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 and 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!

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

Brought to you by Public Goods high-quality everyday essentials, LinkedIn Jobs recruitment platform with 750M users, and ExpressVPN virtual private network service. More on all three below.

This episode is brought to you by LinkedIn Jobs. Whether you are looking to hire now for a critical role or thinking about needs that you may have in the future, LinkedIn Jobs can help. LinkedIn screens candidates for the hard and soft skills you’re looking for and puts your job in front of candidates looking for job opportunities that match what you have to offer.

Using LinkedIn’s active community of more than 750 million professionals worldwide, LinkedIn Jobs can help you find and hire the right person faster. When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit LinkedIn.com/Tim.

This episode is brought to you by ExpressVPN. I’ve been using ExpressVPN to make sure that my data is secure and encrypted, without slowing my Internet speed. If you ever use public Wi-Fi at, say, a hotel or a coffee shop, where I often work and as many of my listeners do, you’re often sending data over an open network, meaning no encryption at all.

A great way to ensure that all of your data is encrypted and can’t be easily read by hackers is by using ExpressVPN. All you need to do is download the ExpressVPN app on your computer or smartphone and then use the Internet just as you normally would. You click one button in the ExpressVPN app to secure 100% of your network data. Use my link ExpressVPN.com/Tim today and get an extra three months free on a one-year package!

This episode is brought to you by Public Goods! Public Goods is the one-stop shop for sustainable, high-quality, everyday essentials made from clean ingredients at an affordable price. Public Goods searches the globe to find healthy, eco-friendly, and innovative products and then packages them using a single, streamlined aesthetic for your home so you can get all of your premium essentials in one place and avoid buying from a bunch of mismatched, single-product brands. Multiple people on my team already used Public Goods, and now, so do I.

Visit PublicGoods.com/Tim to receive $20 off the products in your first Public Goods order using code TIM, with no minimum purchase required! 

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.


  • 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. [42:23]
  • 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. [51:07]
  • 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? [58:16]
  • How did Lloyd respond when reading the first few scenes of Personality, and how did it make Jeff feel? [1:03:10]
  • As Lloyd passed away in 2021, what’s the current status of this play? [1:05:37]
  • 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. [1:08:41]
  • How regional theaters with successful productions feed Broadway, and how enhancement deals work. [1:10:16]
  • 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. [1:12:13]
  • 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. [1:16:31]
  • Where can people go to support, drop off a bag of cash, or just find out more about Personality: The Lloyd Price Musical? [1:20:02]
  • What books does Jeff gift and recommend most often? [1:21:05]
  • The movie that never fails to make Jeff tear up, and a conversation he had with Gregory Peck about it. [1:27:09]
  • 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? [1:31:17]
  • What would Jeff’s billboard say? [1:34:15]
  • Parting thoughts. [1:35:16]


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 600 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.