Free Agent Technologies
Jan 22, 2025
Mason Bennett transitioned from CFL player to digital marketing entrepreneur, leveraging resilience and leadership skills.
When most people think about professional athletes, they often imagine the glory days of the game—high-flying tackles, record-breaking seasons, and championship wins. But what happens when the game ends? For many athletes, the transition from sports to life after the final whistle can be challenging, uncertain, and full of tough questions. Few understand this better than Mason Bennett, a former CFL player who has navigated this transition firsthand.
Born and raised in Winnipeg, Manitoba, Mason's journey into football began at just six years old. Encouraged by his mom, he instantly fell in love with the sport, which soon became the focal point of his life. Football was his world and found its way into everything he did.
As a teenager, Mason realized that his passion for football could lead him further than just high school championships. With a strong work ethic and the support of his high school coach, Mason's athletic potential began to take shape. His journey took a significant turn when he was invited to play for Team Canada in a high school football showcase at Cowboy Stadium in Dallas, Texas. This not only boosted his confidence but also put him on the radar of several Division I programs in the U.S.
While Mason always dreamed of playing at the college level, his academic journey initially lagged behind his athletic one. His grades weren’t always the best, and schoolwork took a backseat to his passion for football. But his coach and mentors pushed him to realize that success in football also depended on success in the classroom. With newfound focus, Mason turned his academic life around, eventually earning a Division I scholarship to the University of North Dakota.
At UND, Mason took his football career to new heights. Not only did he break multiple school records—setting the career and single-season sack records—but he also earned the prestigious title of All-American. More importantly, college became a turning point for him off the field. With the pressure of professional athletics hanging over him, he understood that football wouldn't last forever. This realization pushed him to focus on his studies and career beyond the sport.
Graduating with a degree in communications, Mason's time at UND shaped him into a more well-rounded individual, preparing him for the next phase of his life. As his football career progressed, however, so did his list of injuries. From torn retinas to dislocated fingers, Mason’s rookie year in the CFL with the Hamilton Tiger-Cats was filled with physical challenges. Yet, despite the pain and setbacks, he got the opportunity to play in the Grey Cup—a remarkable honor for any Canadian football player.
By 2024, Mason made the difficult decision to retire from professional football. Though the choice was bittersweet, it marked the beginning of an exciting new chapter. He transitioned from the field to the business world, founding a digital marketing company. This shift wasn’t entirely new to him; Mason had always been fascinated by the behind-the-scenes aspects of sports, like working with sponsors, coaches, and team logistics.
Curious about how people in business development operate, he took it upon himself to learn more, enrolling in online courses and reaching out to mentors in the industry. This curiosity and drive led him to build a career in digital marketing, helping businesses grow and thrive through effective online strategies.
"I think it’s all about finding your ‘wins’ and ‘losses,’" Mason says, reflecting on his entrepreneurial journey. "In sports, it was all about setting goals—sacks, tackles, victories. Now, it’s about setting goals for the business—getting clients, building partnerships, and growing my team. It’s still the same mentality, just applied differently."
As Mason transitioned out of football, he realized the importance of building a strong network—one that not only helped him professionally but personally. This is one of the reasons he believes in the mission of Free Agent, a platform that connects former athletes to one another for support, opportunities, and collaboration.
“Having a network of elite athletes is huge,” Mason shares. “It’s not just about finding a job or career advice. It’s about connecting with people who have been through the same challenges, who understand what you’re going through. There’s an emotional side to the transition that people who haven’t been there just don’t get."
For athletes looking to make the jump from professional sports to the business world, Free Agent provides a unique opportunity to tap into a supportive community. This community isn’t just about finding a job—it’s about connecting with like-minded people who understand the intricacies of transitioning from life as an athlete to life after sports.
One of the most significant challenges athletes face when transitioning out of sports is finding purpose. As Mason reflects on his own journey, he acknowledges the sense of loss that comes when the structure and routine of professional sports are gone. “You wake up one day and realize that you don’t have a game to prepare for, no practice to show up to. It can be incredibly disorienting.”
But Mason credits sports with teaching him resilience and discipline—qualities that continue to shape his life today. "Football taught me how to take setbacks and turn them into comebacks," he says. "Whether you’re benched, injured, or just going through a tough stretch, it’s all about how you respond. Life after football is no different."
This mindset is what drives Mason now as he runs his digital marketing business. “The same discipline and goal-setting that helped me on the field are helping me in my business. In football, it’s about stats. In business, it’s about clients, projects, and growth. Setting those targets is key."
Mason believes that athletes make exceptional candidates for jobs because of the skills they develop throughout their careers—skills that are transferable to any field. “In sports, you learn to handle wins and losses, face adversity, and work as part of a team. You learn leadership, time management, and the importance of discipline. These are things that set athletes apart in the workforce.”
Whether it's tackling a tough project, working under pressure, or learning to bounce back from setbacks, athletes are well-equipped to excel in the business world. Mason is living proof of that, as he continues to grow his marketing business and mentor aspiring entrepreneurs.
When asked to describe Free Agent in one word, Mason doesn’t hesitate: “Innovative.” He sees the platform as a game-changer for athletes transitioning out of sports, offering a much-needed space to connect, learn, and grow.
For Mason, the future is bright—both for himself and for the athletes he supports. "As athletes, we can reinvent ourselves and build new legacies," he says. "It’s all about staying adaptable, continuing to learn, and leveraging the skills we've honed in sports to excel in life after the game."
