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A lot of us have a dream we quietly put away because life gets loud. Today we sit down with Philadelphia-born filmmaker and entrepreneur Derek Shaw, and he’s proof that “later” can still turn into real momentum if you’re willing to start small and keep showing up.

We talk about where Derek’s storytelling starts, from a fifth grade teacher who pushed him to write more, to the years he “sat it in the closet” while working full time, raising a family, and building side businesses. Then comes the turning point that changes everything: he starts writing again after decades, and that decision becomes the bridge to screenplays, production, and building Ruby Street Productions.

Derek breaks down the nuts and bolts of independent filmmaking: buying a cheap camera, making early short films, and turning a weekend hobby into feature projects like Blissfully Unmarried and his dark comedy Bedridden. We get honest about film financing, earning investor trust through reputation, navigating SAG requirements, and why film distribution can be harder than making the movie. Derek also shares what it took to get Bedridden onto Amazon and Apple TV, why he chose self-distribution, and what he’s chasing next with bigger budgets and bigger names.

If you’re into indie film, screenwriting, self-distribution, creative entrepreneurship, and building a sustainable production company, this conversation is packed with practical insight and real-world perspective. Subscribe, share this with a friend who needs a push, and leave a review so more listeners can find the show. What’s one daydream you’re ready to dust off?

Guest Links

Ruby Street Productions

Bedridden on Amazon

Derrick on Insta

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Credits

Music Credit:  True Living by Patrick Moore

Royalty free music license purchased at soundotcom.com