My biggest takeaway is that I knew more than I realized. I was aware of all of these directors first films, and I've even seen most of them, but I just didn't really put together that "this is the way". It makes total sense though. Reminds me of that quote in A Knight's Tale, "How did the nobles become nobles anyways?… they took it, at the tip of a sword." My biggest concern is that I won't be able to write anything compelling. I watch a lot of independent films on tubi, and a lot of "first features" on r/filmmakers that are often touted as being ultra low-budget, and many of them suffer writing pitfalls that make them somewhat hard to watch. I love The Puffy Chair, so I can definitely forgive low production value, but that movie has so much soul, and I'm afraid that's what I might not be able to capture.

The Origin Story At 21, Cooper Raiff wasn’t waiting for permission. During spring break at Occidental College, he grabbed a borrowed camera, two friends, and made a scrappy 50-minute film called Madeline & Cooper. He had no lighting kit, no crew, and no plan beyond making something real. Instead of hiding it, he uploaded the rough cut to YouTube and dared Jay Duplass (yes, that Jay Duplass) on Twitter: “Bet you won’t click this link.” Jay clicked. Jay watched. Jay responded. That moment wasn’t luck—it was proof of concept. Raiff had something tangible that a seasoned filmmaker could recognize. Leveling Up: Shithouse (2020) With Duplass’s mentorship, Raiff turned the short into a feature. He dropped out of college, raised about $15,000 through friends, family, and a Duplass-boosted Kickstarter, and shot guerrilla-style in LA. He did everything—writing, directing, acting, even editing. The result? Shithouse won SXSW’s Grand Jury Prize. IFC Films picked it up. A dorm-room project became an indie film that proved he could finish a feature. Going Big: Cha Cha Real Smooth (2022) The festival win gave him credibility. His next film, Cha Cha Real Smooth, had Dakota Johnson attached as producer and co-star, plus backing from Picturestart and Endeavor Content. Budget: multi-million dollar indie (huge jump from $15k). Festival: Sundance Audience Award. Deal: Apple TV+ bought it for $15 million. That leap wasn’t just about talent—it was the power of proof. Because he had already made a feature, bigger players felt safe betting on him. Today: Beyond Features Raiff’s TV series Hal & Harper premiered at Sundance 2025 with Mark Ruffalo and Lili Reinhart. MUBI picked it up. He also launched his own production company, Small Ideas, to keep creative control. Even after a shelved project (The Trashers, too expensive to finance), he keeps momentum alive because he has proof of execution behind him. Tactical Strategy: How You Can Apply This 1. Start Small, But Start NowRaiff didn’t wait for money, agents, or a studio. He made something scrappy and honest. Your first project doesn’t need a budget—it needs completion.