From Comic Books to Contracts: Simon Pulman and Dealmaking in the Age of Transmedia

"Just to be clear, your father’s dying and you’re choosing to allow that to occur naturally", Noah Wyle as Dr. Michael "Robby" Robinavitch in HBO Max’s The Pitt. 

In his New York office, renowned entertainment lawyer Simon Pulman leans forward, animated as he describes why The Pitt might be the most compelling medical drama in years.

"I think The Pitt is extraordinary in how it marries traditional hospital procedural drama with something that feels very visceral. I think it’s absolutely stellar," he enthuses during our 31 March conversation—a glowing recommendation that has had my wife and I hooked ever since.

Long before becoming a partner at Pryor Cashman, Pulman was like many 80s kids, spending weekends devouring comic books obsessing over games, movies and football.

That perspective gave him something rare: the ability to recognise value in stories that traditional gatekeepers overlooked.

“The Exorcist is what people in their 60s thinks of as a valuable ora IP. Five nights at Freddy's is an actual valuable ora IP."

It's a brutal reflection but a key driver to our conversation. The chasm between old and new media isn't just a cultural divide—it's reshaping the fundamental power dynamics of who controls valuable IP and how deals get made.

When Games and Hollywood Collide: The New Deal Paradigm

"The traditional entertainment deal is the movie studio will want to take everything in that IP except the things reserved," Pulman explains, laying bare the philosophy that has dominated dealmaking for decades.

But that paradigm is crumbling. Video game companies approach IP from the opposite direction: "This is our IP. We’ll give you the right to make a movie. But everything else, we reserve."

The results speak for themselves. 

When Kingdom Come: Deliverance II vaulted over one million sales on its first day of launch, before galloping toward two million copies sold by the end of February, it showed exactly why game studios now have the upper hand.

The crucial difference? The game cost substantially less to produce than a movie, especially in traditional heartlands. This economic reality of increased competition and scale, is why gaming companies now enter negotiations with unprecedented leverage.

"You must honour the feel and fundamental core tenets," Pulman emphasises, speaking about successful adaptations like The Last of Us. "If you change those things, it will not work, because the fans will reject it."

The Community Imperative

"Community is really undervalued by the industry overall," Pulman notes. "The classic Hollywood approach has always been, 'We’ve made a movie. Now let’s think about marketing it.' Whereas you’ve got to go the other direction and think, 'Who’s the audience? How can we energise them?'"

This explains why Five Nights at Freddy’s achieved an $80 million opening weekend despite a day-and-date streaming release—the community was already built and activated.

Risk, Reward, and Individual Incentives

Why does Hollywood continue making sequels instead of taking chances on original content? 

According to Pulman, it comes down to individual incentives.

"Success has many fathers, but failure is an orphan," he observes. "If you advocate for original content and it fails, you’ll lose your job. Whereas with a built-in audience, even if it doesn’t work, you can say, 'You can’t blame me—this book sold this many copies.'"

Despite his analytical approach to the business, Pulman isn’t just a legal strategist—he’s also a genuine fan with his own enthusiasms. As our conversation winds down, he suddenly lights up: "Oh, and I should shout out the new Final Destination movie. I can’t leave that out. Comes out in May. The greatest film franchise of all time."

This moment of unfiltered enthusiasm reveals the passionate fan beneath the industry expert—someone who still experiences the pure joy that entertainment is meant to deliver.

The Future of Entertainment

Looking ahead, Pulman sees an entertainment landscape where distinctions between mediums continue to blur. "Most of the new and original brands are going to come out of other media, particularly gaming, over the next 10 or 20 years," he predicts.

This shift brings both opportunity and existential questions. "Hollywood is risk-averse, but it’s taking a big risk in the long term, because if the value of these catalogue brands diminishes, then it’s going to be left with nothing."

This conversation offered a rare window into how entertainment and deal architecture is evolving. 

Join Simon Pulman and me for the full podcast episode coming soon, where we’ll explore everything from the mechanics of transmedia rights deals to the future of entertainment IP. 

Consider this a teaser to that amazing Purpose Made Podcast. 

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