B Jeffrey Madoff On How Live Arts Helped Teach Courage, Authenticity, Vulnerability & Career Success
An Interview With Vanessa Ogle
We haven’t spoken about failure. What is it? It isn’t something that went wrong, a bad review, or a performance that didn’t go right. There will always be bumps in the road, sometimes big ones, but that’s not failure; it’s part of the discovery process. Failure is giving up on what’s important to you. It’s compromising your values and convincing yourself it was necessary.
The stage is a powerful platform for personal and professional growth. Through live arts, individuals learn to embrace vulnerability, project authenticity, and muster unparalleled courage. These experiences not only shape artists but also prepare them for varied career paths with a distinctive edge. From actors and dancers to directors and behind-the-scenes creators, the lessons learned in the limelight often translate into profound career success beyond the footlights. As part of this series, we had the pleasure of interviewing B. Jeffrey Madoff.
Jeffrey Madoff’s career straddles the creative and business side of the arts. He has been a successful entrepreneur in fashion design, film, and as an author, playwright, and producer. He was an Adjunct Professor at Parsons School of Design, where he created a course called Creative Careers Making A Living With Your Ideas, which led to a bestselling book of the same name.
Madoff has been a guest lecturer at Princeton, Wharton, FIT, NYU and Yale.
His play “Personality”, about Rock and Roll legend Lloyd Price, was a critical and audience success in Philadelphia, Chicago and is currently waiting for a theater on London’s West End.
Madoff’s next book, “Casting Not Hiring”, written with the founder of Strategic Coach, Dan Sullivan, is about the transformational power of theater and how you can build a company based on the principles of theater.
Thank you so much for joining us in this interview series. Before we dive in, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career in live arts?
As a kid, I would draw cartoons, and comic strips that would get passed around the school. I wrote stories and experimented with my father’s 8mm camera. I put together a movie theater in our basement, created soundtracks, and designed posters I’d put up around the neighborhood. Fifteen kids would show up, pay twenty-five cents, and I sold candy bars and popcorn. I wrote a play in sixth grade that was put on for the whole school. My parents were always supportive of what I did. If you discover what lights you up as a kid and can figure out how to do it for a living, you’ll love what you do. I was fortunate enough to do that.
Can you share the most interesting story that happened to you since you started your ?
I have worked with so many fascinating people through my work; Audrey Hepburn, Gregory Peck, Martha Graham, Liza Minnelli, Halston, Walter Cronkite and Lloyd Price, to name a few — and so many others who you have never heard of who have enriched my life.
Having the opportunity to work with and learn from such wonderfully talented people is a huge perk in the work I’ve done. I can’t think of a favorite story because there are so many.
Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Curiosity. Perseverance. Humor.
Curiosity: What’s the story here? How did they do what they do? Why did they do what they did? What were the obstacles along the way. The successes? The problems. The solutions. Why would anyone want to hear the story I’m telling?
Perseverance: How to keep moving forward when everything takes longer, costs more, is more difficult, and the path you thought would lead you there is a dead end — yet you keep going and have the resilience necessary to accomplish what’s important to you. You did what you do for a reason. Remember that reason and the purpose you felt when you started so you can keep going.
Humor: If you don’t have a sense of humor, you’re done. Done. Not only does lacking a sense of humor make you a drag to others, it makes you a bigger drag to yourself. Laughter is the oxygen of your emotions.
I was hired to create a film honoring Ralph Lauren winning a Lifetime Achievement Award. This was for a black-tie event at Lincoln Center, introduced by Audrey Hepburn.
I wanted to tell a very different story about Ralph. Something unexpected that would surprise and engage an audience who had seen it all. I was curious to discover aspects of Ralph’s life that the public had never seen. I watched his home movies and looked through his private photo albums.
The first obstacle was a big one. Ralph. I wanted to start the film with a picture of him as a baby. I got an emphatic “No”. He is a private person. He didn’t want to show those images of his life. I told him we weren’t making a commercial, we were making a movie about Ralph Lauren the man. Not the image. Another resounding “No”.
I didn’t have a convincing argument; I needed a compelling offer. I showed Ralph and his wife Ricky, a film I made for my parents’ 50th anniversary.
When it ended, Ralph said, “I’m crying, and I don’t even know these people.”
“I want the audience to feel what you just felt,” I told him. “Let me start with the baby picture and I can do that.” I persevered and finally got his permission.
Throughout the process, there were many late nights and meetings, but we were able to laugh and enjoy the process. Humor was a stress release and helped us form a bond.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. How has a live performance experience directly influenced a critical decision or leadership style in your professional career?
I am the playwright and lead producer of the “Personality”. My job is to make sure the creative and financial aspects of the play work together to set us up for success. There are decisions that impact both, all the time.
We opened our Chicago run in the summer of 2023. It was a challenging time for theater in general and particularly so for Chicago. Some theaters were shortening their seasons. A few closed. “Personality” received fantastic reviews, and the audiences were phenomenally responsive, but ticket sales were not what we hoped. I had a choice; spend more on advertising and hope that word of mouth would kick in, or close, and put the money toward our next step.
I flew back to Chicago to meet with the cast and tell them we were going to close. I went straight from the airport to the theater so I could watch the show. Once again, our phenomenal cast gave it their all. Once again, the audience was on their feet, cheering and dancing at the end. The playwright side of me wanted to keep the show open — and ticket sales were going up. The producer side of thought how we accomplished what we were after; great reviews, audience response, and publicity. Ironically, the smartest move to keep the show moving forward was to close.
Can you describe a moment on stage that taught you a profound lesson about vulnerability and how you’ve applied that lesson offstage?
