The Creative Executive

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Who really gets paid when a movie hits theaters? Usually it isn't the producer, and it isn't the A-list star.

In this episode of The Creative Executive, Harry Smith (founder of Smith Global Media, real estate developer, and brother of Will Smith) joins Siddhi to explain how money actually moves through the film business.

Harry never meant to work in entertainment. He had an aversion to an industry where "no" rarely means no and "yes" rarely means yes. That changed after a conversation with Will about what it would take to get a major star into a $5 million movie instead of a $105 million tentpole. After talking with A-list actors and Academy Award winners, Harry learned that talent cared about two things. They wanted the movie to be good, and they didn't want it to sit on a shelf. Then came the bigger revelation. Film companies don't exist to make movies. They exist to fill distribution pipelines and hit financial targets. In other words, they're banks.

That insight became the blueprint for Smith Global Media. Sundance, Cannes, and Berlin receive roughly 25,000 submissions for about 100 slots. Harry saw thousands of finished films, with talent already attached, that had nowhere to go. He could acquire a $10 million movie for a $2 million advance, which eliminated production risk entirely. He hired editors and creative directors coming off $100 million productions for a fraction of the cost. As the distributor, he also sat in first position on the waterfall: last dollar in, first dollar out. That meant collecting up to 50% of first-dollar revenue before producers, financiers, or gross talent saw a dime. Distributors also hold what Harry calls "green-light power," because committing to a set number of screens can trigger a film's production financing.

Harry is also candid about what came next. Smith Global Media depended on theatrical releases for 95% of its business. When COVID closed theaters for 14 months, that foundation disappeared. He talks openly about winding the company down and about the embarrassment of closing a business tied to a famous name. He also reflects on building his own identity next to one of the world's biggest stars. People don't call him "Will's brother, Harry." They call him "Harry, Will's brother." As he puts it, "Will was fuel, not the engine."

This episode delves into:

Takeaway: Power in Hollywood doesn't belong to whoever makes the movie. It belongs to whoever controls first position. Ownership is not a title, but knowing where you sit in the waterfall. Subscribe so you never miss an episode of The Creative Executive, and share this with a filmmaker trying to get their movie seen.

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Caleeb Pinkett has produced Cobra Kai, After Earth, and Charm City Kings, but this episode isn't really about the resume. It's about the mentorship, discipline, and one very public failure that actually built his career.

Caleeb traces it back to church pews and history books: a lifelong love of storytelling he didn't recognize as a talent until Will Smith looked at him and said, "you have a gift for storytelling." That single moment of recognition changed everything, and Caleeb is candid about how many people go through life never hearing that sentence, stuck in work they hate because no one ever named what was already there. He credits Sir Ken Robinson's book The Element, the idea that fulfillment lives at the intersection of what you're good at, what you love, and what people will pay you for, with crystallizing his own path.

Before he earned a seat at the table, Caleeb had to pass what Harry calls a series of tests. The first came from boxing trainer Darryl Foster, who trained Will for Ali: Caleeb wasn't getting help until he had a six-pack, not because of vanity, but because discipline over your body is a proxy for discipline everywhere else. The second came from James Lassiter, Will's business partner, who initially didn't want Caleeb around at all. Instead of folding, Caleeb leaned in, reading scripts ahead of meetings and offering notes that made him impossible to ignore, eventually building an 18-year creative partnership.

The most candid stretch of the episode is Caleeb's account of After Earth, his first producing credit and a high-profile box office disappointment. He owns it completely, then makes the case that it was probably the best thing that ever happened to him: had it succeeded, he says, he'd never have been pushed toward the writing and directing career he's building now, a shift filmmaker Lee Daniels predicted years before Caleeb believed it himself.

This episode covers:

Takeaway: Nothing is wasted. Caleeb didn't lose two decades of experience when he pivoted from producing to writing — he carried the network, the perspective, and the failure that finally showed him where he was actually headed.

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Hollywood producer Todd Black has over 80 films to his name and decades-long partnerships with Denzel Washington and Will Smith. In this episode of The Creative Executive, he traces it all back to a ray of light in a movie theater, and opens up about leading through one of the most public crises of his career.

Todd's origin story starts at seven years old in Oklahoma City, faking sick to skip school and ending up at the local mall theater with his mom. He barely remembers the movie, he remembers the projection booth, the ray of light cutting through the dust, creating images out of nothing. That moment planted a seed he couldn't name yet. He went on to USC's drama school not even knowing film school existed, discovered he hated being watched but loved everything else about the creative process, and talked his way from a casting internship at Fox into a full producing deal by his mid-twenties, using nothing but a willingness to say "I don't know" and ask.

