From Accidental Entrepreneur to Second-Half Purpose: The Heath Wilson Story

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In today’s episode of Made to Matter, Adam sits down with Heath Wilson — a successful entrepreneur who built and sold a company to a NASDAQ-listed acquirer and then woke up the next day realizing something he never expected:

Success doesn’t prepare you for the identity crisis that comes after.

Heath’s story is a masterclass in what it means to be a second-half man — someone who’s already climbed the mountain, cashed the check, earned the title… and then suddenly finds himself asking:

“Who am I when I’m no longer the one everyone needs?”

This episode pulls back the curtain on the emotional, spiritual, and practical challenges that ambitious men face after the exit. And more importantly, the path back to purpose.

🔑 What You’ll Learn in This Episode
1. How Heath accidentally became an entrepreneur
Heath didn’t set out to build a company — he stumbled into it by spotting a problem with coworkers and saying, “We can make this better.”
2. The identity crash that happens post-exit
Heath goes from being the needed leader…
…to sitting at a desk with literally nothing to do.
3. The humbling moment that changed everything
One day in New York, he tries to walk into the acquiring company’s office…
only to discover his employee badge spells his name wrong: “Health Wilson.”
He can’t even get past the front desk.
This is the moment he realizes:
“I am no longer important on any level whatsoever.”

4. The emotional fallout of retirement at 43
After the sale, Heath tries to “retire,” spending his mornings reading Scripture, journaling, and working out… but by 10 AM he’s done.
Day after day.
For 45 straight days.
His wife finally sits him down:
“Heath, this is not going to work.”

5. Why men in the second half struggle when work disappears
Heath’s friends are all still working.
His rhythm disappears.
His built-in identity evaporates.
This is the danger Adam warns entrepreneurs about:
You prepare your business for exit —
but you rarely prepare yourself.

6. How Heath rebuilt purpose by building something that matters
Heath begins building a new company centered around wellness, presence, and digital health, serving churches and organizational leaders.
He describes helping teams create rhythms that make them “better at work, at home, and in their relationship with God.”
He also shares insights into their intentional-living technology that helps people break phone dependency and reengage with real life.


So many men believe the exit is the finish line.
But for the men Adam serves — successful, capable, second-half professionals — the exit is often the beginning of the real work:
rediscovering who you are without the title
finding fulfillment beyond achievement
learning to create instead of react
rebuilding identity around purpose, not productivity

Heath’s story is a case study in what happens when the ladder you’ve been climbing disappears overnight — and how you can rebuild a life that matters.



life after selling a business
entrepreneur identity crisis
second half of life coaching
post-exit depression
finding purpose after retirement
founder mental health
accidental entrepreneur story
digital wellness entrepreneurship
Made to Matter podcast
Heath Wilson interview


If Heath’s story hits close to home — if you’ve built success but lost yourself somewhere along the way — Adam’s programs are designed for men exactly like you.