B. Jeffrey Madoff — Dealmaking, The Hidden Persuaders, Working with Ralph Lauren, and Finding the Secret to Life in the Mojave Desert (#526)

Illustration via 99designs

“Everything you do, if your eyes are open, informs everything else you do.”

— B. Jeffrey Madoff

B. Jeffrey Madoff (@madoffproductions) began his career in fashion, becoming one of the top 10 designers in the US before switching careers to film and video production. He has directed award-winning commercials, documentaries, and web content for clients around the world, including Ralph Lauren, Victoria’s Secret, and Tiffany.

His book, which is based on the class he teaches at Parsons School of Design, is Creative Careers: Making a Living with Your Ideas.

He has been a featured speaker at Wharton School, Princeton University, NYU Steinhardt, Google Next, Barclays’ Rise and Verizon on the topics of creating a brand and creativity. He works with private equity firms and investment banks, such as Lazard, to create the brand story for companies that are being sold or startups looking to attract investment.

Madoff is also a playwright and theater producer. His play Personality: The Lloyd Price Musical, based on the life of the titular Rock & Roll Hall of Fame legend, will have its world premiere in March of 2022 at People’s Light theater in Malvern, Pennsylvania.

He graduated with honors from the University of Wisconsin with degrees in philosophy and psychology. He was also on the wrestling team, which, combined with his academic studies, prepared him for a life in the film business.

Please enjoy!

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The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#526: B. Jeffrey Madoff — Dealmaking, the Hidden Persuaders, Working with Ralph Lauren, and Finding the Secret to Life in the Mojave Desert

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear an episode with someone else who’s never been shy about initiating conversations with celebrities in the wild? Give a listen to my discussion with Academy Award-winning producer and New York Times bestselling author Brian Grazer, in which we talk about cultivating curiosity, making high-end connections from lowly places, good producers versus great producers, contacting the difficult-to-reach, what can happen when a good story’s perspective is poorly calibrated for its intended audience, and much more.

#279: The Most Curious Man in Hollywood — Brian Grazer


  • Connect with B. Jeffrey Madoff:

Website | Instagram | LinkedIn | Madoff Productions | Madoff Productions’ Instagram


  • How learning to scratch one’s own itch can launch a career. [05:35]
  • After graduating with degrees in philosophy and psychology, where did Jeff first find gainful employment, and how did this inform his future career path? [08:49]
  • On the informed perseverance it takes to make it over the early bumps of a new path taken — and learning past the point of ignorance. [10:59]
  • In what ways did The Hidden Persuaders by Vance Packard influence young Jeff? [13:21]
  • How did Jeff go from fashion design to film and video production? [15:18]
  • An aside: a Dennis Hopper anecdote Jeff’s never told anyone. [20:23]
  • Why did William S. Burroughs’ lawyer introduce Jeff to people who were starting a production company, and why did they bring him on board even though he was yet unproven in the filmmaking world? [23:40]
  • The difference between a good lawyer and a great lawyer. [26:57]
  • Why does Jeff ask his students to define success at the beginning of every semester at Parsons? What is he hoping to hear, and how has his own definition of success changed over time? [29:02]
  • If engagement in what he’s doing is key to Jeff’s success, what does this feel like? [31:46]
  • How does Jeff choose who to interview for his class? [32:34]
  • An aside: here’s that video of Ferriss Baggins making a salad for Victoria’s Secret models. [33:58]
  • Jeff shares the story about that time he trekked deep into the Mojave Desert to visit a life coach who had insights about the meaning of life to share — for a small fee. [34:56]
  • Learning to sell and manage: Jeff fills us in on Fuller Brush foibles and shoe store monkey business. [42:29]
  • Just to clear things up: Ben Jeffrey Madoff is not the same person as Bernie Madoff. But the Post Office and people using the Manhatten phone book didn’t always know this circa 2007. [51:13]
  • Who was Lloyd Price, how did he change the course of music history, and what led to Jeff writing a play — Personality: The Lloyd Price Musical — about him? [58:22]
  • How did Lloyd respond when reading the first few scenes of Personality, and how did it make Jeff feel? [1:03:16]
  • As Lloyd passed away in 2021, what’s the current status of this play? [1:05:43]
  • How Jeff broke the news to Personality director Sheldon Epps that he has a “no asshole” rule, and why you should never let anybody rob the joy of the process. [1:08:47]
  • How regional theaters with successful productions feed Broadway, and how enhancement deals work. [1:10:22]
  • When publishers rejected the pitch for my first book, a select few did so gracefully. Others, not so much. Did I remember names when it came time to pitch my second book? You bet. Remember: cruelty is far costlier than kindness. [1:12:19]
  • If you’re going to try to do anything in the world, you need to get used to people saying no to you. Here’s how to protect your psyche from rejection and cultivate the empathy to reject others without crushing their morale. [1:16:37]
  • Where can people go to support, drop off a bag of cash, or just find out more about Personality: The Lloyd Price Musical? [1:20:08]
  • What books does Jeff gift and recommend most often? [1:21:11]
  • The movie that never fails to make Jeff tear up, and a conversation he had with Gregory Peck about it. [1:27:15]
  • Has Jeff always had the chutzpah to initiate conversations with celebrities in the wild — like the time he and I encountered a very kind and gracious Jason Statham? [1:31:23]
  • What would Jeff’s billboard say? [1:34:21]
  • Parting thoughts. [1:35:22]


