Jul 21, 2026
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