In this deeply candid and inspiring Part 1 of their conversation, Dwayne Kerrigan 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.
CHAPTERS:
00:00 - Introduction
00:35 - Unplanned Conversations
01:10 - Jaime McKenna
05:15 - Why Can't You Take Compliments
10:38 - What Drives You
12:22 - How Adversity Shapes You
17:45 - Turning Points in Life
24:20 - Step-by-Step Formula for Success
27:48 - Reflecting and Observing Others
29:18 - Importance of a Mentor
29:40 - Accounting Degree Journey
30:55 - Hard Work vs. Smart Work
34:45 - Getting Out of Your Comfort Zone
37:21 - The Challenge of Balance
40:41 - Coaching Techniques
42:24 - Embracing Vulnerability
44:43 - Vulnerability in Leadership
46:35 - Leadership Style Exploration
47:33 - Lessons from the Last 5 Years
50:29 - Gaining Buy-In on Your Vision
54:05 - Team Selection Criteria
55:23 - Promoting from Within
56:40 - Vision and Strategic Planning
57:47 - Leadership No-Go Zones
59:55 - Expectations vs. Culture Fit
01:01:57 - Managing Expectations and Priorities
01:06:36 - Identifying Workaholic Traits
01:10:04 - Challenges of Being Present
01:12:43 - Strategies for Being Present
01:16:03 - Managing Pressure and Uncertainty
01:20:01 - Research Project on Housing Market
01:22:12 - Protecting Your Mental Health
01:26:00 - Mental Health and Females
01:29:34 - Overcoming Mental Health Challenges
01:33:17 - Current Coping Strategies
01:40:30 - Breath Work Techniques
01:43:05 - The Power of Love
01:44:28 - Understanding Archetypes
01:48:30 - Outro
Notable Quotes:
“That fear of having nothing never left me — and it still drives me today.” — Jaime McKenna
“You don’t balance work and life — you integrate them.” — Jaime McKenna
“Discipline isn’t punishment. It’s a gift. It’s how I get my freedom.” — Jaime McKenna
Key Takeaways & Resources:
Themes:
• Resilience Over Privilege: Jaime’s story shows that a successful life and career can be built without family wealth or connections — but it takes relentless discipline.
• The Power of Micro-Momentum: Massive transformation begins with small, consistent steps — not instant miracles.
• You Don’t Have to Be the Smartest: Jaime outworked, out-disciplined, and outlasted many who may have started with more.
• Vulnerability Creates Trust: The most effective leaders are those willing to show their human side.
• Mental Health Matters at the Top: Jaime’s breakdown years after her mother’s death led to a breakthrough that reshaped her approach to leadership.
Connect with Dwayne Kerrigan
Linked In: https://www.linkedin.com/in/dwayne-kerrigan-998113281/ Facebook: https://www.facebook.com/businessofdoingbusinessdk Instagram: https://www.instagram.com/thebusinessofdoingbusinessdk/
Website: www.dwaynekerrigan.com
Disclaimer The views, information, or opinions expressed by guests during The Business of Doing Business are solely those of the individuals involved and do not necessarily represent those of Dwayne Kerrigan and his affiliates. Dwayne Kerrigan or The Business of Doing Business 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.
