From Turtle to Titan: Trend Following with Jerry Parker
In this episode, Damanick Dantes, CMT, founder and portfolio manager at Dantes Outlook, sits down with Jerry Parker, founder of Chesapeake Capital and one of the original Turtle Traders selected by Richard Dennis in 1983. With more than four decades of experience in systematic trend following, Jerry shares insights on risk control, diversification, and why discipline is the foundation of durable performance. The conversation explores how trend following behaves across market regimes, the role of dispersion in today’s environment, and how advisors and portfolio managers can thoughtfully integrate systematic strategies into diversified portfolios.
Dantes Outlook Market Podcast · Jerry Parker
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Show Notes
Key Topics:
- The original Turtle experiment and lessons from Richard Dennis
- Why and how trend following focuses on small losses and large winners
- Volatility-based position sizing and risk management discipline - Diversification across equity markets, currencies, commodities, bonds, and individual stocks
- Current market dispersion and what it means for systematic strategies
- The psychological challenge of sticking with trend during whipsaws and drawdowns
- The growing role of ETFs in managed futures
- How advisors can size and integrate trend-following sleeves within broader allocations
Key Takeaways:
- Trend following is agnostic — it adapts rather than predicts.
- Diversification across a broad global universe improves opportunity and resilience.
- Proper allocation and manager selection matter more than short-term performance.
- No strategy is perfect — understanding drawdowns and behavioral discipline is critical.
Learn More:
- Jerry Parker & Chesapeake Capital: www.chesapeakecapital.com
- Dantes Outlook's RIA & OCIO Services: www.dantesoutlook.com
- Dantes Outlook Substack for ongoing research and portfolio insights: www.dantes.substack.com
Disclaimer: The information presented is for informational purposes only and should not be considered as investment advice nor as a recommendation of any particular strategy, allocation or investment product: before making any investment decision, you should seek expert, professional advice and obtain information regarding the legal, fiscal, regulatory and foreign currency requirements for any investment according to the laws of your home country and place of residence. Investing involves risk, including the possibility of loss of principal. Any forward-looking statements or forecasts are based on assumptions and actual results may vary from any statements or forecasts.
The information presented is for informational purposes only and should not be considered as investment advice nor as a recommendation of any particular strategy, allocation or investment product: before making any investment decision, you should seek expert, professional advice and obtain information regarding the legal, fiscal, regulatory and foreign currency requirements for any investment according to the laws of your home country and place of residence. Investing involves risk, including the possibility of loss of principal. Any forward-looking statements or forecasts are based on assumptions and actual results may vary from any statements or forecasts.
Visit us at www.dantesoutlook.com