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.

In this episode of The Open House Podcast, we sit down with Adrian Sauvageau, a true entrepreneur who’s built multiple businesses from the ground up… and not in the way you’d expect.

From launching a marketing agency that got wiped out by COVID, to pivoting into real estate investing, to building a community-first pawn shop, pet store, and property management business, Adrian walks us through how he turned uncertainty into opportunity.

We dive into:
• How he scaled multiple businesses using partnerships
• The mindset shift from working in the business to working on it
• Why “passive income” isn’t actually passive
• The power of calculated decisions over risky ones
• Real stories from buying, renovating, and selling properties (including a $600K win in under a year)

This is a raw, behind-the-scenes look at what it actually takes to build something meaningful… especially when things don’t go according to plan.

If you’re into entrepreneurship, real estate, or just figuring out how to create your own path, this one’s worth the listen.

Small town life, big city roots, and a fresh take on modern dating.

In this episode of The Open House Podcast, Ben and Richard sit down with Jordana, founder of EpicDates, to talk about her move from Toronto to Simcoe County and how it led to a completely new business idea. What started as a search for community turned into a platform designed to help people connect in real life without endless swiping.

They get into why so many people are leaving the city for places like Midland and Collingwood, the challenges of building community in a smaller market, and what is really going on with dating apps right now.

You will also hear:

• Why meeting people in small towns can feel harder than expected
• How EpicDates is helping singles and couples create real experiences
• The problem with modern dating apps and what people actually want instead
• Why planning better dates can change your relationship
• A few surprisingly good local date ideas you might not have considered

There is also plenty of honest conversation about parenting, hustle culture, and finding a better balance between work and life.

If you want better date nights, stronger connections, or just a reminder of what is possible right in your own community, this episode is worth the listen.

Listen in and maybe plan your next epic night out

What happens when a nurse trades hospital shifts for a teal dog bus full of howling pups?

In this episode, we sit down with Megan, the owner of Tales and Trails Dog Retreat, to unpack how a side hustle turned into one of the most joy-filled businesses in the community. From COVID timing and gut decisions to buying a retired school bus for dogs (yes, really), Megan shares the real story behind building something from scratch, messy moments and all.

We dive into:

• Turning a passion into a full-time business (without a perfect plan)
• The reality of balancing entrepreneurship and motherhood
• Why not every dog and not every client, is the right fit
• The surprising emotional side of running a dog-based business
• And her long-term vision for a rescue or sanctuary that’ll melt your heart

Plus… what it’s actually like inside a bus full of dogs (spoiler: loud, chaotic, and oddly magical).

If you’ve ever thought about starting something of your own or just need a guaranteed mood boost, this one’s for you.

Jacqueline Sunday of Sunday Restoration joins us for a conversation about vintage home decor, entrepreneurship, community, and the courage it takes to build something meaningful. What starts with sump pumps, Roll Up the Rim, and a few laughs turns into a thoughtful discussion about style, sustainability, small business ownership, imposter syndrome, and why collaboration beats competition every time.

Jacqueline shares the story behind Sunday Restoration, how a layoff led her toward a more creative path, and how her Midland shop has become more than just a store. It’s a space rooted in restoration, connection, and giving back. We also get into the challenges of growing a business as one person, the importance of putting yourself out there, and why feeling a little uncomfortable might just mean you’re growing.

This one is funny, heartfelt, and packed with great perspective on community, confidence, and building a life and business that actually feels like you.

This week on The Open House, Ben and Richard sit down with Emily from Emily’s Esthetics to talk about what it really looks like to build a business from the ground up at just 23 years old.

From getting laid off and opening her own business a month later, to growing a loyal client base, hiring a team, and dreaming about one day franchising across Canada, Emily shares the real story behind her success. The conversation dives into entrepreneurship, taking risks before you feel ready, learning to set boundaries, building a brand people trust, and why personality matters just as much as skill when growing a business.

They also get into skincare, self-care, social media, small-town business life, and the balancing act of building something big while still making time to live your actual life. It’s an honest, fun, and inspiring episode for anyone chasing a dream, growing a business, or just trying to figure things out as they go.

Plus: facials, hydrofacials, brows, bestie spa days, and a completely reasonable amount of chest-waxing talk.

If you’ve ever wondered what it takes to bet on yourself and make it work, this episode is for you.

This week on The Open House Podcast, Ben and Richard do something rare (and mildly reckless): they invite on guests they’d never met before hitting record.

Meet Anna and Alex from GB Singles Social

the Georgian Bay-area singles club creating real, in person connection through fun events like trivia nights, bowling, walks, and yes, the occasional euchre tournament. Think less awkward speed dating, more “actually enjoying yourself while meeting new people.”

We talk about how GB Singles Social started in 2025, how they keep events welcoming and safe (including the genius “wing pal” option), why small town dating has its own special plot twists, and what success looks like when your best members literally meet someone and “graduate” out of the group.

If you’re single in the area, know someone who is, or you just miss the concept of humans talking to humans — you’re going to love this one.

Follow & Get Involved
Follow @gbsinglessocial on Instagram for event updates and the sign up form.

Next Event
April 9 at Quayles — euchre tournament night.

As always, thanks for stopping by our open house.