“Everything you do, if your eyes are open, informs everything else you do.” — B. Jeffrey Madoff

“Ignorant, you can learn. Stupid’s forever.” — B. Jeffrey Madoff

“If you’re bored in New York, it’s on you. There is so much going on all the time and I can go hear a jazz concert, see a play, eat at a great restaurant, and walk to all those places. I love it. That’s why flying saucers land in Wyoming. New York, you can’t find a place to park.” — B. Jeffrey Madoff

“I was hired to sell shoes, not be a zookeeper.” — B. Jeffrey Madoff

“Never let anybody rob the joy of the process, because the process is what’s magic.” — B. Jeffrey Madoff

“The sure way to make sure that nothing happens is do nothing.” — B. Jeffrey Madoff

“Pay attention to the road.” — B. Jeffrey Madoff

“Stay curious, keep learning.” — B. Jeffrey Madoff

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform.


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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4 Replies to “B. Jeffrey Madoff — Dealmaking, The Hidden Persuaders, Working with Ralph Lauren, and Finding the Secret to Life in the Mojave Desert (#526)”

  1. One of the funniest interviews & fascinating character on the show in recent memory! Love the rapport between Tim and Madoff.

  2. Hi Tim. I have followed your Friday email for many years. I bought one product you mentioned in the past and it was great. I wanted to purchase the book you recommended this week (This is how you lose the time war)
    I wanted to use your Amazon affiliate link so you got paid but unfortunately I’m in Japan and it did not work for the Japan Amazon store. Not much I can do now but want to let you know in case this type of thing can be changed for the future so you can get your dues.
    Thanks for the great recommendations Tim.

  3. Hi Tim,
    I know you’re really busy and that you get a lot of emails, so this will only take 60 seconds to read.
    I’m a huge fan of yours and have devoured all your content since first reading The 4 Hour Work Week! However, what I have appreciated the most has been your openness and honesty around your struggles with depression. I have suffered from depression for most of my life also, which prompted me to start my own clothing brand offering meaningful clothing for people with depression, which I hoped you may be interested in. The brand is called Solis [Moderator: domain name removed.], and officially launches today! I really hope that it resonates with you!
    I totally understand if you’re too busy to respond, but even a one- or two-line reply would really make my day.
    P.S. Sorry to hijack your comments section, but didn’t know how else to get in touch!