On Sunday, October 9, Richard Rushfield’s phone lit up with the type of jaw-dropper that can really get Twitter going on a weekend: Nikki Finke, legendary Hollywood journalist, dead at 68.

Finke had largely been off the radar since parting ways with her self-made entertainment news website, Deadline, at the end of 2013. But her death from an unspecified “prolonged illness” was no less monumental. Gone was the mythically fearsome woman who, some two decades earlier, saw an opening in the staid landscape of Hollywood’s trade press and drove an 18-wheeler straight through it, lobbing bombs at anyone in her path.

Rushfield had a history of crossing Finke, as the furious messages in his email archives can attest. “Nikki Finke One Step Closer to Dream of Becoming World’s Worst Boss,” declared the headline of a Gawker post Rushfield wrote in 2009. As word of Finke’s demise spread across the internet, Rushfield’s “blood started rising.” Finke was a fearless trailblazer, the eulogies went, who disrupted entertainment journalism and redefined its relationship with the world it covers. Not untrue, but Rushfield saw it as revisionist history, glossing over Finke’s dark side: the toxicity, the bullying, the lies, the sheer meanness. He started belting out an article for his own Hollywood publication, a subscription newsletter called The Ankler.

“This is the story,” he wrote, “of a very troubled writer who used the megaphone of ‘journalism’ to work out her insecurities and issues in a hellstorm of performative rage, all while hiding—ailing, agoraphobic, sick—behind an online persona.… [I]f Donald Trump had been an entertainment journalist, you can see how he would have looked a lot like Nikki.” Still, Rushfield also gave Finke credit where due. “She had the imagination to create a story out of all this,” he continued. “The story of entertainment is not gray, dutiful marching towards the quarterly earnings report—it is wild, colorful characters doing completely ridiculous things, and if you can’t capture life’s rich pageant that way, then you should wonder how accurately you’re representing the true experience of an industry whose business is entertainment.”

You might say Rushfield is capturing life’s rich pageant but without Finke’s malevolence and ethically compromised behavior. The Ankler, which he started in late 2016, chronicles Hollywood in all of its naked theatricality, with a mischievous bent and a sardonic regard for the industry’s towering egos. It’s a sensibility Rushfield has nurtured for years through an array of DIY media projects, from his alternative college newspaper (The Hampshire Hypocrite) to his AOL-era email newsletter (The Barricade) to his early-aughts fanzine (L.A. Innuendo) and now The Ankler. “I seem to have a history of starting troublemaking publications,” Rushfield told me.

The Ankler is expanding as a venture-backed, Substack-hosted business, Ankler Media, for which Rushfield has joined forces with the veteran editor and executive Janice Min, who recently told me the goal is to become “a primary resource about the entertainment business for the largest audience available on a global scale.” Grand ambitions aside, Rushfield remains The Ankler’s beating heart, and his trenchant analysis is the main reason people are willing to pay for it. Which is to say, not everyone is convinced The Ankler can or should be much more than that, or that it can become a bigger player without diluting Rushfield’s boutique appeal. Depending on who you talk to, it’s either a total must-read or, well, not quite so.

Ankler Media will, of course, face hurdles in the punishing digital media economy: subscriber churn, the vagaries of advertising, ever-increasing competition for attention in a world where anyone can start a Substack, the pressures that come with taking money from venture capitalists, and so on. (Plus it’s in the same chase for high-end subscription dollars as Matthew Belloni’s influential Hollywood newsletter at fellow start-up Puck.) “Richard and Janice are world-class experts in building publications people want to read and pay for, and they have opportunities both in subscriptions and ad revenue,” said Brad Flora, the angel investor who worked with Min and Rushfield for Silicon Valley’s esteemed Y Combinator program. “That said, the word and can often be deadly for young companies. Navigating that is a tricky thing for them.”

