The Creative Path From Fashion to Film With Jeffrey Madoff of Madoff Productions

Jeffrey Madoff is the Founder and CEO of Madoff Productions, a company specializing in creating content like commercials, live streaming events, and branding videos for an impressive clientele, including Ralph Lauren and Victoria’s Secret. Before his film career, he started as a fashion designer in Wisconsin and was recognized as one of the top 10 designers in the US. Transitioning to film and video production, Jeffrey has edited and directed award-winning commercials, documentaries, and web content worldwide for renowned brands. He is also a playwright, theater producer, and author of Creative Careers: Making a Living with Your Ideas.

Here’s a glimpse of what you’ll learn:

• [5:52] Jeffrey Madoff talks about his book, Creative Careers: Making a Living With Your Ideas
• [7:20] Jeffrey’s criteria for selecting certain influential figures to include in his book
• [11:00] What is personal and business success?
• [14:56] Workplace fairness and conflict resolution
• [21:16] Jeffrey shares his early accidental yet remarkable entry into the fashion industry and major retail exposure
• [23:35] Lessons learned while building a fashion company to over 100 employees and the value of smaller teams
• [29:26] The unexpected similarities between the fashion business and independent film industries
• [34:17] Why setting proper expectations for a project can turn potential failure into success
• [40:55] Jeffrey discusses the emotional power of storytelling and challenging conventional branding
• [47:35] The significant concepts learned from conversations with Dan Sullivan
• [50:54] The motivation behind writing and producing a play

In this episode…

Have you ever wondered what it takes to pivot careers and dive headfirst into new industries? What lessons could you learn from someone who did this multiple times and excelled in each new venture?

Jeffrey Madoff, a film producer and director, peels back the curtain on his dynamic career, starting as a fashion designer in Wisconsin before becoming a renowned filmmaker and author. His path is punctuated by bold moves, such as launching a fashion brand without a typical background in the industry and transitioning to film production, where he directed award-winning content for major brands. Jeffrey also discusses the inspiration and insights that led him to pen his book, Creative Careers: Making a Living with Your Ideas, aiming to ignite the same passion in others that has fueled his diverse journey. He unveils pivotal moments and the importance of relationships and emotional resonance in his work.

In this episode of Inspired Insider Podcast, host Dr. Jeremy Weisz interviews Jeffrey Madoff, Founder and CEO of Madoff Productions, about turning creative ideas into a lucrative career and navigating multiple industry pivots. Jeffrey discusses his Creative Careers book, personal and business success, his entry into the fashion industry, the transition to film production, and the similarities between the fashion business and independent film industries.

Resources mentioned in this episode:

• Jeffrey Madoff on LinkedIn
• Madoff Productions
• Creative Careers
• Creative Careers: Making a Living with Your Ideas by Jeffrey Madoff

Special Mention(s):

• Dan Sullivan on LinkedIn
• Anything and Everything

Related episode(s):

• “What Inspires Brian Kurtz, VP at Boardroom Inc.?” on the Inspired Insider Podcast
• “Boardroom Inc: Light Bulb Moments after 1.3 Billion pieces of direct mail – with Brian Kurtz [Big Lessons]” on the Inspired Insider Podcast
• “Lessons and Reflections from Three Top Direct Response Marketers with Brian Kurtz, Richard Armstrong, and John Carlton” on the Inspired Insider Podcast
• “[Top Giver Series] How to Keep Your Best Customers And Build Lasting Business Relationships” on the Inspired Insider Podcast
• “Destroying Metabolic Disease With Tom Bilyeu of Quest Nutrition” on the Inspired Insider Podcast
• “Negotiation Tactics From FBI Agent Christopher Voss, Founder of Black Swan Ltd” on the Inspired Insider Podcast
• “Lessons From A Lifetime of Marketing Expertise, with Ken Glickman, Founder of KenGlickman.com” on the Inspired Insider Podcast

Quotable Moments:

• “I never let ignorance stop me, because if you’re stupid, it’s forever. If you’re ignorant, you can learn.”
• “I believe in making your future bigger than your past.”
• “Relationships are the true currency in life.”
• “A brand is a good story that resonates emotionally with people.”
• “Success in business is being in a position to say ‘no’ without catastrophic financial consequences.”

Action Steps:

1. Pursue a career that aligns with your passions and interests, as it leads to a fulfilling and gratifying life: This is effective because it underlines the importance of personal satisfaction in professional success.
2. Be unafraid to challenge norms and advocate for your creative ideas as they can lead to groundbreaking work: Challenging preconceived notions and proposing unique ideas lead to emotional and impactful storytelling.
3. Foster and maintain long-lasting relationships in both personal and professional life: Building strong relationships is essential for success and can provide a strong support network.
4. Recognize the value of setting clear expectations for business projects to frame success positively: This teaches the power of perception in business.
5. Embrace lifelong learning and curiosity to continually grow and adapt in your career: The ability to learn and adapt is paramount in navigating different industries and roles.

