Monday, October 02, 2023  |


Triller Boss Ryan Kavanaugh, Ex Hollywood Honcho, On What’s Missing From Boxing, Why Jake Paul Rocks, And Mike Tyson’s Appeal

Fighters Network

I can only imagine what it must feel like for pro boxers, guys and gals who started out at age seven, kept at it, rose through the amateur ranks, turned pro, dealt with the physical hits and the political and business annoyances, soldiered on to a place where they are looking at getting a title shot and making some decent money….and in comes this YouTuber who picked up boxing as a side hustle ten months ago, and is now headlining a pay per view. Yes, Jake Paul is not universally adored by those in the pugilism profession who are climbing the ranks the time-honored way, without first having become famous in the strange way some folks become celebs in this age of social media.

Teofimo Lopez has ranted a good bit about this Tuber takeover, and it’s clear that he’d be happy if the Jake and Logan Pauls, and the other IG attractions swerved out of the boxing lane, and got back into their own. But Teofimo is not probably going to get his wish, not for a spell, anyway. Jake Paul is headlining a PPV, on April 17th, and he’s the A side, while Ben Askren, the ex UFC practitioner, is relegated to B-side status.


If you are reading this, chances are good that you watched the last PPV event put out by the people formulating the Jake Paul-Ben Askren event, which featured the comeback of Mike Tyson, of sorts, against Roy Jones Jr.

Mike Tyson fought Roy Jones on Npv. 28, 2020 in an exhibition promoted by Triller.

People seemed to be entertained by this exhibition, but I heard more people commenting that night and days after on Snoop’s humor and the Jake Paul KO than about how stellar Tyson looked.

That battle and promotion also drew scorn from plenty of barb tossers, who didn’t understand the appeal of pitting a 53 year old who hadn’t fought since 2005, except against personal demons, against a 51 year old foe who retired from the ring in 2018, after a slow and sad skills slide.

The appeal was apparent to the crafters of the concept, and it’s this–boxing is sports entertainment.

And what is deemed “entertaining” is a wholly different animal today as opposed to ten, twenty, thirty years ago. Hell, even five years ago.

Tyson pulled the sled in promoting his Nov. 28 comeback. That was actually an exhibition, which went eight rounds and featured maybe 5% of the magnetic Tyson ferocity which made him a legit sensation in the mid 80s, and made it so he’s still a relevant public figure 35 years later. The ferocity, as well as–and this is huge–his personality.

Tyson is part train-wreck, part Plato, and the numbers for Tyson-Jones proved that people were still entranced enough by his persona to pony up $50 to satisfy their curiosity. They ponied up, and in the meantime, while waiting to see if Tyson could do to a human being what he did to the coaches’ pads in that 8 second video snippet which excited nostalgists, they learned what Triller is.

Triller, according to the text at the bottom of the release announcing the April 17 event, “is an AI-driven music and social media experience bringing together creators, artists, and brands around the world. Powered by the motto “You Do You,” Triller allows users to create and share videos in mere seconds, backing them with custom music tracks using Mashtraxx editing technology. Celebrities like Alicia Keys, Cardi B, Chance the Rapper, Marshmello, Roddy Ricch, and Eminem regularly use the app to create their own original music videos, while Triller has attracted brands such as Pepsi, Chipotle, Manscaped, Boost Mobile, and more. Triller recently was acquired by Proxima Media.”

OK, you don’t know who Roddy Ricch is, and I don’t, but that only proves that we are out of the honey spot age demo. And it proves, I think, that the people who worked with Tyson on his return to possible glory know what the hell they are doing, and best be respected for that. You maybe want to allow for the probability that this “Tuber trend” will continue to mushroom, and people not getting why it has a great chance to succeed will stay frustrated and without a clue.

Triller’s Fight Club, that’s the name of the consortium of people and entities who will see how close they can come to those Tyson numbers without Tyson being involved. I spoke to the driver-seat talent who is looking to build up this brand, a guy who has a blow-you-away history at building brands, but more so mostly in the “Hollywood” arena.


Ryan Kavanaugh, who Wikipedia was erroneously telling you as of a few weeks ago enjoys the title of president of Warner Bros. Pictures, is a 46-year-old California resident who founded Proxima Media, the controlling shareholder of Triller.

