Beyond The Family Business Creating a Family Legacy that Lasts Generations (Derrick Hunter)
Oct 31, 2025
Derrick Hunter, the second-generation CEO of Calgary's Blue Sky Equities, shares insights on transforming a family business from oil and gas to diversified investments. He discusses lessons from his father about legacy and the shift to U.S. multifamily real estate, highlighting a strategic pivot to mitigate concentration risk. Derrick emphasizes the crucial role of entrepreneurs in family legacies and details his foundation's mission focused on supporting mental health and entrepreneurship. His reflections on family governance reveal the importance of transparency and succession planning.
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Timing A Big Real Estate Win
- Derrick describes buying over 15,000 U.S. apartments between 2008 and 2017 after entering multifamily with a partner.
- He notes strong cash flow, 8% average rental growth, and perfect timing during the global financial crisis.
All-Weather Portfolio Goal
- After a large liquidity event in 2017, Derrick decided to avoid concentrated risk and build an 'all-weather' portfolio.
- Their target: positive annual returns with drawdowns limited to about 10% via uncorrelated asset construction.
Generational Need For Entrepreneurs
- Every generation needs an entrepreneur, Derrick says, because prior approaches won't necessarily work for the future.
- He argues families must adapt to technology and changing economies to keep a business alive across generations.