October 9

How to Make a Living with Your Ideas

Persistence is essential if you want to make a living with your ideas.

If you are someone who is easily discouraged or gives up easily, neither will you make it as an entrepreneur, nor as a creative. This is because it is too hard for you, and there is a false notion that is fostered by social media about how everything will be great all the time.

The only way to put out the energy it takes is to have persistence, and understanding what your motivations are to fuel your persistence because it is easy to lose track of it when you are always up against the wall.

The Unmistakable Creative Podcast is hosted by Srinivas Rao, where you get a window into the stories and insights of the most innovative and creative minds who have started movements, built thriving businesses, written best-selling books, and created insanely interesting art.

In this episode, Srinivas Rao interviews  Jeffery Madoff, discussing his book, “Making A Living With Your Ideas”.

Parental Influence on Career Choices

Jeffrey’s parents were both retailers. Before they got married, his father worked at a shoe store while his mother worked at a department store, both in Akron, Ohio.

Shortly before getting married, his father opened his store, and when they were married, his parents became partners, selling women’s and children’s clothing. There was a point where there were four small specialty stores in Akron.

Therefore, it is seen that Jeffery grew up in an entrepreneurial household. Apart from his parents having their businesses, his sister has her own business as a retailer in Charleston, South Carolina.

Jeffery never received any pontification or lecture about making his way into the world from his parents. His parents were great in terms of modeling by example. His parents had great relations with the people who worked for them, as well as the people outside of work, in terms of lifelong friendships.

He worked in his parents’ stores when he was a kid and learned certain things about the business by doing work.

It was always up to Jerry to find what it was to make a living and what he wanted to do.

Jeffery’s relationship with his sister in terms of their career

Jeffery’s sister Janice, worked at a store with a real talent for selling, buying, and display, giving her a positive talent for reinforcement.

As an independent retailer, she has been in business for about 45 years, which is an incredible testament to her talent.

However, Jeffery did not have an interest in retail. He had known the concept of sales because of his upbringing in his parent’s business where he learned valuable business lessons, which apply to his current life.

He used the same skills to apply it when he was in college for retail sales.

The main difference between his sister and himself was that he had different things that interested him than the things that interested his sister. There is a convergence of interests between them when it comes to theatre, film, or books.

Jeffery’s view on what should be taught to kids at school

In his book “Making A Living With Your Ideas”, there is a bunch to unpack, part of it being, it is necessary to have a job. If a job is defined as “being compensated for the service or product that you are providing”, then everyone has a job.

According to Jeffrey, although he is an entrepreneur and started his company, it is also a job. Many divisions create a false sense of what things are, and it becomes a limiting sense.

For example, many people think that creativity is strictly to do with arts, but Jeffery being within the art, does film, writes books, writes plays, and produces it. Being a writer, producer, and playwright is an art.

Jeffery believes that all things that people do in any form depends on what they do and how they do it. What he means by this is, an entrepreneur is an idea, which is manifest in presenting something for sale.

An entrepreneur creates “something” from “nothing”, that started from an idea. One has an idea at first and has a compelling need to express the idea. Therefore, Jeffery looks at creativity as something different, rather than the traditional and narrow definition of it.

How would Jeffery change the education system as an educator?

Jeffery thinks that creativity in its broadest sense ought to be encouraged.

When Jeffery was in college, he had a double major in Philosophy and Psychology and tried to get a job as a Sage, but all the factories were shutting down at the time.

This never was or is considered as a practical line of pursuit. However, the ideas that Jeffery was exposed to, helped him pay the path for him forward, in terms of critical thinking and how he approaches things.

One of the important ideas is that everything you do, forms everything else you do, and many people do not see the linkage. Real-life lessons are to be taught, part of it being, “if this is what you want to do…then here is how you need to think about it…if you want to make a living with your ideas.”

Jeffery’s Early Days


The ability to approach and engage people quickly is what Jeffery learned when he worked in his parents’ store was a kid.

He did not think about this until he got older and reached a point where he started reflecting on the days where it made him not reluctant to approach people he did not know.

Even when it came to door-to-door sales, being able to engage with people soothed him his entire life.

The Distinction Between having Persistence and Being Delusional

Most stories are written about stories of people who make it unless, for example, the story “The Death of a Salesman” by Arthur Miller, which is probably a common story, but a depressing one.

One of the quotes from the story is “Attention must be paid”, but most people go through life without getting the attention, and is very difficult.

You have to be honest with yourself ie., you have to be realistic because you cannot be the only one in love with the idea. This goes back to the business principle of ‘The Proof of Concept’.

Jeffrey was compelled to write a play on Lloyd who shattered the wall of race records and made a career out of it because he was the first teenager who fell over a million records.

When Jeffry started the play, he was fascinated by Lloyd’s life. He told Lloyd that he knew he could capture his voice and hence wanted to write his story.

Jeffery then conducted a table read (read-through), where a bunch of actors read their scripts, and as a writer, he could understand how it sounds.