Ryan Kavanaugh did the Hollywood thing, and is now involved with the app and platform Triller, which is hosting boxing.

Keep reading to see what Kavanaugh thinks about the next Mike Tyson exhibition.

It makes some sense he’s looking to tweak the paradigm in the boxing space, because Kavanaugh got buzz producing, distributing, and/or structured financing for more than 200 films and generating more than $20 billion in worldwide box office revenue. Kavanaugh, a red-head who lists Albert Einstein as the being who has most influenced his way of thinking, along with his father Jack, had his hand in The Fast and Furious 2-6,300, Social Network, Limitless, Talladega Nights, Step Brothers, Mama Mia! and The Fighter, the 2010 Micky Ward bio-pic starring Mark Wahlberg.

On the TV side, his company refined a model where more parts of production were done in-house, and his instinct for what will resonate made for hits like MTV’s hit “Catfish” and “The Great Food Truck Race.” And Kavanaugh didn’t scoff at sports; Relativity Media which had Rogue Sports, centered on basketball, unveiled a new beefed up sports agency, with Ron Burkle’s Yucaipa Companies, in 2012. It still exists today, as Independent Sports and Entertainment.

A 2015 LA Times piece, which took a look at Kavanaugh’s coffee-spill speed-bump moments as well as his lengthy triumph parade, said that Kavanaugh “sought to rewrite the Hollywood rules of engagement.” It referred to him as one of the “movie industry’s youngest and flashiest power players,” and shared specifics on his rise. Kavanaugh started a venture capital firm in his mid-20s, and then hit Hollywood, with a “Moneyball”-like approach to choosing projects which fueled the to the moon rise of his Relativity Media. His appetite for going with his gut, after crunching numbers and data, and going against established grains, meant that his rise wasn’t parabolic. Haters smirked when it looked like Relativity was getting hammered on the ropes, and smiled when Kavanaugh stepped down as Relativity CEO in later 2016.

Sniping in media would continue, into 2018, but Kavanaugh kept on churning out ideas, cementing partnerships, and figuring out his next plays. Rivals and the envy-fueled maybe assumed that he was down, and would stay out, out of site. He was not–by May 2019, people following his arc understood that he was still in the game, but in a different arena. His new entity was named Proxima Media, and they reportedly lined up a big batch of money to produce up to 10 U.S. films in China, while acquiring a stake in a publicly traded Hong Kong studio. Kavanaugh also noted the trend-line in crypto-currency, inventing a financing tool to fund film, TV, music etc. called Proxicoin, buoyed by reported $100 million investment from investors in Hong Kong.

It’s kind of funny, three years before, Kavanaugh had said no mas, no more Hollywood for me. And now he was tiptoeing back into the film world. And boxing has that same sort of push me-pull you effect on people, I see people exiting the sport, for years, sometimes decades at a time…and then sliding back in like a DM.


By October 2019, it looked like Kavanaugh had a focal point that he was thinking worth his time to try and feed and nurture. Triller had backers believing in the mission to work on “overtaking competitor TikTok.” A release noted that “Triller has grown 500 percent organically year-over-year, with 13 million active monthly users and 60 million total downloads. You’d see, if you gauged the tone of stories on Kavanaugh, that coverage was more favorable, that there was less dart-throwing at someone who stumbled and experienced a comedown from mountainous heights. Triller seemed to be gaining buzz and market share with alignment deals with Snoop Dogg, The Weeknd, Marshmello, Lil Wayne, YoungThug, Kendrick Lamar, Pitbull, Baron Davis, Tyga, TI, and Jake Paul and, along with mega-music managers Gee Roberson, Moe Shalizi, the manager for Marshmello and founder of The Shalizi Group), Amir Cash Esmailian of XO, and Ash Pournouri, and music industry executives such as Shawn Gee, Anthony “Top Dawg” Tiffith, Abe Burns and James Prince.