When I met with the cast and told them we would run for two more weeks, then close, there were a lot of tears, including mine. One of the actors asked, “Did you really fly to Chicago to tell us this in person?” I couldn’t imagine not doing that. Honest communication is important in all aspects of life. It’s not always fun, but I have so much respect for the talent and passion of all those involved, I couldn’t imagine not getting together and letting them know how proud I was of them and my gratitude for the passion they put into their performance night after night.
One of the cast members thanked me for being vulnerable and telling them the truth. Telling the truth doesn’t make you vulnerable, it makes you human.
In what ways has the discipline and creativity demanded by live arts shaped your approach to career challenges and opportunities?
The first thing you have to do is show up. On time. Prepared. Alert. Curious. That’s also true in day-to-day life. Creativity is about problem solving, and art is the expression of a solution. Opportunities only exist if you recognize them as such. That’s why you always need to be alert, prepared and curious.
How do you think the authenticity required in live performances has impacted your personal brand or leadership identity in your career?
The live arts are about action and reaction. How you initiate and react on stage is a representation of real life. Real life is the real thing. It’s not a metaphor. It is. Authenticity on stage doesn’t feel contrived, it feels real, even if it is contrived.
I don’t believe in “personal brand”. If you are calculated about creating it, it becomes a contrivance and is performative. Your personal brand is what people say about you when you leave the room. It’s not a brand, it’s your reputation.
Ok super. Here is the main question of our interview. Based on your experience and research, can you please share “5 Ways That Live Arts Helped Teach Courage, Authenticity, Vulnerability and Career Success?” If you can, please share a story or an example for each.
1 . Courage is the willingness to do something that you don’t know what the outcome will be. It’s a risk. When there is a good outcome, and it is repeated, courage transforms into confidence. This happens constantly in the live arts; an actor in a new part, a dancer learning new moves, a musician learning a new score. It’s compounded because they are working with a new director, a new choreographer, a new conductor and a new cast. The willingness to challenge yourself is the process of going from courage to capability.
2 . A new challenge breathes life into the artist and into their art. The more you avoid your fears, the less you are able to express authentic art, art that is exciting because it pushes boundaries, and the audience connects to the fears and triumphs of the artist. The more you create the more you face your fears and that will help you develop new capabilities.
3 . Live performances are unique because the performers and the crew are vulnerable from the beginning to the end of the performance. Anything can happen; someone can forget a line; a lighting cue is missed, and the actor is in darkness. The music starts too soon — or too late, a piece of the set falls over, a costume is damaged during a wardrobe change, a dancer falls — the possibilities of things going wrong are constant — and there’s a new audience for every performance. I believe that tension not only informs the cast and crew, it also affects the audience in a subliminal way. When you choose a life in the live arts, you are choosing a life that is highly charged, and nerve endings are almost always exposed.
4 . I never set out to be “successful”. I wanted to make people laugh, cry, think and inspire discussion. I wanted to make an audience feel like I feel when I see great work. I wanted to do what I wanted to do and make a good living so I could keep doing it.
It is “show business”. The “show” is what the public sees, the business is what keeps it moving forward. Every time I see a live performance, I am grateful to those who choose the difficult road, whose efforts enrich our lives. I know they had no choice, because those who make their living in the arts have a compelling need to express. Financial success is great, but it’s a byproduct of what you do. A sense of purpose and emotional fulfillment is much harder to achieve.
5 . We haven’t spoken about failure. What is it? It isn’t something that went wrong, a bad review, or a performance that didn’t go right. There will always be bumps in the road, sometimes big ones, but that’s not failure; it’s part of the discovery process. Failure is giving up on what’s important to you. It’s compromising your values and convincing yourself it was necessary.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂
Starting a movement seems overwhelming, so my suggestion is to start doing what you can do, like taking an improv or acting class where you will meet new people. Volunteer at a non-profit or local theater. There is a tremendous amount that can be learned from the live arts that can be applied in everyday life and careers outside the arts, such as overcoming the fear of public speaking, and the importance of listening and making sure the other person knows they are heard. Relationships are the foundation of all pursuits in life. Engage with others, not just those that agree with you. Challenge your fears and watch your courage morph into confidence and capability. Remember; it’s called a play — have fun.
How can our readers further follow you online?
Your readers can follow me on LinkedIn, on Instagram at
@acreativecareer and @bjeffreymadoff and www.madoffproductions.com and www.acreativecareer.com
Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!
About The Interviewer: Vanessa Ogle is a mom, entrepreneur, inventor, writer, and singer/songwriter. Vanessa’s talent in building world-class leadership teams focused on diversity, a culture of service, and innovation through inclusion allowed her to be one of the most acclaimed Latina CEO’s in the last 30 years. She collaborated with the world’s leading technology and content companies such as Netflix, Amazon, HBO, and Broadcom to bring innovative solutions to travelers and hotels around the world. Vanessa is the lead inventor on 120+ U.S. Patents. Accolades include: FAST 100, Entrepreneur 360 Best Companies, Inc. 500 and then another six times on the Inc. 5000. Vanessa was personally honored with Inc. 100 Female Founder’s Award, Ernst and Young’s Entrepreneur of the Year Award, and Enterprising Women of the Year among others. Vanessa now spends her time sharing stories to inspire and give hope through articles, speaking engagements and music. In her spare time she writes and plays music in the Amazon best selling new band HigherHill, teaches surfing clinics, trains dogs, and cheers on her children.
Please connect with Vanessa here on linkedin and subscribe to her newsletter Unplugged as well as follow her on Substack, Instagram, Facebook, and X and of course on her website VanessaOgle.
B Jeffrey Madoff On How Live Arts Helped Teach Courage, Authenticity, Vulnerability & Career… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.