As far as founders go, Rushfield is a curious sort—a gruff and curmudgeonly Gen X’er who wouldn’t look out of place in a film noir. He comes from an irreverent journalistic tradition and sees himself as a foil to the conventional trade press, allergic to the minutiae of carefully leaked studio announcements and agency scooplets.

He’s unique among his peers in that he built a significant brand from scratch with his bare hands, a middle-aged one-man band without the backing or support of a larger organization. He’s also the only one whose name rolls off the tongue with the same alliterative ring as the legendary columnists of yore: Walter Winchell. Hedda Hopper. Army Archerd. Richard Rushfield.

Rushfield is hardly a one-man band anymore. He and Min, who officially teamed up on Ankler Media in early 2022—Rushfield as editorial director and chief columnist; Min as CEO and editor in chief—are now part of a full-time staff of four, including a chief revenue officer and a managing editor. Those four salaries and a freelance budget are the only significant overhead. There’s no physical office, accounting and payroll are outsourced, and Substack handles the back-end tech stuff. The Ankler has enlisted a cabal of regular contributors, among them Rob Long, Peter Kiefer, Jeff Sneider, Vincent Boucher, Nicole LaPorte (Rushfield’s better half, with whom he has two elementary-school-aged kids), Sean McNulty, who writes a morning briefing called The Wakeup, and the Entertainment Strategy Guy, an anonymous data wonk who loves a good chart about the streaming wars. There are three Ankler podcasts and a budding events component. (Think gabfests, screenings, cocktail hours.) Come for the scoop on Michael Lewis’s impeccably timed Sam Bankman-Fried project; stay for the feature about the first hundred days of CAA-ICM.

As with all start-ups, Ankler Media’s finances are opaque. Last spring, after completing Y Combinator, the company raised $1.5 million at a $20 million valuation. The company says it is profitable, with about 50 percent of revenue from subscriptions and 50 percent from advertising, the type where film and television studios pay good money to woo members of the awards-voting bodies. When I spoke with Min in December, she told me The Ankler landed in 38,000 inboxes every day, but she wouldn’t specify the number of paying subscribers, who get the full shebang of content for $17 a month or $149 a year. Rushfield told me that when he moved The Ankler to Substack at the end of 2019, there were about 800 paying subscribers at $40 a year. By the end of 2022, according to Min, subscription revenue had grown by a multiple of nearly 40. (Per my back-of-the-envelope math, that would put The Ankler’s annual subscription revenue a little north of $1 million.)

“I read it the second I see it pop up,” says Richard Plepler, whose post-HBO life involves an Apple TV+ production deal. “They have a little bite, but their bite is always within the bounds of fair play. People read it, people respect it, serious people send it around.” Imagine’s Brian Grazer told me, “People in Hollywood like it. They think it’s titillating and find it largely truthful.” The Ankler’s About page boasts raves from Bret Easton Ellis and media analyst Rich Greenfield. Other satisfied customers include David Zaslav, Patrick Whitesell, Kathleen Kennedy, Donna Langley, and Maureen Dowd, who told me, “I just think Min and Rushfield are smart.”

In conversations with an array of sources, I caught some whiffs that The Ankler may not be as essential to Hollywood’s power class as it’s made out to be. “I think Richard’s excellent, but the diversification of The Ankler feels like a stretch,” said a well-placed source in the agency world who reads Rushfield and The Wakeup but ignores “all the other stuff.” A second knowledgeable agency source concurred: “I just don’t feel like it’s necessary reading. When something like [Bob Iger returning to Disney] happens, you wanna hear what Richard has to say. But the other things on The Ankler, I still haven’t figured out why I’m supposed to be reading them.” A Hollywood heavy hitter told me he subscribes because it helps him make sense of a wildly disrupted industry in a challenging market, but “on the other hand, sometimes it’s a little bit prurient, a little bit claustrophobic, and it’s not always right.” Take this for what it’s worth, but when I asked another top player for his thoughts on The Ankler, he said he couldn’t help because he doesn’t regularly read it.