Security concerns about TikTok helped Triller get runoff business during the summer of 2020, and Kavanaugh started getting ink for this business rebound endeavor. We see “ourselves as the adult version (of TikTok),” he told CNBC in August 2020. “We look at [TikTok] like a stepping stone to Triller,” he said, noting that the app’s content is “a little more risque” and speaking to an older crowd than the TikTok demo. And to a younger crowd–my 10 year old saw a meme announcing that influencer Charli D’Amelio had hooked on with Triller. Mainstream media noticed–in October of 2020, stories on Kavanaugh and Triller appeared in the NY Times, Wall St Journal and Fast Company magazine.

People who had watched Kavanaugh’s ups and then his drop wondered if he wasn’t driving too fast down an unfamiliar lane, though. Whispers ricocheted at the announcement of the decision to put off the Tyson-Triller marriage, originally to unfold Sept. 28. The shift proved sage. The new date for the promotion would be Nov. 28, giving more time to make sure the production went off seamlessly. Tyson had teased he’d be making some sort of ring return, his quick video hits got people born after he had his last fight, in 2005, intrigued. On July 23, he announced “I. AM. BACK.”

Tyson would be back, with new G partners. Triller was in, OGs like Don King were not in the mix for this comeback foray.

There were hurrahs and hoots, too, and it was no sure thing that Triller would do this from-left field marketing foray and not be left with some egg on face. Yes, Tyson had morphed into an OG pugilosopher, but he was and is still the type to speak his peace. And in this age words can get someone in the deep manure pile.

Fast forward to Nov. 28–it became apparent pretty soon after the Triller event started streaming that this would probably work. The event proceeded smoothly, and the tone was right. There was irreverence in the mix, and the hype wasn’t over-board, on air talent didn’t tell watchers that Tyson would be a threat to the Anthony Joshuas and Tyson Furys by late 2021.

The numbers told Kavanaugh and Bobby Sarnevelsht, executive chairman and co-owner of Triller, who was a developer at IBM, and suceeded in real estate and then health care, that they’d succeeded. Revenue rolled in and the buzz spread couldn’t be calculated. Brands that came on board to let some Snoop smoke seep into their persona didn’t regret the choice.

Snoop wants to spark interest in the Triller Fight Club events moving forward.

And so Kavanaugh didn’t regret the play. That seemed to be one message for the taking when we heard that a guy who stole the show for many watchers Nov. 28, Jake Paul, who took a piece of the chin and soul of ex NBAer Nate Robinson, would headline the next Triller boxing event.

Jake Paul would fight Askren…and no, Tyson wasn’t going to be in that mix.

Ryan Kavanaugh offered up solid depth and detail why Team Triller is going deeper into the fight scene sans Tyson in a recent 45 minute Zoom chat.

After we compared some notes on pandemic era existence, on how to juggle work and family and kids running into the Zoom cam space, Kavanaugh told me his thinking on the reason for getting into boxing.


“The sport as a whole hasn’t really evolved,” he said. “The right prescription forward hasn’t been done.” He thought that by melding fighting, and music and fashion, and trying to change the energy, he could offer an alternative that would acknowledge how much the world has changed since everyone knew who “The Greatest” was.

“Boxing kept shrinking, shrinking, shrinking, into such a narrow niche. But, at the end of the day, it’s entertainment. And I’d see fights, and wonder, why is the world not watching? Because boxing looked like it did yesterday!” And he knew he could bring some of his film experience into this sphere. “I wanted to film it like a movie,” he continued. And he thought he could more so present it as a “four-quadrant” attractant, something that would appeal to both males and females, and people over 25 and crucially, those under 25 as well.

Knowing that more explicitly, now maybe you better understand why a Jake Paul might be tapped as a headliner, because you likely understand the width of his appeal. (Or anti-appeal, Kavanaugh knows that the $50 from someone who has a crush on Jake, or wants to see him get his teeth knocked out spends the same.) “And I wanted to make it fun.”

Another thing to know about Kavanaugh, and how he came to this pugilism place. “I didn’t want people to think I’m here to compete with well known purist promoters,” he said. “We can co exist. I actually hope we help other promoters.”

And looking back at the Nov. 28 night of fights and Snoop Dogg comedy, Kavanaugh noted that the Jake Paul KO resonated heavily.

