In this episode, Michael Dermer interviews Steve Madden, who made the Steve Madden brand a household name in shoes. Now has led the brand to endeavors far beyond shoes.  No one knows more about success in the face of the struggle. Steve spent two years in jail when his company was taken public by Stratton Oakmont, the investment firm run by his childhood friend, Jordan Belfor (the character played by Leonardo DiCaprio in The Wolf of Wall Street).  In this podcast, Steve shares his views on:

  • Surviving in jail for two years
  • How we knew he was an entrepreneur
  • Getting caught up in the scandal of Stratton Oakmont
  • His happiest day and loneliest day

“My happiest time was when I came back from prison and I was able to work. It was so exciting to be back at work. It was an amazing year. It went up like a rocket ship.”

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Quotes of Note

  • Jail: “I was thinking of surviving – about getting through it. I knew if I got out I could make an impact.”
  • Donald Trump as President: “To his credit he figured out he is a shitty operator and then he just became a licensing guy. And I give him credit for recognizing that. But of course he touts his operating ability. He is a terrible operator which is why I think he would be a terrible President.”
  • Art and Commerce: “I’ve always been interested in art and commerce as a unit.  As opposed to someone that is just commercially successful or just artistic without success is terribly boring to me. That’s what intrigued me. The idea is to be creative but to ring the register at the same time.”
  • His Start: “I started with $1,100. I finally just took what I had and said I’m just going to start. I’m going to do what I can do. This is all the money I have. And if it’s buying 12 shoes and selling 12 shoes that’s all I am going to be able to do.”
  • His First: “I remember my first sale, the first boot I sold in the Steve Madden store and my first shoe show on my own.”
  • His Favorite Saying: “When you are going through hell keep going. You’ve got to keep going. You’ve got to keep putting one foot in front of another.” (Winston Churchill)
  • The Lonely Entrepreneur:  “The Lonely Entrepreneur – it is a lonely thing. You nailed it.”

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About The Lonely Entrepreneur

The Lonely Entrepreneur Podcast series – called Perspectives – help entrepreneurs with the one issue we all face – the struggle – by changing our perspective on the business and personal issues we all face. We share parts of The Lonely Entrepreneur methodology, crazy stories from our journey and interviews with well-known entrepreneurs about how they have succeeded in the face of their own struggles. Passion and grit is not enough – and it is our goal at The Lonely Entrepreneur to provide perspectives to help each of us become better entrepreneurs each day. Also, we believe that the difference between success and failure is your perspective. In the end, we hope to help the community of startups, entrepreneurs, small business, venture capital, angels, investors, incubators, accelerators and universities unlock the entrepreneurial spirit.

TAGS: struggle, entrepreneur. startup, lonely, investor, stress, succeed, business, learn, Steve Madden, fashion, Stratton Oakmont, Jordan Belfort, Leonardo DiCaprio, Wolf of Wall Street.