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/

—

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.

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.

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.

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

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 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.

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.

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.

What do you get when you mix retail sales, banking, construction, mortgages, and a little Duolingo?
You get Dennis Aguirre.

In this episode of The Open House Podcast, we sit down with Caledon and Vaughan realtor Dennis Aguirre to talk about:

• Building a real estate career from the ground up
• Why client experience beats flashy marketing every time
• The condo market reality in the GTA
• Pricing strategy in a shifting market
• Why time is your most valuable currency
• Young fatherhood, ambition, and learning to love the season you’re in

Dennis shares his journey from overnight banking shifts and insurance contracts to managing new developments and finally stepping fully into real estate in 2021. We dive into what he’s seeing in the Caledon and Vaughan markets, what buyers and sellers need to understand right now, and why playing the long game matters more than timing the perfect move.

We also get real about:

• Balancing business growth with being present as a dad
• The guilt, the grind, and the growth of entrepreneurship
• The power of “no” and protecting your time
• Social media, collaboration, and building relationships beyond your backyard

And yes… there’s plenty of golf talk.

If you’re a young parent building a business, a realtor navigating today’s market, or someone who believes ambition and gratitude can coexist, this one’s for you.

🎧 If you made it to the end… you know what to do.
Send us a message on Instagram and we’ll buy you a coffee.

⭐ Don’t forget to:

• Follow / Subscribe wherever you get your podcasts
• Leave us a rating on Spotify or Apple
• Subscribe on YouTube

Thanks for stopping by our Open House. We’ll see you when the house is open.

Kevin shares the full “what do you even do?” breakdown, including his day job as Art Director at Collaborative House Marketing in downtown Midland (graphic design, web/UI/UX, photo, video, social, basically “if it’s creative, it’s on his desk”), plus his very not small “side hustle” as Kevin Cascagnette Photography, capturing weddings, families, newborns, and those milestone moments that somehow become more valuable every year you keep living.

From there, the conversation goes deep in the best way: why printed photos still matter in a world of endless camera rolls, how Kevin’s love of people turns into “passive networking,” and why he’d rather connect humans than do the whole stiff handshake-and-business-card routine. You’ll hear about his volunteer work with North Simcoe Rotaract (including how it got started and why it’s not as intimidating as people think), his board role with CLH Foundation, and how mentorship is less “guru worship” and more “learn the good stuff… and the stuff you’ll do differently.”

Also on the menu:

• why entrepreneurship is hard but still worth it (especially when you’re not being “corporately seasoned”)
• a surprising amount of heartfelt love for Test Batches and the community builders behind it
• Kevin’s decompression life: convertibles, story-driven video games, and why Red Dead Redemption 2 hits like an emotional freight train
• Ben’s legendary Boston accent cameo (apologies to the entire state of Massachusetts)

It’s funny, it’s thoughtful, and it’s basically a masterclass in how to build a community by simply being a good human—while still finding time to do… literally everything.

If you enjoyed the episode, make sure to follow/subscribe, rate, and leave a review wherever you’re listening (Spotify, Apple Podcasts, YouTube, Amazon Music, etc.). And if you made it to the end: congrats, you’re officially part of the Open House.

What starts as “Ben learns who the guest is in real time” turns into a surprisingly thoughtful conversation about:

• Rotaract (think: Rotary’s younger, fundraiser-and-community-energy cousin)
• Growing up in Tiny and the pull of nature, solitude, and slower living
• Making the leap from a family automotive business into full-time creative work
• The messy middle of entrepreneurship: structure vs freedom, income uncertainty, and trusting the long game
• Jess’ children’s books (The Old Lady in the Shed and Jem’s Unicorn, available at Indigo)
• Why her “poetic prints” hit people right in the feelings (including one hanging in Richard’s office)
• A detour into psychology, Gabor Maté, and how understanding people changes how you move through the world
• The vulnerability of markets, self-promotion, and being both the CEO and the creator of your own art business

Plus: barefoot nature therapy gets debated, a haunted violin movie is discussed, and Ben confirms that toddlers believe every older person is named “Mimi.”

Find Jess here:
Website: artistjessgraham.ca
Instagram: @artistjessgraham

Follow / subscribe so you don’t miss upcoming episodes with more local voices you can actually run into downtown (and yes, please rate the show—future Ben and Richard will thank you).

In this episode of The Open House Podcast, Ben and Richard welcome Jake Lewis a local business operator, new dad, and all around “do whatever the day demands” kind of guy. Jake breaks down what it’s like growing up in an entrepreneur family, working alongside his dad from a young age, and helping run a multi part operation that includes Precision Balancing Services (PBS), KG Bearing & Belting, and yes… a legal cannabis business in Victoria Harbour.

