Indie Film Hustle® - A Filmmaking Podcast

What does a career look like when it spans cult films, Bollywood productions, Hollywood boardrooms, and ultimately a complete reinvention of purpose?

In this episode, Will Keenan shares one of the most unconventional journeys in entertainment. From landing the lead role in Tromeo and Juliet alongside a young James Gunn to producing independent films, working in Bollywood, and eventually becoming an executive at Maker Studios, Endemol, and Streamup, Will offers a rare insider perspective on how the entertainment industry transformed from traditional filmmaking into the digital era.

But this conversation goes far beyond career milestones. Will delivers a brutally honest look at why most independent films fail, how online audiences have become the new gatekeepers of success, why creators should stop waiting for permission, and how YouTube has replaced many of Hollywood’s traditional discovery systems. The discussion culminates in his decision to leave Hollywood behind and create St. Babs, a nonprofit foundation honoring his mother’s legacy, proving that sometimes the most meaningful chapter of a creative life begins after professional success.

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What separates a good cinematographer from one that directors, producers, and talent repeatedly trust with high-pressure productions?

In this episode, cinematographer Jared Hess shares hard-earned lessons from over a decade shooting for ESPN, WWE, Bellator, and major fight promotions. From filming in dangerous neighborhoods and chaotic gyms to working directly with elite athletes and unpredictable environments, Jared explains why technical skill alone is never enough. The real job is managing people, emotions, pressure, and trust while still delivering cinematic images under impossible conditions.

But beneath the stories of cameras and production lies a deeper conversation about collaboration, leadership, and surviving the modern filmmaking industry. Jared breaks down how cinematographers can build trust with directors and talent, why ego destroys sets, the importance of preparation, working without enough time or money, and how maintaining calm energy can completely transform an interview or production day. For indie filmmakers and aspiring DPs, this episode becomes a practical masterclass on professionalism, communication, and visual storytelling under pressure.

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What happens when a lifelong wrestling fan decides to document one of the most chaotic and misunderstood subcultures in entertainment history?

In this episode, filmmaker John Philapavage breaks down the 13-year journey of creating Barbed Wire City, the unauthorized documentary about ECW and the culture surrounding extreme wrestling. From tracking down elusive wrestlers and dealing with conflicting stories to surviving crowdfunding, licensing nightmares, and volatile personalities like New Jack, John reveals the brutal realities of making an independent documentary without studio backing.

But beneath the stories of wrestling chaos lies something much deeper: a masterclass in documentary filmmaking. John explains how trust, persistence, and storytelling discipline became more important than fandom itself. The conversation dives into interview psychology, handling unreliable subjects, crowdfunding mistakes, DIY filmmaking, licensing issues, and why documentaries are ultimately about people—not just the subject matter. Whether you're a filmmaker, wrestling fan, or creative entrepreneur, this episode offers a rare look into what it truly takes to finish a passion project against impossible odds.

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What does it really take to make an independent film with almost no money, no studio backing, and no guarantees?

In this episode, filmmakers Bob Woolsey and Darren Borrowman break down the entire chaotic journey of making their indie feature film Do Something with Your Life—from crowdfunding disasters and broken cameras to film festivals, self-distribution, and the harsh realities of today’s indie film marketplace. Along the way, they share invaluable lessons about collaboration, creativity, and why waiting for permission is the fastest way to never make your movie.

The conversation dives deep into crowdfunding strategy, low-budget filmmaking hacks, horror film distribution, DSLR filmmaking, building long-term creative teams, and the emotional rollercoaster of surviving post-production. Bob and Darren reveal why modern filmmakers must think beyond just making the movie and start planning distribution from day one. This is a masterclass in DIY filmmaking from two creators who learned everything the hard way—and kept going anyway.

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Christopher Downie’s filmmaking journey began the same way many indie filmmakers start—with VHS tapes, cheap cameras, and a deep obsession with movies. But after discovering Kevin Smith’s Clerks and the View Askewniverse films, filmmaking transformed from a hobby into an identity. In this episode, Christopher shares the unbelievable story behind Shooting Clerks, the ambitious biopic about the making of Clerks, and how years of fan films, persistence, and sheer determination eventually earned the support of Kevin Smith himself.

The conversation dives deep into the realities of independent filmmaking: actors not showing up, productions collapsing, hard drives failing days before premieres, crowdfunding chaos, and the constant need to improvise under pressure. But beneath the filmmaking war stories is a larger lesson about creativity itself—that great indie filmmaking often comes from limitations, not resources. Christopher’s story becomes a reminder that the DIY spirit that inspired Clerks decades ago is still alive today.

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