Why the Biggest Number Doesn’t Mean You’ve Won - Jerome Myers

09/11/2025 24 min
Why the Biggest Number Doesn’t Mean You’ve Won - Jerome Myers

Listen "Why the Biggest Number Doesn’t Mean You’ve Won - Jerome Myers"

Episode Synopsis

Everyone wants to know the number: what you sold your company for, the valuation, the payout. But as Jerome Myers reveals, the number is not the finish line. It is only one mile marker on the journey. In this solo episode, Jerome uncovers what truly defines a successful exit: peace, purpose, and freedom. Through powerful stories and practical frameworks, he explains the four hidden levers —structure, timing, control, and alignment — that determine whether your exit becomes an evolution or a regret. 

Founders will walk away with tools to measure success beyond money and to negotiate for a life that feels right, not just a deal that looks good.

[00:00 – 03:30] The Illusion of the Headline Number



The world celebrates the sale price, but that number rarely reflects true success




Founders often chase valuation without understanding its emotional cost




“You can hit your financial goal and still miss your life goal”




[03:30 – 07:30] The Hidden Levers: Structure and Timing



Structure determines how money actually reaches you — not just what’s promised




Beware of earnouts and rollover equity tied to someone else’s performance




Timing affects your freedom; stretched payments can quietly fund your own exit




[07:30 – 11:30] Control and Alignment: The Freedom You Forget to Negotiate



Freedom isn’t automatic after an exit — it’s negotiated




Many founders unknowingly trade autonomy for an employment clause




Alignment between values and culture is the silent determinant of post-exit peace




[11:30 – 15:30] Redefining Winning: Beyond the Transaction



Create a non-negotiables list — your personal term sheet




Identify your true freedom number after taxes and fees




Measure deals through the Freedom Compass: control, connection, meaning, and sustainability




[15:30 – 19:00] The Power Questions That Reveal True Value



Founders lose leverage when they ask for valuation instead of impact on the future self




Strategic questions expose power dynamics — “Who controls the capital stack post-close?”




Emotional readiness is key: “Do I know what I’m walking toward?”




[19:00 – 21:30] Exit as Evolution, Not Ending



The exit isn’t closure — it’s a portal to who you’re becoming




Peace is the ultimate return on investment




“The company was never the dream; it was a vehicle for it”




Key Quotes:

"You can hit your financial goal and still miss your life goal." - Jerome Myers

“If you do not define your non-negotiables, someone else will, and it will not be for your benefit." - Jerome Myers

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