You’ll hear about
• The reality of “gray collar” work: admin one day, factory installs the next
• How Midland has changed (and hasn’t) from poutine in the old mall food court to Amazon at your door in a blizzard
• Why community, family dinners, and staying connected with friends matters more as you get older
• How becoming a dad changes everything (including sleep schedules, in hilarious ways)
• The surprisingly meaningful side of gaming and lifelong friendships built through World of Warcraft
• A quick detour into F1 fandom, because obviously

It’s warm, funny, and full of small town perspective with big life lessons. Hit play, throw it on while you shovel (again), and come hang out.

New episodes drop every Tuesday. If you enjoyed this one, share it with a friend, leave a rating, and drop us a comment with your feedback.

Connect with us
Ben Robitaille: www.bensells.ca
Richard Thompson: www.georgianbaylending.com

We talk goals we are excited about, fears we are not pretending do not exist, and how we actually plan a year when life includes businesses, families, mortgages, and the occasional existential spiral at 2 a.m.

This is a real conversation about what success actually looks like now. Not just revenue or growth charts, but energy, presence, health, and showing up properly for the people who matter most. We unpack how we set goals, how we measure progress, where we have screwed it up before, and what we are doing differently this time around.

If you are an entrepreneur, a parent, a partner, or someone trying to build a full life instead of just a busy one, this episode is for you.

Listen in, reflect a little, steal what works, and feel free to reach out if something resonates.

Connect with us
Ben Robitaille
ben@bensells.ca
www.bensells.ca

Richard Thompson
richard@georgianbaylending.ca
www.georiganbaylending.ca

If you enjoyed the episode, subscribe, leave a review, and share it with someone who is also trying to do a lot without losing themselves in the process.

We talk about Richard’s journey to becoming a mortgage broker, the twists, risks, and moments that shaped how he approaches both business and people today. He also shares how he met his wife and built a life with her, before we detour into legendary family humour, including the long-running joke about multiple generations of children being conceived on the same mattress. For the record: no, that did not actually happen, but the fact that he lives in his grandparents’ house makes the story way funnier.

It’s candid, funny, self-aware, and surprisingly thoughtful, a reminder that behind every professional is a human being with a story that didn’t come from a LinkedIn headline.

If you enjoy real conversations, good-natured oversharing, and laughs with a bit of depth underneath, this episode is for you.

Contact & Connect

Ben Robitaille
Real Estate Agent
🌐 www.bensells.ca
📧 ben@bensells.ca
📱 705-535-0913
📸 Instagram: @benrobitaillerealtor

Richard Thompson
Mortgage Broker
🌐 www.georgianbaylending.ca
📧 richard@georgianbaylending.ca
📸 Instagram: @georgianbaylending

Ben Robitaille | ben@bensells.ca

@benrobitaillerealtor

Richard Thompson | Richard@georgianbaylending.com

@georgianbaylending

The learn more give the wonderful Amber a follow on instagram:

@shecomesfirst.av

You can also follow your hosts:

@benrobitaillerealtor

@georgianbaylending

Thanks for listening!

Mercedes pulls back the curtain on how Junior Achievement empowers students across the province by bringing real-world financial education directly into classrooms. From budgeting and saving to entrepreneurship and career readiness, she shares why these programs matter now more than ever — and how early financial confidence can shape a young person’s entire future.

We dive into the challenges students face today, the gaps in traditional education, and the inspiring impact JA has on communities across Ontario. Mercedes also talks about what drew her to the organization, the stories that keep her motivated, and how educators and volunteers can help support this mission.

Whether you're a parent, teacher, business owner, or someone who wishes you had been taught this stuff earlier in life, this is a conversation you don’t want to miss.

Connect with us:
Ben Robitaille — ben@bensells.ca
Richard Thompson — richard@georgianbaylending.com

Elle Social | https://www.instagram.com/e.l.l.e.social/

Jess on Insta | https://www.instagram.com/jessicaradecki.realestate/?hl=en

Courtney on Insta | https://www.instagram.com/mrscourtneycorfield/

Connect with your hosts

https://www.instagram.com/theopenhousepodcast/

We talk about what inspired them to launch Pulse, the real stories behind their clients’ transformations, how nutrition plays into everyday energy and performance, and why creating a supportive community matters just as much as the food on your plate. Expect practical tips, honest insight, and a whole lot of passion for helping people live stronger, healthier lives.

If you want to feel motivated, informed, and maybe slightly guilty about skipping breakfast this morning, this episode has your back.

Connect with your hosts
Ben Robitaille: ben@bensells.ca
Richard Thompson: richard@georgianbaylending.com

From understanding the role of insurance to finding balance between risk and reward, this conversation is packed with insights for entrepreneurs, homeowners, and anyone looking to take control of their financial future.

Connect with your hosts:
📩 Ben Robitaille — ben@bensells.ca
📩 Richard Thompson — richard@georgianbaylending.com

Follow The Open House for more real conversations with the people shaping business, finance, and community life around Georgian Bay.

In this episode, Sharelle McArthur and Chrissy Wood share how their friendship and determination helped raise over $360,000 to buy an airboat for a Southern Georgian Bay fire department. Along the way, we talk community, theatre, parenting, and the heart behind giving back.

Real stories. Real people. Real conversations.