Was It Chance?

#42 - Jeff Madoff: Creating more PERSONALITY!

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It turns out this guest is the older version of our very own Alan Seales. Get ready for excellent Dad jokes and a lot of laughs. Seriously though - Jeffery Madoff has a wildly inventive and creative brain and a masterful entrepreneurial spirit. For Jeff, barriers are simply not something that exists because his creative spirit always finds a way to thrive. 

Jeff is a Fashion designer, teacher, author, playwright, and producer who helps dispel the myth that artists can’t be good business people and that good business people can’t be creative! 

Jeff has directed award-winning commercials, documentaries, and web content for clients such as Ralph Lauren, Victoria's Secret, Tiffany, Radio City, The American Academy of Dramatic Arts, and Harvard University just to name a few.

He’s also the writer and producer for “PERSONALITY” a play based on Rock and Roll Hall of Fame artist, Lloyd Price that just opened in Chicago in June 2023.

Connect with Jeff on LinkedIn, Instagram, and his website. 

Get Jeff’s book: Creative Careers: Making a Living with Your Ideas

See Personality in Chicago


  • Make sure to follow this podcast everywhere you find podcasts, leave a rating and a review, and slip into our Instagram DMs at @wasitchance.
  • More about Heather via @heather_ vickeryandco on Instagram and Threads, @Braveheather on TikTok, and listen to The Brave Files
  • More about Alan via @theatre_podcast on Instagram and listen to The Theatre Podcast with Alan Seales


    • EPISODE TAKEAWAYS:

    • Jeff had no plan on what he was going to do but he was always seduced by ideas.
    • Fashion design was never a passion but an opportunity. 
    • He did have some merchandising experience from his parent's business when he was younger.
    • Jeff put his designs on the back of a motorcycle, headed to Chicago, and made a name for himself.
    • We make sense of our lives through the rearview mirror.
    • By the age of 22, Jeff had over 100 people working for him.
    • When Jeff decided to move to NYC he lost his financial backing. So he closed his company in Wisconsin and took off.
    • As a young man with long hair in the 70’s Jeff had to prove he had financial backing in order to be taken seriously. 
    • Jeff has embraced opportunity over and over again through meeting other people, embracing storytelling, and being willing to simply try things that interested him.
    • If you’re paying attention everything you do plays a part in everything else you do.
    • It’s easier to start at the top and work your way down. You never know until you try and there’s no reason not to go big.
    • Jeff believes that you shouldn’t say no to yourself.
    • You shouldn’t say no to yourself. If you’re passionate about something give it a try. There are enough people that will say no to you. Don’t say no to yourself.
    • Jeff was his own fallback position. There was no other Plan B.
    • He focuses on the goals rather than the obstacles in the way.
    • The way to “run distance” is to break it down into smaller milestones and then celebrate those milestones.
    • Perseverance is more important than talent.
    • Jeff says he’s smart enough to know what he doesn’t know.
    • After being a guest speaker for a class at Parsons, Jeff took a job as a part-time professor (he was actually hired by Tim Gunn!). His class is about Creative Careers.
    • The way you talk to yourself makes a big difference in how successful you’ll be.
    • Opportunities are not opportunities if you don’t recogonize them. 
    • It was absolute chance that Jeff was introduced to Lloyd Price and that’s what eventually led to Jeff writing and producing Personality which is now running in Chicago.
    • Don’t wait for someone else to make magic happen in your life, do it yourself.
    • There’s courage and there’s confidence. Confidence is a capability that comes from repetition. Courage is stepping off the edge of the cliff and not knowing what’s going to happen. 
    • Doing a play is like a start-up.

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      Was It Chance?By Alan Seales, Heather Vickery & Broadway Podcast Network