In this first installment of a two-part conversation, host Diana Cassidy-Bush sits down with Kara Enright, the driving force behind Enright Cattle Company.

What begins as a conversation about farming quickly unfolds into a powerful story about innovation, resilience, and building a modern agricultural brand from the ground up.

Kara grew up immersed in rural life, where farming wasn’t just a career — it was a way of life shared by entire communities. But as agriculture evolved, so did the realities facing family farms. With limited land and resources, Kara and her husband had to think differently about how to build a sustainable future in farming.

Instead of scaling through land and herd size alone, Kara focused on building a brand — creating a direct connection between farm and consumer. What followed was an entrepreneurial journey that expanded far beyond selling beef.

From supplying chefs and restaurants to launching leather products made from their own cattle hides, creating a boutique farm store inside a converted grain silo, hosting immersive farm dinners in a crop circle, and even acquiring a local blueberry farm, Kara has continually reimagined what a modern farm business can be.

This episode explores how legacy farming knowledge, creative thinking, and a willingness to adapt can transform a traditional agricultural operation into a thriving rural enterprise.

And perhaps most importantly, Kara shares what it means to lead in an industry where women are still often underestimated — and why that challenge only fueled her determination to succeed.

Learn more about Enright Cattle Company: https://enrightcattlecompany.com/

Episode Timestamps:

00:00 - Welcome to Country Club

00:45 - Meet Kara Enright of Enright Cattle

03:12 - Growing Up Farming

05:16 - Work Ethic Lessons

05:54 - Agriculture Is Evolving

07:03 - Women in Farming

08:20 - Building a Beef Brand

09:54 - From Markets to Restaurants

13:37 - Leather Goods from Hides

17:19 - Grain Bin Farm Store

21:45 - Dinner in the Crop Circle

24:54 - Buying a Blueberry Farm

28:00 - Keeping Local Food Alive

Key Takeaways:

1. Agriculture isn’t disappearing — it’s transforming

2. Building a brand can sustain a smaller farm

3. Relationships can open unexpected opportunities

4. Use the whole animal — and create value from it

5. Authentic experiences build powerful connections with customers

6. Entrepreneurship often starts with curiosity

7. Women are redefining leadership in agriculture

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: info@thedcbteam.ca

This podcast is for educational purposes only - real estate isn’t one-size-fits-all! Every deal, market, and situation is unique, so be sure to get professional advice tailored to your needs. If you’d like to discuss your real estate journey, we’d love to chat - reach out anytime. Thanks for listening!

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: