Jerry Parker

Jerry Parker is one of the original Turtle Traders. In December 1983, he answered an ad in the Wall Street Journal, flew to Chicago, and was selected for Richard Dennis's legendary trading program. He was taught to trade alongside a small group of recruits, and over four years generated roughly 150-200% annual returns following Dennis's system. When the Turtle program ended, Parker launched Chesapeake Capital in Richmond, Virginia in February 1988. He's been running trend following strategies ever since, and recently brought that approach to the ETF market with TFPN (Blueprint Chesapeake Multi-Asset Trend ETF).

On this episode, Jerry sits down with Brad to talk about the Turtle origin story, why he built TFPN to trade roughly 400 instruments including individual stocks, and his conviction that trend following belongs at the center of a portfolio rather than at the margins.

From Accounting to the Turtles

Parker started in public accounting in Richmond, Virginia. He passed his CPA exam, got his certificate, and immediately started looking for the exit. He knew corporate accounting wasn't for him. He interviewed for an assistant role with a commodity trader in Richmond and didn't get the job. A few months later, he saw the Wall Street Journal ad for Richard Dennis's Turtle program and applied. Dennis was settling a bet with his partner Bill Eckhardt about whether great traders were born or made. Dennis believed they could be taught. He gave each Turtle roughly a million dollars and a few weeks of training, then set them loose. The core philosophy: follow the system, take every signal, don't override the rules. Parker describes it as being "handed a career." He was 25 years old.

After the program ended, Parker launched Chesapeake with the same core approach. For decades, he ran a traditional managed futures business, trading primarily through the CTA structure. The move to ETFs was driven by a desire to bring trend following to a broader audience. Parker believes the strategy has been unfairly confined to the alternatives bucket, and the ETF wrapper makes it accessible to any advisor or retail investor who wants exposure.

How TFPN Works

TFPN stands for Trend Following Plus Nothing. The fund trades roughly 400 instruments across five sectors: stocks, commodities, currencies, interest rates, and some crypto. What's unusual is that about half the portfolio is individual stocks, which sets it apart from traditional CTA strategies that typically trade only futures contracts on indices and commodities. Parker added individual stocks because he saw an opportunity to apply trend following signals to a much larger universe of liquid instruments, which improves diversification and creates more independent bets.

Every trade has a predetermined stop loss of roughly 10-15 basis points of total portfolio risk. The system enters positions when price trends confirm across multiple timeframes and exits when those trends break down. There are no fundamental inputs, no earnings estimates, no macroeconomic forecasts. It's purely price-driven. Parker emphasizes that the key to trend following isn't any single trade but the aggregate effect of hundreds of small bets where losses are cut quickly and winners are allowed to run. The math works because the occasional large winner more than compensates for the frequent small losses.

Why Trend Following Belongs in the Core

Parker makes a passionate case for reclassifying trend following from an alternative strategy to a core portfolio holding. His argument: trend following has positive expected returns in both up and down equity markets because it can go long or short any instrument. When stocks enter a bear market, the system shorts them or shifts to long positions in assets that are trending up (like bonds during a flight to quality, or commodities during inflationary periods). This creates a return profile that is genuinely uncorrelated to traditional 60/40 portfolios.

He points to 2022 as a case study. When both stocks and bonds fell simultaneously, trend following strategies had one of their best years because they captured the commodity rally and shorted bonds as rates rose. Parker argues that any strategy capable of generating positive returns during a year when the traditional portfolio got destroyed deserves more than a 5% alternative allocation.

Key Takeaways

• TFPN trades roughly 400 instruments across five sectors, with about half the portfolio in individual stocks, which is rare for a trend following fund.
• Every trade has a predetermined stop loss of roughly 10-15 basis points of total portfolio risk, with the system designed to cut losses quickly and let winners run.
• Parker was one of about a dozen traders selected for Richard Dennis's Turtle program in 1983, generating 150-200% annual returns over four years before launching Chesapeake Capital in 1988.
• In 2022, trend following strategies posted strong positive returns while both stocks and bonds declined, demonstrating the genuine diversification benefit Parker advocates for.
• Parker believes trend following is misclassified as an alternative and should be a core allocation, citing its ability to generate positive returns in both rising and falling equity markets.

Listen to the full conversation on Spotify, Apple Podcasts, or YouTube.