Scott Woolley
Scott Woolley’s story doesn’t read like a résumé — it reads like an adventure. From stocking shelves in a Long Island supermarket to stacking up more than 150 entertainment awards (yes, including four Emmys), his path has been anything but predictable. In 1999, he was crowned Ernst and Young’s Entrepreneur of the Year, a title that surprised everyone except those who’d watched him turn wild ideas into thriving businesses again and again.
A true builder at heart, Woolley has launched companies across industries the way some people collect coffee mugs. And he’s not done yet. Today, he and his wife continue to dream up and drive forward new ventures with the same spark, curiosity, and fearless creativity that carried the “supermarket kid” far beyond anything he once imagined. Along the way, he’s also become a storyteller — the author of several books, including a cookbook – Cooking for the Family, his memoir – From Ordinary To Extraodinary, and Pitch Sell Sold, with his fourth book, Entrepreneur Life, now underway.
It’s proof that an extraordinary life isn’t born — it’s built, one bold leap at a time.
Early Years
Before Scott Woolley became a globe-trotting TV producer and entrepreneur, he was a kid with a backstage pass to the world’s greatest rock-and-roll education. While his friends were worrying about midterms, Scott was hustling through the halls of Swan Song Records — the legendary label behind some of the biggest names in music history.
He started as an intern while attending St. John’s University, but it didn’t take long before the NYC office noticed his drive. Soon he was the guy making sure every major album landed exactly where it needed to — in the hands of radio stations, concert promoters, and tastemakers who would send those records into the stratosphere.
And these weren’t just any albums. Scott cut his teeth helping to push releases like Led Zeppelin’s “Coda,” Robert Plant’s “Pictures at Eleven,” Jimmy Page’s “Death Wish 3,” Bad Company’s “Rough Diamonds,” and more. Decades later, in 2025, the official Led Zeppelin website even featured a story about Scott — a full-circle moment that honored the kid who once ran records across the city for rock legends.
But Scott’s early life wasn’t just about vinyl and backstage passes. When he wasn’t at Swan Song, he was relieving store managers at his father’s chain of grocery stores so they could go on vacation — a grounding counterbalance to the whirlwind of the music world.
And because Scott was never one to choose just one path, from ages 17 to 21 he was already producing and staging concerts of his own. Hall & Oates, INXS, The Police, The Kinks, The Go-Go’s, Adam Ant, Marshall Tucker, The Kinks, The Allman Brothers, The Ramones — the list reads like a who’s-who of music’s golden era, and somehow he was booking them before most people choose a major in college.
Those early experiences didn’t just foreshadow his future — they built the foundation for it. Music, business, grit, and a dash of audacity… the perfect ingredients for the extraordinary life he was about to build.
The Grocery Store
Before the Emmys, the global adventures, and the behind-the-scenes moments with rock legends, Scott Woolley’s empire began in a place most people overlook: the grocery store aisle. But leave it to Scott to turn even a supermarket into a launching pad for something extraordinary.
What began as a young man learning the ropes of his father’s grocery business quickly evolved into Scott opening his own chain of upscale gourmet markets — stores that didn’t just sell food, but redefined what a supermarket could be. Long before “artisan,” “chef-crafted,” or “gourmet experience” became trends, Scott was already building one of the nation’s most innovative privately owned upscale supermarket and liquor chains.
His vision didn’t just turn heads — it caught the attention of legends. When Lee Iacocca and President Ronald Reagan needed someone they could trust to cater the grand reopening celebrations of the Statue of Liberty during Fourth of July week in New York harbor, they turned to Scott’s supermarkets which were located in South Florida. It’s not every day a grocery chain gets hand-picked to serve America’s most patriotic party.
But Scott wasn’t done innovating. Decades before digital signage and in-store media became mainstream, he launched a trailblazing concept: a full-blown in-store TV network. Twenty-four large screens, strategically placed where customers waited, delivering food education, cooking ideas, and store offerings — basically turning grocery shopping into edutainment before the word even existed.
And then came the moment that changed everything.
In Boca Raton, a frequent customer kept stopping by — a guy with a larger-than-life grin and an even larger legacy: Jerry Lewis. Lewis took Scott under his wing, teaching him the craft of editing, producing, directing, and the magic (and madness) of Hollywood. Those conversations, those stories, and those informal masterclasses would quietly reroute Scott’s entire life, opening the door to the entertainment world that would later define his career.
Scott’s grocery stores weren’t just supermarkets — they were the birthplace of his entrepreneurial daring, his creative spark, and the mentorship that nudged him from gourmet aisles to global stages. A reminder that sometimes the extraordinary begins right between the produce and the deli counter.
