In this episode of The Country Club Podcast, host Diana Cassidy-Bush sits down with Greg Gaylord, owner of Gaylord Hardwood Flooring, to explore what it truly means to go away, come back home, and grow a global business from a small town.

After going away for school and gaining perspective beyond his hometown, Greg made the intentional decision to return—raising his family locally while continuing the legacy business his parents founded in 1985. What began as a small, family-run operation has grown into an internationally recognized hardwood flooring company, supplying custom floors to builders and homeowners across North America and beyond.

This conversation dives into leadership succession, craftsmanship, sustainability, and the power of relationships in building long-term success. Greg shares how staying rooted in core values, listening closely to clients, and making thoughtful, incremental improvements have allowed the company to evolve without losing its identity.

This episode is a reminder that success doesn’t always mean leaving—it can mean coming back, staying rooted, and building something meaningful that lasts.

Episode Timestamps

00:00 – 02:00 | Welcome to The Country Club Podcast & episode introduction

02:00 – 03:10 | The origins of Gaylord Hardwood Flooring (founded in 1985)

03:10 – 04:20 | Growing up in a family business & early lessons

04:20 – 05:30 | Choosing to carry the legacy forward

05:30 – 06:40 | Leadership challenges & growing in a competitive market

06:40 – 08:00 | Balancing tradition with innovation

08:00 – 10:10 | Building global reach from a small town

10:10 – 11:20 | The power of referrals & long-term relationships

11:20 – 12:45 | Featured projects & Netflix exposure

12:45 – 14:30 | Hardwood flooring trends: low maintenance & natural finishes

14:30 – 16:10 | Quality, sourcing, and what buyers should know

16:10 – 17:30 | Sustainability & the value of buying local

17:30 – 19:00 | Choosing to raise a family in the community

19:00 – 21:20 | The showroom renovation & creating an experience

21:20 – 22:45 | Family, business, and community connection

22:45 – 25:45 | Personal stories & family moments

25:45 – 28:15 | The legendary company limo story

28:15 – 30:45 | Final reflections & closing thoughts

Notable Quotes

1. “You don’t have to leave home to build something exceptional.”
2. “Innovation doesn’t always mean big breakthroughs—it’s about getting better every day.”
3. “People want their floors to look like wood again, not a piano.”
4. “There’s nothing more sustainable than buying local and building to last.”
5. “Referrals come from relationships, not transactions.”

Key Takeaways

1. Legacy businesses thrive when core values stay intact—even as markets change
2. Global success can grow organically through trust, referrals, and consistency

In this solo episode of The Country Club Podcast, host Diana Cassidy-Bush kicks off the new year with a refreshing, grounded conversation about real estate goal-setting—one that prioritizes clarity, lifestyle, and long-term planning over market predictions and media noise.

With headlines shouting forecasts and opinions at every turn, Diana offers a calm counterpoint: planning beats predictions every single time. She walks listeners through how to slow down, reflect on where life has actually landed them, and use real estate as a tool to support—not complicate—the life they want to build.

Whether you’re considering buying, selling, downsizing, upsizing, investing in a cottage, or simply getting organized for the future, this episode provides a simple, realistic framework for thinking about real estate in one-, three-, and five-year horizons. It’s thoughtful, reassuring, and deeply practical—perfect for anyone who wants to move forward with confidence instead of pressure.

Timestamps

00:00–00:45 – Welcome to The Country Club Podcast & show positioning

00:45–01:33 – Why this conversation matters right now

01:33–02:24 – January noise, reflection, and real life priorities

02:24–03:30 – Predictions vs. planning in real estate

03:30–04:15 – Why your home should support your lifestyle, not stress it

04:15–05:15 – Lifestyle questions driving real estate decisions

05:15–06:15 – Country living, cottages, and lifestyle shifts

06:15–08:15 – Starting where you actually are (without judgment)

08:15–09:45 – Common buyer mistakes in a noisy market

09:45–10:45 – Interest rates, timing myths, and financial comfort

10:45–12:30 – Seller mistakes: pricing, renovations, and strategy

12:30–13:15 – Strategy vs. seasonality

13:15–14:30 – The 1-, 3-, and 5-year planning framework

14:30–15:15 – Asking better questions about your future

15:15–16:30 – Planning as a way to create options, not pressure

16:30–17:30 – Closing thoughts, planning worksheet & next steps

Notable Quotes

“Planning beats predictions every single time.”

“A good real estate plan isn’t about guessing the market—it’s about understanding what you want your life to look like.”

“Your home should support your lifestyle, not keep you up at night.”

“Good strategy will almost always outperform good timing.”

