The Calgary Sessions with Jeff Humphreys

Jeff Humphreys
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The Calgary Sessions: A podcast about the awesome people who make Calgary what it is. I'm Jeff Humphreys, and I'm here to share stories of locals who inspire us, from the big wins to the tough times.. Join me for real talks that get to the heart of our city. This show is all about connecting with the different voices in our community. Whether you've lived here forever or just got here, The Calgary Sessions is all about the amazing journey stories of people adding to our city's vibe.

  1. 7H AGO

    Adrian Stimson: From Tribal Councilor to the Art Studio

    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 people into some of the toughest conversations in our culture. From facing a gauntlet of racism in rural Alberta schools to being embedded with Canadian troops in Afghanistan, this conversation is about the search for a true vocation and the resilience required to find it. In this episode, we talk about: The Mid-Life Pivot: Why Adrian left a 10-year political career to become a student again. The "Tickle, Slap, and Hug": A real-world framework for navigating hard truths through art. Life in Afghanistan: What Adrian observed while embedded with the troops in Kandahar. Siksika Culture: The responsibility of protecting the language of pictographs and Blackfoot history. Leading AUArts: Taking one of Canada’s premier art institutions into its 100th year. Connect with Adrian Stimson: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram Connect with Jeff Humphreys ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Podcast Location & Production: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios⁠

    1h 36m

  2. MAR 25

    Burn the Boats: Total Commitment with Tommy Wheeldon Jr.

    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 "nomadic" childhood taught him to find comfort in uncomfortable situations and why he believes every high-performer needs to schedule time for "play" to stay sharp. We also explore the "Sunrise and Sunset" of a career—a powerful framework for navigating transitions and helping people find their purpose long after the game (or the job) is over. In this episode, we talk about: The "Burn the Boats" Strategy: Why total commitment requires severing your retreat lines. Gifting Yourself "Play": How hobbies like golf provide the mental clarity needed for high-stakes leadership. Career Transitions: Managing the "sunset" of a professional journey and finding a new identity. The Power of Mentorship: Lessons from the legendary Southern family and building a community at Spruce Meadows. Connect with Tommy Wheeldon Jr.: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠ Connect with Jeff Humphreys ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Podcast Location & Production: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios⁠

    1h 30m

  3. MAR 18

    "Never Be the Smartest Man in the Room" | Peter Izzo

    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 finish high school, to being 16 years old and driving himself to junior high because he was "out ofsync" with his peers. He also opens up about the difficult ultimatum from hisfather that forced him to choose between his own independence and taking the business out of the family basement to build what it is today. Inside the conversation: The "Old World" Tension: The struggle to modernize a business when the previous generation prefers torun it out of the home. The Railroad & The Classroom: Working overnight on the LRT lines while calling in your ownschool absences at age 18. Entrepreneur vs. Businessman: Why "seat of the ass" entrepreneurs are a different breed than those with a traditional business plan. Defining Success: Why Peter believes success is an internal belief, not a perception of being "the Golden Globe." Connect with Peter Izzo: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠ Connect with Jeff Humphreys ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Podcast Location & Production: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios⁠

    1h 41m

  4. MAR 11

    Vince Fowler: From Paratrooper to Coaching CEOs

    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 moment in Grade 6 when he decided he wanted to become a Canadian paratrooper. That early decision shaped his identity, discipline, and relationship with adversity. Years later, after navigating high-performance environments and personal challenges, he began exploring the deeper psychological work required to understand behaviour, resilience, and personal growth. The conversation explores the connection between military mindset and entrepreneurship, why understanding human behaviour matters for leadership, and how high-performing people often have to rebuild themselves after intense periods of achievement. Jeff and Vince also discuss discipline, identity, decision-making, and what it means to truly embrace the difficult parts of life in order to move forward. Connect with Vince Fowler: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn Connect with Jeff Humphreys ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Podcast Location & Production: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios⁠

    2h 20m

  5. MAR 4

    Michelle Morgan: Acting, Directing and Creative Identity

    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 she makes decisions. We discuss moving from performer to director, managing energy on set, and the kind of inner work that allows creative careers to last. If you’re navigating your own creative path, this conversation offers an honest look at longevity, identity, and staying inthe work without forcing it. Connect with Michelle Morgan: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠ Connect with Jeff Humphreys ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Podcast Location & Production: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios⁠

    1h 22m

  6. FEB 25

    Pete Estabrooks: How Fitness Replaced Addiction and Reshaped His Life

    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 actually takes to change direction. Now in his 60s, Pete is still racing, still competing, and still training. This is a conversation about consequences, daily choices, and what happens when someone commits to rebuilding their life one habit at a time. Connect with Pete Estabrooks: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram Connect with Jeff Humphreys ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Podcast Location & Production: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios⁠

    1h 56m

  7. FEB 18

    Drezus on Finding His Voice Through Hip Hop and Culture | Ep 190

    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 and the work of healing. Nothing polished. Just the reality of shifting from reacting to life to taking responsibility for it. We also get into what it means to carry your roots publicly, how culture shapes confidence, and how success eventually turns into service. It’s less about music and more about what happens when you stop hiding who you are. Connect with Drezus: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠ Connect with Jeff Humphreys ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Podcast Location & Production: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios⁠

    1h 37m

  8. FEB 11

    Rob McLeod: Starting Late, Failing Often, and Staying With It | Ep 189

    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 about losing his mom at 18, and how that kind of loss doesn’t always show up as a dramatic turning point. Sometimes it quietly shapes how deeply someone commits to their work, and how they define success for themselves. We spend time on failure too. Not as a lesson, but as a reality. Rob shares what it means to attempt something again and again without immediate results, and how repetition, patience, and self-awareness matter more than talent or recognition. This conversation also touches on the gap between visibility and value. World records and attention don’t always translate into stability, and Rob reflects honestly on what it takes to build something that lasts. At its core, this episode is about starting later than expected, questioning your own motivations, and choosing to play the long game. Connect with ”Frisbee Rob” McLeod: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube Connect with Jeff Humphreys ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Podcast Location & Production: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios⁠

    1h 22m
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About

The Calgary Sessions: A podcast about the awesome people who make Calgary what it is. I'm Jeff Humphreys, and I'm here to share stories of locals who inspire us, from the big wins to the tough times.. Join me for real talks that get to the heart of our city. This show is all about connecting with the different voices in our community. Whether you've lived here forever or just got here, The Calgary Sessions is all about the amazing journey stories of people adding to our city's vibe.

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