The Calgary Sessions

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

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

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

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

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

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

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠

Connect with Jeff Humphreys

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Podcast Location & Production:

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios⁠

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

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 without losing the basics.

Connect with Dane Thorogood:

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website

Connect with Jeff Humphreys

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Podcast Location & Production:

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios

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 you invent on demand.

We get into what clarity actually costs, why preparation is a form of respect, and why “balance” is not the word when two serious crafts are involved. It is a grounded look at craft, responsibility, and what it means to stay honest when the room is paying attention.

Connect with our guest, Felipe Alberto:

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠

Connect with Jeff Humphreys

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠

Podcast Location & Production:

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios

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 running a shop, the emotional weight that comes with client-facing work, and the kind of conversations that happen in a tattoo chair. Mike also speaks openly about alcohol addiction, choosing sobriety, and why cycling became a necessary replacement structure in his life. Movement, routine, and showing up consistently play a big role in how he manages his mental health.

There’s also time spent on community within tattoo culture, working alongside his son, and what it looks like to build a steady life without chasing anything bigger than what’s in front of you.

Connect with our guest, Mike Peace:

• ⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠Instagram

Connect with Jeff Humphreys

• ⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠

Podcast Location & Production:

• ⁠⁠⁠⁠⁠⁠⁠⁠Off Set Studios