Film Investment is Stupid. That's Why Smart People Do It.

When a dentist contacted me last month wanting to invest in movies, I asked him a simple question:

"Do you hate money?"

He laughed. I didn't.

After nearly 2 decades structuring media and entertainment deals from Malta to Mumbai, I've learned something profound about film investors - they're not as dumb as everyone thinks. They're just chasing something money can't buy.

Let's be clear: As a pure financial play, film investment makes crypto look conservative. When 80% of movies lose money and success metrics include "well, we only lost half," you're not dealing with rational economic behavior.

Yet every year, a fresh crop of successful people - doctors, tech founders, private equity partners - line up to roll the dice on celluloid dreams. The interesting question isn't why most films fail. It's why brilliant people keep investing anyway.

The Dentist's Dilemma

Back to our dentist. He didn't really want to know about pre-sales estimates or tax credit stacking. He wanted stories he could tell at dinner parties that didn't start with "So this impacted molar..."

Think about it. That crypto millionaire who just backed a documentary? He's not analyzing comparable sales data. He's imagining himself at Sundance, holding court at the après-ski, casually mentioning his "little film project."

The lawyer who put $100K into an indie feature? She's not dreaming of backend points. She's picturing herself at the premiere, wearing something that definitely isn't from Brooks Brothers.

Bernard Arnault and François-Henri Pinault didn't just pump billions into Hollywood because they ran out of luxury brands to buy. They know that cultural capital compounds better than money ever could.

The Three Types of Film Investors

After watching countless deals, I've identified three distinct species in the film investment ecosystem:

The Social Climber

This person already has the Patek Philippe. Now they need something interesting to say while wearing it. Film investment buys them into conversations they couldn't enter otherwise. It's a social lubricant more effective than the Dom Pérignon they're also probably invested in.

The Frustrated Artist

Usually a highly successful professional who chose pragmatism over passion early in life. That M&A partner backing experimental short films? He still has a dog-eared copy of Cassavetes on Cassavetes in his desk drawer.

The Empire Builder

They're playing a longer game. They understand that entertainment shapes culture, and culture shapes commerce. These are the luxury conglomerate titans and tech moguls who see film investment as part of a broader influence portfolio.

The Real ROI

The actual return in film investment isn't measured in dollars. It's measured in access.

When LVMH launches a film studio, they're not trying to compete with Universal. They're buying their way into rooms where culture gets created.

This is why serious players structure film investments like venture capital - they expect most to fail but know one hit changes the narrative entirely. Except unlike VC, even film investment failures can pay social dividends.

• That producer's table at Chateau Marmont? More valuable than box office points.

• That festival VIP lanyard? Better than backend participation.

• That story about how you helped discover the next Greta Gerwig? Priceless.

When a tech founder backs an indie feature, they’re not seeking ROI. They're seeking legitimacy in a world their money alone can't access. A $600M exit from a software company gets zero props at the Vanity Fair Oscar Party.

A Better Way to Lose Money

Does this mean film investment is always a financial black hole? Not necessarily. There are intelligent ways to structure entertainment investments that can mitigate risk and even generate returns.

But the smartest film investors know something the ROI-obsessed miss: Some things are worth losing money on.

Like that dentist? He ended up backing a documentary. Not because the numbers made sense, but because he was tired of being the guy who could only talk about fluoride at dinner parties.

Now he's the guy who can casually mention his film premiered at SXSW.

Worth every penny he lost.

Want to learn how to really play this game?

March 2025 in Malta, we're gathering a small group of investors who understand that cultural influence yields better returns than interest.

The Negative Pickup maintains absolute discretion regarding content and participation. This guide is for informational purposes only. Consult qualified professionals before making investment decisions. Though if you're doing it right, those professionals are probably already in Malta.