Ever wonder what happens when estate planning meets complex family dynamics? In this raw and revealing episode, Sara sits down with second-generation entrepreneur and author Cindy Arledge, whose family built a $10 million legacy from the ground up—only to face unexpected conflict when their wealth transfer strategy fell short. Cindy opens up about her family's journey, sharing hard-won wisdom on estate planning and the emotional landmines that even the most loving families encounter when it comes to inheritance. Drawing from both heartbreak and hope, she breaks down how families can navigate generational wealth transfer, tackle tough conversations about succession planning, and create comprehensive estate plans that strengthen bonds rather than break them. Whether you're protecting modest assets or substantial wealth, Cindy's story is a powerful reminder that successful estate planning isn't just about financial inheritance—it's about preserving family unity for generations to come.
About Cindy:
Cindy Arledge, MBA helps families create lasting legacies by planning for generational success. Her passion was ignited by the most painful experience of her life—losing her relationship with her brother over a shared inheritance. Determined to find a better way, Cindy reverse-engineered a practical, common-sense solution to prevent end-of-life challenges from tearing families apart.

She developed a proven framework that equips proactive families to prepare their members for roles as caregivers, fiduciaries, and builders of generational wealth.

As a second-generation real estate investment entrepreneur, best-selling author, and family matriarch, Cindy is dedicated to helping families thrive across generations.
Her Books:
Family Emergency Handbook
The Legacy Family Way
Curse of Inheritance
Cracking the Inheritance Code
My Camino, My Life
Connect with Cindy:
CindyArledge.com
On LinkedIn
Cindy recommends the following website for families to take the first step in elevating their planning efforts: FamilyCareGivingResources.com
Referenced in this Episode:
The Ostrich Paradox: Why We Underprepare for Disasters by Robert Meyer

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