86. The Art of Living, Leading, and Letting Go with Jaime McKenna

In this deeply candid and inspiring Part 1 of their conversation, Dwayne sits down with Jaime McKenna — President of Real Estate at Fengate Asset Management — for a raw, no-filter look at what it takes to go from near-poverty to managing billions. Jaime shares the deeply personal story of losing everything in her university years, climbing out of debt, overcoming imposter syndrome, and redefining leadership in a high-stakes, male-dominated industry. If you’ve ever doubted your path or wondered how top leaders push forward through fear, shame, and uncertainty — this is your episode.

Timestamps:

00:00 — Why Jaime shares her story: The power of shedding shame

02:00 — A breakdown of Jaime’s career and early hardships

05:00 — The root of her humility and difficulty with compliments

09:30 — How fear of scarcity became fuel for her success

14:30 — Tuna cans, $7 haircuts & the truth behind survival mode

18:00 — Baby steps, big vision: The method behind her comeback

23:00 — Creating vision when no one else is coaching you

26:00 — Studying for a CPA with VHS tapes & Swiss Chalet

30:00 — Why discipline is the real secret weapon (not motivation)

34:00 — Work-life integration, not balance

38:00 — Vulnerability and the power of human leadership

44:00 — What Jaime looks for when building elite teams

50:00 — Leadership through transitions and letting people go

55:00 — Be nice, be direct: How to lead with both heart and clarity

1:03:00 — Real workaholism vs. the art of joyful, purposeful work

1:08:00 — The power of breathwork and managing internal pressure

1:18:00 — Jaime’s battle with anxiety after the loss of her mom

1:28:00 — Rebuilding mentally, emotionally, and spiritually

1:35:00 — Rewriting identity, leading with heart, and shedding the labels

Notable Quotes:

“That fear of having nothing never left me — and it still drives me today.” — Jaime McKenna

“If you’re not uncomfortable, you’re not growing. That’s your cue to step up.” — Jaime McKenna

“Discipline isn’t punishment. It’s a gift. It’s how I get my freedom.” — Jaime McKenna 

Key Takeaways & Resources:

• Jaime’s story shows that a successful life and career can be built without family wealth or connections — but it takes relentless discipline.
• Massive transformation begins with small, consistent steps — not instant miracles.
• Jaime outworked, out-disciplined, and outlasted many who may have started with more.
• The most effective leaders are those willing to show their human side.
• Jaime’s breakdown after her mother’s death led to a breakthrough that reshaped her approach to leadership.

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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.