Success Story with Scott D. Clary Eddie Wilson - 100+ Companies Exited (Aspire Tour Founder) | The Most Expensive Education
Jan 20, 2026
Eddie Wilson, serial entrepreneur who built and exited 100+ companies and founded the Aspire Tour and Empire OS. He discusses learning acquisitions after an early loss. He explains building community-first businesses, scaling through operator-to-investor shifts, and the loneliness and purpose struggles that follow big wins.
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Early Exit That Sparked His Acquisition Path
- Eddie Wilson describes being forced to sell his ad agency at 24 after overbooking ads and lacking capital, initially feeling ripped off.
- He reframed the outcome as getting seven years of his life back and vowed to learn acquisitions and never exploit others like that buyer did.
Buy Potential, Not Just Distress
- Do target businesses where owners feel stuck at a certain profit because mindset, not capability, often blocks growth.
- Believe you can apply different vision and systems to unlock more value than the current owner sees.
Get Operational First, Then Acquire
- Do build operational capability across multiple assets before scaling acquisitions so you can leverage shared services.
- Use early roll-ups as a training ground to create a bench of operators and systems.