Episode Transcript

Intro 0:01 

You are listening to Inspired Insider with your host, Dr Jeremy Weisz.

Jeremy Weisz 0:22 

Dr Jeremy Weisz here, founder of inspiredinsider.com, where I talk with inspirational entrepreneurs and leaders today, is no different. I have Jeffrey Madoff and Jeffrey, you can check them out at acreativecareer.com and madoffproductions.com. Jeffrey, before I formally introduce you, I always like to point out other episodes. People should check out our other podcast dear friend, Brian Kurtz, who you know very well. He may be the only one who’s been on three times over the past decade. Just an amazing human being, direct response marketer, we were talking a little bit and Jeffrey, you’ll talk about this, which is, what does success mean? And this is one of the things I really admire about Brian, because I see him, and he’s a family man.

He has amazing relationships, and to me, that is huge success. And I really admired him from the get go. And I know you’re very cut from the same cloth and very similar. And know Brian well. So check those out. He sent over 2 billion pieces, I think, of direct response in his career. And so there’s something he learned there. Tom Bilyeu, the founder of Quest Nutrition, who Jeffrey you have actually interviewed too, and you talk about him in your book. And that was a really good one. He started Quest Nutrition. Chris Voss, Never Split The Difference. Another favorite episode again, I know you know Chris as well. Ken Glickman lessons from a lifetime of marketing expertise. And so the funny thing is, I’m surprised we didn’t meet earlier, Jeffrey, because there’s so many connections. I know Michael Rodrick has talked about you and so many people. But check those episodes out on inspiredinsider.com and this episode is brought to you by Rise25.

At Rise25 we help businesses give to and connect to their dream relationships and partnerships. And how do we do that? We do that by helping you run your podcast. We’re an easy button for a company to launch and run a podcast, and we do the strategy, the accountability and the full execution. Jeffrey, we’ve talked about this. We’re kind of like the magic elves that run in the background and make it look easy for the hosts, so they can create amazing content, create amazing relationships, and run their business. For me, you know, the number one thing in my life is relationships, and I’m always looking at ways to give to my best relationships, and I found no better way, over the past decade, to profile the people in companies I most admire and share with the world what they’re working on.

So if you’ve thought about podcasting, you should, if you have questions, you can go to rise25.com and it’s funny, because Jeffrey, you’ve even mentioned podcasting in your book, and it’s under the realm of consistency, right? And so I think I’ve been publishing around two episodes a week for over 10 years, because I love it, and I learned a lot from this. It made me study the life and the work of Jeffrey Madoff, which is hugely valuable for me. So I suggest everyone check out his book. And when you go to acreativecruiter.com you can check it out there. And big thank you to Bill Cates, who runs a marketing agency, who it’s funny, it takes Bill to introduce us, who I don’t know that well, as opposed to all the other people. But thanks, Bill and check out hereisyourfire.com.

So without further ado, I want to formally introduce Jeffrey Madoff. He’s the founder of Madoff Productions, and they collaborate with ad agencies, public relations firms, directly with clients to produce commercials, live streaming events and other content. He’s very selective at this point with the people he works with, but I’ll talk about some of his work and who he’s worked with over the years. He actually began his career as a fashion designer, okay? And if you’re thinking the amazing streets of New York or LA, you’d be wrong. Okay, he started a likely place, I guess you’d call it, in Wisconsin, but actually, he was chosen one of the top 10 designers in the US. Built a Company to over 100 people. He ended up switching careers to film and video production, and he’s edited and directed award winning commercials, documentaries and content from clients like Ralph Lauren, Victoria Secret, Revlon, Gucci, Godiva and so many more.

Also they’ve helped private equity firms too, investment banks as well. So they have a wide range of clients. He’s authored, as I mentioned, Creative Careers: Making a Living with Your Ideas. It was an Amazon bestseller. It was based, actually, in the class that he developed and taught at Parsons School of Design. And he’s a playwright and producer, and the play is called Personality, the Lloyd Price Musical he’s been a featured speaker on creating a brand and creativity. At the Wharton School, Princeton. NYU Google Next and many others. And the most important part of his whole bio is he went to University of Wisconsin, and fun fact, he was on the wrestling team, of all things. So don’t mess with Jeffrey. Jeffrey, thanks for joining me.

Jeffrey Madoff 5:14 

Thanks for having me on. And I guess that about wraps everything up. I have nothing to add. Very good. Thank you.

