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Trump, Triller, and the return of Ryan Kavanaugh

After billionaire status and bankruptcy, Ryan Kavanaugh is seeking a new path to moguldom with Triller, the dark horse TikTok rival endorsed by the Trumps.

Trump, Triller, and the return of Ryan Kavanaugh
(Left to right) Steven Mnuchin, Ryan Kavanaugh, and Donald Trump. [Photo: Graeme Jennings-Pool/Getty Images (Mnuchin); Jason LaVeris/FilmMagic via Getty Images (Kavanaugh); Nicholas Kamm/AFP via Getty Images (Trump)]
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Teenage fans of the addictive short-form video genre probably have never heard of Ryan Kavanaugh, the onetime Hollywood bad boy now back in the limelight thanks to his ownership of Triller, a video sharing app with a long-shot chance to dethrone TikTok, its more popular rival. The jockeying for young eyeballs between the two companies has mostly taken a backseat to Donald Trump’s lunatic efforts to pry TikTok’s user data from the hands of its Chinese owners. But Kavanaugh is well known around Los Angeles for his own Trumpian exploits—and a similar flair for salesmanship.

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“We call ourselves the new MTV,” he says earnestly, when we spoke on a recent autumn afternoon.

Kavanaugh made his name with Relativity Media, the entertainment company he founded in 2004, which claimed to use sophisticated algorithms — the “Monte Carlo method,” in the parlance of Wall Street — to take the risk out of film financing. It was a seductive pitch, and Kavanaugh sold it with infectious energy, even when Relativity was losing gobs of money. (The Zach Galifianakis and Kristen Wiig heist-comedy Masterminds, for instance, earned hardly a tenth of the $125.4 million that the studio predicted.) An increasingly lavish lifestyle was also part of the marketing: in 2011, Variety named him Showman of the Year, and in 2013 he landed on the Forbes billionaires list. For years, Kavanaugh remained always one step ahead of his creditors — right up until the moment that Relativity Media declared bankruptcy (twice).

Of course, no one loves a redemption story more than Hollywood, and Kavanaugh’s might be a fitting capstone to this terribly twisted year. When Kavanaugh and his partner at Proxima Media, Bobby Sarnevesht, took a majority stake in Triller in 2019, lawmakers were just beginning to raise national security concerns about TikTok’s Chinese parent company, ByteDance. Now, Triller and Kavanaugh stand to benefit, at least on a paper, from a perfect storm of booming tech valuations, SPAC mania, and Trump’s ongoing efforts to ban or to force a sale of TikTok.

Equally covetable is Triller’s growing user base of 15- to 27-year-olds, a demographic that corporate America is desperate to reach and that Kavanaugh says is Triller’s target audience. “Brands all want to be there,” Kavanaugh tells me with his relentless manic energy. “You can’t really market to them.” But there they are on Triller, getting paid to post zany videos, lip-syncing and dancing and marketing Red Bull to one another.

Kavanaugh tries some modesty — “I just like to stay way under the radar,” he says — but he’s pretty giddy about Triller. Constitutionally incapable of not seeking the spotlight, Kavanaugh has recently been on CNBC talking up Triller and boasted to The New York Times about poaching social media stars with seven-figure deals; Sarnevesht, who serves as executive chairman and runs the day-to-day with CEO Mike Lu, has launched a Twitter campaign to hammer TikTok as “an arm of the Chinese government.” When I called Kavanaugh at home, in Southern California, he was eager to show me how Triller works on his new Galaxy Z Flip. Even with the occasional demonstration glitches, Triller looks and feels like another win for Kavanaugh, hyperbole and all.

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Kavanaugh understands as well as anyone that if TikTok fails, Triller has a better chance of succeeding. “Protect your family and our country do not use #tiktok,” Kavanaugh tweeted last year, shortly after he and Sarnevesht bought into Triller as part of a $28 million capital raise at a $130 million valuation. (Bytedance, TikTok’s parent company, has denied that it sends user data back to China.) Triller got lucky in June, when India banned TikTok, leading to a surge in Triller downloads there, and again in July when Trump began his anti-TikTok rampage.

Nowadays, Kavanaugh says, Triller is up to 231 million downloads worldwide and has 65 million active monthly users. (The monthly user number is a matter of some dispute. Earlier this month, Business Insider cited six former employees who asserted Triller’s user numbers were wildly inflated — a charge Triller denied.) TikTok, by comparison, has been downloaded more than two billion times globally and has about 100 million monthly users in the U.S.

But investors can appreciate an underdog. There has been another round of equity raised at a $250 million valuation, and now Kavanaugh and his bankers at UBS are finishing up one more — for $250 million at a $1.25 billion valuation — rumored to be led by Ron Burkle, the billionaire supermarket magnate who knows Kavanaugh from the old Relativity Media days. A source close to the company says that Proxima has invested more than $150 million in Triller, with help from Taiwan’s Fubon Financial Holding and Indonesia’s GDP Venture. Other investors include Pegasus Tech Ventures and music stars Snoop Dogg, The Weeknd, Lil’ Wayne, Rowdy Rich, Maverick, and G. Robertson. (Triller has also teamed up with Centricus, a London-based investment firm, to make a long-shot bid for TikTok, though a ByteDance spokesman characterized it as an unsolicited inquiry.)

