What happens to your business, your wealth, and your family if you’re not around tomorrow?
In this episode of the Relentless Growth Podcast, Chase Calhoun and Jack Maher dive into one of the most overlooked—but most important—topics for entrepreneurs: succession planning and building a lasting family legacy.
Chase shares insights from a recent GoBundance workshop focused on legacy, generational wealth, and family businesses, along with the practical steps he’s been taking to create a succession plan for his companies and investments. The conversation covers everything from protecting your family financially to designing businesses that can operate without you.
Jack brings the perspective of being second generation in a family construction business, discussing the realities of passing down companies, preparing the next generation, and why most family wealth disappears within three generations.
They also explore the challenges of leaving wealth to your kids without removing their motivation, how communication can prevent family conflict around money, and why entrepreneurs should start thinking about legacy much earlier than they typically do.
Whether you're a business owner, investor, or entrepreneur building something meaningful, this episode will challenge you to think long-term about your business, your family, and the impact you want to leave behind.
Why every entrepreneur needs a simple succession plan
Protecting your family with life insurance and financial planning
How to structure businesses that can run without the founder
The “three-generation rule” and why most family wealth disappears
The debate around leaving money to your children
Why communication and transparency are critical in family businesses
How to start building a multi-generational legacy
If you’re building a business and want it to outlast you, this is a conversation you don’t want to miss.
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In this episode, we discuss: