The Dwayne Kerrigan Podcast 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.
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Disclaimer The views, information, or opinions expressed by guests during The Dwayne Kerrigan Podcast are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Dwayne Kerrigan Podcast is not responsible for and does not verify the accuracy of any of the information contained in the podcast series. The primary purpose of this podcast is to educate and inform. Listeners are advised to consult with a qualified professional or specialist before making any decisions based on the content of this podcast.