Why 75% of Business Owners Regret Selling

Why 75% of Business Owners Regret Selling

July 21, 2026 · 43 min

About this episode

This episode discusses the reasons why 75% of business owners regret selling their business and how to plan for life after the sale.

Most business owners celebrate the sale. Most also regret it. In this episode of the Measure Success Podcast, I sit down with Bob Bedritis, founder and managing director of Oswego Private Wealth Management and a certified exit planning advisor, to discuss why nearly 75% of owners regret selling their business, the "wealth gap" that blindsides them, and how to plan the most important act of your life — the one that comes after the business. We cover: • Why nearly 75% of business owners regret the sale — and the wealth gap driving it • The real math of a deal: how $5M on paper becomes $1.5M in your pocket • Why exit planning is really growth planning that should start 5 years out • Making yourself dispensable, not indispensable, so the business runs without you • Your "third act" — building a life of significance after you step away Watch the full episode and ask yourself: if you sold your business tomorrow, would you know what comes next? Connect with Bob: LinkedIn: https://www.linkedin.com/in/bob-bedritis-certified-exit-planner%C2%AE-crc%C2%AE-05140613 Website: OswegoPrivateWealthManagement.com

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