This should be Vice’s moment. We have a narcissistic fabulist in the White House. There’s rioting in the streets. The nation is the world leader in coronavirus. The country is mired in a deep recession. The rich keep getting richer, and the poor are getting poorer. The Black Lives Matter movement has never been more potent. California and Oregon are burning up. And there is a presidential election coming up in a matter of days that may or may not determine the fate of the world’s oldest democracy. If ever there were a confluence of momentous events that screamed, “This moment is made for Vice Media!,” in all its edgy millennial-ness, this would be it.

And yet, what is the most popular show on Vice TV? Why, it’s Dark Side of the Ring, a docuseries about seminal moments in the history of pro wrestling. The Season Two finale, aired May 19, analyzed the bizarre death of Owen Hart, who fell 80 feet inside a wrestling ring. The episode got the biggest audience yet—626,000 viewers, including 390,000 of desired 18–49 types.

Then, this week, Vice News had a scoop that broke through on Twitter: Jeff Toobin, a New Yorker writer and CNN commentator, reportedly masturbated in front of his colleagues on a Zoom meeting. (He was suspended by The New Yorker and is on leave from CNN.)

Standing by: Gavin McInnes, one of the three founders of Vice, attends an alt-right protest in New York, 2017.

To think that just three years ago Vice News, then on HBO, brought us Elle Reeve’s mesmerizing 22-minute, behind-the-scenes march with white supremacists—of “Jews will not replace us!” infamy—through Charlottesville. For that reporting, Reeve won a Peabody Award, as did Vice News Tonight. Nowadays, Reeve has moved on to CNN, and HBO has moved on from Vice News. They are not the only ones who have left. The talent loss inside the company has been epic: Josh Tyrangiel, the former editor of Bloomberg Businessweek who was brought in to run Vice News Tonight, now heads up documentary filmmaking at Eden Productions, the five-year partnership between Apple TV and former HBO head Richard Plepler. Derek Mead, the editor in chief of Vice Media, left in June. Respected journalists such as Kim Kelly, Matt Taylor, Lauren Oyler, Callie Beusman, and Claire Ward have all joined the Vice diaspora; even the irreverent comedy duo Desus & Mero have split. In the past three years, Vice’s workforce has shrunk from 3,000 to about 2,000.

Most notable among the employee turnover, however, is Shane Smith, Vice’s larger-than-life co-founder who, back in the day, was known to have spent $300,000 on a board-of-directors dinner at the Bellagio, in Las Vegas. (In fairness, he had reportedly won $1 million in the week prior, gambling, with particular success coming at the blackjack tables.) He resigned from the day-to-day management of the company after The New York Times revealed in December 2017 allegations about the sexist, misogynist side of the company’s culture. Shocker: some of Smith’s bros found themselves accused of harassment and racial bias after having filled Vice with young, attractive women. By the time he left, though, Smith had already pulled many of his millions out of Vice and decamped to Los Angeles, where he and his wife, Tamyka, restored a sprawling Santa Monica estate that had been featured in the shoot-out scene in Beverly Hills Cop. Smith bought it sight unseen for $23 million (for perspective, a staff writer at Vice earns $57,000 a year, according to Glassdoor), and in 2016 he let The Wall Street Journal inside to visit with him, Tamyka, and their two children. These days, Smith keeps a lower profile but can at times be spotted driving around Beverly Hills in a huge, white-on-white Rolls-Royce Phantom convertible.

If ever there were a confluence of momentous events that virtually screamed, “This moment is made for Vice Media!,” in all its edgy millennial-ness, this would be it.

The fact is you won’t hear much from Smith these days. After Vice’s spin through the #MeToo movement, he’s gone silent. (He declined repeated requests to be interviewed.) Officially, he’s Vice’s executive chairman of the board of directors and the only time you’ll hear from him is if you watch Shelter in Place, a Vice TV show where Smith “chats” with “experts, thought leaders and political figures.” Yet it’s Smith whom many people would no doubt like to chat with, and ask him a few questions. Such as: Was your long tenure as head of Vice just a case of insane hubris—like that of Adam Neumann’s at WeWork? Or will your actions bring down the house of cards that Vice seems to be?