“When you focus on direction instead of decisions, you give yourself time—and time creates clarity.”

Key Takeaways & Value for Listeners

1. Tune out the noise.

Predictions change weekly. Your life goals matter more.

2. Start where you are—honestly.

Real planning begins with acknowledging your current season without judgment.

3. Avoid rushed decisions.

Most real estate mistakes come from reacting, not from lack of information.

4. Think in layers, not deadlines.

The 1-, 3-, and 5-year framework creates flexibility and confidence.

5. Let real estate serve your life.

Homes, cottages, and investments should support how you want to live—not the other way around.

Resources Mentioned

1. Real Estate Planning Worksheet – Linked in the show notes
2. (Designed to slow the process down and help clarify...

In this highly informative episode of The Country Club Podcast, Diana Cassidy-Bush welcomes Chartered Professional Accountant Ben Bryden from Wilkinson & Company to break down one of the most misunderstood and most consequential topics in real estate: capital gains tax.

Ben walks listeners through the whirlwind of tax changes proposed since 2024, explaining what was supposed to happen, what actually happened, and what property owners should know as we approach 2026.

Whether you own a cottage, rental, farmland, or you’re thinking about selling in the next few years, this conversation gives you the clarity you need to plan confidently and avoid surprises.

Key Takeaways

1. The Capital Gains Inclusion Rate Remains at 50% as of this recording

Despite the upheaval from 2024–2025, the proposed increase to a ⅔ inclusion rate was cancelled in March 2025, leaving the long-standing 50% rate in place. This eliminates the urgency sellers once felt but future budgets may still bring change.

2. Timing Matters—Your Income Year Affects Your Tax Bill

Consider selling in a year where your income is lower to reduce the marginal tax rate applied to your gain. Selling early in a calendar year can defers tax payment to the following April.

3. The 12-Month Rule Automatically Applies

If you sell a property within 12 months of buying it, the profit is generally treated as business income (100% taxable) rather than a capital gain (50% taxable). Only specific life events may qualify for exemptions.

4. The Principal Residence Exemption (PRE)

For people with multiple properties (house + cottage), thoughtful planning is key. You must choose which property to designate for PRE based on accrued gain per year. If you use the PRE on a cottage sale, future gains on your primary home may become taxable.

5. Mixed-Use Properties Have Special Rules

If part of your home is used for rental or business purposes:

• You may need to apportion the sale value between personal and income-producing use.
• Using more than 50% of your home for business can jeopardize the PRE entirely.

6. Land Size Matters

The principal residence exemption typically covers the home + up to ½ hectare (1.24 acres) of land. Additional land may be taxed separately unless you can prove it’s necessary to the home’s use.

7. “Change of Use” Can Trigger a Taxable Event

If you convert a principal residence into a rental (or vice versa), the CRA treats it as a deemed disposition—a taxable capital gain—even if you don’t sell the property. You can avoid this by filing a special election with your tax return. Missing the election can result in penalties and unexpected taxes.

8. Keep Every Receipt for Capital Improvements

There is no 7-year rule for cost-base documentation.

• Improvements that increase value (steel roof, addition, upgraded countertops) raise your adjusted cost base and lower your eventual capital gain.
• Repairs that simply restore condition (new shingles, repainting) do not count as capital improvements.

9. Estate Transfers Can Trigger Capital Gains

When someone passes away:

• Property transferred to a spouse rolls over tax-free.
• Property transferred to children triggers capital gains at fair market value.
• Large real-estate-heavy estates may face liquidity issues without planning.

10. Special Rules Apply to Farm Properties

Farms actively used in a farming business may qualify for:

• The Lifetime Capital Gains Exemption (LCGE)—now up to $1.25M
• Or special rollover provisions for transferring farmland to...

In this episode, Diana Cassidy-Bush sits down with Brian and Joanna Milligan, owners of Milligan Meats — the beloved local butcher shop that’s become a cornerstone for both year-round residents and weekend cottagers.

What started as a dream to stay close to home and community has turned into a thriving business built on passion, trust, and old-fashioned service. The Milligans’ share how they took a leap of faith, transformed a massive building into a welcoming local hub, and created a workplace that feels like family.

Whether you’re a small-town entrepreneur, a weekend visitor, or someone dreaming of your own “someday” business, this episode is full of inspiration, laughter, and lessons in leading with heart.

TIMESTAMPS

00:00 – 02:00 | Welcome to The Country Club Podcast — Diana introduces the Milligans and their story of starting Milligan Meats in Cloyne, Ontario

02:00 – 05:00 | From Alberta to Ontario — How Brian and Joanna met and how his lifelong butchering experience led to the dream of owning their own shop.