The heart of the episode is the story of Antwone Fisher: a security guard with an extraordinary life story, a college roommate teaching screenwriting in South Central after the LA riots, and Todd using his own honeymoon money to buy the man a computer so he could write it himself. It took three more years to get Denzel Washington on board, who'd told Todd back in 1989 not to call him again until he found a script that made his heart do something. That relationship led directly into The Pursuit of Happyness, which brought Todd into Will Smith's orbit and became, in his telling, the best shoot of his career.

The conversation doesn't shy away from the hardest chapter either: the 2022 Oscars incident, which hit right as Todd's film Emancipation was awaiting release. He's candid about watching it unfold the call from Denzel in the middle of it, and the advice from his own father that got him through it: life isn't always fair, as a kid or as an adult. Todd closes with what he considers the real throughline of a lasting creative career: find one piece of material you love, read the classics to understand story, and let fear drive you instead of stopping you.

This episode covers:

About Todd Black

Todd Black is a Hollywood producer with over 80 films to his credit, known for championing stories that blend commercial appeal with deep human resonance. His producing credits include Antwone Fisher (2002), The Pursuit of Happyness (2006), Seven Pounds (2008), Donnie Brasco (1997), The Equalizer series, and Emancipation (2022). He maintains long-standing creative partnerships with Denzel Washington and Will Smith, and has worked with directors including Denzel Washington, Gabriele Muccino, Mike Newell, and Antoine Fuqua. Beyond film, Todd and his wife, screenwriter and designer Ruth Black, have built a successful real estate business (10 spec houses with clients including Viola Davis) and recently launched Maison Ruff, a high-end clothing store on Melrose Place in Los Angeles. Todd began his career as a casting director at 20th Century Fox before becoming an independent producer in his mid-twenties and the youngest member of the Academy of Motion Picture Arts and Sciences at the time.

Takeaway: No single moment, good or bad, defines a career. Todd's built his on the willingness to ask questions he was embarrassed not to know the answer to, and on refusing to let one public crisis undo decades of partnerships built on trust.

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What does it take to sustain a family business when the stakes are global, and the spotlight is intense?

In this episode of The Creative Executive, Harry Smith—financier, real estate developer, and lifelong business partner to his brother Will—joins Siddhi to reflect on three decades of balancing family ties with the demands of the boardroom.

Only 30% of family businesses make it to a second generation. The list of legendary dynasties that fell apart is striking. The Dassler brothers, founders of Adidas and PUMA, parted ways and never reconciled. The Gucci family nearly destroyed its own empire. Harry openly shares that he and Will have faced similar challenges: sibling rivalries, personal baggage, and heated conflicts. These were magnified by the scale of their success. What set them apart, he reveals, was their commitment to avoiding low blows. They also created a habit of pausing mid-disagreement to ask, "Is this Harry my brother speaking, or Harry my CFO?" That simple question became a key safeguard. It ensured business disputes didn't erode their personal relationship.

The discussion also touches on the often-overlooked imbalance of recognition in family partnerships. Harry recalls pitching a low-risk venture with the potential to generate a few million dollars annually. He was met with indifference by a board accustomed to the massive successes of I Am Legend, Hitch, and Hancock. "It was tough to compete," he confesses. Presenting a $5 million opportunity to a group focused on $150 million movie years was a challenge. Nonetheless, he persevered. He built a career spanning real estate development, private equity, nonprofit initiatives, hospitality, film distribution, and entertainment ventures. Collectively, these contributed to $9 billion in box office revenue.

At its heart, this episode explores authenticity as the ultimate competitive advantage. Harry compares this to Kobe Bryant, who began his career emulating Michael Jordan. Over time, Kobe evolved into the Black Mamba—someone entirely original rather than a mere imitation. Harry shares his "Top Five" framework for decision-making. This involves identifying the five things that truly bring you joy (with money notably absent from the list) and using them to guide every major choice. He also provides a behind-the-scenes glimpse into Will's memoir journey. This included a visit to Oprah's estate, where she declared it the best memoir she'd ever read.

This episode delves into:

Takeaway: The families who survive going into business together aren't the ones without conflict. They're the ones who build guardrails, like knowing exactly which role is talking in any given moment, so the business can get hard without the relationship paying for it.

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The Creative Executive is a show built for the modern creative economy, where artists are becoming founders, executives are becoming storytellers, technology is reshaping every industry, and the people with the greatest ideas often lack the mentorship and business fluency to move those ideas through the world. The show brings together leaders from entertainment, entrepreneurship, technology, and culture to unpack how they built what they built, what they learned, what they got wrong, and what it takes to manifest the life and career their talent was made for.

Hosted by Harry Smith and Siddhi Sundar. Launching October 8, 2026