Jeremy Weisz 5:22 

I had to include all of that because it’s a pretty storied career and keeps going. And I just wanted to start with kind of the origin of the book which came out of your talks. I know you talk all over, so if someone is looking for a Keynote or a speaker, they can go to a creative career and contact Jeffrey directly, but talk about the original book and what came out of Parsons School of Design.

Jeffrey Madoff 5:52 

Well, the course that I teach, which has the same name as the book, Creative Careers: Making a Living With Your Ideas, came about because people said, this is such a cool class, but you have like, 60 students and some people, actually, people we know in common, audited the class, but it was about getting the ideas out there, because ideas need to be shared in order to have any value. And so, for a few years, people were telling me, write a book, write a book. And I said, yeah, but then what do I do with it? Because I knew nothing about the publishing world at all, or even getting an agent, or any of that. And once I started focusing on that, I learned a lot about it, and I’m still learning about it, and the idea of the book was to just spread these ideas and hopefully trigger people in a way that would help them pursue the kind of dreams, passions, desires they have, and make a living with the things they love doing.

Jeremy Weisz 6:57 

You include a lot of interesting stories, and not just your stories, but other people’s stories in here. Talk about some of the reasons you chose some of these people. I know you mentioned Kathy Ireland a bunch of times. You talk about Damon John, you talk about, I mentioned Tom Bilyeu. What was the thought process on including some of these people in the book?

Jeffrey Madoff 7:20 

It’s the same process for everybody, which is, do they have an interesting story? Do I care about what they do? You know, because, like you, I don’t think I’d want to spend an hour talking to somebody that I don’t care about what they do. So what they do is interesting. So up on the screen, there you have Michael Arad, who designed the 911 Memorial, which is an extraordinary thing. I mean, his work is going to be around forever. It’s like talking to whoever designed the Lincoln Memorial or the Washington Monument. I mean, it’s kind of incredible. Kathy Ireland, I happen to have shot Kathy for Ralph Lauren. Ralph Lauren collection, late 80s, mid 80s, and my wife found a picture of she and I together.

I didn’t really know that she had grown a multi-billion dollar global business, and then just pure serendipity, I saw a commercial or a segment, a new segment about her and what she had done. So I reached out to Kathy and sent her the picture of the two of us together, and she came in and did my class at Parsons on entrepreneurship. But it was great. Damon, John and I met through a mutual friend to Joe Polish, and Damon and I just immediately hit it off, because we both had fashion backgrounds. Ended up knowing a lot of people in common, and so, it was all about, wow, they’re doing really interesting stuff, Tim Ferriss becomes a global sensation with the 4-Hour Workweek, which probably it should be called the 60-hour workweek.

But 4-Hour Workweek became a phenomenon. And I think it’s just really interesting. What people do enjoy read. She’s a host on MSNBC. She has her own program and the read report, and she’s I’m fascinated by journalism, by what is news, by the discussions around that. So I’ve kind of got boundless curiosity. And all of the people that I have in are, I suspect, not unlike you, people that I’m really interested in talking to, if I could sit down and just have a cup of coffee with them, it’s just I learn from them, and it fuels my curiosity. And I think curiosity fuels creativity. So it all works together.

Jeremy Weisz 10:03 

I do want to talk about what does success mean before we get to you. And I know it’s not just money and things, it’s family. And if you’re watching, there is an audio part, but there’s a video part too. So if you’re watching the video you’re looking right now. We’re at Madoff Production website, and you can see all these things that you produced, from Victoria’s Secret to these runways, this kind of, I think, of what does success mean? And I know you’re big in family, but what does your wife think, I mean, this is the work, like you’re filming this stuff, right? And she sees a picture of Kathy, Kathy Ireland, you’re with these celebrities. You’re with Victoria’s Secret models. What’s that conversation like with your wife when she sees these things, or when you go back?

Jeffrey Madoff 11:00 

Well, my wife, we met, actually on a job about God, probably 37 years ago, and she was a model. And because you tend to meet the kind of people that you work with and hang out with, and says she knows the business. And honestly, I could make a bunch of funny cracks, but it was never an issue. It’s like people would say to me, oh, God, you traveled with the Victoria’s Secret models. And, wow, wow.

What was that like? What was like getting up at five in the morning and doing the shoot, which was fun, but it’s a lot of work. And you finish the day, and then you have a pre-production meeting for the next morning, and it was a lot of fun. It’s great making images with the models. And the ones that I worked with and had the pleasure of working with, were very professional. This is their profession, and they take it seriously. And so it never was a thing. I could make up some orgy story, but the reality is, we’re all there working.

Jeremy Weisz 12:26 

Yeah, no, so talk about what success means to you?

