I spent the last 45 minutes listening to a man call his customers “my girls”, need I say more? The Steve Madden sat down with former Stanford roommates Phoebe Gates (yes, Bill Gates’ daughter) and Sophia Kianni, and went full origin story, dupe culture, Mary Janes, Gen Z, and struggles. Even his tanning girl slid in the Burnouts’ Tik Tok comments section just to bless it all, talk about cult following. Here’s everything.
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When Your Career Starts Because Rent Is Due
There’s nothing like a harsh wake-up call. Madden drops out of college, University of Miami, the phone rings. Not a venture capitalist, not a business angel, just his dad, telling him to figure out what he’s going to do next because the family funding was over. Brutal, but hey, we all owe him one I guess? He lands a job in a shoe store and learns everything you could learn really, which if you ask him, started with “waiting on hysterical women selling them shoes”.
At the time, he lives in small-town Lawrence, near Queens, while his friends are 21, getting their first NYC job, taking the railroad, pretending to be grownups, making fun of him for staying behind with a shoe horn sticking out of his pocket. I mean, super practical, but really?
Early Fame: Before Hashtags and Dupes, There Were Mary Janes… or Lous
The first shoe that went viral under the Madden name, was a Mary Jane, sorry, a Marylou. Early on, Madden noticed that nobody paid attention to the youth market, so naturally, he did. He tweaked the classic with some fresh little twists and the phone suddenly started ringing. Inspiration to success at its finest. There’s even a reference in “Wolf of Wall Street”. Jake Hoffman, who hung out last with Madden the day before the podcast was filmed, played him in the movie, but that came with the cost of having shoes thrown at him after 1993’s IPO during broker chaos. Glamorous, right?
The conversation went on with duping, and Madden’s hot takes were hotter than platform sandals in 2014. “I’m a f***ing pirate. In fact, I want to get a tattoo of a pirate.” Gold, literally. When it comes to designing new pieces, Madden “just has a feel for it”. He described the label as “a big stew”, stirring around the hottest luxury designs and making them their own (affordable too). Inspiration comes from the streets, back in the day, he’d stroll through the West Village, soaking in what everyone was wearing. If a shoe is walking three NYC blocks three different times, that’s basically it, but besides design, speed to market is everything to the Steve Madden company. Moral of the story is, if there’s a Gucci shoe taking over SoHo, better be sure a similar one is on the way to get the Steve Madden special.
Real CEOs Get Stress Pimples Too: Prison, Ego, Struggles
“Someone asked me yesterday, ‘What did you do? I want to be like you.’ I said I suffered a lot.” And really, that’s part of the Steve Madden story. From the 1993 IPO with Jordan Belfort’s firm, yes, the “bucket shop” scheme his childhood friends cooked up, he indeed was the product. Lesson learned though, sometimes you raise money you didn’t think you could, survive the chaos, and somehow it pays off.
Prison? Survival first, creativity maybe later. Reputation? Already questionable since 15. Ego? Constant battle. I mean, I get it, having your name tied to a multi-billion dollar empire starting from zero, surely has its ups and downs, I could imagine the fight of detaching yourself from it. I could also imagine late-night self-talks, anxiety breakouts and bad hair days, ouf.
He came back to Steve Madden, after being forced to let go, with a bunch of loyal, trusted and trusting people keeping the lights on. My favorite takeaway from this podcast would be, know what you’re not good at. It’s totally fine to suck at numbers or tech as a creative, it’s a crime not to bring in people who don’t. Hire smart, ride-or-die people. Period. Payoff comes later, and it won’t be money or success, it will be spotting a girl in your shoes in a random shared elevator. That’s CEO validation right there. Luck optional, but highly recommended.
Steve Madden, the man unofficially adopted by Gen Z, who one day just decided to go with it, is the perfect example of what happens when goals, instinct and a slightly delusional level of confidence align. Copying or not, he built an empire by watching people on the street, trusting the right ones, and surviving everything from Wall Street schemes to prison cafeterias. In a world obsessed with overnight success, he’s our proof that the real win is longevity. And let’s be honest, the true reward is still spotting a stranger in your shoes on the way to the 12th floor.
