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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Origin Story And Name
- Derrick recounts Blue Sky's origin as his father's oil-and-gas venture transitioned into a family investment company in 2001.
- He explains the name comes from a stratigraphic formation tied to their first well, not a metaphorical 'blue sky.'
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.