05:00 – 07:30 | Taking the Leap — Buying the building, trusting instincts, and Joanna’s creative vision that shaped the shop’s welcoming aesthetic.

07:30 – 10:30 | Creating the Milligan Experience — Why “old-fashioned” customer service never goes out of style.

10:30 – 13:30 | Building a Happy Team — The Milligans’ share how they cultivate harmony, fun, and respect among staff.

14:00 – 17:30 | Supporting Local, Building Community — How the shop supports farmers, bakers, and artisans; plus a touching story about a local charcuterie board maker.

17:30 – 20:30 | Seasonality and Growth — From summer crowds to hunting season, the rhythm of small-town business life.

20:30 – 24:00 | Adaptation and Expansion — Growing the team, expanding products, and balancing busy seasons with purpose.

24:00 – 28:00 | Secret Ingredients & Customer Favorites — Rib eyes, hamburger patties, barbecue sauce, and those famous chicken bobs.

28:00 – 30:00 | Final Reflections — The power of loving your work, giving back to the community, and finding joy in small-town life.

NOTABLE QUOTES

“I design everything by feel. When it feels right, I know it’s right — and so far, that hasn’t led us wrong.” — Joanna Milligan

“How can you not love your job when it’s all built around community, laughter, and good food?” — Diana Cassidy-Bush

KEY TAKEAWAYS

• Big Dreams Don’t Need A Big City: You can create a thriving business in your small town.
• Follow your instincts: Big dreams often start small — and scary. Trusting your gut pays off.
• Create experiences, not transactions: The Milligans built their success on connection, conversation, and care.
• Community is everything: Supporting local makers and farmers strengthens everyone’s success.
• Growth can be joyful: Even long hours feel lighter when your work aligns with your values.

RESOURCES & LINKS

• Milligan Meats, Coyne, ON — Visit in person or follow on social media for product updates and local stories.

Connect with Diana Cassidy-Bush:

Facebook: https://www.facebook.com/DianaCassidyBushRealEstate/

Instagram:

Myth: Small towns can’t sustain world-class arts.

Reality: They’re thriving.

In this episode of The Country Club Podcast, host Diana Cassidy-Bush welcomes Tim Porter and Emily Mewett of Tweed & Company Theatre, a powerhouse proving that rural Ontario is alive with creativity, culture, and opportunity.

From their start in 2009 to becoming one of Ontario’s top performing arts companies, Tweed & Co. has shattered expectations by bringing Broadway-level productions, concerts, comedy, and original Canadian works to intimate small-town stages.

Tim and Emily share how community support, collaboration, and bold vision turned a local dream into a cultural destination. They also bust the myth that you need a big city to build a big career in the arts—showing how small-town stages can create some of the most personal, memorable experiences anywhere.

🎭 Whether you’re an artist, entrepreneur, or someone chasing a dream in a smaller community, this conversation will inspire you to see rural life in a brand new light.

Timestamps

00:00 – 01:30 | Welcome to The Country Club Podcast – celebrating rural life, community, and opportunity.

01:30 – 03:30 | Meet Tim Porter & Emily Mewett from Tweed & Company.

03:30 – 05:30 | Why small-town theatre offers a more personal, meaningful experience.

05:30 – 07:30 | Community collaboration: local businesses and audiences rally behind the arts.

07:30 – 09:30 | The early days—renting venues, selling tickets at the Tweed News, and hustling for donors.

10:00 – 12:30 | Becoming one of Ontario’s youngest professional theatres.

12:30 – 14:30 | The turning point: new venues, big productions like Mamma Mia, and thousands of new audience members.

14:30 – 17:00 | Recognition, awards, and proving rural theatre is not “small scale.”

17:00 – 19:30 | Audience and performer feedback—why people can’t wait to come back.

19:30 – 22:00 | Investing in the future: youth programming, skill development, and hands-on learning.

22:00 – 24:30 | Why rural arts matter and how to experience them yourself.

24:30 – 26:00 | Closing thoughts: thriving careers and vibrant communities beyond the city limits.

Notable Quotes

• “It’s not small scale—it’s world-class talent in a more intimate setting.” – Tim Porter
• “The sense of community here is stronger. Success in one business leads to success across the town.” – Emily Mutt
• “We just need to get people in the door once. Then they’re sold.” – Tim Porter
• “The arts aren’t just alive outside the city—they’re thriving.” – Diana Cassidy-Bush
• “Our audiences here are so appreciative, because for them, it’s not just another show—it’s an experience that matters.” – Emily Mutt

Resources & Takeaways

• Tweed & Company: www.tweedandcompany.com – find tickets, merch, and program details.
• Recognized as one of Ontario’s top performing arts venues and winner of multiple arts & tourism awards.
• Young Company Program & High School Projects: Offering students hands-on experience in performance, stage management, costume design, and more.
• Community Power: Small-town arts thrive because of partnerships with businesses, service groups, and passionate volunteers.
• For dreamers: You can build a creative career—and a fulfilling life—outside the city.

