Different Teams

For some, it began to feel like they no longer sat on the same team as the founders, rather they lived different experiences, separated by wealth and power.

Monthly all-hands meetings became increasingly acrimonious. Staff bombarded management with questions about topics from return to office requirements to standards for promotions. The mood was openly adversarial and tense, according to people who were present during these exchanges.

Earlier this year, the format of the monthly meetings was changed. Instead of an open forum, executives replaced the conversations with presentations given by various guest speakers on generic corporate topics.

Meanwhile, staffers felt real issues within the Democratic Party should have been more openly discussed. The war in Gaza in particular pitted employees against each other and their bosses. Some people said the hosts weren’t empathetic enough toward Palestinian suffering, or understanding of pro-Palestine protestors.

The spokesperson noted that Vietor has talked about the war in Gaza regularly on Pod Save the World, including with former Deputy National Security Advisor Ben Rhodes, and called for a ceasefire in late October during a live taping of Pod Save America in Cleveland.

Staffers purposefully placed links to pro-Palestinian news coverage in an internal Slack channel to ensure the founders and top executives saw it, hoping to encourage discussion. They changed the status emoji next to their names to a watermelon, which has become a symbol of support for Palestine. Some also wore the traditional Palestinian head covering, a keffiyeh, to the office to draw attention to the cause.

Some staff pushed the founders to address the issue internally and foster conversation for a company-wide audience, but they never did. The founders and Treat instead held office hours during which staff could come to them to talk confidentially, the spokesperson said.

These divisions stoked animosity that culminated in office disputes. Earlier this year, one producer was discussing pro-Palestinian student protestors, according to people familiar with the exchange. Someone else overheard the conversation and thought the producer had uttered a slur. The incident was reported to human resources, which investigated the claim and cleared the producer of any wrongdoing, though the producer later quit rather than endure the highly-charged workplace culture.

The producer declined to comment.

After the producer left, Treat and Favreau addressed the staff and told them such distractions were unacceptable. The team needed to step up and focus on the election, they said.

Indicative of the relentless pace, in June, over the week of the Biden-Trump debate, the Pod Save America team released four episodes.Photographer: Jayme Kaye Gershen/Bloomberg

Favreau acknowledged sometimes being at odds with Crooked Media’s younger staff in a recent podcast interview with David Axelrod, the chief strategist for former President Barack Obama’s political campaigns and the founding director of the University of Chicago Institute of Politics.

“They let us know when we seem too old or we don’t get it,” Favreau said on the Axe Files. “It’s a constant process of learning and like trying to understand the change that’s happening in younger generations without being like, you know, the old man on the lawn yelling at kids kind of thing.”

He imagines his staff thinks, “you know, you’re not that aware.” Long Hours

To gear up for the election and counteract the advertising market downturn, Treat enacted a strategy to build a newsroom that could more readily react to and cover political stories on the fly. She also doubled down on what already worked — that is, founder-hosted shows, especially Pod Save America. The flagship program upped its release schedule from two days a week to three and tacked on a bonus, subscriber-only feed in addition to regular live shows around the country and additional, breaking-news episodes.

That often meant working long hours with no clear policy about comp time, on that show and others. At least one staffer worked 12 days straight. Other staffers said they regularly put in 12-hour days.

Indicative of the relentless pace, in June, over the week of the Biden-Trump debate, the Pod Save America team released four episodes, two of which were recorded from live shows that required staff to travel to New York and Boston with the co-hosts. Members of the team worked extra hours to produce the additional content.

Meanwhile, just as election season began to kick off in earnest in May, Lovett took more than a month off. Seemingly, the election could wait — he’d gone to compete on the CBS reality TV show Survivor.

“It was glorious,” he said on The Late Show with Stephen Colbert in June after his return. “And, sometimes, I imagine being away from my phone for longer, maybe forever. We don’t have to live like this anymore… but keep listening to the podcast.”

Disagreements aside, Crooked Media positions its mission as being bigger than any one person, and the staff is united in working to achieve their goals. The whole company is fighting to keep Trump out of office, and the stakes are high, as the hosts often remind their listeners.

After weeks of political upheaval and Biden’s dramatic decision not to run again, the Democrats have rallied around Vice President Kamala Harris as their nominee, and the Pod Save America hosts can refocus their staff and audience on the path to victory in November.

"We're coconut-pilled," Favreau said, as he, Lovett and Vietor raised a glass of a coconut-flavored drink to Harris, a palm tree-shaped balloon floating in the studio background in a recent episode of Pod Save America. The toast was a reference to a speech Harris made last year that has turned the “coconut tree” into a symbol of her campaign. "We're all coconut-pilled, just like everybody else."