Smoke and Mirrors

After being perceived as the red-hot center of Millennial-based media culture for the past decade or so, Vice’s place is harder to pinpoint now. Some of it is still edgy and provocative. But increasingly the impact of its work feels more like the proverbial trees falling in the forest. On top of that, there is the brain drain, along with the ongoing existential advertising crisis across much of digital media—all of which has many investors wondering what the deal is with Vice these days.

The answer depends on whom you ask. Top executives at Vice tell you the present is pretty damn fabulous, while the best is yet to come. Former employees—or at least those willing to speak out despite confidentiality provisions in their contracts—say Vice is an unmitigated disaster and it’s only a matter of time before TPG, its private-equity overlord (TPG also has a stake in Air Mail), takes control of the company and tries to salvage what it can of its $450 million preferred-stock investment, made in June 2017 at an ungodly valuation of $5.7 billion. In short, Vice has become the ultimate Rorschach test. And that makes Vice utterly au courant in the Late Trump Era of closed minds and hardened positions.

Trophy days: Smith (third from left) celebrates at the 2014 Emmys.

Those who remain at Vice—it claims to be the world’s largest youth-media company, reaching 390 million people a month—now work in five business lines. There’s a so-called digital business that produces 1,700 pieces of content a day—Snapchat, TikTok, Facebook, and YouTube videos, plus written editorials—for and affiliated sites in 35 countries around the world. It is supported, as best as can be expected these days, by digital advertising and content production. There is a nightly news program, formerly on HBO, that is now on its own streaming channel, Vice TV, and a weekly docuseries on Showtime. The fully distributed cable-television channel has more than 30 million monthly viewers and is distributed in France, Australia, and the U.K. Its fourth business line, Vice Studios and Pulse Films, produces feature-length films such as The Report, about U.S. torture policies in Iraq, which starred Adam Driver. The unit also makes commercials, including the Emmy-nominated ad “Bounce,” for Apple AirPods. Vice’s fifth line of business is Virtue, an ad agency, which does work for Cholula Hot Sauce, among others.

After Smith got drummed out, however, it fell to an adult to clean up the stinking mess the boys had made in the frat house. In this case, Nancy Dubuc, a gifted TV hand who spent five years as the C.E.O. of A&E networks. She took the top job in March 2018. No surprise, Dubuc is an ardent believer in Vice.

“Vice has never been more needed,” she tells me. “You’re dealing with a cultural revolution, a generational reckoning. This should be our Super Bowl moment.” Dubuc knows Vice well, thanks to her time at A&E. In August 2014, it made a $250 million investment in Vice, at a $2.5 billion valuation, and she was A&E’s representative on the Vice board of directors. In November 2015, A&E agreed to let Vice take over its H2 channel and to relaunch it as Viceland, now Vice TV. The long-suffering Vice investors tapped her for the top job, hoping she could turn things around. “I thought it was a great opportunity,” she says. “I love the brand.”

Was Smith’s long tenure as head of Vice just a case of insane hubris—like that of Adam Neumann’s at WeWork? Or will his actions bring down the house of cards that Vice seems to be?

Dubuc joined at a difficult moment in Vice’s history. The December 2017 New York Times exposé revealed Smith’s Vice to be home to a nearly out-of-control bad-boy culture, rife with allegations of sexual harassment and defamation. There were four settlements between women and Vice, and “more than two dozen other women” told the Times they had “experienced or witnessed” episodes of “unwanted kisses, groping, lewd remarks and propositions for sex.” Dubuc said she went into Vice with her “eyes wide open. I knew it would be a transformation, first and foremost. I was not under any illusion that I was going to walk in and the job would be done. I said often I took the harder job for less pay, and I’m fully aware of that.”

