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

EPISODE · Jul 21, 2026 · 36 MIN

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

from Mechanics of Money · host Sam Silverman | Silverman Capital

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 crisisWhy 60% of the people you spend the most time with vanish after an exitThe Transaction Illusion and why money only solves two levels of Maslow's hierarchyThe mountain metaphor: ascent, summit, and the descent nobody talks aboutWhy $15M in cash can feel smaller than $3M a year in incomeWhat happens when operators become capital allocators overnightJerome's Five Scars of Success and the $44M client who wouldn't take a vacationWhy Die with Zero changed how his clients think about spendingThe scholarship text on Mother's Day and what fulfilled founders actually spend onThe purpose formula founders already know but forget to apply to themselvesTopics 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, entrepreneurshipGuest: Jerome Myers, CEPA, MBA, Founder, Exit to Excellence | https://www.linkedin.com/in/jeromemyersNewsletter: https://www.mechanicsofmoney.coWebsite: https://silvermancapital.comSubscribe for weekly conversations on private markets, alternative investments, and the mechanics behind building real wealth.#exitplanning #founderpsychology #postexitlife #transactionillusion #mechanicsofmoney #wealthmanagement #privatemarkets #entrepreneurship #founderexit #capitalallocation

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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 an...

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

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