It was a Thursday night in SoHo, the kind of crisp evening when the city’s energy hummed quietly beneath the streetlights. It was a little after 8 p.m., and the usual flood of tourists had thinned out. In their place were the stylish locals—fashionably understated, effortlessly cool—cruising down the cobblestone streets like runway models on a casual stroll. This is what I love about SoHo: the people-watching. And tonight was no exception.
Stephen R. McFadden and I had just finished dinner at Kenn’s Broome Street Bar, where the burgers had been nothing short of exceptional—juicy, perfectly charred, a hint of caramelized onions still lingering in the air as we left the restaurant. We trekked down Broome Street, j-walking past oncoming cars, until we landed on the corner of Broome and West Broadway across the street. That’s when I pulled out my travel mic, always in my bag just in case, and asked Steve if he was up for a conversation. He’s the kind of guy who’s always down, and tonight was no different. I hit record, and with the cool night air wrapping around us, we jumped into a conversation that spanned decades of friendship and his incredible journey as a creative.
Listen to Our Conversation
For over 25 years, Stephen has been one of my closest friends, someone I met at the University of Southern Mississippi in 1999 when we were both young men chasing degrees in Radio, Television, and Film. Our bond has never been about networking but about collaboration, friendship, and a shared love for storytelling. He’s been there through every step of my creative career, from our early days working together on student short film projects to the creation of New York Said, and it’s not an exaggeration to say he’s as much a brother as a friend.
But tonight wasn’t about me. It was about Stephen—his work, his life, and the principles that have guided him through a career spanning from corporate hallways to freelance freedom.
From Jackson to the World: The Early Years
Born and raised in Jackson, Mississippi, Stephen grew up with a creative itch, but it wasn’t until he decided to pursue video that he fully realized where that drive would take him. “I knew I was a creative when I had to figure out what I was gonna do,” he said. “Video was the ticket. Once I found it, I knew that was the path.” That path led him from Mississippi to the open seas, where he worked as a Norwegian and Royal Caribbean television coordinator on cruise ships.
Working on those ships wasn’t just an adventure but a crash course in efficiency and resourcefulness. “The biggest thing I learned from working on cruise ships was how to shoot with the edit in mind,” Stephen explained. “Most of the things I shot had to be on TV later that night or the next morning. There was no time to overshoot or overthink. You had to be precise.”
That precision became a cornerstone of Stephen’s creative philosophy. He wasn’t just learning how to film—he was learning how to tell a story quickly, succinctly, and beautifully. “Back then, we used to sell DVDs at the end of the cruise,” he recalled. “The edit was already built. I knew exactly what shots I needed for each segment, and once I had them, I could move on.”
The Florida Chapter: Miles Media and a Pivotal Decision
After his time on the open sea, Stephen’s journey brought him to Sarasota, Florida, where he joined Miles Media, a company specializing in tourism videos for destinations around the U.S. It was a job that seemed almost tailor-made for him—a blend of travel, storytelling, and video production. Stephen traveled across the country for a few years, filming promotional videos for various tourist destinations, capturing everything from golf courses to alligator farms.
However, as the financial crisis of 2008 swept across industries, Miles Media, like so many other companies, faced cutbacks. Stephen, along with many others, was laid off. It could have been a devastating blow, but his next move was one of the most pivotal decisions in his career. Instead of accepting the full severance package from Miles Media, Stephen negotiated to have the cost of the company’s video equipment deducted. Although his final payout was smaller, he walked away with the essential gear that would become the foundation for his freelance career.
“I didn’t have a camera or any gear at the time, but I knew I needed it to freelance,” he explained. “So I asked them to deduct the cost of the equipment from my severance. I walked out of there with a camera, a tripod, and a whole microphone set.”
With this equipment, Stephen returned to his roots as a freelancer, but this time with a renewed sense of purpose and freedom. Sarasota became his creative playground, where he shot original content, shared his work on Facebook, and gradually built a portfolio that would later open doors. “People started asking me to make stuff, and they were paying me to do it,” he said.
Back to New York, Back to Square One
Stephen’s return to New York in 2015 was anything but simple. At 35, he had experience, but in the city’s relentless creative hustle, names on a resume didn’t hold much weight if nobody recognized them. Starting from scratch, he tapped into the city’s freelance networks and temp agencies, building a client list from scratch.
In those early days, he took gigs anywhere they came—two days here, a week there. “I had to prove myself all over again,” he said. Slowly, his portfolio grew, and soon enough, Stephen produced fashion videos, even working with Emily Ratajkowski on a shoot. “New York is a gauntlet,” he admitted. “But it’s also full of opportunities if you stick with it.”
The Pivot to Corporate: A Masterclass in Business
By 2018, Stephen found himself in New York City, navigating a new chapter in his creative career. He joined IFundWomen, a venture-backed platform supporting female entrepreneurs, as a video producer. The role offered more than a steady paycheck—it became a masterclass in business.
Working at a startup taught Stephen about the mechanics of raising capital, building pitch decks, and developing business strategies. “It wasn’t just about making videos anymore,” he reflected. “It was about understanding the business side of things—how to talk to investors and create content that would drive results. I learned the language of KPIs and quarterly earnings.”
He also learned the importance of being adaptable. “At IFundWomen, we had to evolve constantly,” Stephen said. “We weren’t just making videos—we were offering coaching services, teaching entrepreneurs how to tell their own stories.” That flexibility is something he advises all creatives to embrace. “You’ve got to be nimble in this industry,” he said. “Be willing to evolve and adapt.”
Lessons in Resilience
After five years with IFundWomen, Stephen returned to the freelance life, working with major brands like Vita Coco and Vivvi, a high-end childcare company in New York. While freelancing offers freedom, it also comes with uncertainty. “There are peaks and valleys,” he told me, “and you’ve got to be prepared for the valleys.”
That’s where his concept of “float money” comes into play—a financial cushion he’s saved up during the more lucrative times. “Float money is essential,” Stephen said. “It’s what keeps you going when the work dries up. You can still pay your bills, take your girl out, and keep working without panicking.”
Through it all, Stephen and I have lived by a simple but powerful creative philosophy: “Create the work you want to be hired to do.” Early in his freelance career, Stephen embraced this fully, focusing on projects he was passionate about. Clients began seeking him to create similar content as his work gained visibility. “Even if they didn’t want exactly what I was making, they knew I was capable,” he said.
The Long View
When I asked Stephen what the most important lesson from his creative journey has been, he didn’t hesitate. “Be nice to people,” he said. “The world’s harsh enough as it is. Treat people well, and they’ll remember that.”
It’s a simple mantra that has served Stephen well over the years. His kindness, humility, and dedication to his craft have earned him clients, friends, collaborators, and a creative family spanning cities and industries. As he continues to navigate the world of freelance, corporate gigs, and personal projects, Stephen McFadden remains grounded in the values that have carried him through hard work, humility, and always keeping the bigger picture in focus.
As we wrapped up our corner talk, I felt an overwhelming sense of gratitude—not just for the friendship Stephen and I share but also for the example he sets. His story reminds me that while success in the creative world may be unpredictable, what matters most is how you navigate the journey with kindness, perseverance, and a relentless commitment to your craft.
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