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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