Eddie Wilson - 100+ Companies Exited (Aspire Tour Founder) | The Most Expensive Education
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Eddie Wilson, known as the "King of Exits," has owned over 140 companies and successfully exited more than 100 of them. He's the founder of the Aspire Tour, one of America's largest business mastermind events, and leads Collective Influence, a private equity firm with holdings across multiple industries. Wilson also created the Empire Operating System, a methodology for scaling and exiting companies. Beyond business, his foundation Impact Others feeds and educates nearly 5,000 children daily and supports anti-slavery initiatives globally.
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➡️ Talking Points
00:00 – Intro
01:29 – Eddie Wilson’s Origin
10:16 – The Mindset That Makes or Breaks Businesses
11:33 – Learning the Art of Acquisition
14:12 – Operator vs Investor: Mastering Both
16:08 – Why Hiring Is Still Hard at the Top
20:18 – The Truth Behind Eddie’s First Exits
22:19 – Why Timing Changes Everything
26:06 – Sponsor Break
28:38 – The Most Overlooked Acquisition Opportunities
32:15 – Building a Real Community
39:18 – Depression After Success
48:05 – Sponsor Break
49:59 – When Success Feels Empty
53:39 – How Self-Work Changed Eddie as a Founder
54:55 – The Loneliness of Winning
57:17 – Eddie’s Frustration With Young Entrepreneurs
1:05:14 – Why Ego Is the Real Enemy
1:10:36 – Eddie’s Next 10-Year Vision
1:11:25 – Advice to His 20-Year-Old Self
1:17:58 – The One Lesson He’d Teach His Kids