Mechanics of Money

Why Founders Get Depressed After Selling Their Company | Jerome Myers, CEPA

Sam Silverman | Silverman Capital Season 1 Episode 21

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0:00 | 36:26

What happens when you sell your company, deposit more money than you've ever had, and immediately feel worse than before?

Sam sits down with Jerome Myers, Certified Exit Planning Advisor, founder of Exit to Excellence, and author of Your N.E.X.T.: Finding Fulfillment After Your Exit. Jerome built a $20 million division from zero in a single year inside a Fortune 550 company, walked away on principle, then later discovered what he calls the Founder's Exit Paradox: founders who win on paper and quietly fall apart afterward. 

He now coaches founders through what comes after the transaction: the identity loss, the relationship collapse, and the spending paralysis that no advisor prepares them for.

In this conversation:

  • Jerome's origin story and the $2B founder who said he still hasn't beaten his crisis
  • Why 60% of the people you spend the most time with vanish after an exit
  • The Transaction Illusion and why money only solves two levels of Maslow's hierarchy
  • The mountain metaphor: ascent, summit, and the descent nobody talks about
  • Why $15M in cash can feel smaller than $3M a year in income
  • What happens when operators become capital allocators overnight
  • Jerome's Five Scars of Success and the $44M client who wouldn't take a vacation
  • Why Die with Zero changed how his clients think about spending
  • The scholarship text on Mother's Day and what fulfilled founders actually spend on
  • The purpose formula founders already know but forget to apply to themselves


Topics covered: exit planning, founder psychology, post-exit depression, identity crisis, transaction illusion, hedonic treadmill, capital allocation, Maslow's hierarchy, private equity, founder fulfillment, giving policy, buy box, accredited investors, wealth management, entrepreneurship

Guest: Jerome Myers, CEPA, MBA, Founder, Exit to Excellence | https://www.linkedin.com/in/jeromemyers

Newsletter: https://www.mechanicsofmoney.co
Website: https://silvermancapital.com

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