My guest today is fashion designer and entrepreneur, Steve Madden. Steve started his first company back in 1990 with a mere $1,100 selling shoes out of the trunk of his car and today his company is worth over $3 billion. Along the way, he struggled with alcohol addiction and went to jail for over two years for stock fraud. Steve’s story of both failure and success is captured in his new book, “The Cobbler”, which we discuss in this podcast episode.

The 5 questions I ask in this episode:

1. After you dropped out of college you got a job as a traveling salesman for a shoe company but didn’t have a driver’s license because you had so many DUIs. This didn’t stop you from being successful at your job though. How did this early experience shape you as a business person and become the foundation for your future company?
2. What motivated you when you were building your company from scratch and how were you able to grow the brand while simultaneously battling your alcohol and drug addiction?
3. In your memoir, you talk openly about the high and low points in your life. One of your lowest points was when the FBI arrested you for participating in a “pump and dump” scheme that was orchestrated by Jordan Belfort and illustrated in The Wolf of Wall Street movie. What led you down that path and what lessons did you learn during your 2.5-year prison term that can be applied to business and life?
4. You credit your team for many of your company’s achievements and I find in business that hiring is stressful and time-intensive. What are some of the unconventional hiring strategies that have allowed you to build a team that led to your success?
5. What is your best piece of career advice?

Follow Steve’s journey:

• Brand
• Book