In February,Kurt Meinicke three former Obama administration staffers sat on stage in Brooklyn at a podcast/radio festival talking politics with New York City Mayor Bill DeBlasio, a month after the inauguration of Donald Trump.
As far as choirs go, it was an easy one to preach to.
"Doing an event at BAM is not just preaching to the choir. It's inviting them on stage and doing a Rockettes-style dance," cracked Tommy Vietor, one of the three to interview the mayor.
Such is the tenor of one of the newest and most irregular media startups of the moment — biased, funny, and cautiously self-aware.
Vietor's a co-founder of Crooked Media, a new media company that burst onto the podcast scene with "Pod Save America" and "Pod Save the Word," both of which rank in the Top 25 for podcasts on iTunes. Vietor—formerly Barack Obama's national security spokesman—started the company along with former Obama speechwriters Jon Favreau and Jon Lovett.
As they tell it, the fact that the company exists at all is still something of a surprise. Favreau and Vietor started a political consulting company in 2012 after leaving the Obama administration, and the three of them were pitching a TV show that never materialized.
Then, in March 2016, Favreau and Dan Pfeiffer (another former Obama staffer) appeared on The Bill Simmons Podcastto wax poetic on the 2016 primaries. Not long after that, Bill Simmons, who'd recently started The Ringer, gave them their own podcast that would eventually be called "Keepin' It 1600." The show quickly found traction, thanks in part to the timeliness of an insidery-but-fun look at the election, combined with the existing podcast audience that Simmons commands at the Ringer. Meanwhile, Favreau, Pfeiffer, Lovett, and Vietor already had chemistry from their years of working together, with their booking of guests bolstered by their strong personal networks of contacts (like then-Secretary of Labor Tom Perez, and New York Timesreporter Maggie Haberman).
That's something that's still serving them now as an independent company. Their fourth podcast featured the final interview of Barack Obama as president.
Despite that success, starting a media company wasn't exactly the kind of thing Vietor, Favreau, and Lovett had in mind. The show was a success, but they figured that once Hillary Clinton won—something they took for granted as a foregone conclusion, and later had to own up to post-election—they'd move on.
Then it happened: Hillary lost. Trump won. And a media company was formed.
"The podcast—The Ringermade that possible," Lovett said. "When Trump wins, that's what made Crooked [Media] possible."
The trio formed Crooked Media in the days immediately following the election, and have been working to build it out since. The decision to leave The Ringer, which provided the reach on which their show built its audience, came out a desire to push into activism.
Crooked Media is based in podcasts and media, but rallying people around causes and inspiring action is a big part of what the three hope to achieve.
"I think The Ringerwas fine with having some partisan people on doing political writing and podcasts," Favreau said. "But there's a difference between being a commentator with partisan views, and having this little mini-brand within your company that is telling people to go to town halls and vote for people and organize.
"I don't think that fit within The Ringer's larger mission, and Bill [Simmons] understood that within about two minutes of talking to him," Favreau said.
Right now, Favreau, Vietor, and Lovett are still the only full-time employees, though they're working on hiring more people and developing other ideas. That hiring will be key. The three of them were aware of how Crooked Media could look from the outside—three white, left-leaning men with podcasts.
"We're trying to recruit new voices because we don't think that you can base the company on just the three of us," Vietor said. "We also don't want to be a company that is offering the perspective of three white guys who worked for Obama. We want to have a diverse set of voices on a diverse set of issues."
To that end, Crooked Media's third podcast is its first hosted by a woman. Ana Marie Cox, senior political correspondent for MTV News, is the host of "With Friends Like These," which will center on the political divide.
Outside of podcasts, live and edited video is next. They've talked to investors, but aren't necessarily looking to raise money just yet. Lovett said they have been surprised by the amount of revenue they've been able to generate based off the podcasts as well as some merchandise.
And there's the chance to do more events. Though their first event proved to be a home game, Vietor said they want to get out of their bubble.
Of course, there's a company to build in the meantime while still doing the podcasts. When Vietor spoke with me for this story, Donald Trump was hosting his first press conference.
When asked why he didn't move our phone call, Vietor responded, "I have it paused on my Tivo."
"It's just a practical question of minutes in the day," he said.
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