Entertainment Industry
At a moment when most people might have settled into a successful career, Scott Woolley did something very on-brand — he pivoted. Hard. Leaving behind the thriving supermarket world, he chased the passion that had been tugging at him since his Swan Song Records days: television and film.
That leap of faith became Five Star Entertainment, a company born with nothing but ambition, creativity, and Scott’s refusal to think small. It didn’t take long before the industry realized something special was brewing.
Under Scott’s leadership, Five Star became a powerhouse, quickly growing to over 220 employees, producing over twenty-five nationally broadcast television series that aired in 53 countries. And that was just the beginning. Scott and his team also created content for Fortune 500 companies, major sports franchises, world-renowned music artists, and hundreds of national commercials — all with the signature “Woolley polish.”
As Five Star soared, Scott spotted gaps in the industry and filled them before anyone else saw the opportunity. He built an in-house syndication department that not only distributed his own shows but represented programs from other producers. Then he expanded globally, launching an international sales division to bring Five Star’s content to audiences around the world.
But Scott’s innovation didn’t stop at production and distribution. He built a 30-person branded entertainment team dedicated to integrating sponsors directly into show content — a move so ahead of its time, networks began knocking on his door for guidance.
One of those calls led to a landmark partnership with Lifetime Television, transforming The Balancing Act from a modest 30 minute Saturday series into a five-day-a-week, one-hour national morning show. It was a defining moment, proving Scott didn’t just understand the entertainment industry — he was reshaping it.
In the years that followed, Scott’s footprint grew into something extraordinary. He ultimately created over 1,400 episodes of television, produced several feature films, delivered hundreds of national commercials, and crafted dozens of comedy and music specials.
And here’s the best part: he never stopped. To this day, Scott continues producing major television specials every year, still fueled by the same passion, curiosity, and fearless creativity that pushed him to take that first leap.
For Scott Woolley, entertainment isn’t just an industry — it’s a lifelong adventure.
National Radio Shows
Just when it seemed Scott Woolley had conquered every corner of television, he shifted gears once again — this time into the world of radio. And in true Woolley fashion, he didn’t ease in quietly. He launched “Inside the NHL,” a weekly show that quickly became the go-to source for hockey fans across North America.
Broadcast straight from the Five Star studio complex — the same creative hub that fueled his television empire — the show delivered breaking news, insider updates, and the kind of behind-the-scenes access only Scott could pull off.
“Inside the NHL” didn’t just succeed; it became the foundation for a whole new branch of his media career. What started as his inaugural radio venture opened the door to a string of successful national shows, proving once again that Scott doesn’t just enter an industry — he leaves a footprint on it.
Whether it was TV, film, commercials, or radio, Scott’s instinct was always the same: go big, innovate boldly, and give audiences something they can’t get anywhere else.
Digital Video Library
By 2004, while most producers were still wondering what this “internet video thing” might become, Scott Woolley was already ten steps ahead — digitizing thousands of hours of content and preparing for the future everyone else had yet to see.
He took his massive archive of TV episodes, specials, concerts, and films and began repackaging them for online distribution, recognizing early on that the web would transform how the world consumed entertainment. It was a bold move, but bold moves were becoming something of a Scott signature.
Partnering with a close friend, he launched Classic Video Archives, a passion project that grew into a monumental undertaking. The two painstakingly built one of the largest privately held digital libraries in existence — more than 21,000 titles strong. From rare music performances of the 1950s to modern films and vintage gems thought to be lost to time, the archive became a living museum of pop culture.
Today, Classic Video Archives reaches audiences in over 70 countries, streaming through digital platforms, mobile carriers, and online portals worldwide. What began as a vision to preserve great content has become a global entertainment vault, giving new life to decades of cinematic and musical history.
Scott didn’t just collect videos — he safeguarded culture, opened access to forgotten treasures, and helped usher thousands of classic titles into the digital age. It’s a legacy of preservation and innovation woven together, perfectly in line with the rest of his extraordinary journey.
Classic Video Archives continues to stand as a testament to Scott Woolley’s instinct for what’s coming next — and his commitment to making sure the past stays alive, available, and unforgettable.
The Balancing Act
By 2010, Scott Woolley had already conquered television, built a syndication machine, and produced one of Lifetime’s most successful shows — The Balancing Act. So naturally, he did what only a true entrepreneur would do: he sold the hit series and his state-of-the-art 39,000 square foot production facility to make room for his next creative chapter.
The sale wasn’t an ending — it was Scott clearing the runway. Free from the daily demands of a bustling studio, 230 employees and he shifted his focus toward the fast-growing world of internet content, feature films, high-end TV specials, and documentaries. He wasn’t slowing down; he was leveling up.
