Episode 17: The Uncomfortable Truth of Family Business Transitions w/ Tom Deans

In this episode of The Do Diligence podcast by Sleeping Giant Capital, host Derrick McIver welcomes Tom Deans, acclaimed author and global thought leader on family business succession.

Tom shares insights drawn from his own experience running and selling a multi-generational manufacturing company and from his three-book trilogy on family wealth and succession planning, including Every Family’s Business, Willing Wisdom, and The Happy Inheritor. He challenges conventional wisdom around gifting family businesses, advocating instead for transparent conversations, third-party valuations, and the critical importance of having next-generation owners risk their own capital.

Listeners will gain a candid look at the often-avoided family dynamics that derail succession plans — from unspoken promises to sibling rivalries — and learn why secrecy can destroy both wealth and relationships. Tom also explores why building a sellable business should be every founder’s goal, how to view a business as a tool for wealth creation rather than legacy, and how family meetings and clear governance can preserve harmony across generations.

With humor and data, this conversation reframes what it means to transition a family business and offers actionable steps for owners, heirs, and advisors seeking to protect both wealth and family unity.

To learn more about how Tom thinks, visit his website: https://www.thomaswilliamdeans.com/