Jeffrey Madoff 12:33 

Well, to me, what success means, there’s business success and there’s personal success. And to me that’s a distinctive difference. Business success, to me, is being in the position to say no, without any catastrophic financial consequences, so I can do what I want to do. And personal success is the integrity and the maintenance of the relationships that are most important to me and really loving others and being loved back. That’s personal success, and so I am very fortunate most of my closest friends I’ve known for most of my life, pre-kindergarten, third grade.

And so relationships, I think, are the true currency in life. I know you believe that too. So business is one thing, and I like it because I do fun work. I work very hard, but I’m paid well for it, and get to travel, meet interesting people and all of that, and that’s all great, because I wouldn’t consider myself successful if I hated what I did, even if I made a lot of money. That’s not success to me. Success is directly tied in, and this is business and personal into gratification and fulfillment.

Jeremy Weisz 14:19 

I want to touch on some fun stories and lessons from different parts of your career. Okay, I want to start with one of my favorite stories from the book, Monkey Poop. Okay.

Jeffrey Madoff 14:37 

What chapter that? For the title of the book actually.

Jeremy Weisz 14:44 

Hopefully has a better subhead if you named it that. But talk about the lessons there, and what was the scene surrounding this?

Jeffrey Madoff 14:56 

See, I’m in an interesting position now, Jeremy, because. I could say, I don’t know what you’re talking about, focusing on Monkey Poop, but there is a real story behind it, as you know. I’m from Akron, Ohio originally, and there was a new shopping mall that was opening, and I needed a job, and I think I was 16 or 17, and the shoe store, family shoe store was going to be opening, and they had placed an ad for someone who was and in those times, you could actually be more specific in advertising for a job than you can now. So they wanted somebody who was married over 22 and had at least two years of shoe selling experience. I was 16, single and never sold a shoe, but I had sold things before.

I did door to door sales. I did all kinds of stuff. So the boss, there’s two lessons here. The guy that ran the store said, you know, look, I really enjoy you. You’re fun, you’re a bright kid, but you meet none of the criteria for the job. I can’t hire you. I can’t do it. I’d love to do it. I just can’t do it. And I said, well, I convinced you, and you got to be harder to sell you than selling a pair of shoes. And he said, look, I just can’t do it. It’s just against the company policy. And so as I’m leaving, he came out after me, said, Jeff, Jeff. And he stopped me, said, all right, you got the fucking job, and I left. So what happened? He said, you’re right. If you could sell me on yourself, that’s a lot harder than selling a pair of shoes.

He got the job. So I love the fact that he was broke with policy, because he saw in me some promise that could help their business, which, in fact, I did. And so that was really cool. Well, because it was a family shoe store. Now we get to the real meat or the poop of this issue. They had a monkey in the back of the store which would never fly these days. Yeah, it’s so bizarre, is true. And, so one of the first conflicts I had when I was there, because I was by far the youngest salesperson in the store. And the assistant manager said to me, cleaning out the monkey cage. And I said to him, do you clean out the monkey cage? He said, no, I told you to clean out the monkey cage.

I said, I’ll take my turn if everybody else does it, but I’m not going to do it if everybody else doesn’t do it. He said, well, you’ll do what I tell you. And I said, no, I won’t. I wasn’t hired to be a zookeeper. I was hired to sell shoes. And Bob, the manager who hired me, overheard the conversation, and he stepped in, and he said, Jimmy, who was the assistant manager, why don’t you show us all how to clean out the cage, and from now on, we’ll all take our turn, and we’ll all do that job. And I thought that was really great, that I felt heard, acknowledged, and that Bob had a sense of fairness about him. And I wasn’t going to do that just because I was the youngest.

I was hired for the same reason everybody else was, sell shoes. So if part of the job that we all share in is cleaning up monkey poop, okay, I’ll take my turn, but I’m not going to be the only one that does it. And the monkey, whose name was solo. And at that time, which was in the late 60s, everybody thought there was a monkey naming contest, and we store employees are the ones that decided on the winning name. And everybody thought that it was solo, based on Napoleon solo, who was a James Bond like character in a very popular TV show called The Man from UNCLE. That’s not why we named him solo. We named him solo because what the monkey did all day long was masturbate and Pearl feces. And so we thought solo would really be a perfect name, because it describes what that monkey does in the store. And so, mothers would be with their kids, and she’d want to try on.

She has to go. Go look at the monkey. Kids. And then she’d glance over there and see the monkey furiously trying to please itself get away from the monkey cage. So it was nuts. It was very funny. Fortunately, ASPCA policy has made it so that that kind of thing doesn’t exist anymore, but it was a weird sideshow at a family shoe store.

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