TTU14: “You’re going to make a lot of money doing this…” ft. Jerry Parker – 2of2

TTU14: “You’re going to make a lot of money doing this…” ft. Jerry Parker – 2of2

Today we will continue our conversation with Jerry Parker the founder of Chesapeake Capital and widely known as the most successful Turtle ever.

After wrapping up his position with Richard J. Dennis as a famous “Turtle,” he went on to start his own asset management firm, Chesapeake Capital Corporation.

In this episode we discuss the evolving CTA industry and the story of Chesapeake. It’s a powerful story from one of the most successful people in the industry. We really hope you enjoy it.

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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:

  • How the research and complexity of systems has a backwards effect to making money
  • Challenges with entering stock markets with CTA strategies
  • Why counting the trades and analyzing sample size is what most investors forget to ask when seeking fund managers
  • Where the CTA managers have failed investors
  • How Jerry Parker handles emotions during drawdowns
  • Why markets have changed so that longer term focus has proven more successful
  • Learn about the philosophy of “The Markets are the Heroes”
  • Important lessons from a long, successful career in the CTA industry
  • What is it that keeps investors from Turtle CTAs and choose larger financial organizations
  • Why we see a skewed distribution towards profitability of long side trades and short side trades
  • The key legacy traits left behind by the Turtles and if the experiment could be replicated now
  • Why Jerry Parker’s contribution to the CTA space will be that he sticks with the plan and be the last one going down with the trend following ship
  • Lessons for upcoming CTA managers from Jerry Parker
  • Debunking trading cliches like, “you never go broke taking a profit” and “exits are more important than entries”
  • Personal habits that have contributed to Jerry Parker’s success
  • How Jerry Parker would start if he were to start all over again

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Resources & Links Mentioned in this Episode:


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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