Kavanaugh is also fielding calls from Wall Street dealmakers who want to buy Triller and take it public by merging it into a special purpose acquisition company, Wall Street’s latest craze, known as SPACs. According to a source familiar with the conversations, Triller has had nine SPAC offers and is seriously pursuing five of them. One of the calls Kavanaugh has been fielding from the SPAC community, the source shares, is from former House speaker Paul Ryan, who has just closed on a $360 million blank-check company of his own. (Ryan did not respond to a request for comment.)

To hear Kavanaugh tell the tale, it’s Proxima’s ability to find unique opportunities that others might overlook that made his investment in Triller possible. He says Triller began as “utility tool” for musicians who didn’t want to go into a studio every time they wanted to make a music video. “There’s not a huge market for that,” he says. But he notes that Triller’s “roots are in music” and its founders smartly cut streaming deals with Sony, Warner, and Universal for access to “90-plus percent of the world’s music.” Triller raised a seed round of $4.5 million in May 2016 and then another $5 million from Carnegie Technologies, in February 2018.

“It’s the very first social app that we [say] ‘completes the circle,'” Kavanaugh explains. “The audience gets access to music that they otherwise wouldn’t have to use and share and influence. The artists, managers, labels, they get paid.” He says The Weekend put his album out exclusively on Triller and got 109 million views. “Not only is there money,” he trills, “but it’s a place where a lot of people go to interact with their favorite artists in a very raw format.”

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Trump’s video pissed off some Triller employees. Five of them quit when Kavanaugh wouldn’t remove it, but Kavanaugh was unapologetic.

For all Kavanaugh’s hustle, it was probably Donald Trump’s TikTok fight that put Triller on its higher trajectory. Soon after Proxima invested in Triller, “out of the blue,” Kavanaugh says, “we woke up to Trump doing a MAGA challenge on Triller.” The idea, apparently, was to get Triller users to post MAGA-related videos, with the winner invited to the White House. Soon after, Kavanaugh placed a call to Steven Mnuchin, the Treasury Secretary and onetime co-chairman of Relativity Media. According to a well-informed source, Kavanaugh told Mnuchin it was a pretty big deal that Trump had posted to Triller but that he wished Mnuchin had given him a heads up. They had forged a close bond, after all, during Relativity’s highly litigated collapse. But Mnuchin didn’t take the bait. He told Kavanaugh he would connect him with the White House communications team. (Secretary Mnuchin did not respond to a request for comment.)

Trump’s video pissed off some Triller employees. Five of them quit when Kavanaugh wouldn’t remove it, but Kavanaugh, until recently a regular GOP donor, was unapologetic. “We can’t just cut someone off if we don’t like them,” he told the Triller staff. Meanwhile, the Trumps were finding new reasons to love Triller. When it was reported that the president’s June rally in Tulsa, Oklahoma, had been undermined by TikTok users reserving tickets they never intended to use, Donald Trump Jr. began posting videos to Triller extolling its virtues as a TikTok alternative. Triller, Don Jr. said, would not “weaponize” user data.

According to the well-informed source, Kavanaugh called Mnuchin again, this time offering to share with the Treasury Secretary what he knew about TikTok. “It’s really, really, really scary what they actually can do,” Kavanaugh says. But Mnuchin didn’t want to hear it. Once again, Kavanaugh had to reassure his employees that Triller was not taking sides in the political battle, even though Triller stood to benefit from TikTok’s woes. “As long as they are not doing anything that hurts people, we allow freedom of expression,” Kavanaugh reminded the Triller troops, who now number more than 300 worldwide. This time, none of them quit.

Regardless of what happens to TikTok — if it’s shut down, or sold, or whatever — Kavanaugh only sees upside. If TikTok is sold or goes public at a distressed price — say, $60 billion, from the $75 billion it’s currently valued at — “that’s a great mark for us,” he says. Even if Triller is worth only 10% of TikTok, that’s still $6 billion. And if TikTok gets banned? “More people come to us,” he continues. “Either way, we’re kind of a win-win out of the scenario.”

Does this mean that Ryan Kavanaugh is on a return path to billionaire status? Does making 12.5x his money on paper in a year make him a player again? He admits he’s been lucky with Triller, and that the investment remains illiquid (unless someone like Paul Ryan can negotiate his exit). But at 45 years old, Kavanaugh is taking the longer view. He has two young children and is presumably wiser than he was in his hard partying heyday. And he’s cautiously optimistic. “I’ve had ups and downs and lefts and rights,” he says. “On this one, I just wanted to be stable.”


William D. Cohan is a journalist and author of six books, including his latest, Four Friends: Promising Lives Cut Short.