What do a raccoon in the attic, a call center job taking 100+ calls a day, and a leap from Royal Bank of Canada into entrepreneurship all have in common?

This episode.

We sit down with Joel Fox, co-founder and COO of Ownright, to unpack the real story behind building a company from scratch, and why it’s a lot less glamorous (and a lot more valuable) than most people think.

Joel walks us through:

• The unexpected lessons from his early career (including getting yelled at about mutual funds… a lot)
• Why leaving a stable corporate role is both terrifying and necessary
• The reality of starting a business during COVID—and what actually goes into those first few months
• How a frustrating real estate closing experience turned into a scalable business idea
• The truth about raising money, building a pitch deck, and finding the right investors
• Why most people underestimate the importance of their real estate lawyer (until it’s too late)
• We also get into the mindset side of things, fear, failure, and how to make decisions based on what you’ll regret not doing.

And yes… we do eventually address the raccoon situation.

If you’re an entrepreneur, thinking about making the leap, or just want a behind-the-scenes look at how modern real estate services are evolving, this one’s worth your time.

This one’s got everything… small town grit, big life pivots, and a barbershop that somehow turned into a community hub.

We sit down with Chris Walsh, the owner of Hemingway’s Barbershop, to talk about his journey from the hospitality grind to building one of Midland’s most talked-about local businesses. From chasing snow in Banff to opening a shop (and now expanding into Muskoka), Chris breaks down what it really takes to bet on yourself… and win.

We get into:

• Walking away from a stable job to go all in
• Building a business from scratch (literally… tools and all)
• Why community > competition
• The reality of entrepreneurship no one talks about
• And how a barbershop became a place people actually want to hang out

There’s also a solid mix of laughs, life lessons, and yes… a raccoon rave in the attic.

If you’ve ever thought about starting something of your own, this episode might just be the nudge you needed.

👉 Check out the upcoming Hemingway’s Barbershop Golf Tournament here:
https://events.golfstatus.com/event/2026-hemingway-s-barber-social-club-golf-tournament/

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Thanks for watching and listening. If you’re enjoying the show, make sure to subscribe, share it with a friend, and we’ll see you at the next one.

What do a peanut butter porter, a paint store, and a small-town success story have in common? This episode.

We sit down with longtime Midland entrepreneur Jamie Tripp to unpack the journey behind building not one, but multiple businesses in our community. From discovering Midland by accident in the 90s to running a paint store for nearly three decades, Jamie shares what it really takes to take risks, adapt, and grow in a small-town market.

We get into:

• The unexpected move that changed everything
• What it’s like buying a declining business and turning it around
• The power of timing, including riding the HGTV wave
• Building multiple businesses while raising a young family
• Why small towns like Midland, Penetang, Tiny, and Tay are quietly some of the best places to live and build

There’s also a real conversation about entrepreneurship, community, and why sometimes the best opportunities aren’t planned at all.

If you’ve ever thought about starting something of your own, moving to a smaller community, or just want a behind-the-scenes look at how local business actually works, this one’s worth your time.