Why Operators Struggle to Become Investors

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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