40 Strategy Blog

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: ...

What is wealth really for? In this episode of the Measure Success Podcast, Carl sits down with Tyson Ray, CEO and Founding Partner of Form Wealth Advisors, to discuss building wealth that creates a better life. Tyson shares lessons from his career helping business owners, a powerful experience in Israel that reshaped his perspective, and why financial success should always support purpose, relationships, and legacy. Together, they explore retirement, succession planning, giving while you're living, and how business owners can avoid spending their lives chasing more money without enjoying what they've built. Listen now for practical wisdom on wealth, leadership, and measuring success beyond your balance sheet. Connect with Tyson:  LinkedIn https://www.linkedin.com/in/tysonray/   Book Total Succession:  https://totalsuccession.com/   Website https://totalsuccession.com/     Check out this episode!

What happens after you achieve financial success? In this episode of the Measure Success Podcast, Carl sits down with Mark Podolsky, known as "The Land Geek," to discuss passive income, AI, entrepreneurship, and finding purpose beyond financial success. Mark shares how he transitioned from investment banking to building a successful land investing business and explains why creating systems is the key to gaining both financial freedom and time freedom. Together, Carl and Mark explore how AI is changing the way businesses operate, why leaders should think of AI as an operating system instead of another tool, and why success ultimately comes down to relationships, purpose, and being present. Listen now for practical insights on building wealth, using AI with intention, and measuring success beyond the bottom line. Connect with Mark:  LinkedIn https://www.linkedin.com/in/thelandgeek/   Facebook https://www.facebook.com/thelandgeek   Twitter https://twitter.com/TheLandG...