The Calgary Sessions

Rob Sawchuk returns to The Calgary Sessions as the first repeat guest on the show, and this conversation carries a lot more than the episode 200 milestone. Jeff and Rob talk about what changed over the past six years, from building for other people and working out of the basement to opening Turkey & Pistols, stepping further into music, and trying to build a life that actually fits. It’s a con...

Lana Rogers is the founder of Gentle Lion Communications, but this conversation is about a lot more than marketing. We talk about burnout, self-awareness, hospitality, accidental entrepreneurship, and what it looks like to build a business without following the usual blueprint. Lana shares how years of working in restaurants shaped the way she reads people, creates experiences, and leads a team. S...

April Brown is the founder of Rootbar, but this conversation is about more than building a salon brand. We talk about the discipline that shaped her early, from competitive soccer to starting in the hair industry at a young age, and how that same drive carried into entrepreneurship. April opens up about burnout, divorce, COVID as a reset, and the time and space she needed to get clear on what she...

Jill Dewes spent years in the high-stakes world of advertising,eventually becoming a partner at Daughter Creative. But long before the big brand launches and the 80-hour work weeks, she was a student with a degree in Ancient Greek history—a move she admits was "really unemployable" at the time. In this episode, Jill shares the breaking point that brought her to Calgary. After a decade of...

What makes a person walk away from a decade of stability in tribal politics to start over as a "starving student" at 40? In this episode of The Calgary Sessions, Adrian Stimson shares the grit it takes to move from a position of political influence into the uncertainty of an art studio. We dig into Adrian’s "Tickle, Slap, and Hug" approach—his unique way of using humor to bring...

What does it actually take to go "all in" on a vision? Tommy Wheeldon Jr., the Head Coach and GM of Cavalry FC, joins the show to share the story behind the "Burn the Boats" mentality that helped him build a professional soccer club in Calgary from a blank canvas. This isn’t your typical sports interview. Tommy dives into thehuman side of leadership, discussing how his "no...

What does it actually take to sustain a family legacy withoutlosing your own identity? In this episode, Peter Izzo (President of CappuccinoKing) joins Jeff Humphreys to pull back the curtain on the reality of the immigrant work ethic and the transition of a multi-generational Calgary brand. Peter shares the unfiltered stories of his upbringing—from working the railroad night shift while trying to...

In this episode of The Calgary Sessions, Jeff sits down with Vince Fowler, a performance coach who works with CEOs and entrepreneurs across North America. His work focuses on understanding human behaviour, the decisions leaders make under pressure, and the psychological patterns that shape leadership and impact. Vince shares the story behind his path, beginning with a difficult upbringing and the...

Michelle Morgan has spent nearly two decades working as an actor, including a long run on Heartland, and has more recently stepped into directing. In this conversation, we look at what it actually means to build a creative career over time. She talks about nearly choosing a different path early on, how her confidence has shifted between her 30s and 40s, and whyintuition has become central to how s...

Pete Estabrooks has been part of Calgary’s fitness culture for decades, but his story didn’t begin in a gym. As a teenager, he was arrested for armed robbery and spent time in jail. In this episode, Pete shares how boxing became structure, how running replaced destructive highs, and how discipline slowly rebuilt his identity over time. We talk about responsibility, aging, addiction, and what it ac...

Drezus is a Plains Cree hip hop artist and storyteller whose work is rooted in identity, resilience and culture. We talked about what it was like growing up feeling different, carrying anger, and not really knowing where to put it. Hip hop became the place where he figured out how to speak. Not just through music, but through understanding who he was. He’s honest about masculinity, fear, ceremony...

In this episode of The Calgary Sessions , I sit down with Rob McLeod , also known as Frisbee Rob. Rob didn’t find his path early. He didn’t discover frisbee until after high school, and long before it became his work, teaching and helping others were already part of who he was. We talk about what it’s like to grow into something over time, without a clear plan or early certainty. Rob also opens up...