With his trademark instinct for spotting opportunities before they became trends, Scott ventured into sports entertainment and took on another ambitious project: the “World Series of Boxing.” Partnering with the Olympic governing body and global sports giant IMG, produceing a groundbreaking boxing series designed to shake up the industry. The show brought together elite athletes from around the world and delivered a fresh, high-energy format that resonated with viewers across North America.
Each move Scott made during this period showed the same pattern: see the opening, trust the instincts, dive in. His ability to navigate an evolving entertainment landscape — and continuously reinvent himself within it — is a testament to his vision, courage, and relentless drive.
Today, he’s not just creating content — he’s charting new territory, shaping industries, and proving once again that extraordinary things happen when you refuse to stand still.
NHRA Nitro Funny Car Team
In 2012, Scott Woolley took a sharp turn into the high-octane world of motorsports, teaming up with NHRA Nitro Funny Car driver Alexis DeJoria and her father, entrepreneur and philanthropist John Paul DeJoria, to launch Alexis DeJoria Racing. True to form, Scott wasn’t just a partner — he became the engine behind the operation.
He orchestrated major sponsorship deals, built endorsement partnerships from the ground up, and crafted a sponsorship strategy that put the team on the map long before the first race of the season. His knack for creating value where others see chaos translated perfectly to the fast, fiery world of NHRA racing.
But Scott didn’t stop at sponsorships. He dove into brand-building with the same intensity you’d find on the starting line. He developed a robust retail merchandise line that helped transform the team’s identity into a recognizable and coveted brand. And with PR and marketing running through his veins, he led a talented crew in rolling out attention-grabbing campaigns that won over fans everywhere the team competed.
In the early stages, Scott stepped in as President, steering daily operations, shaping the team’s culture, and guiding Alexis DeJoria Racing through a successful launch. His leadership laid the foundation for what would become a respected and competitive force in the NHRA world — a team built with grit, vision, and a whole lot of horsepower.
Under Scott’s early stewardship, Alexis DeJoria Racing didn’t just join the NHRA circuit — it arrived with authority, speed, and a brand strong enough to leave its own mark on the sport.
Retail Products
Scott Woolley’s entrepreneurial reach extends far beyond television studios and racetracks — he’s a master of turning ideas into products people can hold, taste, and experience. Through his company, The SW Group, Scott oversees a diverse portfolio of brands and businesses, each reflecting his signature blend of creativity, innovation, and relentless drive.
From TW Interiors, a high-end interior design company celebrated for its craftsmanship and elegance, to The Scott Woolley Entertainment Company, a hub of creativity producing captivating content across mediums, Scott’s imprint is everywhere. He also brings cutting-edge experiences to life through TW Audio Video, delivering immersive audiovisual solutions that push the boundaries of entertainment.
Scott’s entrepreneurial creativity doesn’t stop there. His collaborations with iconic spirits brands like Patrón and Jack Daniel’s led to the creation of indulgent liquor-infused cakes — a playful fusion of flavor and sophistication. He’s also helped launch innovative products like Intellergender and John Paul Pet Shampoo Products, demonstrating a keen eye for spotting trends and opportunities.
When it comes to retail, Scott isn’t just thinking about ideas — he’s putting them on shelves. With a combination of vision, strategy, and execution, he’s managed to place products in an astonishing 24,000 stores in just eight months, a feat that speaks to his unmatched ability to navigate the retail landscape. He’s even leveraged this expertise to help celebrity friends like Dan Marino and Kristi Yamaguchi launch their own product lines, turning concepts into reality.
Through decades of innovation, Scott Woolley has proven that retail isn’t just about selling products — it’s about creating experiences, shaping trends, and turning vision into tangible, unforgettable success.
Design & Real Estate Ventures
If multitasking were an Olympic sport, Scott Woolley and his wife would take home the gold. Together, they are constantly immersed in the world of design, remodeling, redesigning, and redecorating a minimum of 14 homes at any given time — each one a unique canvas reflecting their signature mix of style, innovation, and attention to detail.
But their creativity doesn’t stop at transformation. Ever the entrepreneurs, they are also developing and flipping one or two homes simultaneously, blending business acumen with design expertise to turn properties into striking, high-value masterpieces.
Whether it’s reimagining interiors, sourcing the perfect furnishings, or orchestrating a full-scale renovation, Scott and his wife thrive in the fast-paced, ever-evolving world of real estate and design. Their projects are a testament to their passion for creativity, their eye for beauty, and their knack for turning vision into tangible, stunning results — all while keeping a dizzying number of balls in the air at once.