“He stole the show,” Kavanaugh told me. “He did. He brought youth to the event.” Partners, like WeedMaps, were pleased with the breadth of the makeup of watchers. DraftKings, too, saw a moonshot surge in interest, visits and signups, from the Triller/Tyson offering. Kavanaugh was told that partners were getting buzz bumps like they’d get from a Super Bowl spot, in fact. The tech people told him that the Tyson on Triller click through rate was ludicrously high, as compared to norms, that about 10% of people looking at an ad clicked it.

So, we’ll see more of these, then. Kavanaugh wants to have every show set up like a movie set, and to have a different visionary “direct” each event. He is not interested in opening it up and selling tix, because that means they’d have to serve a couple masters. On April 17, if you watch the six matches you’ll see more camera coverage, which is possible because there’s no worry of fans telling the camera guy to get down.

You will notice also that the last one got centered on Tyson’s comeback to the space. This time, marketing will more so center on the fight. And if anyone who followed the Kavanaugh Hollywood chapters is wondering how sure of himself is with this play…”If I was certain this is a sure thing, I would go in a lot bigger,” he allowed. He likes his chances for succeeding, though partly because, “I’m coming at it not knowing what I’m not allowed to do.”

He foresees four Triller boxing events in 2021, he told me. We then discussed how “this” space got more crowded, how the success of the Tyson exhibition bred others thinking they could succeed similarly. The Fanmio/Floyd Mayweather deal, he told me, didn’t surprise him. Mayweather was to fight on Feb. 23, taking on Logan Paul, the older brother of Jake Paul. Fanmio, which is a web-based platform which offers virtual meet n greets with people like Gaten Mattarazo of “Stranger Things” and Zachary Levi from “Shaazam,” and Mayweather, was to put the show together.

Fanmio is still selling the Mayweather PPV even though no re-set date has been set or announced.

One Solomon Engel is the Fanmio helmer and he said that he wanted to build up something beyond a one off. Tickets to watch the Mayweather exhibition versus Logan, who would probably be out weighing “Money” by up to 40 pounds, were put on sale. A gimmick, which saw the PPV price rise notably after ticket sales surged, meant that someone could could pay $24.99, but after the planners say they sold 1 million PPVs, their friend would be charged $39.99. The next tier is $59.99, and right now, the Fanmio website is charging $59.99. Yes, that means Fanmio is saying they’d received two million orders for the Mayweather-Logan Paul exhibition. Starting Feb. 11 the PPV price would be $79.99, and the website still indicates that the fight is on track to happen Feb. 20. On Feb. 2, word dropped that the Feb. 23 promotion was being postponed, and it would be re scheduled.

Kavanaugh has kept his eye on how that all is progressing. He knows that some people might lump all exhibitions together. “It does concern me,” he said. “Fanmio is a website, with some kids from “Stranger Things” available for meet ‘n’ greets. It’s smoke ‘n’ mirrors,” he asserted. “There’s not even an app.” He didn’t seem to think that it will play out that the Fanmio/Floyd event will be able to be re-set successfully. “Maybe if Al Haymon takes it over.”


And speaking of the changing of plans and such…Kavanaugh surely did contemplate, after the Nov. 28 event finished, what the next one might look like. But did his conception of the the next one change when Mike Tyson did his post-fight press conference? When Tyson told people that he was happy that he went the distance, and that he’d blew spliff before fighting, and this was who he was now, he was no longer the snarling human pit bull, who’d leap on a foe and seek to bludgeon them into submission?

Discussions with Tyson certainly proceeded with Kavanaugh and company after the Nov. 28 success. Evander Holyfield has been discussed as the foe for Tyson’s second exhibition. But terms would have to be hashed out. The first one had been a success, yes, from several metric points. But Kavanaugh knew that some of the reasons that people tuned in to the first exhibition wouldn’t be present leading into the second one. And that a certain number of people who watched the first exhibition had certain expectations, of a degree of intensity on display from Tyson. And plenty came away comprehending that yeah, it’s real hard to turn back the clock, that the ingredients for making a dynamo of assaultive splendor, at age 20, reduce as decades pass.

