Why do 75% of Exits Fail? | Michael Winn, Co-Founder & Partner at Chartered Wealth Partners

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Michael Winn of Chartered Wealth for the first installment in a new mini-series on one of the biggest questions founders face: why do so many exits fail? Michael breaks down the surprising statistic that 75% of founder exits are unsuccessful, and explains why selling a company is not just a transaction, but a deeply personal, financial, and strategic process.

Michael shares the three areas every founder must align before an exit: business readiness, financial readiness, and personal readiness. While most owners focus on whether the business is valuable and transferable, Michael explains why the emotional side is often the most overlooked and the most dangerous, especially when founders lose their identity, purpose, and daily adrenaline after the wire hits.

Jess and Michael also explore real client stories, including founders who walked away from $300M+ deals, struggled after $120M exits, or discovered that their “magic number” was not what they thought. The conversation dives into estate planning, wealth gap analysis, tax mitigation, spouse alignment, and the importance of preparing for life after the sale long before the deal closes.

Whether you’re actively preparing to sell, years away from an exit, or building a business you may never sell, this episode is a practical and eye-opening guide to avoiding founder regret and creating an exit on your terms, not the buyer’s.

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