90. How to Build a Lasting Legacy - with Charlie Leichtweis

Most family businesses don’t survive beyond three generations. Less than 3% make it to the fourth. Why? Because growing a business and sustaining a family at the same time is an incredibly complex challenge. In this episode of Leadership That Sells, I sit down with Charlie Likewise, business veteran and author of The Power of Legacy, to uncover the secrets to long-term family business success.

Charlie breaks down the three biggest decision-making areas that determine whether a family business thrives or fails: purpose, direction, and legacy. We explore how generational engagement plays a crucial role in succession planning, why governance is often misunderstood, and the steps every family business leader should take to ensure continuity across generations.

If you’re leading a family business and want to secure its future, this episode is packed with actionable insights.

• Define your purpose. Align the family and business around a clear mission to guide decision-making.


• Engage the next generation early. Start succession planning long before leadership transitions are needed.


• Build strong governance. Establish clear structures for decision-making without stifling family relationships.


• Prepare for tough conversations. Conflict is inevitable—having open discussions prevents crisis-driven decisions.


• Think long-term. Avoid short-term gains that could compromise the business’s future sustainability.

[03:10] - The shocking statistic: why 97% of family businesses fail before the fourth generation [08:25] - How to align your family and business around a shared purpose [14:40] - Why governance is misunderstood (and how to make it work for your business) [20:55] - The role of generational engagement in building leadership and succession plans [29:30] - How to balance business sustainability with family expectations

• The Power of Legacy by Charlie Likewise


• Connect with Charlie Likewise at expertsinhow.com

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