“The fight wasn’t a KO, there wasn’t any blood, there was no winner,” remarked Kavanaugh. And yes, there would be interest in Tyson v Holyfield as an exhibition, but the price has to work. “Triller does have first and last look at all Mike Tyson fights, and we’ll look at them as they come.”

Kavanaugh to me is talking smart business, and not getting swept up in the Tyson of today narrative. “People watched to see the Tyson from back in the day, and they didn’t see that crazed intensity. And I don’t know that you’ll see that again, that old Mike Tyson. And that’s not what fighting is about. People want to see that passion and heart!”

The debate will continue, as long as the Paul brothers are plying this side-hustle trade. It arose on a recent “I AM ATHLETE” podcast. The pod is co-hosted by Brandon Marshall (36 years old ex NFL wide receiver who made the Pro Bowl six times), who might be dismissed by some as being a deluded fool, being that he said he wants to face off with Deontay Wilder despite never having had a single damn fight, amateur or pro. But he had Jake Paul on, and asked him what his skill-set is.

“YouTube is one of the hardest things in the world,” Jake Paul responded. “It’s work ethic, marketing, creativity and being entertaining. I made a new video every day for 300 days straight. You have to get people coming back every day. You can only name a few of us, because we’re actually talented and dedicated.” YouTube is actually harder than boxing, the 24 year old Paul continued.

“There’s a lot of fighters who aren’t happy with your position in boxing,” Marshall said. “Are you helping or hurting the sport?”

“Boxing saved me in a lot of ways,” said Paul. “Mentally, I was lost and boxing helped me find a purpose. I think it’s positive that I’m taking my audience and showing boxing to them.” His audience, by the way, includes 14.6M followers on Instagram and 20.3M suscribers on YouTube.

More people know who these two are than they do the top ten pound for pound active boxers.

“This is the way now,” said Marshall in agreement. “The bravado and the entertainment, that’s what sells. If you play in the NFL, you get paid regardless of what team you’re on or how they do financially. It’s different in boxing!”

If you check out the Paul IG, you’ll see his default pose features a middle finger flip. I don’t know about you, but that resonates with me. The way the world is, all the bullshit that’s out there, I’m sorta with Jake Paul. So, he’s tapping into an emotional zone that is where about 150M American adults reside. It’s a wide and deep pool. Add to that, you maybe think his antics are buffoonish and shallow. But he’s savvy, he gets what works now, how many younger people think and what they want to see and respond to. The kid is canny, I offer. Know what two accounts he follows on Instagram? His own management company, so he can field offers, and Triller. There’s no room for sentiment, beyond focus on making opportunitities and money, and it shows a singular focus. Yes, it’s a narrow type of savvy, it’s not implied that he’s looking to be a great role model or save some portion of the world. It’s limited, but honest.

I’m in the Kavanaugh camp here, and not in the purist camp. I will say to people who bemoan “YouTuber” fights featuring neophytes lacking in form and technique, “You ever see how the place comes alive when on the rink two hockey players drop the gloves and flail away? How is their form? People respond to the passion and the fury.”

And people responded when Jake Paul came out and showed those attributes against Nate Robinson on Nov. 28. In pro boxing today, powers aren’t “wrong” when they back fighters who possess superlative technique. But they don’t always understand that it comes off like watching physical chess when a Shakur Stevenson or whoever dissects his opponent, and out-boxes the man in dominant fashion. The key word is “out-boxes.” The issue is, for too many portions of too many rounds, in too many fights, people might tune in to see a fight, and instead they see a display of technical superiority. They tuned in to watch a FIGHT! So a relative shitload of people tuned in to watch Caleb Plant beat Caleb Truax last weekend, on a PBC on Fox offering. How many of those people are newbies who might have said, yeah, OK, Plant is good, but what’s new on Netflix? Where is the fury and fire and killer instinct?

Kavanaugh gets that.

That’s why I wouldn’t think to dismiss his Triller Fight Club out of hand, or be one who craves seeing his plan brought to the altar built and maintained by purists, and sacrificed in the name of the sanctity of the sport. That adherence to old school “values” mindset, refusing to adapt to the times and the tastes of rising generations, can and does lead to increasing irrelevance and a slow slide to extinction.