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July 31, 2025 30 mins

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In this first of a four part series, we'll examine why it is that 75% of the business owners regret their business sale after the first year, a statistic that challenges conventional success measures. What if the key to a fulfilling post-business life isn't as much in your financial metrics, but in your personal values? Join us, Matthew Grishman and Jim Gebhardt, on the Whole Wealth Journey Podcast as we explore the profound connection between personal planning and meaningful entrepreneurship. Inspired by the lessons from our fathers, we dive into the world of crafting a life beyond work. From our experience with entrepreneurs in transition post sale of their companies, we emphasize the role of personal planning in shaping a fulfilling journey once life in the business is gone.

Amidst the noise of financial success, have we forgotten the human element? We'll spotlight the often hidden pitfalls of entrepreneurship.a statistic that challenges conventional success measures. We invite you to rethink these metrics by integrating personal fulfillment and future identity into your financial planning. We illuminate the importance of knowing who you want to become after the sale, beyond just maximizing business value, to prevent post-sale regret and nurture a more holistic definition of success.

Fear of losing identity—could this be the silent saboteur in business transitions? As we gear up for our four-part series on personal planning for entrepreneurs, we confront this overlooked barrier. Entrepreneurs often struggle to envision life beyond their current roles, yet it's crucial for a successful transition. We look deep into the dynamics between builders and sustainers in business partnerships and the unsettling prospect of retirement for those who thrive on creation. Through our candid reflections, we offer a roadmap to prepare for the journey beyond entrepreneurship, ensuring clarity and a purpose-driven future.

As mentioned in the episode, you can find the Amazon link to the book "Who Not How" HERE

Learn more about The Whole Wealth Journey and get periodic updates or helpful content by getting on our email list HERE. Entrepreneurs, exit strategies and personal financial planning before the sale are topics you can count on every episode. You can follow us on Instagram @thewholewealthjourney.

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