The High Functioning Struggler: Kenny Stoddart on What Happens When the Executive Who Has It All Together on the Outside Is Falling Apart on the Inside

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He was a millionaire by 24. He spent 27 years as an executive in cybersecurity — traveling the world, closing deals, chasing quotas and high achievers clubs. And it almost killed him. Not metaphorically. He had cancer. He battled alcoholism. He lost himself so completely in an identity built for someone else that he didn't know who he was anymore. 

Then he asked for help. And everything changed. 

In this episode of Undiscovered Entrepreneur: Get Across the Start Line, Kenny Stoddart — founder of Iron Mind Advisors and self-described helper of the "high functioning struggler" — joins Skoob for one of the most honest and courageous conversations the show has ever had. From burnout and recovery to imposter syndrome, identity, and what it actually takes to start over at 51, this episode is for anyone who looks like they have it all together on the outside while quietly struggling on the inside. 

What You'll Learn: 

• How 27 years of chasing quotas and high achievers clubs cost Kenny his identity — and nearly his life
• The shift from identity loss (cybersecurity) to identity gain (coaching)
• Why the "high functioning struggler" is Kenny's ideal client — and why they're everywhere
• Why you can't change the world around you until you change your world first
• How to go from "I can help anybody" to finding the one target market that fits
• Why not succeeding out of the gates is actually a gift — and what the bumps teach you
• Why asking for help is the biggest sign of strength, not weakness
• The imposter syndrome moment that hit a decorated executive in his first entrepreneur room
• Why passion is what differentiates you in a crowded market — because you are the differentiator
• How student athlete identity loss mirrors executive burnout — and what Kenny does about it
• Why boundaries, rest, and wellness aren't soft skills — they're survival skills
• Kenny's six-month goal: master's degree graduation, big stages, and a business with a bow on it

Timestamps:
 

• [00:00:00] – Introduction & Welcome
• [00:01:00] – Meet Kenny Stoddart: 27 Years in Cybersecurity and the Career That Almost Killed Him
• [00:02:30] – From Identity Loss to Identity Gain: The Pivot That Changed Everything
• [00:04:00] – We're Both Just Getting Started: The 10% Behind You Worth Bringing Along
• [00:05:00] – Millionaire at 24 and Still Missing the Most Important Piece
• [00:06:00] – Operating Through Someone Else's Lens: Why the External Win Felt Empty
• [00:07:00] – You Have to Wear Your Brand — Passion Is the Only Differentiator
• [00:08:00] – Change Your World First — Then Change One Person's World
• [00:09:00] – From "I Can Help Anybody" to Finding the Right Target Market
• [00:10:00] – The Freedom of Being Your Own CEO — And the Responsibility That Comes With It
• [00:11:00] – The Entry-Level Price of Entrepreneurship: Grinding Is the Cost of Getting In
• [00:12:30] – Grateful for Not Succeeding Out of the Gates: Why the Bumps Were Necessary
• [00:14:00] – Learning From People One Month Ahead and One Month Behind You
• [00:16:00] – Burnout Again? Setting Boundaries Before History Repeats Itself
• [00:17:00] – Morning Walks, Meditation & Why Wellness Is a Survival Strategy
• [00:19:00] – Cancer, Alcoholism & the Moment Kenny Finally Asked for Help
• [00:22:00] – Student Athletes and Identity Loss: Helping Them Get Ahead of the Curve
• [00:23:00] – We Don't Know What's Going On Inside Someone Else's Head
• [00:24:00] – Networking With Entrepreneurs: The Best School You'll Never Pay For
• [00:26:00] – There's No Competition — Only People Who Can Help Each Other
• [00:29:00] – Authenticity, Ethics & Being Proud of What You've Built
• [00:30:00] – One Piece of Advice: Walk Into the Room Like You Belong There — Because You Do
• [00:34:00] – Fear Is Healthy — If You're Not Scared, You're Not Thinking Big Enough
• [00:35:00] – Kenny's Six-Month Goal: Graduation, Big Stages & Putting a Bow on the Business
• [00:39:00] – How to Find Kenny, Iron Mind Advisors & the Free Identity Assessment

Free Tools:
🧠 Free Identity Assessment: ironmindadvisors.com/assessment
🏆 Student Athlete Assessment: theathletecheck.com/assessment

Connect with Kenny Stoddart:
🌐 ironmindadvisors.com
📱 Instagram: @ironmindskenny
🎓 Graduating: Liberty University, Master's in Clinical Mental Health Counseling — Nov/Dec

Subscribe & Leave a Review:
If Kenny's story made you want to raise your hand and ask for help — or walk into a room you've been afraid of — please subscribe, leave a review, and share this with someone who needs to hear that asking for help is the biggest sign of strength there is.

🎙️ Undiscovered Entrepreneur: Get Across the Start Line — new episodes dropping regularly.
 

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