Rushfield’s fans appreciate how he swims against the current. “He runs counter to groupthink in the town,” said a senior executive at a major media company. “He can be a much-needed contrarian voice.” Here was Rushfield’s take on Disney’s ouster of Bob Chapek, a move portrayed as a hastily assembled palace coup that even Iger didn’t see coming. “It’s amazing how quick a narrative has come out here. Almost like they had it ready to go: the vote of no confidence from the deputies, the sudden phone call, the summons-back to destiny. All comes together very cleanly and nicely. Everyone on the same page. Nothing to see here. No conspiracy—involving Bob I anyway. Who was just minding his own business, working on a World War II book when the call of destiny came.”

The target that helped put The Ankler on the radar in its early days was Netflix. “This was kind of the height of Netflix boosterism,” Rushfield recalls. “Everyone was saying, ‘This is the miracle! Why would anyone else even think of starting a streaming company? They should all just shut down their companies and give their libraries to Netflix!’ And I presented a contrarian voice on that.” Rushfield in 2018: “What if competition at the bottom stays so intense that Netflix is never able to command anything like monopoly power and has to start shrinking its offerings while raising its rates. In the olde timey economy, that’s what folks call a death spiral.”

Netflix is far from a death spiral, but one of the biggest media stories of 2022 turned out to be the company’s stunning subscriber stumble. The streamer lost almost half its stock value and came to be seen as a potential acquisition target. I asked Rushfield if he felt vindicated. “I wanna jump up and down,” he said, “and yell ‘I told you so’ every day.”

Rushfield, 54, grew up in Pacific Palisades and attended Santa Monica’s prestigious Crossroads School, where he overlapped with future hotshots like Matthew Greenfield, Jay Sures, Brett Morgen, Jason Blumenthal, Maya Rudolph, and Jack Black. Rushfield’s younger sister, the TV writer Alexandra Rushfield, was friends at Crossroads with Jenni Konner, who went on to showrun HBO’s Girls with Lena Dunham. At Hampshire College in Western Massachusetts, Rushfield frequented punk shows—X, Sonic Youth, Nirvana, Henry Rollins (he saw Black Flag in high school)—and wrote a decidedly gothy senior thesis about Jacques-Louis David’s paintings from the French Revolution (Marat bleeding to death in a bathtub, etc.). After graduating, he followed the grunge-era playbook of loafing around without a plan. Then he landed an entry-level gig with the ’92 Clinton campaign, sharing a small cigarette-smoke-filled office with Noah Shachtman, now editor in chief of Rolling Stone. “Even when we were kids, he was a figure from a different era,” Shachtman recalls. “I felt like he had stepped out of a Raymond Chandler novel.”

After working as a field organizer for several other Democratic campaigns, Rushfield pursued a writing career. His first byline, a front-of-book item for Los Angeles magazine, highlighted a stand-up comedy show featuring rising stars like David Cross, Bob Odenkirk, Patton Oswalt, Margaret Cho, and Janeane Garofalo. (He became friends with a lot of these folks.) “I think it ran two sentences and I got $25,” Rushfield recalls. In 1998, he and his friend Adam Leff conceived a Spy-inspired trend-forecasting charticle, “The Intelligence Report,” which caught the eye of Graydon Carter. He gave them a contract with this magazine, where the column appeared several times a year until 2010. (Rushfield has also written a few features for Vanity Fair.) By the mid-2000s, Rushfield was working as a web editor at the Los Angeles Times, where a print higher-up once told him the only reason people wanted the online versions of articles was so they could print them out to read in the bathtub. He embraced the web, where he ended up spending the majority of his professional life. In 2009, Rushfield left the Times to become West Coast editor of Gawker. He then wrote a book about American Idol and did tours of BuzzFeed, Yahoo, and, finally, HitFix, where he was editor in chief before the site was acquired in 2016. “The second half of my career was working on every website, essentially,” he told me.