Rising from Smoke and Mirrors …

By now, the Vice origin story has been fully burnished. It was founded in 1994 in Montreal as a counterculture magazine by Smith and two partners, Suroosh Alvi and Gavin McInnes, who bluffed their way from one opportunity to the next. (Vice is a “company built on a bluff,” proclaimed New York magazine in a 2018 profile.) There was the seminal 1999 move to office space on West 27th Street, in Manhattan, complete with 25 employees and espresso machines. But that chapter quickly ended in tears during the bursting of the dot-com bubble, when the money of the company’s main investor evaporated. There was the move thereafter to a loft in Williamsburg, Brooklyn, and a return to a shoestring budget. In 2006, Vice sought to diversify, starting Virtue to provide creative content to brands hoping to reach a younger audience. The next year, thanks to a $2 million investment by Viacom (later bought back), Vice started, an early version of a digital-video Web site.

In the major-league-bluff department was Smith’s head fake in 2010 that convinced Intel to give Vice $25 million to create branded content that would help promote Intel’s chips in a different way. According to New York, which reported the story, Smith was determined to fool Intel executives into thinking Vice was more substantive than it truly was, so he convinced the architecture firm across the hall from Vice to leave their offices. Vice’s 50 employees then zipped in and created a Potemkin village of Brooklyn hipness that impressed the Intel executives sufficiently to hand over the money.

The bluff became the Vice paradigm. “When you look at the supernova rise of it, you can’t overstate the impact that Shane had, not just on Vice, but on digital media as a whole,” says one former Vice executive. “I do believe that billions of dollars were raised off his argument that this is obviously young people running away from MTV. They’re running away from linear and they’re all going to go to digital. This was the future.” Smith, he continues, was really good “at scaring the hell out of the legacy players” and at making “this phenomenal argument that basically Vice represented the young people, who were going to tear down the walls, and unless you got in bed with Vice, you were going to lose your entire market share with young people.”

After Smith got drummed out, however, it fell to an adult to clean up the stinking mess the boys had made in the frat house. In this case, Nancy Dubuc.

As digital media gained prominence, old-line media executives were freaking out; Smith played them. Indeed, he had an almost preternatural gift for being able to sell baby-boomer media executives on the notion that only he could connect them with the oh-so-coveted millennial viewers. In 2012, Rupert Murdoch invested $70 million in Vice at a valuation of around $1 billion. In 2014, A&E and TCV, a Silicon Valley venture-capital firm, invested $250 million each at a $2.5 billion valuation. Such was Smith’s prowess that, in 2015, he got Disney—with its mostly deserved reputation for wholesome content—to invest $400 million in Vice at a valuation of between $4 billion and $4.5 billion, including the investment it already had in Vice through its stake in A&E.

Over and over, Smith told his investors the Big Payday was coming. But it never did. “Shane was extremely good at doing deals and really comfortable there,” the former executive says. “Back in the day, he would do print-magazine deals with Converse, and then he graduated to digital deals. Then he graduated to the Intel and Unilever deals. Then he graduated to the investment deals, TV deals, film deals. He is a phenomenal deal-maker. He balks. He connives. He plots. He takes a deal. He goes back out, shops it around to other people. He’s really good at it.”

One Step Ahead of the Sheriff?

From the outset, Smith was about getting out one step ahead of the sheriff. Or Disney, News Corp, and TPG. The plan, according to former executives, was always to raise money at higher and higher valuations and then figure out a way to sell to a larger company or to take Vice public. “The company was always kind of built to be sold,” says the former executive. “There was always a lot of speculation around what was going to happen to Vice. Would Vice go public? Would it get bought by Viacom? It was in conversations with Time Warner for an investment; maybe it could be something else. Would Vice get sold and be bought by Disney?” (According to one longtime observer, Smith turned down a rumored $5 billion offer from Disney because “it wouldn’t have made him even a billionaire.”) The problem is: What happens when the exit strategy disappears? It seems Smith thought the rules didn’t apply to him. He believed the management and operational problems that had racked Vice for years would become someone else’s problem to solve when he sold the company. That’s a great solution. Until, as one executive said, “All of a sudden no one wants to buy and you really haven’t built anything for the long haul.”

From the beginning: Suroosh Alvi, one of the co-founders of Vice.

Even still, one former Vice honcho says, there was a moment there where Vice looked like it could hit on all cylinders. “Viceland had Desus & Mero,” this person says. “Vice News Tonight was on HBO. And it was pretty clear that there was this brief window where the model forward was to make shows no one else will make.... You can be the place.”

