitly or explicitly?

My mom was a homemaker who did various odd jobs, and my dad was a machinist who had no high school education, but he was able to retire early with a sizable real estate portfolio. When I was 9 years old my dad told me that all of the greatest and wealthiest people in the world owned real estate. He said, “Real estate son … you can touch it!”

When I was 12, my dad took me to the mall to meet with a representative at CIBC to open my first bank account. Dad explained that it was important to build a good relationship with your bank and said they will be a useful partner over time and actually work for you. I am still banking with CIBC today.

When I was 9 years old my dad told me that all of the greatest and wealthiest people in the world owned real estate. He said, 'Real estate son … you can touch it!'
Donovan Bailey

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I bought my dad’s real estate portfolio from him when I was 21. Today I still share his philosophy: Regardless of where we are in the market cycle, one of the absolute pillars of my investment portfolio is my real estate holdings. You can buy high and sell higher!

Growing up I had the good fortune to enjoy a great community. I got to be around a huge support system of entrepreneurs – people who wanted to pay it forward, who spent a lot of time talking with me about how to be productive and be successful in life.

How has your career evolved since you retired as a professional athlete? Tell us about some of the investment irons you have in the fire at Bailey Inc.

When I was a professional athlete, I realized there would be a window of opportunity, and my responsibility was to take advantage of that window. Along the way I was always exploring and getting to know various people who were experts in their industries. I’ve had some amazing advisors, and living in Oakville I’ve been around people with generational wealth. This has been a great environment to be able to watch how friends and families live life in a happy and healthy way – balanced with fiscal health.

I am regularly approached by investors who have exited their first or second companies and have moved on to their next startup. I either get asked to invest myself in these new projects or help their company with my global network and/or by lending my brand. This is where I find my sweet spot to be today – I am currently invested in five startups. I’m involved in fintech, I own a shoe company (with a focus on data collection from the sole of the shoe), I’m exploring the psilocybin and cannabis spaces, I own a hot sauce company, and the pillar of my portfolio continues to be real estate.

You are a sought-out motivational speaker, too. What other projects are you involved in?

Well, there is no retirement with motivational speaking! I love lending a hand inspiring younger generations of athletes to be productive with their lives.

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I also have a TV show that recently debuted on CBC called Canada’s Ultimate Challenge. It is a reality competition show, with regular Canadians coached by me and five other coaches. Each episode takes place at an iconic Canadian location, where the teams compete in challenges that will test them physically and mentally.

I’ve signed a book contract with Penguin Global for release in the fall of 2023. This book will detail my background and what motivated me to invest in myself and achieve greatness.

And along with my co-host Jason Portuondo I have a podcast called Donovan Bailey Running Things. Every week we pick three or four topics from what happened the week before – it’s just a conversation between two friends.

What is the biggest thing you have learned throughout your career as an athlete and business person?

My number one priority is to invest in my body.

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When I started out as a professional athlete I spent over 60 per cent of my earnings investing in my body. I bought the best food (I had to eat six meals a day), the best physio, whatever it took to achieve my goal of becoming the greatest athlete on the planet. At age 54 I’m no longer competing, but I make sure to get regular exercise, eat high quality food and sleep well. As you get older it is important to find a structure that works for you. I eat a healthy breakfast, lunch and dinner, and in between I snack on fruit and nuts.

What advice would you pass along to the next generation of entrepreneurs?

My best advice to others is to live a balanced life and focus on four priorities:

Take care of your body and your mind.
Listen attentively to experts. Ask a lot of questions and spend more time listening than talking.
Surround yourself with like-minded, motivated people.
Travel a lot! Travel is the greatest education that any human can get. I’ve visited 200 countries. See how other people live – dance to their music, drink their wine and look at their art.

Responses have been lightly edited for clarity and length.

Barbara Stewart wealth Canada — Barbara Stewart

Barbara Stewart is a Chartered Financial Analyst (CFA) with 30 years of investment industry experience. She spent five years as a foreign currency trader, more than two decades as a portfolio manager for high-net-worth entrepreneurs, and for the past six years she has been performing interview-driven research for financial institutions around the world. Barbara is a keynote speaker for CFA Societies, banks, stock exchanges and industry conferences globally, and she is a columnist for CFA Institute and Canadian Money Saver magazine. She is on the advisory board of Kensington Capital Partners and also is the Ambassador for the Kensington Women’s Forum. In addition, 13 years ago Barbara saw a need to challenge outdated financial industry stereotypes and share positive messages about women and money. Today, Barbara is recognized worldwide as one of the leading researchers in women and finance. Her Rich ThinkingÂ® global research papers quote smart women and men of all ages, professions and countries and are released annually on International Women’s Day, March 8. To find out more about Barbara’s research, visit www.barbarastewart.ca.