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.
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