417. Betting On Yourself & Stacking the Odds with Jeffrey Madoff

Feb 7, 2022 | Interviews, Podcast

YouTube video

As a podcast guest, Jeffrey Madoff, presented about a thousand different angles and directions to take the conversation. We begin the journey in the grocery store cereal aisle, where, as an eighth grader, he dabbled in cognitive neuroscience and the hidden brain training that goes into product merchandising. From there, we hit the neighborhood streets, where, at the ripe old age of sixteen, Jeffrey became the nation’s top selling Fuller Brush sales representative.

He goes on to describe his 50-year love affair with life in New York City before we unpack the valuable lessons he learned in the film industry, world of fashion, and his fifteen-year teaching career at Parsons School of Design.

Jeff, who authored “Creative Careers: Making a Living With Your Ideas” in 2020, walks us through the mindset and leadership practices that have allowed him to pursue and achieve the collective life experience of many individual people, combined. His inspiring story is a great example of when betting on yourself goes incredibly right.

In This Conversation We Cover:

  • [3:00] Jeffrey’s early interests and sales success
  • [12:10] Turning his attention (back) to fashion
  • [15:53] Making the jump to New York City
  • [21:23] Learning the movie industry
  • [28:18] Business motivations and priorities
  • [30:57] Living by creativity and curiosity
  • [46:28] Rapid fire questions



Work Hard Play Hard is a production of Crate Media

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Ciao! We’re Rob & Kim. Over the past two-decades we’ve lived by one motto, “Excuses are over. it’s time to live!”

In August of 2021, we put our motto to the test, sold everything and moved our family to Italy.