(Bloomberg) -- As one of the most influential media outlets for Democrats, the liberal podcast Pod Save America is trying to help listeners make sense of the chaotic US presidential election.
But at a pivotal moment in American politics, the divisions on display in the Democratic party are also playing out inside the progressive media powerhouse, pitting members of the young, idealistic staff against the more moderate hosts and founders of parent company Crooked Media.
Issues such as the war in Gaza and a stalled union-organizing push have consumed many staffers at a time when there’s little room for distraction. Long hours and a broader retrenchment in the podcasting industry have contributed to the mounting tensions, according to 15 current and former employees who asked not to be identified discussing internal issues.
Worse still, many employees have been disappointed to learn that a company espousing progressive ideals of equality isn’t immune to more common workplace complaints — from promotions to office romance. In the past three years, Pod Save America has cycled through three senior producers and a third of Crooked Media’s employees have left since January 2023.
The show’s hosts had long been ardent supporters of President Joe Biden’s re-election campaign. They quickly tempered their enthusiasm for the incumbent, however, following his dismal debate performance against Donald Trump on June 27, becoming some of the first high-profile pundits to question whether he should step aside. But some of the staff had become disenchanted with Biden long ago and said they were frustrated their concerns weren’t better reflected in the popular show much earlier.
Unlike the well-oiled machinery of the right, left-leaning partisan organizations struggle to define their message because the party itself is “so diverse in its makeup,” said Johanna Dunaway, research director at the Syracuse University Institute for Democracy, Journalism, and Citizenship.
“Democrats have a lot more of a big tent party,” she said. “It’s harder to have a consistent party platform and messaging.”
Clear Messaging
To the founders, Crooked Media’s message has always been clear: help Democrats win elections.
Started in 2017 by three former Obama administration staffers, Crooked Media and its flagship Pod Save America has become the political left’s answer to conservative talk radio. The program’s “no bullshit” format quickly garnered a following and helped propel the hosts — founders Jon Lovett, Tommy Vietor and Jon Favreau, plus Dan Pfeiffer – to celebrity status.
On the back of that success, the group expanded to include a publishing imprint, live events, merchandise and a subscription offering with nearly 20,000 members. The founders also launched a get-out-the-vote initiative and political action committee called Vote Save America, which has generated more than $57 million since 2018 for Democratic candidates and causes, according to a company spokesperson. In June, the founders and Josh Halloway, a TV writer, released Democracy or Else: How to Save America in 10 Easy Steps, which instantly became a New York Times bestseller.
Crooked Media now regularly produces and releases 14 podcasts, half of which are hosted by the founders, including Pod Save the World, Offline with Jon Favreau and Lovett or Leave It. Seven years after its launch, Pod Save America remains the company’s biggest show – it was the 30th most popular podcast in the US in the first quarter, according to Edison Research. Crooked Media’s show line-up, which also includes limited series, generates 25 million monthly downloads, according to the spokesperson. Pod Save America averages around 12 million monthly downloads and YouTube streams.
The company’s idealism and influence attracted a cohort of young activists who saw the organization — media startup meets grassroots political campaign — as a way to make an impact on the US political landscape. Many joined after stints in politics. Almost all the major Democratic candidates sat for interviews on Pod Save America during the 2020 election primary, signaling how important the company had become for the party’s heavyweights.
After Biden’s 2020 win, the company’s profile kept growing. In March 2022, Crooked Media signed a distribution and ad-sales agreement with SXM Media, the ad-sales branch of Sirius XM Holdings Inc., worth $150 million over three years, according to people familiar with the arrangement. Six months later, it scored an investment from Soros Fund Management, representing the group’s first outside financing, which provided the fund founded by billionaire George Soros a seat on its board.
At the same time, the company appointed its first chief executive officer, Lucinda Treat, formerly the chief legal officer at Vice Media Group. Its staff had, by that point, grown to 88 employees.
Crooked Media was suddenly flush with cash and status. But instead of rallying the crew, the business’ high profile within the Democratic Party fractured the group, just as the global podcasting industry also began undergoing convulsions of its own.
Following years of profligate spending, advertisers started pulling back their budgets. With fewer ads, one of Treat’s first moves as CEO was to cull programs that didn’t deliver large audiences. One of the underperforming shows was Hot Take, hosted by climate essayist Mary Annaïse Heglar and climate reporter Amy Westervelt. It was canceled in December 2022.
Red Flags
In a blog post published in March 2023, Heglar said the hosts saw “a lot of red flags” as they negotiated their contract with Crooked Media, including “our very apparent ideological differences with the heads of the network. Suffice it to say that Amy and I were far, far to the left of just about every show I’ve heard in the Crooked universe.”
Signs of belt tightening emerged elsewhere, including job cuts.
In response to workplace conditions, the Crooked Media staff agreed to join the Writers Guild of America East in early 2023, though they have yet to reach a contract agreement with the company.On July 29, the Guild filed an unfair labor practice charge against Crooked Media over claims of union-busting tactics of excluding some allegedly eligible staff members from the collective bargaining unit.
“It’s a shame when a progressive company like Crooked Media fails to live up to its own values and attempts to union-bust," said WGAE President Lisa Takeuchi Cullen. "The Guild fully expects Crooked Media to stop playing politics with its workers' livelihoods and settle this first contract without delay.”
A spokesperson for Crooked Media said the company voluntarily recognized the union immediately and that two-thirds of its employees are in the unit. The disagreement with the union is over five roles that were not included in the initial recognition agreement, the spokesperson said.
"We have been engaged in good faith discussions about these roles and expect to continue that discussion in three days of bargaining this week,” the spokesperson said.
Among the most pressing issues for many staff were promotions, which felt hard to obtain and occasionally caused resentment when they did occur, according to several current and former employees. The spokesperson said there have been 25 promotions with pay increases in the last 18 months. But one move in particular rankled the workers.
One staffer rose swiftly through the ranks, getting three promotions over two years, reaching a position that reports directly to the CEO. The person spoke openly to colleagues about having a close friendship with co-founder Lovett and talked about staying at his home to dog-sit. Earlier this year, the two informed the human resources department that they were dating.
The relationship began about a year after the employee’s last promotion, according to the spokesperson, who noted that Lovett is not a manager and is not involved in discussions about promotions. The employee declined to comment.
The three founders and the CEO declined to comment for this article through a spokesperson.
Not all former employees agreed with their colleagues’ complaints. Some said the workplace at Crooked Media mirrors any other media company in the throes of an election cycle. At least the staff still had jobs amid a broader media industry slowdown, and the company offers generous benefits, including unlimited vacation and free health insurance. What’s more, political divisions are found in almost every office Slack channel.
But for some, the layoffs and perception of a lack of a clear career ladder jarred with the big payday the founders received from the Sirius and Soros Fund deals. Favreau, one of the youngest speechwriters to have worked at the White House, reportedly bought a home for nearly $10 million in Los Angeles in early 2023. Images on social media showed him and his wife schmoozing with celebrities like Chrissy Teigen and John Legend.
Some of the Crooked Media staff said they resented Favreau’s real estate dealings. They interpreted it as a signal of the founders talking like progressives but enjoying the wealth of the privileged class, particularly during a tough time in the podcast market, according to several staffers.
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.
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."
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