B. Jeffrey Madoff — The Hidden Persuaders, Working with Ralph Lauren, & More | The Tim Ferriss Show

Tim Ferriss and longtime friend B. Jeffrey Madoff cover Madoff's winding career from running a Wisconsin clothing company at 24 to teaching himself film production in New York. They explore the idea of 'scratching your own itch' (rooted in a conversation Madoff had with Ralph Lauren), how informed perseverance carries you through dozens of rejections, and how to evolve your personal definition of success toward engagement. Madoff shares vivid stories from his early days, brushes with figures like Dennis Hopper and William Burroughs, and the headaches of sharing a surname with Bernie Madoff. The conversation closes on graceful rejection, favorite authors, a Gregory Peck anecdote, and Madoff's new theater and podcast ventures.

• Ralph Lauren told Madoff he has kept his pulse on the consumer for decades because 'I know who my consumer is because I am the consumer', the essence of scratching your own itch.
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• Madoff's Wisconsin financial backer refused to keep funding the business if Madoff moved to New York, forcing him at 24 to decide whether closing the company meant he was a failure.
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• His father's lesson, 'money comes and goes, time only goes', drove his decision to close the business and move to New York.
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• The mystical 'life coach in the Mojave Desert' parable was entirely made up by Madoff to end his book, with the real point that there are no secrets, only hard work and perseverance.
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• The shoe-store monkey was named 'Solo' not after Napoleon Solo from The Man from U.N.C.L.E. but because all the monkey did was masturbate.
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• When the Daily Beast asked Madoff to cut a line about wealthy people cloaking themselves in religious and philanthropic causes to inoculate against criticism, he refused; HuffPost ran it unchanged, launching about 50 articles for them.
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• Madoff told Lloyd Price 'you're the messenger, this story is bigger than you,' and Price said he had waited years for someone to say that, beginning their collaboration on the musical.
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• Madoff's first job after college was in a Madison boutique in the base of a notorious rooming house, where the impulse-buy items by the register were hash pipes and rolling papers.
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• Starting out, Madoff was so naive about clothing he thought fabric on the bolt was wholesale; he distinguishes 'ignorant you can learn, stupid's forever.'
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• Tim and Madoff first met in 2007 or 2008; Madoff helped with many of the exercise photographs for The 4-Hour Body.
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• Madoff was offered an acting role in a film adaptation of William Burroughs' 'Junkie' that Dennis Hopper was to direct and star in, but predicted (correctly) it would never get made.
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• Madoff interviewed Taylor Swift, though Tim notes it was as part of a Victoria's Secret job, not his Parsons class.
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• Before selling shoes, Madoff worked door-to-door as a Fuller Brush man and once accidentally handed a customer oven spray instead of hairspray, she bought it anyway.
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• Lloyd Price's 1952 song 'Lawdy Miss Clawdy' broke down the 'race records' wall, became the first record to sell over a million copies, and is considered a cornerstone of rock and roll.
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• Madoff recommends pairing Michael Lewis, Daniel Kahneman and Amos Tversky's heuristics-and-biases work, Timothy Wu's The Master Switch, and James Gleick's The Information.
  01:22:58
• Madoff recounts Gregory Peck telling how Harper Lee gave him her father's pocket watch on the To Kill a Mockingbird set, which Peck rubbed during his Best Actor acceptance speech.
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• Asked for his billboard message, Madoff offered the literal 'pay attention to the road' and the metaphorical 'stay curious, keep learning.'
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