He grew up immersed in two family businesses, so when he speaks about succession battles, personality clashes, and the weight of legacy, he draws from real-life experience. Today, Stephen combines decades of firsthand leadership with expertise in psychometrics, leadership development, and entrepreneurship to help family businesses sidestep drama, nurture future leaders, and ensure the right people—family or not—are in the right roles.

But Stephen’s work goes beyond preparing for the next in line. He is an enthusiastic advocate for NextG Entrepreneurs: those navigating the tension between honoring tradition and pursuing their own ambitions. Stephen empowers them to launch ventures with confidence, whether within the family business or on their own path.

His talks and training sessions—such as “Build a Killer Family Business, Without Killing Your Family,” “Pruning the Family (Business) Tree,” “Sibling Showdown,” “Finding Your [in]-Side Hustle,” and “Black Sheep Breakout”—deliver refreshing honesty and strategic clarity about the messy realities of working with those you love (and sometimes want to strangle). 

https://stephenshortt.com/

http://www.yourlotandparcel.org

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