The Ankler almost didn’t happen. After HitFix, Rushfield was accepted to the USC Rossier School of Education to pursue a graduate degree in teaching. Around the same time, inspired by the success of The Information, Jessica Lessin’s subscription-powered tech-news publication, he started sending an email digest to a small group of friends, who started showing it to their friends, who then forwarded it to their friends. Before he knew it, he had an impressive distribution list. “It started getting passed around very quickly to the executive class,” Rushfield told me. He decided against USC Rossier and put his eggs in The Ankler instead. “It took me time to get up the guts to put down a paywall, but I made that leap.”

Rushfield first met Min at the Golden Globes about a decade ago, “stuck at the kids’ table in the back,” Min joked. A former People and InStyle reporter and editor who became a mid-aughts media star as the editor in chief of Us Weekly, Min was in the midst of her celebrated reinvention of The Hollywood Reporter, which she ran until 2017. In 2021, as Min recovered from a brief stint at the train wreck that was Quibi, she and Rushfield started talking. “The Ankler had come to my attention because people were forwarding it to me, pretty senior people in the industry,” she recalls. “My thoughts were that entertainment was undergoing these crazy upheavals, both culturally and in the business model, and nobody was really owning that conversation.” They made it official with a New York Times piece shortly before Christmas and entered the Y Combinator program several months later. “In Silicon Valley terms,” Min said, “Richard would be ‘the product.’ ”

The Ankler is no stranger to courtship. Penske Media, whose near-monopoly on major entertainment titles includes THR, Variety, Deadline, Billboard, and Rolling Stone, made a number of overtures up until several weeks before Rushfield and Min announced their business relationship. (Variety put an offer on the table in 2019 to add The Ankler to its newsletter lineup; later, Penske Media boss Jay Penske pursued an acquisition.) Additionally, Puck had conversations with Rushfield prior to its own launch. Min and Rushfield later explored partnerships with Axios and Lessin, an early Ankler booster who’d welcomed Rushfield into The Information’s inaugural accelerator program. Ankler Media’s decision to remain independent—albeit with investors—and to continue publishing on Substack, where they’re part of a growing crop of full-fledged publications, reflected a desire to “control our own destiny,” as Min put it.

What does The Ankler’s destiny look like? Min envisions “a universe of bundled subscriptions” and a push into international markets. “The story of streaming is that it hit the ceiling in the United States before it was supposed to,” she said. “So everyone’s saying, ‘Let’s try to make money somewhere else,’ aggressively looking toward markets like Japan, India, Latin America, and that’s a great story.” When I asked for a pie-in-the-sky target of paid subscribers, she didn’t flinch: “a hundred thousand.” If they manage to get there—that’s a lot of paying subscribers!—it won’t have been easy. “I think they’re off to a tremendous start, but the road ahead is hard,” said Lessin, one of Ankler Media’s investors. “It’s a really difficult, long path.”

In early 2018, Lessin hosted Rushfield and the other members of The Information’s first accelerator class at her home in San Francisco. Over dinner, she asked her guests to describe their five-year aspirations. When it was Rushfield’s turn, he said, “What drew me to newsletters was the chance to really write something meaningful and to be able to do your best work. If, five years from now, I could be doing that on a stable basis, I’ll be thrilled.”

Here we are, five years later. I called Rushfield late one night while wrapping up this piece and read back his quote from Lessin’s soiree. “I couldn’t believe I was getting away with speaking so honestly and freely about this industry back then,” he said. “I still can’t believe I’m getting away with it.”

HAIR, CHECHEL JOSON (MIN); MAKEUP, TAYLOR BABAIAN; GROOMING, STACY SKINNER; TAILOR, HASMIK KOURINIAN. SET DESIGN, BETTE ADAMS. PRODUCED ON LOCATION BY PRODUCTION SQUAD. FOR DETAILS, GO TO VF.COM/CREDITS.