My Guest
Today’s guest is Chris Hillier, an entrepreneur, investor, author, and longtime operator in the world of small and mid-sized businesses. He co-founded Benefit Health Advisor during the Great Recession, returned to Colorado after earning his MBA from Stanford, and over the next sixteen years helped grow the company at more than 30% annually in revenue and more than 40% annually in EBITDA.
Along the way, Chris also acquired a struggling insurance underwriting business that was nearing shutdown, helped grow it nearly fifteenfold, and ultimately sold both businesses. In 2018, BHA was acquired by Acrisure, after which Chris spent roughly five years inside 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 covers growth, specialization, profitability, acquisitions, time management, and how his views on ambition, family, and success evolved after the exit.
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The Case for Focus, Profitability, and Saying No to Growth for Its Own Sake – In The Trenches
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Episode Summary with Timestamps
- 00:00 Introduction and Chris career background
- 03:11 Chris Hillier’s entrepreneurial journey and early career
- 09:08 Timing and economic conditions for starting a business
- 14:16 Challenges of business growth and managing expansion
- 20:45 Focus, specialization, and market niche strategy
- 28:31 Customer selection and firing problematic clients
- 29:47 Balancing growth with profitability
- 35:22 Work-life balance and time management as a CEO
- 41:12 Myth of entrepreneurship for flexibility and time
- 48:55 Acquisition of distressed company and risk management
- 55:35 Exit strategy and post-exit experience
- 01:03:17 Post-exit life, learning, and new priorities
- 01:11:43 Managing personal relationships and time with family
- 01:16:39 Most meaningful lessons learned in the past year
- 01:18:14 Trust, character, and evaluating people
- 01:19:43 Resources and ways to connect with Chris
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Thanks to our Sponsors
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