The Calgary Sessions

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...

What happens when the one thing that defines you is gone? Dr. Matt Brown had his entire life planned: play pro football, then become a surgeon. But a single helmet-to-helmet hit ended his career, broke his neck, and shattered his identity. In the darkness that followed, he felt "gutted like a fish" and asked himself a question that would change his life: "Who is Matt Brown without f...

What does it take to lose the business you built from scratch and then come back to create an even bigger success? This week, we sit down with Hailey Seidel, the founder of Calgary’s luxury pet hotel, The Petropolitan, for a masterclass in resilience, branding, and grit. For 20 years, Hailey has been a force in the pet care industry, but her path was anything but straight. Her journey started by a...

What if the key to unlocking your highest potential wasn't about pushing harder, but about becoming more authentic? My guest this week, Kayti Simonson, shares her profound journey from a high-achieving lawyer and athlete running on adrenaline to a resilient competitor guided by energy and intuition. Kayti is a Calgary-based lawyer and three-time HYROX world championship competitor who seemed t...

I've always been fascinated by the moments that change everything. Not the big goals we set, but the unexpected turns that truly define us. My guest this week, Cari Din, calls these powerful moments "interruptions". Cari is an Olympic silver medalist in artistic swimming and an award-winning Kinesiology professor. She was incredibly open about her journey, from the intense focus of b...

What if the biggest risks lead to the most meaningful rewards? My guest this week, Christine Goudie, is the definition of that question. As the Co-founder and CEO of Granville Biomedical, she has forged a unique path driven by a desire to use her design skills for good, starting with a one-way ticket out of Newfoundland with just $250 in her pocket. In our chat, Christine took me through her incre...

What does it mean to shape ideas for a living? In this episode, Shelley reflects on what it takes to shape meaningful ideas, how to trust your gut in creative decisions, and what it feels like to stay curious over time. Her stories reveal how culture takes shape through consistent and thoughtful choices. A few themes that run through the episode: • Creating space for conversations that matter • Ma...

Jamie Parker didn’t plan to become an entrepreneur. He worked a lot of jobs, spent time on wildfire crews, and started roasting coffee in a garage before anything looked like a business. That business became Canadian Heritage Roasting Company. This episode isn’t about overnight success. It’s about figuring things out by doing the work, staying committed when there’s no clear payoff, and navigating...

Marco Carducci is still in the game, competing at a high level, leading on and off the field, and figuring it out as he goes. In this episode, Marco reflects on what it took to make it in pro soccer, what nearly pulled him away from it, and how he's found a healthier way to thrive without losing himself in the process. He opens up about growing up in Calgary, the pressures of early success, the id...

Trent McClellan didn’t step on stage until he was 30. No plan, no roadmap. Just a feeling he couldn’t ignore. We talked about what it took to go from a full-time day job to late-night open mics, touring small towns across Alberta, and eventually landing on 22 Minutes. Trent shared the less visible side of his career. The mental discipline. The self-doubt. The pressure to define success without tyi...

Crystal was chasing the Olympics when she was diagnosed with MS. What came next was unexpected, but the way she handled it shaped everything that followed. In this episode, we talked about competing at a high level, what it’s like to face a sudden diagnosis, and why Crystal started rethinking the healthcare system from the inside. We also got into the early days of the Branch Out Foundation and th...

Dr. Karen MacNeill and I talk about what it really takes to perform under pressure. Whether you’re an athlete, leader, or just someone trying to keep it together in tough moments. She shares honest stories about setbacks, the mindset shift from fear to freedom, and how mental fitness makes the difference when it counts. We talk about resilience, finding balance, and why clarity and purpose matter...

Ross has done a lot in his life: firefighter, nurse, musician, speaker, and now the host of a TV show. What really stood out was how all those parts of his story came together. We talked about service, identity, and the tension between being who you are and who you're expected to be. Ross shared what it’s like to discover his Métis roots later in life, the lessons that come from frontline work...

I sat down with Nicole Robertson, a journalist and founder of Muskwa Productions, to talk about where her voice comes from and how she’s used it to tell hard stories for nearly 30 years. With Cree and Scottish roots, she spoke about growing up between cultures and the early experiences that shaped her sense of identity. We talked about the loss of her childhood friend Neil Stonechild, her early re...

In this episode, I sit down with Emma Harding, a voice coach and artist development expert who grew up backstage in the British rock scene and later built a creative life in Calgary. We get into what it really means to unlock your true voice, how healing your past can change your performance, and why community matters more than chasing perfection. We also talk about ADHD, imposter syndrome, and th...

Daniel Plenzik built a steady career as an electrical engineer before deciding to leave it behind. What started as a personal passion for winemaking turned into a full-on commitment to craft spirits, leading to a Calgary distillery that quietly produced the best brandy in the world. We talked about what it really takes to step away from security, how long-term thinking shapes every decision, and w...