In the major-league-bluff department was Smith’s head fake in 2010 that convinced Intel to give Vice $25 million to create branded content that would help promote Intel’s chips in a different way.

The pièce de résistance—or so it seemed at the time—was the 2017 deal Smith cut with TPG. He could have done the deal at a $4.5 billion valuation. He could have done the deal at a lower valuation than what TPG agreed to and on better terms. Instead, he got greedy, according to a former executive, and opted for the higher valuation—$5.7 billion—which came with tougher terms that included guaranteed payments of $400 million in cash and stock between 2020 and 2024 (since renegotiated by Dubuc) and a provision that TPG’s preferred stock would get paid back before any other equity holder got a payout. In other words, Smith agreed that if the valuation of Vice slipped, TPG would own more and more of the company, diluting other shareholders. “Look,” Smith told people, according to an executive, “it’s going to look bigger for us. It shows strength. Then I’ll sell it the next year.” After the TPG deal, Smith went on CNBC and started primping for an I.P.O. The TPG deal was, he said, “what we would do if we were going to go public … start building our book, and bringing in revenue on a sort of hockey-stick basis.”

Little more than a year later, however, the high, unsustainable valuation, the operational dysfunction, the searing consequences of the #MeToo scandal, the rapidly declining ad revenues for digital-media businesses, all of which had been threatening to submerge Vice, were now problems Dubuc had to confront. Says one competitor: “Savvy people always questioned how much brand value Vice really had outside of media circles, whether the Vice consumer, this sort of mythical motorcycling, tattooed, badass young-male consumer ever existed in the first place. I just don’t know how many of these so-called cool millennials really existed.” For her part, Dubuc says she’s tried to “instill some strategy behind every decision” and create a “culture of a lot more information sharing with the board.”

Changing the tune? Nancy Dubuc, the new C.E.O. of Vice Media, at the company’s headquarters.

Yet the problems have continued to mount. Speaking at the New York Times DealBook conference in November 2018, Dubuc told Andrew Ross Sorkin that Vice would be profitable in 2019. That did not happen. (Smith once boasted that, by 2016, Vice would have $450 million of EBITDA, or earnings before interest, taxes, depreciation, and amortization—an important measure of profitability on Wall Street—on $1 billion of revenue. That did not happen, either.) Dubuc tells me that Vice will be profitable—by that she means at the EBITDA line—in the fourth quarter of 2020, “barring any other bizarre pandemic situations that we aren’t foreseeing,” on more than $600 million of annual revenue. She declines to be more specific about the company’s financial picture, its valuation, or its shareholders. “That’s private information,” she says. But what’s publicly known isn’t great. When Disney completed its acquisition of 21st Century Fox, in March 2019, it inherited the $70 million stake that Rupert Murdoch had bought at a $1 billion valuation. (Murdoch reportedly was glad to be done with Vice.) Within two months, Disney wrote off the value of its $510 million stake in Vice to zero. (That’s right: zero.) That doesn’t mean Vice is worth nothing, only that Disney and its accountants probably don’t expect there to be a payback anytime soon—if ever.

There are other problems, too. Shrinking the company by a third has taken its toll on morale. There was a layoff of 250 people announced in February 2019 and another 155 people laid off in May. The May layoff was a consequence of the pandemic, Dubuc says, and of the ongoing contraction in the digital-advertising market. “I don’t know that there is a company out there, especially in media right now, that hasn’t been touched by the impact of the pandemic,” she adds.


