87. Real Estate, Recessions, and Smart Investing with Jaime McKenna

In this powerhouse follow-up episode, Jaime McKenna, President at Fengate Real Estate, returns to unpack the intersection of leadership, housing economics, and strategic foresight in times of uncertainty. She candidly reflects on navigating imposter syndrome, the true nature of financial literacy, and the real estate crisis threatening Canada’s future. From affordable housing and capital flow challenges to why boring businesses often win — this episode delivers practical, hard-earned wisdom for young professionals, seasoned investors, and business owners alike.

Timestamps:

00:00 — Opening quote: The master in the art of living

01:45 — The power of purpose and leading in male-dominated industries

03:00 — Battling imposter syndrome and the myth of the perfect path

05:30 — Why flexibility and awareness win in uncertain times

07:00 — Moving forward in a spin cycle of rhetoric and judgment

10:00 — Capital tightness and real estate development under pressure

12:45 — Canada’s looming housing catastrophe: What’s ahead

16:00 — Why Fengate shifted from condos to high-rise rental apartments

18:45 — Gen Z & Millennials: Renting by choice, not failure

22:00 — Real estate vs. luxury consumption: A Chanel purse lesson

26:30 — Three levels of housing reform Canada urgently needs

29:00 — The broken municipal approval system and hidden costs

33:00 — Is now the time to buy condos? The case for discounted inventory

39:00 — Investing strategies: Seniors housing, data centers, industrial space

42:00 — Apartment cap rates explained — and how to win with vanilla investments

49:00 — Renovate vs. build: When spiffing up isn’t worth the risk

53:00 — How tariffs and global instability are reshaping the market

56:30 — The danger of complacency and Canada’s productivity dilemma

1:03:00 — Is a majority government the only way forward?

1:09:00 — The final word on resilience, leadership, and gratitude for the journey

Notable Quotes:

“Courage doesn’t mean you know you’ll be right — it means you act anyway.”

— Dwayne Kerrigan

“The goal isn’t to eliminate problems. The goal is to upgrade the quality of your problems.”

— Dwayne Kerrigan

“Every square of adversity is a part of the quilt of your life.”

— Jaime McKenna

Key Takeaways & Resources:

• Adaptability Over Strength: In today’s market, it’s not survival of the fittest — it’s survival of the most flexible.
• Imposter Syndrome Is Universal: Even top executives question their path. Keep building, one block at a time.
• Now is the Window: With capital tight and developers frozen, long-term thinkers can seize undervalued condo opportunities.
• Housing: From Crisis to Catastrophe: Supply is frozen while demand climbs. The next 3–5 years may be pivotal.
• Boring Wins: Apartments and industrial space may lack flash but offer stability and strategic growth.
• Real Estate ≠ Quick Cash: Real value lies in patience, planning, and resisting shiny object syndrome.

Connect with Dwayne Kerrigan

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