Doing a play is like doing a startup. As you cross different thresholds, you need to get more financing. The play was performed in front of an audience followed by a ‘29 Hour’.

A year later, it was viewed by a much bigger audience who saw the entire production.

Each step along the journey, Jeffrey was establishing Proof of Concept, where there was an audience of people that liked the play.

Even when he was designing, as his adult career, the clothing had to sell. The first thing he did was put out the clothing he designed at a boutique he was working at, and it sold quickly.

This is what Jeffrey means by being “realistic”. You need to put your idea out there and see if people will pay for it while testing it along the way. This is the real distinction between being persistent and being delusional.

People can be reluctant to take the risk to put their work out there. Jeffery was hungry to put his work in front of an audience because this is the matrix in staying in business. He also mentions that doing business is a survival skill if you want to make a living with your ideas.

Finding the right Role Models for Success

Jeffrey thinks that people worship false Gods ie., it can be a possible measure of success, culturally, that people use, to have accumulated a lot of wealth. This does not necessarily mean that they are happy or fulfilled.

Jeffrey’s grandmother once said, “It’s better to be rich and healthy than poor and sick.” The idea of trying to measure yourself against the outlier of success, for example, Ralph Lauren or Steve Jobs, is a false notion because what is it that you are looking for in your life?

One of the things Jeffrey was fortunate enough to learn at an early age was, when he was 21 years old, he had about 110 people working for him, a salesforce, and an office in New York as well as Los Angeles, which was horrible.

He realized that one of the things he did not want was to work with so many people at the time. His nose was pressed up the window of success, that from the outside it seemed to look successful, but from the inside, it was not making him happy.

What made him happy was the process of creating things and doing this, while all the other things were uninteresting to him.

You should not ask yourself “What is society’s measure of success?”, but rather, “What brings satisfaction to you?”

The question also arises if you can make a lot of money, more than you will ever need? However, if you are miserable, does the activity that brings income for you make you successful?

Real-Life Examples

Jeffry mentions that Ralph Lauren, Opera, or Steve Jobs, did not start big, but as small independent businesses.

One of the necessary conditions of building an empire like the above-mentioned businesses is an obsession.

The driver is the person behind the business, who is obsessed with the notion of success.

Many people do not ask themselves the question of what drives them to be successful, whereas other middle-aged people often ask themselves, “Is this all there is?”

Jeffrey also mentions that he knows many wealthy people who experience a sense of emptiness and lack of purpose because they thought they have found a solution to a hole they were trying to fill themselves, but it did not do so.

Jeffery’s Experience Writing and Producing a Play

While Jeffery was going through a read-through for his play, he looked around to find 55 people in the room, and thought to himself “This is pretty damn cool!”

All the people in the room had a common script that he wrote and was going to be a part of something that he had built.

If the play is successful, it will sell tickets, hence, it becomes a business.

His real satisfaction would arrive when he has his major commercial run, but it is also to be able to pause, reflect, appreciate what you have done. Many people are not able to give this reward to themselves, which leads to a lot of frustration and unhappiness.

How to turn a Story into a Business

Jeffrey points out that a story does not have to be educational or entertaining, it can be both. There are no boring subjects, but there can be many boring teachers.

As a writer of a play, Jeffery seeks a story as something that the audience is compelled to know what is going to happen next.

There is a problem which is set up, and how is the problem solved? This is basically what a story is.

An engaging story requires talent on the part of the author as well as the engagement of the audience to be curious as to what will happen next.

Without this, you will not have engagement, and without engagement, you do not have a story worth hearing.

How to turn Ideas into your Business

A friend of Jeffery’s, Chris Moss, made a statement, “Never take advice from someone you wouldn’t change places with.”

Once again, Jeffery talks about the ‘Proof of Concept’ ie., you cannot be the only one in love with your idea.

You have to put it out there to test it, and if you are afraid to do it, you have to ask yourself, “Why haven’t I put it out to test yet?”

If it is an expensive hobby, and if you can afford it, while the hobby gives you fulfillment, that’s great!

However, if you hope to turn it into a business, then you need to have the Proof of Concept. You also need to know the basics of business, which at some point you need to have more money coming in than going out.

Jeffery thinks that it is an individual’s determination of what they want out of it. What stops many people is their fear and self doubt they have, in terms of putting their ideas out to see if there is real interest in it, because it can be a shattering blow if you find out that nobody is interested in your idea.

Jeffery’s thoughts on what makes someone an Unmistakable Creative

Jeffrey says that this is a question that should be posed to the receiver or the audience.

As the creator of something, you have your intact because you can put out something that you think is your best material, and it can fall off flat.

Jeffrey things to make someone unmistakable is their ability to learn from, and turn around, from what initially may be perceived as a failure, and to keep moving forward. Having a distinctive difference can make you an unmistakable creative.

Connect with like-Minded Creatives

Join our listener tribe, a private social network for listeners of The Unmistakable Creative Podcast. You can meet other listeners, discuss episodes, and engage with the creative community just by signing up!

Connect with Jeffery:

Creative Careers


Film Company



You may also like