Connect with Diana...

In this inspiring episode of The Country Club Podcast, host Diana Cassidy-Bush sits down with longtime educator and leader Louise Gunning, who has dedicated her career to shaping rural schools and communities in Ontario. From building new schools and leading through delays, to designing online learning during the pandemic, Louise shares her story of resilience, innovation, and heart.

Together, Diana and Louise explore how rural schools are at the heart of their communities—providing not only academics but also wellness programs, food security, and life opportunities for students. Louise also opens up about combining elementary and secondary schools under one roof, the surprising breadth of extracurricular activities available in small communities, and the essential role of parents, businesses, and neighbors in supporting education.

Whether you’re a parent considering a move to the country, an educator facing change, or simply curious about life and learning beyond the city, this conversation will leave you with wisdom, encouragement, and a deeper appreciation for the power of community in education.

Timestamps

00:00 – 02:00 | Introduction

02:30 – 04:30 | Louise reflects on the challenges that shaped her as a leader.

04:30 – 06:30 | Saying “yes” to challenges and encouraging growth outside comfort zones.

06:30 – 08:30 | How rural communities and schools nurture student wellness.

09:00 – 11:30 | Building Ontario’s first K–12 virtual school during the pandemic.

12:00 – 14:30 | The benefits of combining elementary and secondary schools.

15:00 – 17:30 | Clubs, musicals, carnivals, and sports—surprising opportunities in small schools.

18:00 – 20:30 | Schools as wellness hubs: breakfast programs, grocery pantries, and mental health supports.

20:30 – 22:30 | Advice for parents: public health resources, asking for help, and leaning on community.

22:30 – 24:30 | Louise’s leadership wisdom: lead with empathy, model resilience, and don’t underestimate kids.

24:30 – 25:30 | Closing reflections and call for listener questions.

Notable Quotes

• “We should never underestimate one another—children or adults.” – Louise Gunning
• “You don’t need fancy classrooms to thrive. What you need is a shared vision and determination.” – Louise Gunning
• “Rural schools are the heart of the community. Everyone knows everybody, and that creates a powerful safety net for kids.” – Louise Gunning
• “Transitions are tough, but leading with empathy and modeling healthy coping strategies makes all the difference.” – Louise Gunning
• “Our kids are often stronger and more resilient than we are.” – Louise Gunning

Connect with Diana Cassidy-Bush:

Facebook: https://www.facebook.com/DianaCassidyBushRealEstate/

Instagram: https://www.instagram.com/dianacassidybush

Linked In: https://www.linkedin.com/in/diana-cassidy-bush-aa2318b6/

YouTube: https://www.youtube.com/@dianacassidy-bush2027

Website: https://dianacassidybush.ca/

Email:

In this episode of The Country Club Podcast, host Diana Cassidy-Bush welcomes family physician Dr. Charles Mustard—who’s spent 19 years serving Tweed, Ontario—to unpack the unique landscape of wellness and healthcare in small-town life. From Dr. Mustard’s journey swapping urban pace for rural roots, to myth-busting assumptions about diversity and medical services in rural Ontario, you’ll learn how to leverage team-based clinics, allied health professionals, and nature’s restorative power to thrive beyond the city limits. Whether you’re a newcomer or a longtime resident, discover actionable tips for accessing primary care, building meaningful community connections, and embracing a balanced, health-first lifestyle in rural Ontario.

Timestamps:

00:00:00 – Intro: Welcome to The Country Club—beyond dress codes & tee times

00:00:30 – Podcast mission: more than buying property—plan, seize opportunities, build future

00:01:00 – Listener Q&A Recap: Lisa’s question on meeting people while working from home

00:02:30 – Episode focus: wellness & healthcare in rural Ontario with Dr. Charles Mustard

00:03:00 – Guest Intro: Dr. Mustard’s 19-year journey from urban practice to Tweed

00:04:00 – Dr. Mustard’s background: from North & cities to rural family practice

00:05:00 – Recruitment then & now: persistence of colleagues, team-based care models

00:07:00 – The rise of interdisciplinary rural clinics & why young docs want them

00:09:00 – Surprises: rural diversity, social connectedness & true “cradle-to-grave” care

00:10:30 – Personal adjustment: physician vs. spouse’s path to community involvement