And then there’s Refinery29. Last October, Vice agreed to acquire the digital lifestyle publisher geared toward women, in a mostly stock deal reportedly valued at around $400 million. There had been leaks about the deal for months. Refinery’s investors, including Discovery and AT&T (through its acquisition of Time Warner), traded their Refinery stock for Vice stock. The deal reportedly valued the combined companies at $4 billion, 30 percent less than Vice alone was valued in the TPG deal. (Dubuc declines to share the financial details of the transaction.) It was Dubuc’s first big strategic move, and some observers wondered why she wanted the company, especially since, like Vice, it was no longer profitable, either. “That was a Hail Mary,” says a Vice competitor. “To make moves to try to have some strategic direction. It was a weird tie-up.” One wag told the New York Post the combination was “Misogyny meets Feminism.” Dubuc anticipated the doubters. “We know some will think of the old VICE stereotypes and ask, how can the ‘bros’ ever mesh with the feminists of Refinery?” she wrote in her memo announcing the deal. She added that because of the acquisition, women would comprise more than half the Vice workforce. “And, for all of us who don’t identify in the binary,” she concluded, “our company will remain committed to celebrating gender in all its beautiful expressions.”

But the ink was barely dry on the deal when Dubuc discovered that women can be mean to women, too. In early June, Ashley Ford wrote on Twitter about her experience at Refinery29. “I worked at Refinery29 for less than nine months due to a toxic company culture where white women’s egos ruled the near non-existent editorial processes,” she wrote. “One of the founders consistently confused myself and one [of] our full-time front desk associates & pay disparity was atrocious.” Another writer, Ashley Alese Edwards, also on Twitter, described how the editor in chief of Refinery29 called her into her office and “in a very threatening tone” reprimanded her for raising concerns about an essay on immigration written by a white actress from Texas. The essay, according to Edwards, later received a wave of criticism. She wrote that her editorial concerns were routinely ignored as were efforts to win pay equity for her writers.

According to one longtime observer, Smith turned down a rumored $5 billion offer from Disney because “it wouldn’t have made him even a billionaire.”

On June 8, Christene Barberich, a co-founder of Refinery29 and its top editor, resigned. “I’ve read and taken in the raw and personal accounts of Black women and women of color regarding their experiences inside our company at Refinery29,” she posted on Instagram. “And, so I will be stepping aside.” In early July, Amy Emmerich, the site’s president and chief content officer, also resigned. Emmerich, says one competitor, was “absolutely mission-critical for that business.” In September, Refinery29 hired Simone Oliver, who has The New York Times, Allure, and Facebook on her résumé, to replace Barberich.

How did Dubuc miss the signs of the toxic work culture at Refinery29, especially given Vice’s #MeToo problems? “It was a big disappointment about the deal,” she tells me. “We did a lot of due diligence around this issue, specifically—because of our sensitivities to it…. It didn’t show up or surface through any of the background checks, through any of the H.R. files. I think that was very frustrating for us.” She says the problem arose because neither Refinery’s H.R. department nor legal teams reported to the C.E.O., a fact she has since changed. She knows she has her hands full, yet again, focusing on repairing some torn cultural fabric. Like many companies across America, she says, “we’re always going to be dealing with cultural issues.”

And in Other News

It’s not all bad news at Vice, far from it. In August, Vice News Tonight—formerly on HBO, now on Vice TV—got 18 Emmy nominations. To further argue the point that Vice still has plenty of talent despite the workforce cuts, a person close to the company says, “If you go through the Emmy nominations that we just had, all of those people are still here, and nobody who left was nominated.”

Vice lords: Rupert Murdoch and son James.

Dubuc has managed to find new money, despite the ongoing financial difficulties. In May 2019, Vice raised $250 million of debt from a consortium of hedge funds led by 23 Capital that included Fortress Investment Group, now part of SoftBank, and an investment fund related to George Soros. Dubuc declined to share the terms, but it was likely expensive, given the circumstances. It was the first capital the company had raised since the TPG investment. Then, last October, to coincide with the Refinery29 deal, James Murdoch—estranged son of Rupert—bought a small equity stake in Vice, thought to be around $25 million, at a reported $4 billion valuation. “That was favor money,” says the Vice competitor. Murdoch, who joined the Vice board, declined to be interviewed.

Disney wrote off the value of its $510 million stake in Vice to zero. (That’s right: zero.)

