TTU13: Lessons From the Most Successful Turtle of All-Time ft. Jerry Parker – 1of2

TTU13: Lessons From the Most Successful Turtle of All-Time ft. Jerry Parker – 1of2

Imagine you found an advertisement in the newspaper offering a position with a one sentence application process.

Would you take it?

What if it was for a position where you would learn a proprietary trading system in which you would trade solely for owner of the firm?

What if that man was Richard Dennis?

Our next guest took that position in 1983 and it changed his life forever, for the better. He found himself with what was to become a famous title, a Turtle. He was given the opportunity to manage a million dollar account with specific rules to follow. Rules that he would learn to love and perfect.

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50 YEARS OF TREND FOLLOWING BOOK AND BEHIND-THE-SCENES VIDEO FOR ACCREDITED INVESTORS - CLICK HERE

In This Episode, You’ll Learn:

  • About the Turtles and how the unique experiment grew into the Managed Futures/CTA Industry
  • How Wall Street Leaks inspired Jerry into understanding the industry
  • How Jerry encountered trend following for the first time
  • The One Sentence culture in Richard J. Dennis’s office
  • How to excel at unprecedented tests from leading traders
  • What it was like moving to Chicago to train as a Turtle
  • What the Turtle training was like and the mindset provided in the training
  • The most challenging thing about Trend Following when Jerry started with Richard Dennis
  • About the transition from Turtle Trading to starting his own organization, Chesapeake Capital in 1998
  • The evolution of Chesapeake’s strategy from day one after leaving Richard Dennis’s program
  • The early focus on diversification and adding new markets
  • Issues with trying to improve the original Richard Dennis
  • The shift in investor expectations with the growth of institutional investment organizations while operating on of the largest CTA firms in the industry
  • Why it’s best to take an optimal loss rather than a small loss
  • On the meaningfulness of track records and what else investors should be encouraged to explore when choosing an investment management decision

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The advertisement Jerry responded to in 1983:

Richard J. Dennis and CD commodities is accepting applications for the position of Commodity Future Trader to expand his established group of traders. Mr. Dennis and his associate will train a small group of applicants in his proprietary trading concepts. Successful candidates will then trade solely for Mr. Dennis. They will not be allowed to trade futures for themselves or others. Traders will be paid a percentage of their trading profits and will be allowed a small draw. Prior experience will be considered, but is not necessary. Applicants should send a brief resume with one sentence giving their reason for applying.

Resources & Links Mentioned in this Episode:

  • The Barefoot Trader (Article about Richard Dennis in Wall Street Journal)
  • Learn more about Richard J. Dennis the founder of the Turtle program

Follow Niels on Twitter, LinkedIn, YouTube or via the TTU website.

IT’s TRUE ? – most CIO’s read 50+ books each year – get your FREE copy of the Ultimate Guide to the Best Investment Books ever written here.

And you can get a free copy of my latest book “Ten Reasons to Add Trend Following to Your Portfoliohere.

Learn more about the Trend Barometer here.

Send your questions to info@toptradersunplugged.com

And please share this episode with a like-minded friend and leave an honest Rating & Review on iTunes or Spotify so more people can discover the podcast.

Follow Jerry Parker on Twitter.

Copyright © 2025 – CMC AG – All Rights Reserved

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PLUS: Whenever you're ready... here are 3 ways I can help you in your investment Journey:

1. eBooks that cover key topics that you need to know about

In my eBooks, I put together some key discoveries and things I have learnt during the more than 3 decades I have worked in the Trend Following industry, which I hope you will find useful. Click Here

2. Daily Trend Barometer and Market Score

One of the things I’m really proud of, is the fact that I have managed to published the Trend Barometer and Market Score each day for more than a decade...as these tools are really good at describing the environment for trend following managers as well as giving insights into the general positioning of a trend following strategy! Click Here

3. Other Resources that can help you

And if you are hungry for more useful resources from the trend following world...check out some precious resources that I have found over the years to be really valuable. Click Here

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