00:12:30 – Defining wellness in the country: nature, balance & social ties

00:14:30 – Encouraging patients: hobbies, exercise & mid-day routines to connect locally

00:16:00 – Available services: team clinics, allied health & local specialists

00:19:00 – Comprehensive care: palliative support & family involvement

00:21:00 – Access tips: attaching to clinics, virtual care options & emergency fallback

00:23:00 – Evolution of primary care: chronic disease, EMRs & an aging population

00:24:30 – Doctor-patient bonds: confidentiality, rewards & community trust

00:26:00 – Dr. Mustard’s self-care: gardening, screened porch zen & travel adventures

00:28:30 – Closing thoughts & call for listener questions

00:30:00 – Outro: follow, consult professionals & stay tuned for more rural insights

Notable Quotes

“Social connectedness is a huge determinant of health.”

“There’s almost a spiritual connection to nature that people develop.”

Key Takeaways

1. Embrace Team-Based Care: Seek attachment to local interdisciplinary clinics—physicians, NPs, social workers, dieticians—sooner rather than later.
2. Leverage Nature: Encorporate outdoor activities—gardening, biking, mindful walks—to boost mental and physical wellness.
3. Build Community: Join hobby groups, volunteer committees or local events to accelerate social connectedness.
4. Own Your Care: Family doctors in rural areas often manage chronic conditions you’d otherwise see specialists for—empower yourself with regular check-ins and open dialogue.
5. Plan Ahead: Understand your local healthcare network—virtual options, allied services, emergency protocols—to navigate care seamlessly.

Connect with Diana Cassidy-Bush:

Facebook: Diana Cassidy-Bush, Sales Representative Royal LePage ProAlliance Realty | Tweed ON

Instagram:

In this episode of The Country Club Podcast, host Diana Cassidy-Bush dives into one of the biggest challenges for newcomers to rural and small-town living: forging genuine connections and making your house feel like home. Drawing on listener Rebecca’s question about balancing lifestyle goals with investment strategy for recreational properties, Diana shares a hybrid approach and then shifts gears to practical, actionable tips on how to intentionally build community. From identifying your personal interests to showing up consistently at local events, this episode equips you with the blueprint to turn your new hometown into a network of friends, neighbors, and opportunities. Whether you’re volunteering at the farmer’s market or hosting your own backyard gathering, Diana guides you through the steps to become a recognized—and valued—member of your rural community.

Timestamps

00:00 – 01:00 | Welcome & Podcast Introduction

01:00 – 04:00 | Listener Question: Balancing Lifestyle & Investment for Recreational Properties (the “Hybrid Approach”)

04:00 – 05:00 | Topic Overview: Building Community & Connection Beyond the City

05:00 – 07:00 | Step 1: Identify Your Interests—From gardening and wellness to sports and culture

07:00 – 09:00 | Step 2: Engage in Local Activities—Farmer’s markets, craft fairs, hiking groups, sports leagues

09:00 – 10:00 | Step 3: Leverage Local Businesses—Coffee shops, hardware stores, pubs as community hubs

10:00 – 12:00 | Step 4: Show Up & Be Consistent—Volunteer groups, seasonal events, being a familiar face

12:00 – 13:00 | Step 5: Embrace Rural Culture—Adopt the slower pace, join Facebook community groups, attend fundraisers

13:00 – 14:00 | Call to Action & How to Send in Your Questions

14:00 – 15:00 | Outro: Subscribe, Follow & Final Thoughts

Valuable Resources & Key Takeaways

Hybrid Approach Checklist

• Weeks per year you’ll use the property personally
• Income needed to cover costs or break even
• Seasonal calendar mapping (personal, family, friends, guest bookings)

Community Engagement Roadmap

• Interest Inventory: List hobbies, passions & family needs
• Activity Audit: Research local events, clubs, volunteer groups
• Business Partnerships: Introduce yourself to local shop owners & baristas

Action Steps

• Volunteer
• Attend weekly social gatherings: card nights, fitness classes, sports leagues
• Host your own meet-up: coffee chat, potluck dinner, nature walk

Digital & Social Tools

• Join community Facebook groups for event updates
• Follow local business Instagram pages for pop-up markets
• Use Nextdoor or local forums to announce meet-ups

Mindset Shift

• Commit to consistency—attend at least one event per week
• Say “yes” to invitations, even if outside your comfort zone
• Embrace every interaction as a seed for deeper connections

Connect with Diana Cassidy-Bush:

Facebook: https://www.facebook.com/DianaCassidyBushRealEstate/

Instagram: https://www.instagram.com/dianacassidybush

Linked In: