Paychecks to Purpose: The 8 Exits of a Founder - Jerome Myers

Your Next: A Guide to Finding Fulfillment After Your Exit Hosted by Jerome Myers

Most people think money is the biggest barrier to leaving their job—but they’re wrong. In this powerful mastermind session, Jerome Myers joins real estate investors and corporate pros to reveal the real cost of walking away: emotional, mental, and operational.

Drawing from his leap from corporate at the peak of success, Jerome shares hard-earned lessons on why most exits fail, the myths of passive income, and what truly makes wealth worth building.

If you're dreaming of leaving your W2 or already have, this conversation will shake your assumptions and refocus your purpose.

Press play and discover what it takes to build a life of freedom and fulfillment.

[00:00 – 04:57] Real People at the Edge of a Leap

• Investor intros: career paths and exit goals
• Common thread: W2 jobs and uncertainty
• Jerome sets the tone for real talk

[04:58 – 11:45] Jerome’s Exit Story

• Built a $20M division—then told to downsize
• Choose values over comfort and quit
• Faced with cash flow struggles with no plan

[11:46 – 20:59] Freedom Numbers & False Starts

• Most don’t know their real “freedom number.”
• Passive income takes time and capital
• Going from six figures to zero is a real risk
• Know what life—not lifestyle—costs

[21:00 – 34:15] Chief Everything Officer

• Startup life is messy, lonely, and intense
• You’ll do everything—from admin to investor calls
• Visibility is leverage, not vanity
• Faceless brands fail in today’s market

[34:16 – 48:15] Purpose Over Passive

• Real estate cash flow isn’t instant
• Wealth comes from exits and expertise
• Consulting often beats syndication
• Purpose fuels fulfillment; money alone doesn’t

[48:16 – 59:00] Doubt, Purpose & the Real Work

• Doubt lingers, even with a plan
• Mission matters more than ego
• Money without purpose leads nowhere
• We exit to do our real work

Key Quotes:

“The biggest mistake I made in my transition from an employee to a founder was trying to build a faceless brand.” - Jerome Myers

“The only way your life ever matters is if you are positively impacting the lives of other people.” - Jerome Myers

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