There are careers that follow a straight line, and then there are careers like Will Keenan’s—the kind that seem to zigzag across every corner of the entertainment industry before revealing a larger pattern. What began with an unexpected audition for a Troma film eventually led him through independent cinema, Bollywood productions, digital media empires, and executive boardrooms. Along the way, he accumulated a rare perspective on what it actually takes not only to survive in entertainment, but to continually reinvent yourself as the industry evolves.
Will’s story begins shortly before graduating from NYU when he landed the lead role in Tromeo and Juliet, a cult production from Troma Entertainment that was written and heavily shepherded by a young James Gunn. At the time, Will wasn’t even familiar with Troma’s reputation. What he thought would be another creative opportunity quickly became the launchpad for a filmmaking education unlike any classroom could provide. Troma’s low-budget, guerrilla-style approach forced everyone involved to wear multiple hats, solve problems creatively, and learn every aspect of production from the ground up. As Will explains, “Troma was my film school.”
After Tromeo and Juliet, Will found himself immersed in the booming independent film scene of New York during the late 1990s. It was a fascinating period when indie filmmaking was thriving, festivals were gaining influence, and filmmakers believed they could break through without studio backing. Yet even during those years, Will began noticing the harsh economics of independent film. Projects required years of work, financing was difficult, and success stories were far less common than most aspiring filmmakers realized. Despite appearing glamorous from the outside, many productions struggled simply to recoup their budgets.
One of the most valuable lessons from the conversation revolves around budgeting and screenwriting. Will argues that many writers unknowingly sabotage their own projects by writing scripts that are far too expensive to produce. Instead of focusing on what they can realistically make, they create stories loaded with locations, characters, and logistical challenges that immediately push budgets into unrealistic territory. His advice is simple but powerful: write the version of the film you could actually produce. If the story resonates, larger production companies can always expand the scope later. Starting small dramatically increases the odds of getting the project made in the first place.
As traditional independent film became increasingly difficult to sustain, Will saw another revolution beginning to emerge. Long before many industry professionals took online video seriously, he recognized that YouTube and digital platforms were changing audience behavior. Rather than continuing to fight for shrinking opportunities in traditional indie filmmaking, he made a bold move into digital media. That decision ultimately led him to Maker Studios, where he joined during its early growth stage and helped oversee its explosive expansion before its eventual acquisition by Disney. Later, he would hold executive leadership roles at Endemol and Streamup, placing him at the center of the creator economy years before it became mainstream.
Perhaps the most provocative idea Will shares is that today’s filmmakers should stop obsessing over gatekeepers and start building audiences directly. Throughout the conversation, he repeatedly emphasizes that online platforms have become the new discovery system. “The new getting discovered at Schwab’s drugstore is the internet,” he explains. Rather than waiting for a festival, manager, studio, or distributor to validate their work, creators now have the ability to publish content immediately and prove audience demand themselves. This shift fundamentally changes how careers are built.
That philosophy extends to networking as well. Will admits that early in his career he underestimated the importance of relationship building. Over time, however, he learned that opportunities often emerge from long-term connections rather than isolated moments of brilliance. Some of the most important career advancements he experienced came from relationships cultivated over decades. Talent matters, but relationships frequently determine whether that talent ever gets the chance to be seen.
The final chapter of Will’s story may be the most unexpected. After achieving significant success in both traditional and digital entertainment, he chose to step away from Hollywood and create St. Babs, a nonprofit foundation named in honor of his mother. While it may seem like a dramatic departure from filmmaking, it actually reflects the same entrepreneurial spirit that guided every phase of his career. Once again, he identified a mission, assembled resources, and began building something from the ground up. The medium changed, but the creative process remained remarkably similar.
For filmmakers, writers, and creators, Will’s journey offers a powerful reminder that careers rarely unfold according to plan. The industry changes. Technology evolves. Opportunities emerge from unexpected places. The people who thrive are often the ones willing to evolve alongside those changes rather than fight against them.
