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Episode 35 features one of the original Turtle Traders. \u201cWhat\u2019s a Turtle Trader\u201d you ask?\nThe story involves Richard Dennis, a great trader from the 1970\u2019s. As the story goes, he made his first million by about age 25. By the early 80\u2019s, he was worth about $200 million. Around this time, the movie \u201cTrading Places\u201d came out (two millionaires make a bet on the outcome of training a bum to be a financial whiz, while taking a financial whiz and, effectively, turning him into a bum). Richard felt he could similarly train a financial no-nothing, turning him into a great trader. Richard\u2019s partner felt it wouldn\u2019t work. So they made a bet. (Though as you\u2019ll hear on today\u2019s podcast, Jerry doesn\u2019t actually believe there was ever a bet.) Regardless, how\u2019d it turn out? Three or four years later, the group Richard trained had made, on aggregate, around $100 million.\nThe episode starts as Meb asks Jerry how he became involved with Dennis, trend following, and the Turtle Traders. Jerry was hooked on the idea of trend following from the beginning. Meb suggests that many people either \u201cget it\u201d or they don\u2019t \u2013 meaning they get hooked, buying into the strategy completely, or not.\xa0For many people, the philosophy just doesn\u2019t take.\nEventually the program ended, after which Jerry moved back to Virginia and started Chesapeake, which basically consisted of a telephone, a quote machine, and his trading rules. Jerry tell us how the company grew and how its trading systems developed. They\u2019ve gone from trading around 20 markets to well over 100 now. Meb asks in terms of conditions, what\u2019s been the most challenging market for Jerry in his career at Chesapeake? His answer \u2013 the market since 2008.\nThe conversation eventually steers toward leverage and volatility. Meb says how most people don\u2019t realize how they can tamp down a volatile market through trend following and managed futures. Jerry agrees, and adds that you want to \u201cmake the same (volatility) bet\u201d despite different markets, to maintain consistency.\nMeb then asks why so many investors, retail and institutional alike, have such small allocations to trend following. Jerry gives us his thoughts, pointing toward the inherent bias people have for equities. He also believes most investors truly don\u2019t realize how powerful diversified trend following can be.\nJerry thinks people have it backward\u2014they see trend following as an add-on to some other strategy, when in fact, it\u2019s the core. Start with the CTA strategy and maybe add some long-only equities.\nThe conversation then turns toward common investor mistakes, most notably the tendency to hold losses and sell winners short. Simply put, the behavioral side of investing is extremely challenging. This causes Meb to wonder what will happen to the roboadvisors when a bear market finally begins. Specifically, with it so easy to pull your cash out of a roboadvisor (and no live advisor to stop you), how many investors will allow fear to make them liquidate their positions?\nThere\u2019s tons more in this episode, including how Jerry lost 60% in one day, the differences between technical analysis and trend following, the \u201cturtle program\u201d of the future, and the one market that won\u2019t allow futures trading. Do you know which one it is? Find out in Episode 35.\nLearn more about your ad choices. Visit megaphone.fm/adchoices