Ryan Kavanaugh is back with a new tech start up. Chad Salvador/for SkillHouse at Park City / Shutterstock Remember him?
Ryan Kavanaugh, the high-flying mogul whose Relativity Media flamed out into one of the biggest bankruptcies in Hollywood history in 2015, has a new and surprising side hustle. Sources tell Page Six Hollywood that the one-time BFF of Leonardo DiCaprio and Bradley Cooper is now advising a Chicago-based startup, SuperFile, that’s getting more buzz for swaggy branding than actual tech.
We hear Kavanaugh’s Knight Global invested $30 million into the company’s Series B round and is helping attract more funds for the venture founded by Shane Valdez. A source familiar with the operation says SuperFile has raised some $80 million from the likes of “Million Dollar Listing” bros Josh and Matt Altman, “Everybody Loves Raymond” actress Patricia Heaton and her husband, Brit actor David Hunt, and “Watcha Say” singer-songwriter Jason Derulo.
We hear one SuperFile investor became alarmed when he witnessed some allegedly extravagant spending at the company including a $400,000 Louis Vuitton luggage set on display, apropos of nothing, in the lobby of the company’s West Loop offices.
The flashiness of SuperFile might even remind Page Six Hollywood readers of Relativity at its height, when Kavanaugh would commute via helicopter from his Malibu spread to the company’s Beverly Hills offices and throw bashes at the Hotel du Cap in Cannes.
SuperFile hasn’t yet released its “trackable, unhackable, takebackable” system that covers such formats as PDFs, JPGs and MP3s. It is scheduled to launch in September. (The company’s site says “early reservations are full” for its file control product, adding there’s “limited early access” and that it’s in “active evaluations and pilot programs.”)
But its logo is already emblazoned on the jerseys of MLS pro soccer team Los Angeles FC. And fans who attended the Daytona 500 in February couldn’t have missed the SuperFile signage on driver Shane van Gisbergen’s No. 97 Chevrolet thanks to the startup’s multiyear partnership with Trackhouse Racing.
“Basically, there is no actual product,” huffed a skeptical source of the business plan. “They’re doing all this stuff, getting all these investors involved, and Ryan Kavanagh is right in the middle of it.”
Valdez pushed back on that characterization — and insists that there is a real product that is launching in September. “It’s not just branding. It’s real activation, using our technology inside that ecosystem as a proving ground for something much bigger,” he says of the NASCAR spending. “I’d rather be the biggest tech company in NASCAR than the smallest tech company in F1.”
Valdez also insists the pricey luggage is an important symbol of what SuperFile is trying to accomplish.
“Think about a brand like Louis Vuitton. For the first time, certificates of authenticity and proof of ownership can actually be controlled and transferred with the asset itself,” Valdez adds. “That’s a big part of where this is going.
Kavanaugh — who was once one of Hollywood’s most prolific financiers, and a producer on projects including “Limitless” and “The Fighter” — did not comment.
One investor who kicked the tires now questions SuperFile’s “increasingly flashy” spending. But another investor dubbed Valdez “the real deal” with two PhDs in engineering as well as a list of Hollywood credits (under the name Shane Ryan Valdez) including directing “American Idol.”
The SuperFile pitch deck we viewed is 14 pages, some of which are taken up by a single sentence like: “Have you ever sent a file you wish you could take back?” Indeed. Buzz words abound, like “revolutionary” “first of its kind” and “disrupt.”
According to a 2024 article in USA Today, Valdez, who previously founded the ad agency Realm, boasts “an illustrious career managing campaigns for iconic events like the Oscars and ‘American Idol.’” But the fine print of the article also notes: “Members of the editorial and news staff of The USA Today Network were not involved in the creation of this content,” and the piece ends with SuperFile’s tagline, “SuperFile: Secure Every File. On Every System. Everywhere.”
The piece also mentioned that SuperFile partnered with GenTV for an “extraordinary” beta test. Not mentioned is that the influencer-focused platform is owned by … Kavanaugh. Last year, Curtis Jackson, aka 50 Cent, filed a lawsuit against GenTV looking to block the streaming platform’s inaugural film “Skillhouse.” That film was produced by … Valdez. (We have reached out to GenTV for commnent.)
A pitch deck also lists Jono Matt, a Hollywood screenwriter, as an advisor. Matt calls SuperFile a “game-changer for screenwriters” because it will allow scribes to “finally track which directors and actors are engaging with the material.” (Which does sound like a good idea.) Matt’s bio notes he’s “known for” “Sons of Anarchy” and “Glee.” But on those two hits, he was an assistant to writer Paris Barclay. (Matt does appear to be appear to be a hot, on-the-rise writer with a Verve partner as his agent and several projects in development including one at Netflix with DiCaprio’s Appian Way, called “Captain Planet,” about a superhero who “teams up with young environmentalists around the world to protect the planet.” But he’s not exactly David Koepp.)
Regardless, SuperFile has plenty of true believers including Heaton, we hear. (The actress didn’t respond to a request for comment.) And in a nine-plus minute sizzle reel being presented to investors, former National Security Agency director Keith Alexander, who served under George W. Bush and Barack Obama, tells would-be backers: “I’ve met a lot of brilliant people in my career. Shane is one of the best. He’s the kind of person that can take a company like this all the way.”
For his part, Kavanaugh is still producing movies like the upcoming “Killing Satoshi,” and he pulled off something of a feat by luring an actual A-lister in Doug Liman to direct the movie about the titular, mythical Bitcoin creator as well as Oscar winner Casey Affleck and “SNL” alum Pete Davidson to star. (Valdez is a producer on “Killing Satoshi” as well.)
As an investor, Kavanaugh became a cryptocurrency proponent after Relativity’s demise, which has kept him living large long after the Relativity heyday was behind him. And even the Kavanaugh skeptics have to give him credit for getting on that train early.
Ultimately, Valdez says SuperFile shows great potential in Hollywood, where leaks and piracy are commonplace.
“This is the moment it all changes for how your script, your song or your content,” Valdez tells us. “You don’t have to say ‘don’t share this’ anymore. You can just send it and share with confidence, knowing it stays controlled, traceable and yours wherever it goes.”
As for the pitch deck that was leaked to us, we suddenly were unable to access it from our computer hours after reaching out to Valdez and Kavanaugh — a sign that perhaps SuperFile works as advertised.