The catalyst for the James Murdoch investment might have been Jesse Angelo, the former C.E.O. and publisher of the New York Post, and best man at James’s wedding. In June 2019, Angelo joined Vice as president of global news and entertainment. He runs three of Vice’s five business lines: news, TV, and digital. He bleeds Vice now, too. “The corporate cadence of Vice is remarkable,” he says. “Ideas that would take three months to come to fruition at other companies go from being an idea to being launched in a week. It’s unlike any other media company on earth.” He hates the “myth,” as he calls it, that Vice has a sexist “bro” culture. “My two E.V.P.’s who run my news business and report directly to me, the two top people in my newsroom, are women of color. Finding another news organization in America that can say that, there isn’t one.” He also disputes the idea that Vice is not capturing the Zeitgeist. “If you look at what we did out of Minneapolis, out of Portland, out of the Covid moment, I would put that up against any organization on earth, and I think we come out ahead,” he says. “This narrative of ‘Oh, why isn’t Vice thriving in this moment?’ is bullshit.”

And yet, mistakes continue to be made. As the coronavirus spread in the U.S., Morgan Hertzan, a Vice executive vice president, hired Scott Galloway, the podcaster and outspoken N.Y.U. professor, and Anand Giridharadas, the MSNBC regular and best-selling author, to have their own streaming shows. Both have developed followings across a variety of media platforms for their frank views on race, privilege, and culture. It seemed the lights were still on at Vice. But when the contracted runs of both shows ended, the plug was pulled on them for different reasons: Galloway needed to reduce his workload, he says, and as for Giridharadas, his show was canceled for lack of ratings, according to a tweet he wrote that has since disappeared.

One person who has worked for Vice struggles to understand why it is so “dysfunctional”—his word. “I can’t overstate the extent to which it’s full of people who are not good at their jobs,” he continues. “You can get into race and identity and all the fancy questions. But step one is just being good at your job. No one who had a better option ended up at Vice. The decision-making was just erratic. They’re chasing relevance instead of trying to chase a philosophy that would make them relevant.”

Looming above everything else at the moment for Vice is its ongoing lack of profitability. And what that will mean for its investors and how patient they will be over time. Without profits, the bloom will be off the rose and the days of stratospheric valuations may be over. If the valuation of Vice gets near $700 million—the $250 million in debt owed to the hedge funds and TPG’s $450 million preferred-stock investment—then the real fireworks will start. Some people think we’re already there. “The question is: Will Vice be worth less than $700 million?” asks one outside observer. “And I think that’s a real possibility.” He says the valuation question is compounded by the fact that there are unlikely to be any serious buyers for Vice right now. “It’s a death spiral,” he continues. “There’s no solution. No one is going to step forward to buy it.” He says it’s likely that TPG is already thinking about how to recover its investment by taking control of the company and possibly selling it off in parts. The non-TPG investors will get wiped out because of the contractual provisions of TPG’s investment. “The company is a complete zero,” he concludes. “There’s very little positive you can say about the execution of Vice, and it’s just going to get worse. If and when TPG seizes control of the asset, they’re going to have to do a complete overhaul of the leadership, would be my guess.”

“TPG strongly supports Nancy and the entire leadership team at Vice,” says TPG spokesman Luke Barrett. “They have transitioned the company to one that is generating increasing contracted, global and diversified revenue streams. Suggestions that TPG has any plans other than our support of leadership and the company’s continued progress are totally false.”

Smith, riding high in 2013, in Vice’s Brooklyn offices.

The person who has worked with Vice has given much thought to how the company has gotten itself into such a serious financial predicament. “It is difficult to meet the tremendous journalistic burden and opportunity of this moment if you don’t know who the fuck you are,” he says. “There is a place for many different identities in this new eco-system. Vanity Fair is not The New York Times. Vanity Fair has a relationship to high society and elite culture. There’s a place for that. The New York Times is not ever going to call Donald Trump a “Fascist,” and I’m fine with that. That’s the reason it’s been there 150 years, and I trust them to do what’s right to keep the name of The New York Times. Fox News has its name, which is destroying America, but its name is clear. It knows who it is, and it knows what its purpose is. I think Vice has no spine, no soul, and no bones, and they are going to meet this extraordinary moment as a kind of pile of skin.”

William D. Cohan is a Writer at Large for AIR MAIL