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Steve Madden on The Question You Must Ask Yourself to Build a Company of Value The apparel company founder shares his business philosophy.

By Nina Zipkin

Courtesy of Steve Madden

Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

In 1990, Steve Madden launched his eponymous shoe company with only $1,100 in the bank. In the first few years of the business, he introduced his chunky platform shoes that would soon be synonymous with the decade and opened his first storefront in New York City.

By the middle of the 1990s, the business was bringing in more that $38 million in sales. His second decade in business, the company grew to great heights. In 2000, Steve Madden's 50th store opened and those sales numbers climbed to more than $200 million.

And then 2002, Madden's world was turned upside down. He was convicted on charges of stock fraud and sentenced to 31 months in federal prison. He resigned as CEO of the company, yet, he continued to serve as a creative consultant while behind bars.

In 2005, the company opened its 100th store and when he was released from prison that same year, he returned to his role as CEO.

Over the last 13 years, Madden has also launched ventures that incorporate his passion for music, holding a regular concert series and starting a record label called 5Towns. He has worked with big names like Lady Gaga, Katy Perry and Mary Kate and Ashley Olsen.

A documentary about his experience building the company called Maddman: The Steve Madden Story is currently available on Netflix, iTunes and Amazon.

Today, the company owns nine apparel brands, including Betsey Johnson, and has partnerships with Rebecca Minkoff and Kate Spade. It is valued at around $2.8 billion.

We caught up with Madden to ask him 20 Questions and find out what makes him tick.

This interview was edited for clarity and brevity.

Related: Health and Beauty Mogul Bobbi Brown Shares The Biggest Time Sucker -- and What You Can Do About It

1. How do you start your day?
People have routines for safety, I would say. I think it's a form of protection before you start your day. Lately I haven't been sleeping well at night, which I don't really mind. It's just that I have trouble getting up in the morning. So the big thing is I start my day an hour behind where I probably should be. But I figure I'm more productive. And of course now at this point in my career, I'm able to do that.

2. How do you end your day?
I end my day usually by watching a TV show [with my family] or reading the news, mostly on Twitter. With my children I have some shows that we watch together.

3. What's a book that changed your mind and why?
I would say that Moneyball by Michael Lewis was a very influential book on me. It is about baseball and some different philosophies of the game. But deeper than that, it was more about value.

4. What's a book you always recommend and why?
I have recommended books to get people to start reading, as I've met some people that don't read. And I say, well you've got to get a trashy novel. I have recommended novels to get friends interested in reading, because you've got to start exercising that muscle. So I would say, The Godfather by Mario Puzo is a great novel. Or Kane and Abel by Jeffrey Archer or The Other Side of Midnight by Sidney Sheldon.

Related: This Entrepreneur Shares The Lesson Every Founder Must Learn to Be a Powerful Leader

5. What's a strategy to keep focused?
I have Attention Deficit Disorder. I find what's helpful to me is a rabbit's foot of some sort that you can hold on to that kind of keeps you grounded. Some kind of good luck charm. I try to keep that on me wherever I go. I'm smart enough to know that trinket is not bringing me luck but there's something grounding about having it. Like, I've got this, and I'm okay I'm. I recommend that to people who have trouble focusing.

6. When you were a kid what did you want to be when you grew up?
I wanted to be in show business -- work at a motion pictures studio. I just liked the idea of it. I thought about maybe being a golf pro, but I wasn't good enough. Those were the two goals. Instead of show business, it was the shoe business.

7. What did you learn from the worst boss you ever had?
A big lesson is you should pay your bills. And you should try to keep your word. I think most people try to keep their word, but there's a lot of gray areas.

8. Who has influenced you most when it comes to how you approach your work?
My father. He influenced me with his prioritization. I suppose that has stayed with me. There are people that don't have a good sense of priorities when it comes to business, and they don't usually win. That was the big thing I got from my dad, "first things first."

9. What's a trip that changed you?
My trip to a federal correctional facility. That was a trip that changed me.

Related: This Successful Entrepreneur Shares The Trick That Helps Her Tell The Difference Between Being Productive and Being Busy

10. What inspires you?
I'm inspired by a lot of art. All different kinds of art. Music and painting, things like that are very creatively inspiring to me.

11. What was your first business idea and what did you do with it?
Probably scalping tickets. I was little boy, and my father's company had hockey tickets. I hated it; I still do. I was given the tickets and I took my friends to the city, I was 11 or 12 and took the train into New York. I scalped the tickets, and I took my friends to Tad's Steaks. And then I went back in there, bought tickets and scalped them again. I started doing that and I really enjoyed it. I actually did it for a couple of years. It wasn't about the money, it was mostly about the action.

12. What was an early job that taught you something important or useful?
I worked in a shoe store. The owner was very particular about certain things. One of the things you had to do was wear shoes he sold. The girls, not the guys, because it was a women's shoe store. I do that today. If somebody's not wearing a Steve Madden shoe, they are off the floor. What kind of message does that send?

13. What's the best advice you ever took?
Run your business within your means. Do what you can do and only do what you can do. And keep going. If it was 100 pairs of shoes that I could afford [to make], I stayed in that. I never was a big borrower.

14. What's the worst piece of advice you ever got?
I suppose borrowing money is a bad piece of advice. The advice that money is so cheap, why not put a little debt on your balance sheet? That's bad advice for an entrepreneur.

Related: Use This Successful Entrepreneur's Scheduling Secret to Have Your Most Productive Day

15. What's a productivity tip you swear by?
Try to finish an idea. See if you can finish it and not leave it open. That sort of helps [going into the next day]. I've heard John Lennon talk about that, actually. He always tried to finish a song and that always resonated with me.

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I'm into news as a hobby, so I'll hop on Twitter, Instagram. When you have a moment, waiting for the train, [it clears your mind.]

17. What does work-life balance mean to you?
It doesn't mean anything to me. Everything is one. Life and work are one to me. Any entrepreneur would tell you that.

18. How do you prevent burnout?
You need to sleep. And I play golf, that helps me relax.

19. When you're faced with a creativity block, what's your strategy to get innovating?
You have to get out and walk around.

20. What are you learning now?
As a founder of a very large company. [How do you value] the company and the success of the company, over one's ego, that's the struggle? You've got to put the company first. [My question now is] How can I add value now? Some of the things I did to get us here don't work anymore, because we're a huge corporation. So I have to figure out what I'm going to do and find people who do those things better than me. That's what's next.

Nina Zipkin

Entrepreneur Staff

Staff Writer. Covers leadership, media, technology and culture.

Nina Zipkin is a staff writer at She frequently covers leadership, media, tech, startups, culture and workplace trends.

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