Steven Bowles didn’t take the typical path to entrepreneurship. After spending nearly a decade in sales and business development, he found his calling in wealth transfer planning and life insurance advisory services. For seven years, he worked inside a family office advisory group, gaining invaluable experience helping ultra-high-net-worth families structure their finances, protect their assets, and transfer wealth across generations.

Today, Steven runs an independent life insurance advisory firm that specializes in advanced wealth transfer planning for high-net-worth families, business owners, and investors. In this interview, Steven shares his journey from employee to entrepreneur and the challenges he faces running an independent advisory.


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Steven Bowles
January 6, 2026

The largest intergenerational wealth transfer in history is here. According to The Federal Reserve, Americans born before 1965 hold more than $105 trillion, or 63% of household wealth in the U.S. Over the next two decades, the Great Wealth Transfer will see most of that passed on to younger generations.