A working class kid from the poor part of Connecticut, Jared Dillian somehow managed in 2001 to land a job as a trader at Lehman Brothers, the then-prestigious investment bank. Wearing cheap suits from the Mens Wearhouse, he found himself out-of-place among the Armani-clad Ivy League set on Wall Street. But he loved trading and made a lot of money in the process. In this candid conversation, Jared shares frank insights into the incredible stress of trading and the mental health that became apparent as his career progressed. Those persistent mood swings turned out to be a symptom of undiagnosed Bipolar disorder, which resulted in him spending three weeks in the psychiatric ward, a place he described as “a very healing environment." After Lehman went bankrupt, Jared pivoted to a successful writing career. Today, he is the Editor of The Daily Dirt Nap, an investment newsletter providing daily market commentary and insight to traders and very serious investors. He has also written two books: Street Freak: A Memoir of Money and Madness, a gripping read which chronicles his time as a trader with Lehman Brothers from 2001-2008, and the novel, All The Evil of this World, which Paul is looking forward to reading.   Jared graduated from the US Coast Guard Academy and earned his MBA From University of San Francisco. When he’s not writing or taking care of his 5 cats, he is making music under the name, DJ Stochastic. He lives in Pawleys Island, South Carolina.

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Topics covered in this episode include investments, trading, Wall Street, Lehman Brothers, writing, mental health, bipolar disorder, OCD, Bloomberg, Matt Levine