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Today’s guest is Chris Hillier, an entrepreneur, investor, author, and longtime operator in the world of small and mid-sized businesses. He was the co-founder of a company called Benefit Health Advisor, which he started with his brother and father in the midst of the Great Recession. Over the subsequent sixteen years, he grew revenue at a staggering rate of 30% annually, and grew EBITDA by more than 40% annually over that same period.

Along the way, Chris acquired a struggling insurance underwriting business that was nearing shutdown, helped grow it nearly fifteenfold, and ultimately sold both businesses in 2018, after which he spent five years inside of the larger organization that had acquired him. Today, Chris invests in and advises entrepreneurs, teaches at the University of Denver, and is the author of "It’s About Time" and "Built Different".

Our conversation today covers growth, the benefits of specialization, the revenue growth vs profitability trade-off, time management at both a personal and professional level, and how his views on ambition, family, and success have evolved after his exit.