Last Thursday evening, members of The Bulwark’s paid-subscriber Substack community were invited to ask hosts Sarah Longwell, Tim Miller, and Jonathan V. Last anything that was on their mind. Several wanted to know how to engage with MAGA supporters in everyday life.
“We’re all gonna have different answers,” Last said, kicking things off. “I will give you my answer as somebody who lives his entire life in the real world surrounded by Trump people: In my view, the best thing I can do is to—”
“Rub their face in shit,” Miller interrupted.
Last, entirely unfazed by Miller’s quip, continued, saying, “Live my life with love and generosity, to sort of show them that people like us don’t have horns.”
Longwell chimed in, “You guys, he’s lying to you right now!” Last protested: “I am not lying to you! Hand to God, that’s how I roll in the real world.” Miller and Longwell rolled their eyes, suggesting Last was less charitable in private. “I get a string of text messages from him,” Longwell said. “‘These fucking idiots,’” Miller joked.
At its peak, the livestream saw more than 3,000 active viewers, including fellow Substacker Chris Cillizza, with many chatting it up throughout. To Longwell, publisher of The Bulwark, this type of unfiltered community conversation is what subscribers are truly paying for. “I think the alchemy between us has been the parasocial relationships,” she tells me. “People feel like they are friends with us. One of us represents them.”
The media upstart, launched in 2019 by “Never Trump” Republicans, is thriving in a second Donald Trump term, with the outlet expecting to reach 100,000 paid subscribers by the end of May and 1 million general subscribers by the end of June. Since The Bulwark publishes little content behind a paywall, readers are presumably dropping $100 or more annually for a Bulwark+ membership to engage with the site’s prominent voices—and one another. “The thing that people really pay for is to go deeper with the community,” says Longwell, adding that the site could easily “convert much more aggressively if we put more things behind a paywall. But we like to say you can’t save democracy from behind a paywall.”
The Bulwark has already evolved since its earlier incarnation, which came in the wake of The Weekly Standard’s demise; it’s now meeting a new Trump era—and the resistance emerging alongside it—by expanding its capabilities for original reporting and video. The outlet boasts 1.25 million subscribers on YouTube, though, like other outlets trying to grow audiences on the platform, it’s still honing its strategy, wary of how an algorithmic tweak can throw things off course.
Still, even while enjoying recent success, Miller says he would trade it all to not have to live through another Trump presidency. “I’d gladly not be hitting this milestone and be covering whatever is happening in Kamala Harris’s first 100 days,” he tells me. “But you know, that’s not what the fates had in store for us.”
Early in his career as a Republican operative, Miller saw his future self serving as an administration’s press secretary. That’s now “a dream that’s dashed,” he says, due to his willingness to express a point of view through The Bulwark. Miller, who previously served as a top aide to Jeb Bush during the 2016 presidential campaign, argues that he has since been “exiled by our party”—something he discusses regularly in content—though he adds that “the audience appreciates that candor.” (Miller has also been willing to acknowledge his own missteps in GOP politics that helped give rise to the Trumpist right.)
Recently, Miller has been channeling his full energy into the outlet’s YouTube offerings, posting videos on the platform usually six to eight times a day. The channel features a range of content with headlines like “Trump’s Latest Interview Should FREAK YOU OUT” and “MAGA Cultists Are IN FOR IT! Tariff Agony INCOMING!” Many videos include a thumbnail picture showing Miller with a look of astonishment mixed with disgust on his face, and many feature discussions with a range of guests, including Michael Steele, Tom Nichols, Derek Thompson, and George Conway.
Around the time of heightened discussion around whether Joe Biden would drop out of the 2024 presidential race, Miller started putting more effort into the outlet’s YouTube content, with Longwell agreeing that they needed to not only meet their audience on the medium, but also understand “that the platform demands a certain way of presenting oneself.” It’s “just the language that people on the platform speak,” Longwell adds, also admitting that it was “difficult” at first to translate their written commentary—the presentation of which “looks a lot more like The Atlantic”—for the YouTube crowd, but “engaging in that platform’s language has really helped us grow there.”
Once they saw steady growth, Miller noticed what the platform’s algorithm was rewarding, leading to the channel’s transition into its current style. “There’s an adjustment to: How are we going to package the content in a way that will do well on YouTube so we can maximize the number of people that see it?” He remains acutely aware of not going “overboard,” saying that “you don’t want to mislead,” but adding that “it’s just the nature of the game.”
While initially known primarily for commentary, the outlet has invested in a lean but effective newsroom, one led by Politico, Daily Beast, and HuffPost veteran Sam Stein, who was drawn to what The Bulwark was building.
Stein had a desire to get back to the “upstart mentality,” which he experienced early in his career at places like HuffPost, where he was the site’s first reporter. “You have more freedom to be punchier and more direct with your reporting and more provocative with your headline writing,” he says. “That was all really alluring.” By the spring of 2024, Stein took matters into his own hands, reaching out to Miller to inquire if The Bulwark was hiring. “He’s like, ‘No, we’re not hiring. We have enough reporters.’ And I was like, ‘What about me?’” Stein recalls. Miller put him in touch with Longwell, to whom he pitched his experience at establishment outlets as an asset to help the independent media venture “operate and grow.”
Something that also made “the jump attractive is that The Bulwark had a more multimedia dimension to it,” compared to Politico, Stein tells me. “The chance to do some video was an added bonus.” (Stein, like Miller, is a familiar face to MSNBC viewers.) However, Stein expressed a bit of concern about “overinvesting” in YouTube, given how the news media has been burned before by social media algorithm changes. “It’s just—we’ve all lived through those episodes where you rely a lot on third-party platforms. We’re highly aware of that,” he says. “I just don’t want to get to a place where something changes and we’re like, Oh no, we overdid it.”
With that being said, Stein is ensuring the editorial future of the publication by building out the outlet’s reporting prowess through Substack newsletters. “It was really Sam’s vision to bring on a SEAL team of really talented people who he thought could take The Bulwark from a niche commentary space to a mainstream publication that still had a certain perspective,” Longwell tells me.
That team has included the likes of Adrian Carrasquillo covering immigration, Jonathan Cohn covering the administration’s institutional dismantlement, and Lauren Egan covering how Democrats are fighting back. The “cherry on top” for Stein was poaching Will Sommer from The Washington Post to cover the online right. “Over the years, the weird characters that he came to cover with his expertise, they’ve become like power brokers,” Stein adds, specifically referencing Sommer’s coverage of Laura Loomer. “There was, from the top down, a recognition that we are at a place editorially where we need to supplement our great essay writing, commentary, and analysis with original reporting, and that there’s almost a moral rationalization around hiring people who can dig in” on these specific subjects, Stein says.
Still, The Bulwark won’t allow recent success to provide a false sense of confidence about the “economics of this industry,” according to Stein, who tells me, “We’ve seen plenty of outlets overextending in times of success.” The Bulwark is “doing things strategically,” he adds, “and with an eye toward making it sustainable from a business standpoint.”
The Bulwark has an opportunity to differentiate itself in the marketplace, suggests Longwell, as consumers see major media and tech companies as “kowtowing” to the administration. “Our authenticity has been a big part of the draw,” Longwell says, adding, “There’s a combination of the fracturing of the old media environment, along with Trump coming in, that has just created kind of the perfect storm in which we’ve been able to really thrive and grow.”
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