(from left) Dan Pfeiffer, Jon Lovett, Jon Favreau, and Tommy Vietor after they filmed Pod Save America's live HBO show on September 28, 2018, in Los AngelesJessica Pons / Getty

Before the Pod Save America podcast even existed, there was Keepin’ It 1600, a breezy political roundtable hosted by four strategists and speechwriters who used to work in Barack Obama’s administration—Jon Favreau, Dan Pfeiffer, Jon Lovett, and Tommy Vietor. In the lead-up to the 2016 presidential election, they offered their perspectives from campaigns past, discussed strategies for Democratic nominee Hillary Clinton, and commented, aghast, on the rise of Republican nominee Donald Trump. “I thought of Keepin’ It 1600 as the last thing I was gonna do in politics,” Pfeiffer recalled recently in an Atlantic interview with the four hosts.

The election, of course, didn’t go the way they expected, and that initial calculation about Keepin’ It 1600 quickly shifted. We had “watched political punditry for all those years, become frustrated by it, and now we had a podcast where we could blow off some steam,” Favreau said. “What changed with Trump’s election was us thinking—instead of us being purely reactive to political punditry, instead of us talking about what might happen—we should talk more about what should happen.” Keepin’ It 1600 became Pod Save America, which is part of Crooked Media—a larger network of podcasts, opinion writing, and grassroots organizing geared toward left-wing activism.

The entire enterprise has now found its way onto television, with four Pod Save America specials airing Fridays on HBO in the weeks leading up to the November 6 midterm elections. The episodes show the four hosts—and special guests—visiting battleground states such as Florida, Georgia, and Texas; talking with Democratic Senate and gubernatorial candidates; and essentially acting as a get-out-the-vote operation. (The hosts are on tour; HBO films and airs their live shows.) Crooked Media is an unusual mix of entertainment, news, and engagement, designed to exist in a media ecosystem where Democrats often struggle to push their message through. In a way, the hosts have become something they often rail against—political pundits—except that, unlike many MSNBC and Fox News commentators, they’re transparent about their advocacy.

The quartet spoke with me in New York in the middle of their tour and laid out how their approach to broadcasting and organizing has evolved during Trump’s presidency. Lovett, the funniest of the group (he created the sitcom 1600 Penn after leaving the Obama White House), is also the most eager to upend his party’s reputation for equivocation. “Democrats spent a long time thinking about electability and then losing all the elections,” he said. “What we wanted to talk about is not how it’ll play, not about polls, not about the horse races, but what do we want candidates to advocate for?”

That question pointed Pod Save America to figures such as Beto O’Rourke (running for U.S. Senate in Texas), Stacey Abrams (running for governor of Georgia), and Andrew Gillum (running for governor of Florida). Though they’re not perfectly ideologically aligned, they’re all running more openly left-wing campaigns in conservative-leaning states where Democrats are often told to tack to the middle. To Lovett, Donald Trump’s election was “permission” to cast that advice aside. “Republicans paint everything that Democrats have been for as socialism, too far to the left, as extreme, and it didn’t matter how moderated it was, it didn’t matter that Obamacare started out as a compromise,” he said. “You might as well say what you’re actually for, and show what you really are.” (Lovett has previously written for The Atlantic.)

Pod Save America is an expression of that kind of bullishness, which is much more commonplace in conservative media. The show has tapped into a young, progressive audience that’s keen to push back in an openly hostile political climate, and delighted to wear Crooked Media T-shirts branded with slogans like “Repeal and go f*ck yourself.” “The [podcast’s] listenership is a little less siloed or bubbled than you’d think,” Vietor said. “I think Texas is the third-, fourth-, or fifth-biggest state for [our] listeners. We’re not a candidate; we’re not trying to get votes. We’re just trying to inspire people to get engaged and think about democracy.” The HBO specials reflect that sense of group enthusiasm; the show is a cross between a comedic panel and a grassroots rally, with the live audience giving things a grander vibe than the podcast (which airs twice weekly).

