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How Olympic captain Martha McCabe transitioned from a swimming career to entrepreneurial success.

Her business provides a platform for Olympians to mentor youth.

By Hailey Eisen

Finding purpose after retirement can be one of the greatest challenges an Olympic athlete will face — but for Canadian swimmer Martha McCabe, the lessons learned through a career in sport proved to be just what she needed to embark on an entrepreneurial journey. 

By age 27, Martha had earned a bronze medal at the FINA World Championships in Shanghai and a silver medal at the Pan American Games in Toronto. She had been named Top Canadian Female Swimmer after placing fifth at the London Olympics in 2012 and was captain of the Canadian swim team at the 2016 Rio Olympics. But she was ready for something new.

After years of focusing all of her energy and attention on swimming, Martha founded Head to Head Canada, an organization that provides Olympic athletes with a platform to mentor youth, promoting resilience and mental well-being. She attributes her success to her family’s support, unique education opportunities, and a healthy dose of resilience built from the failures and obstacles she encountered throughout her sporting career.   

Born and raised in Toronto, Martha moved to Vancouver for university with the sole focus of training with a breaststroke specialist who’d recently joined the school. Her first year of university coincided with the 2008 Beijing Olympics.  

“It was my first year in Vancouver, my first year truly focusing on my swimming, and my whole life revolved around the sport,” she recalls. “I had set a personal goal of qualifying for those Olympic games.” When she fell short, Martha says she was devastated. 

“At 18, I had a lot to learn, and that first heartbreak was an important part of my journey,” the 31-year-old recalls. In fact, that first failure is something she still draws upon today when mentoring youth. “From that moment I realized that nothing is certain, and the only way to be successful is to focus on the day to day.”


I had never had a real job before, I’d never used a calendar to set up a meeting — and while it may sound wild, most Olympic athletes don’t have the opportunity to experience that kind of work.


In the four years between 2008 and 2012, Martha says she grew as a person and an athlete. “I think being an athlete provides you with many accelerated life lessons. By the time I graduated UBC and qualified for the 2012 London Games, I was extremely focused and not afraid to fail.” 

Although she didn’t make it to the podium, Martha did finish fifth and beat her own personal best time. “I wasn’t nearly as devastated as I had been in 2008, and I focused my energy on meeting other athletes and enjoying that Olympic experience.”  

She then moved back to Ontario to reflect on what would come next. “I knew then that I needed a balance; I was done university and I wanted to do something outside of swimming while also continuing to train.” 

Though she’d studied kinesiology at UBC, Martha says she was more interested in business and considered doing her MBA upon graduation. “I felt that the business environment was more similar to the sporting world.” Synchronistically, Martha came across the RBC Olympians program and was hired to work as a marketing co-ordinator for the bank in a flexible role that gave her the opportunity to continue swimming.  

“I had never had a real job before, I’d never used a calendar to set up a meeting — and while it may sound wild, most Olympic athletes don’t have the opportunity to experience that kind of work.”

In 2015, Martha won a silver medal at the Pan Am Games in Toronto and as the 2016 Rio Olympics approached, she knew she was nearing the end of her career. As co-captain of the Canadian swim team, Martha went to Rio but her personal performance was not as good as she’d hoped. “Watching the young athletes perform at those games was by far the most memorable experience,” she says. “It was incredible leading that team.” 

For Martha, the next logical step was to support other athletes and young people in their own journeys — but the key to success would be finding a way to build a business around her aspirations.    

“It started with a 60-day drive across Canada,” Martha recalls. “There’s a small window after you’ve been to the Olympics when you’re relevant, and I knew I had to maximize that demand and do something with it.”

Having secured sponsorship, Martha travelled from Victoria, B.C. to St John’s, Nfld., sharing her experiences and expertise with young athletes both in and out of the water. “I did 55 presentations and clinics, and it was the perfect way to test the market and see if my idea for a business was viable.” 

From that journey, Head to Head was born. What started as presentations delivered by Martha and a few teammates has grown to include a roster of more than 30 Canadian Olympians, including hockey medalist Jayna Hefford, four-time canoe-kayak-sprint medalist Adam van Koeverden, and bobsleigh competitor Neville Wright. 

To launch Head to Head, Martha turned to her dad’s experience as an entrepreneur and relied on his support as she navigated new waters. “As with my swimming career, I had assumed starting a business would be easier than it was — and from every rejection I learned and evolved.” 

Martha wanted to give other Olympians the experience she’d had. “Retirement can be challenging, and I wanted to extend the opportunity to other athletes to share their stories and influence the lives of kids.” She began to develop a training program to streamline the content Head to Head would deliver. “Just because you’re fast doesn’t mean you can speak or work with kids, so from the beginning I was very selective in who I chose to join the program.” 

After running the business for nearly two years, Martha says she was suffering, like many entrepreneurs, from imposter syndrome. “I had a lot of self-doubt, like who was I to be running this business? I didn’t have any formal training or education and I felt it would be useful to get some.” 

Another synchronistic opportunity presented itself to Martha, this time in the form of a Master of Management Innovation & Entrepreneurship. Thanks to a partnership between the Canadian Olympic Committee and Smith School of Business, Martha was one of many national team athletes given the chance to go back to school after a career in competitive sport. Martha continued to work on her business while in the program, grateful for the opportunity to garner advice and support from Smith’s coaches and professors. “I received a formal education, really valuable business strategies, and above all I got a huge boost in confidence.” 

Shortly after starting the master’s program, Martha worked up the confidence to hire someone to help run Head to Head. She sought support from the faculty and coaches at Smith to go through this process and choose the right candidate — something she feels she wouldn’t have been able to do on her own. 

With education and experience under her belt, Martha continues to inspire youth with a focus on managing anxiety and nerves while achieving one’s goals and full potential. This summer, Martha decided it was time to come out publicly — realizing there was more of her story that could help others. “I had been so focused on swimming when I was younger and there were no female athletes in swimming who were gay, so I dated guys without realizing something was always missing.” 

While Martha hopes that soon stories like hers won’t be a big deal, until then she wants to provide the type of strong and proud LGBTQ+ role model she never had growing up. 

“Kids tend to look up at Olympians as superheroes, which is why I share my story,” Martha says. Her ultimate goal is to let kids know that they too can achieve their dreams. That the key to a better life is to remain open to possibilities and perspectives. And that taking care of yourself, staying active, and writing down your feelings and tracking your well-being can all contribute to improved mental and physical health. 

Special skills, strategies and strengths are needed to turn an idea into a viable venture, whether in a startup or within a corporation. Smith’s Master of Management Innovation & Entrepreneurship equips you for that success.