How Steve Madden Went From College Dropout to Billion Dollar Fashion Mogul With Only $1,100

In this episode of The Burnouts, Steve sits down with Phoebe Gates and Sophia Kianni to share the true story of how he went from a college dropout selling shoes in Queens to building one of the most influential footwear companies in the world. He talks about the early instincts that set him apart, the moment he knew he had something special, and the creative philosophy that has kept his brand relevant for more than three decades. Steve also opens up about the twists and turns of his journey — including learning hard lessons during the Wolf of Wall Street years and stepping away from the company before returning more focused and energized than ever. He reflects on the loyalty of his team, the power of staying close to the customer, and why speed, instinct, and obsession with product remain his North Star. Plus: the story behind his first viral shoe, his unfiltered take on dupe culture, the trends he loves (and hates), how Gen Z made him go viral again, and the fashion advice he wishes everyone knew earlier. Whether you’re building a brand, navigating a major life pivot, or chasing a creative vision, this conversation is a masterclass in staying true to your instincts, evolving with culture, and building something that lasts. Chapters 00:00 – Growing up in Queens and falling in love with shoes 01:45 – Dropping out of college and learning retail 03:20 – Starting Steve Madden with $1,100 06:00 – Product instinct, speed to market, and early hits 08:45 – Becoming a “pirate” in fashion 11:00 – The Wolf of Wall Street years and the IPO 14:00 – Prison, addiction, and rebuilding his life 16:30 – Reinventing the Steve Madden brand 18:00 – Dupe culture, controversy, and staying relevant 20:00 – What he hates (and loves) in fashion today 22:00 – Designing shoes women actually want 23:30 – AI, TikTok, and the future of trend cycles 26:00 – Lessons from failure and advice for young founders 🔗 FOLLOW US Phoebe Gates Sophia Kianni Steve Madden 🔥 FOLLOW THE BURNOUTS Instagram TikTok LinkedIn 📲 Support What We’re Building Phoebe and Sophia aren’t just your hosts — they’re the founders of Phia, a fashion-tech app helping shoppers find the best prices across retail and resale. Download Phia for free in the App Store. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.