Templ Brewing co-founder Dane Thorogood shares the hard reset that changed how he shows up at work and at home. His path runs through high-performance sport, family business, and addiction, then into the day-to-day habits that keep him grounded. On the business side, we talk about learning sales through reps, building a scrappy system with people you trust, and growing in the non-alcoholic space w...

Felipe Alberto Paredes-Canevari performs Peruvian musica criolla and works in civil litigation. This conversation is about standards. The kind that come from taking the work seriously, whether you are carrying someone’s legal problem or stepping on stage with a tradition that has real history behind it. Felipe talks about identity as something shaped by lineage and lived experience, not a story yo...

In this episode of The Calgary Sessions, I sit down with Mike Peace. Mike talks about growing up after immigrating as a kid, experiencing trauma early, and leaving school sooner than expected. He shares how restaurant work led him into tattoo shops, what it was like to learn the craft by watching rather than being taught, and how tattooing has changed over the years. We talk about opening and runn...

Some businesses grow fast and disappear. Others last through exits, downturns, and restarts. In this episode, Shawn Freeman talks about why relationships are the real structure holding a business together. Not as a value statement, but as something tested through building companies, selling one, stepping away, and starting again. The conversation moves through how trust compounds quietly over time...

Fear shows up quietly. It shapes how we make decisions, how we measure progress, and how long we stay in situations that no longer feel right. In this episode, I sit down with Dr. Laura Hambley Lovett , an organizational psychologist, researcher, and author, to talk about what happens when logic, effort, and planning stop being enough on their own. We explore why life can start to feel like a cons...

Life doesn’t usually offer clarity when you need it. In this episode, reflects on what it means to keep moving forward through uncertainty. From early responsibility and family instability to becoming a husband, father, and leader while still figuring things out, his story unfolds without clean timelines or clear answers. Michael is a Canadian speaker, author, and founder whose work has grown out...

Cassie Hawrysh has lived most of her life in high pressure environments. She grew up around adults, learned responsibility early, and carried that into sport where effort and expectations shaped almost everything she did. When she became one of the top skeleton athletes in the world, the drive that pushed her forwardalso became the thing she had to untangle. This episode looks at what happens when...

Some people grow up fast because life demands it. Teika did. She carried responsibility early and learned to pay attention young. That awareness shaped how she understood people, how she stayed steady in difficult moments, and howshe found confidence in structure and discipline long before tattooing entered her life. This episode gets into the experiences that shaped her thinking. The pressure of...

Success rarely comes from a straight line. Nic Beique built Helcim into one of Canada’s most respected fintech companies, but the road that shaped him was full oftiming, luck, perseverance, and the kind of complicated lessons that make you who you are. In this episode, Nic talks openly about the parts of growth people don’t see. The doubt that shows up at every level. The moments where confidence...

What if you don't need a "5-year plan" to be successful? We're all pressured to find our one "passion" and follow a perfect, linear path. But what if that's not how the most interesting careers are built? Laura Naaykens is a former NCAA athlete who, after an injury, found herself in a complete identity crisis. She didn't have a grand plan; she just started... fi...

Manifestation isn't just "thinking positive." It can be a practical, daily tool, as simple as a specific morning routine—from a cold plunge to how you write in a journal—that you use to run your life and business. These insights come from Brent Boucher, a Calgary entrepreneur whose story is a perfect example of what I call "grey thinking". He built his business from a place...

How do you build a life when your childhood is defined by instability? Brent Boucher is a Calgary entrepreneur who built a successful motorcycle shop and finance company from scratch. But his journey started in a place of deep trauma, navigating family mental health crises and leaving school in Grade 11 just to pay the bills. In this conversation, Brent shares the unconventional origin story of hi...

Dr. Matt Brown had his entire life planned: pro football, then medical school. He details the "helmet to helmet" hit that ended his career and the "messy" mental health transition that followed. He discusses the stigma that kept him from seeking help and the pivotal moment he sat on the field and asked, "Who am I without football?"—and heard "deafening... silence." Ep177 Guest: Dr. Matt Brown, Men...