You Only Die Twice

Former athlete turned respected voice in sports media, Donnovan Bennett shares the real story behind his journey — from playing football at Western to carving out a space in one of the most competitive industries in Canada.In this conversation, we dive into identity beyond the jersey, the grind it took to break into sports media, and the behind-the-scenes realities most fans never see. Donnovan opens up about how lessons from the locker room — discipline, preparation, resilience, and teamwork — became the foundation of his journalism career.This isn’t just a sports conversation. It’s about betting on yourself, building transferable skills, and understanding how who you are shapes what you become.If you’re an athlete thinking about life after sport, a creative trying to break into media, or someone navigating your own transition — this episode is for you.Subscribe for more conversations at the intersection of sport, culture, and personal growth.

In this episode, we sit down with Nakissa “Keesa K” Koomalsingh — founder and CEO of HOOPQUEENS and the visionary behind Canada’s first paid women’s basketball league.What started as frustration from lived experience quickly became a movement. After seeing the gaps, barriers, and lack of opportunity for women athletes, Keesa didn’t wait for change… she built it. HOOPQUEENS has grown into more than a league — it’s a full ecosystem supporting girls and women from youth development all the way to the pro level, on and off the court.We talk about the moment that forced her to pivot, the reality of women’s sports in Canada, building community, confidence, mentorship, and why creating your own space can be more powerful than fighting for a seat at someone else’s table.This is a conversation about sport, leadership, resilience, and redefining what opportunity looks like.Subscribe for more conversations with athletes, creators, and people building culture from the ground up.

In this episode, we sit down with Aryan Sharma, a former Western University basketball player and CEBL draftee, to talk about life after sport — and why content creation is becoming a natural next chapter for athletes.Aryan played four collegiate seasons at Western University, appearing in 101 games and helping lead the program to an OUA second-place finish and a U SPORTS semifinal. He posted a career-high 37 points against Laurentian, grabbed 13 rebounds versus Nipissing, and was later selected second overall by the Montréal Alliance in the 2023 CEBL U SPORTS Draft. Off the court, he was also recognized with the Dr. Craig Boydell Award for Academic Excellence & Community Service.Since stepping away from competitive basketball, Aryan has shifted his focus to building an audience online. While he’s had viral moments across short-form platforms, his real edge lies in understanding how to grow, engage, and monetize smaller, highly connected audiences — especially for creators who don’t aspire to chase a million followers.This conversation explores:- How athletes can transition their competitive mindset into content creation- The identity shift that comes with leaving sport- Why small audiences can be more powerful (and profitable) than massive ones- How to build trust, community, and consistency onlineWhether you’re an athlete navigating life after sport, a creator just getting started, or someone looking to build something meaningful online, this episode offers a grounded, honest look at the journey.

How does someone from a town of just 20 people in Newfoundland end up sharing the court with LeBron James, Kobe Bryant, and the U.S. Dream Team?In this episode, we sit down with Carl English — one of the most accomplished and overlooked players in Canadian basketball history. From growing up in one of the smallest communities in the country to becoming a national champion, elite scorer, and international professional, Carl’s journey is a masterclass in belief, resilience, and outworking expectations.Carl takes us behind the scenes of what it really takes to reach the highest levels of basketball — the pressure, the sacrifice, the mental battles, and the moments that defined his career. He opens up about what it was like to compete against the world’s best, represent Canada on the global stage, and navigate life when basketball is no longer your entire identity.This isn’t just a basketball story.It’s a story about chasing something bigger than where you come from — and proving that greatness can come from anywhere.Whether you’re a hooper, a sports fan, or someone trying to build something of your own, Carl’s story will change the way you think about what’s possible.In this episode:• Growing up in a tiny Newfoundland town• Becoming a national champion and elite scorer• Playing professionally around the world• Facing legends like LeBron, Kobe & Team USA• The mental side of chasing greatness• Life after basketball

A talent like David didn’t go D1. After injury cut his career short, he built something from the ground up instead. @justbe_dt answers what happens (and who you become) when the dream changes. #YouOnlyDieTwice

What we all have in common goes far beyond the jersey. That’s what Friday is all about. Identity shifts, plot twists, and reinvention. Akil spent two decades narrating everyone else. Friday, he becomes the story.20+ years behind the mic, the camera, and culture itself. Now the real headline: fatherhood, rebirth, and what chapter comes next.Come for the media mastery, stay for the human evolution.

Some journeys don’t just test you — they remake you.Walid went from world-stage Taekwondo phenom to rock bottom after injuries tore his career apart and his identity with it. But what followed wasn’t a collapse… it was a reconstruction.Season 3 opens with a story about rebuilding from the inside out.

Born and raised in Toronto, Jevohn Shepherd carved a path from local courts to global arenas. From starring at the University of Michigan to suiting up for Team Canada, his pro career took him across Europe — with stops in Germany, Italy, the Netherlands, and Romania.Now a familiar face on TSN and the Raptors broadcast team, Shep joins us to talk about what comes after the final whistle. In this episode, he opens up about the mental, emotional, and professional challenges of transitioning out of sport — and how he's found new purpose on the other side.This is a real, unfiltered conversation about identity, reinvention, and what athletes need to hear as they face life beyond the game.

@BreysChoice made her mark at @UNCGwbb, leading with grit, vision, and a smooth mid-range game that turned heads. Basketball was in her DNA, and her future in the game was undeniable.
After building a successful career on and off the court and starting a family, life threw her another test: cancer. Open and vocal about her diagnosis, she fought through that transition with the same resilience that defined her playing days.
Today, Brey is still shaping basketball culture. As the founder of @OTG3x3 and head coach at @LayUp_Basketball, she’s dedicated to creating safe, empowering spaces for young athletes to learn, grow, and thrive.
Her relationship with @SupermanJohnson, a former @WindsorExpress guard, captured hearts when his one-on-one proposal at Falstaff Community Centre went viral. But beyond the headlines is a story of loyalty, recovery, and a deep love for the game. And each other.

@hannaahall’s journey didn’t stop at buzzer-beaters and NCAA tournament runs. After leading Canada in assists at the 2016 FIBA U17 Women’s World Championships and earning All-MAC honours with the Buffalo Bulls, Hanna faced the question every athlete must eventually ask: What’s next?In this episode, Hanna opens up about her transition out of sport, the mindset shift it took, and how she’s navigating life after basketball.