When winning still doesn't feel like winning, the problem was never the goal.
It was the why you were chasing it.
Adam Roach built and exited multiple companies....
a tennis club in Beverly Hills, three real estate franchises, a SaaS business.
And none of it was enough.
In this episode, I sit down with Adam to unpack that feeling of emptiness.
We go back to the moment he calls his beach chair moment: the realization that chasing success on repeat was a dead end.
But that decision came with a cost.
Adam opens up about the identity hangover that followed and a very practical reason he couldn't afford to stay stuck (an $18,000-a-month reason, to be exact).
He also talks about the framework he borrowed from Donald Miller's Hero on a Mission—which now runs everything he does: the difference between being the hero of the story and being the guide.
As we continue pulling on that thread, Adam shares the exact language he uses to bring himself out of hero mode when speaking with his coaching clients, peers, and even family! If you've ever wondered why success still feels empty... or why the more you achieve, the more there seems to be left to prove, this conversation is for you.
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📌 What's covered in this episode:
00:00 — Podcast Intro
01:12 — Meet Adam Roach
04:16 — Success vs. Significance
05:54 — The Beach Chair Moment That Changed Everything
09:36 — Why You Need an Advisory Board
12:28 — The Identity Hangover After Success
16:50 — The $18,000/Month Wake-Up Call
22:27 — Stop Being the Hero. Become the Guide.
28:25 — Why Empathy Beats Solutions
30:18 — Feel This or Fix This?
33:54 — From Hero to Guide
43:10 — The 59-Question Coaching Experiment
47:02 — Final Leadership Advice
🔔 Don't miss an episode!
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💬 Where do you wish someone would guide you a little more, and be the hero a little less?
Drop it below.
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🎙️ About Uncommon Leadership:
I'm Michael Hunter, founder of Uncommon Teams.
On the Uncommon Leadership Podcast, I sit down with founders, executives, researchers, and leadership thinkers to explore what it really means to lead in today's world.
Together, we unpack the intersection of leadership, psychology, resilience, and culture—because I believe the best leaders don't just build successful businesses. They build environments where people can do their best work and become their best selves.
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Speakers in this episode of the Uncommon Leadership Podcast:
Adam Roach | Guest
Adam Roach is an entrepreneur, business coach, and Founder of I Love Coaching Co. After building and scaling multiple businesses, he now helps coaches and entrepreneurs create purpose-driven businesses through the REAL Coach Method, empowering them to build lasting impact.
Connect with Adam Roach:
Michael Hunter | Host
Michael Hunter is an executive coach, leadership strategist, and the founder of Uncommon Teams. Drawing on his experience working with leaders at tech giants like Microsoft and Salesforce, Michael helps founders and Heads of People align personal fulfillment with sustainable business success.
Work with Michael Hunter:
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🎵 Music Credits:
Title: Soft Background
Author: DmitriySimf
Source: Envato
License Code: BTGYS9EML4