Divided social-media feeds, partisan podcasts, and a splintered media landscape suggest a country that’s unable to bridge its ideological differences, and Pod Save America is certainly part of that, speaking to a devoted but self-selecting audience. The extreme partisanship online, Lovett said, “is a natural response to a new experience, which is being neighbors with everybody. We are so close to so many people all the time, [and] so many views that used to be harder to access or harder to reach are in your face. I think some people respond to that by protecting themselves and siloing themselves off; some people go crazy and respond to every tweet.”

“We think of bubbles as: There’s a liberal bubble and a conservative bubble,” added Favreau. “But there are also different communities that care about different issues ... that aren’t political. We don’t really think we’re going to pierce the conservative bubble anytime soon, but we have been thinking, over the last couple years: How do we reach people who may have the same values that we have, but don’t necessarily pay as close attention to politics?” As a result, political outreach is a crucial cog of the Crooked Media machine: Its website includes a ballot guide and the registration aid Vote Save America.

But to Pfeiffer, “conservative” and “liberal” media cannot be easily compared. “When you look at studies of media diets, conservatives consume only conservative media, which is trash,” he said. “Liberals consume mainstream news: CNN, The New York Times, NBC, ABC … You have these outlets on the right whose job is to try and win elections for Republicans. Prior to Crooked Media, there was really nothing like that on the left: a media outlet centered on encouraging progressive activism with an actual goal.” The show is, in a way, an answer to Fox News and the other right-leaning news outlets that exasperated the Pod Save America hosts when they worked for the Obama White House.

“People ask us if we’re biased. Yes. I wear it on my sleeve; I donate money, I speak at fund-raisers. I tell you that,” Vietor said. “I think there is a way to do this [in a way] that is a little more honest.” Pod Save America is attempting to combat the “asymmetry of the bias,” he explained, whereby left-leaning editorial boards for outlets such as The New York Times try to give ample space to right-wing voices, but the same (in his eyes) does not happen at right-leaning organizations such as The Wall Street Journal.

“We try to make sure that the facts and information we provide people are true, and when they’re not and we make mistakes, we try to correct them,” Favreau said. “While we’re biased and have an opinion, that’s different from allowing yourself to be a propaganda machine.” That belief, to him, is what sets Pod Save America and the Crooked enterprise apart from the partisan news organizations they’re opposing. “You have to fight it by calling it out for what it is. I think print journalists do a great job of this. I think television networks do a poor job.”

“I think the problem that Democrats have failed to grapple with is: How do we adjust our strategies and tactics and how do we build campaigns to adjust to this new media environment?” Pfeiffer added. In the old world, “the way you got your message [out] was you told it to the press, and the press told it to voters. … We believed that the media had the power and the authority to put consequences on politicians who lied. That is not true anymore, so we are just screaming into the void.”

Pod Save America was created out of the quartet’s shock that the widely predicted outcome of the 2016 election—the victory of Hillary Clinton—didn’t come to pass, but the project has been fueled by the combativeness of politics since then. As the hosts look to the midterms and beyond, they’re careful not to predict anything, having been burned by the many data-fueled guarantees of Clinton’s win in 2016. “Never again will we cherry-pick information in that way to make people feel good. Right now, it’s fucking 50-50 at best that [Democrats] take the House and likely lose the Senate. I think that kind of honesty is hopefully motivational,” Vietor said.

The future holds a different kind of ideological battle for the podcast, one that all its listeners might not agree on. “Once this is over, whether we win or lose, the next conversation is: Who do the Democrats want to put forward in 2020?” Favreau said. “In some ways, it’s more liberating: What do we want to stand for. Who do we want to talk about?”

“We’ve said for so long, ‘Now is not the time for infighting.’ The day after the election, [we said] ‘Let’s do it. Infighting as much as you want!’” Lovett joked. Pod Save America didn’t exist during the 2016 primaries, but its hosts’ ideas are now being put to the test. “The antidote to pessimism is not optimism—it’s activism,” Favreau mused. The coming years appear to promise plenty of all three.

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