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...