Why Crooked Media is succeeding where Air America failed

It turns out podcasting is a much better delivery mechanism than radio.

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There are few things liberals envy more than conservatives’ grip on the talk radio market. Every single weekday, rightwing hosts ranging from Rush Limbaugh to Michael Savage inject pure, unmitigated spin into the media diets for tens of millions of Americans, and there really is no leftwing equivalent.

This reign began in the 1980s with the abolishment of the Fairness Doctrine and then solidified with the passage of the Telecommunications Act of 1996, which allowed large media conglomerates to buy up hundreds of local stations and thereby guarantee national distribution for their hosts. By the early 2000s, figures like Limbaugh wielded significant influence within the Republican Party, and Democrats feared that a dearth of liberal counterparts would place the party at a permanent disadvantage.

Air America was supposed to eliminate that disadvantage. Launched in 2004 in dozens of markets across the U.S., the company framed itself as the left’s answer to rightwing radio. Al Franken helmed the primetime slot, and over the next few years it built up a weekly audience in the millions and carried shows hosted by celebrities like Jerry Springer and Janeane Garofalo. It launched the career of Rachel Maddow and arguably set the stage for Franken’s successful Senate run.

But Air America struggled to remain afloat almost from the very beginning. It quickly burned through its initial investments and had to be bailed out several times. It constantly changed ownership and its mounting debts drove it to its first bankruptcy filing in 2006. And though Franken beat Limbaugh in a handful of urban markets, radio stations constantly dropped its programming, and none of its shows came close to reaching Limbaugh’s audience of 20 million listeners.

In 2010, a mere six years after it debuted, Air America threw in the towel and liquidated its assets. Conservatives crowed, and liberals once again despaired at the GOP’s ability to pipe its agenda directly into cars of a sizable portion of the U.S. electorate. What’s worse, Fox News’s far right primetime lineup had achieved its own level of TV dominance.

But then something interesting happened. In 2016, four former Obama administration staffers launched a politics podcast under The Ringer. It was called Keepin’ It 1600, and it built up a modest following, though its hosts always intended for the show to be a limited series that ended after the election. “We didn’t want to be the people who criticized the White House just to be interesting, nor did we want to be to the Clinton administration what Hannity now is to the Trump administration,” Dan Pfeiffer, one of the cohosts, told The New York Times. “We all assumed the election was the end of the road for us.”

You know what happened next. Trump’s win changed the dynamic for what their podcast could be. The day after the election, they began brainstorming the idea that would evolve into Crooked Media -- a company that aimed to blend leftwing punditry with direct political activism. Pod Save America, the company’s flagship podcast, launched in 2017, and it was an instantaneous blockbuster. Within a month, it had its first million-download episode, and by 2019 it was pulling down 2 million downloads per broadcast. Advertisers embraced the podcast and it sold over 100,000 tickets to its live shows. Its founders plowed that money directly back into the company, and over the next four years it launched 19 shows, an HBO series, and a contributors network that publishes articles to its website.

What’s more, it’s become a veritable force in electoral politics. The podcast has raised millions of dollars for campaigns, registered tens of thousands of young people to vote, and has become a widely sought-after pitstop for any Democratic candidate running for an important office.

Crooked Media is achieving what Air America couldn’t. “With a shoestring budget and no organizational backing,” wrote The New York Times, “its hosts seem to have created something that liberals have spent almost two decades, and hundreds of millions of dollars, futilely searching for: the left’s answer to conservative talk radio.”

But how did it pull this feat off? While the two companies ostensibly had similar goals, they took vastly different approaches to format, distribution, and growth. Here’s why Crooked Media is succeeding where Air America failed:

Growth

One reason Crooked Media has achieved such an effective product-market fit is because it relied entirely on organic growth. It launched Pod Save America on a shoestring budget, and after its explosive success its founders began turning down investors who wanted to plow money into the company. “I was like, ‘We don’t need you people. We’re making money hand over fist!’” co-founder Jon Lovett told Vox.

Instead, Crooked Media funded its expansion entirely through its own profits. One industry executive estimated that Pod Save American alone was generating $5 million in annual revenue during its first year. The co-founders reportedly didn’t take a salary in those early days, and instead put the revenue toward the production budgets of new shows. Several of its shows were hosted by Pod Save America co-hosts -- Jon Lovett hosts Lovett or Leave It; Tommy Vietor hosts Pod Save the World; Jon Favreau hosted a narrative podcast called The Wilderness -- which allowed for cross pollination of audiences and swifter growth.

Air America went the opposite route. Instead of launching a single flagship show and growing the company from there, it debuted with a huge lineup of programming, an incredibly expensive endeavor. It also spent like a drunken sailor, blowing $70,000 on a launch party and then almost immediately burning through its initial $6 million investment before racking up an additional $2 million in debt.

It went on to raise an additional $13 million or so, but its high costs kept it perpetually on the brink of bankruptcy and limited its ability to adapt within the marketplace.

Technology and distribution

Crooked Media’s timing was perfect, and not just because it was a liberal network launched under one of the most unpopular GOP presidents in modern history.

In 2017, billions of people across the world owned a smartphone and could easily download a podcast episode with the tap of a button. What’s more, this was post-Serial, when podcast listenership was exploding. Pod Save America essentially caught a huge wave and was able to ride it as it grew in intensity. It helped that the younger age demographics coveted by advertisers over index on podcast listening.

Air America, on the other hand, faced significant headwinds from the start. Many rightwing hosts are distributed by media conglomerates like iHeart (formerly Clear Channel), which have strong market penetration via well-placed, powerful radio stations. Air America didn’t have near that kind of coverage. “Because conservatives were so entrenched on heritage stations,” wrote Alan Colmes in 2010, “the progressives on Air America were relegated to smaller, less powerful, under-performing signals that could not compete with their more established counterparts; certainly not without lots of promotion and time to develop, both of which were denied in most cases.”

As a result, many potential Air America fans simply couldn’t access its programming. And even if you were within antenna range of the network, you were unlikely to follow any shows that didn’t air during your work commute (on-demand audio was still in its infancy). It did launch an internet stream, which reportedly reached 1.3 million listeners a week. But online audiences were tiny back then, and very few national advertisers, if any, were investing in internet streaming.

One could argue that if Air America had launched a decade later, it would have done so as a podcast network and sidestepped most of these hurdles.

Format

One of the best critiques of Air America’s approach to programming came from Tim Miller, a former Crooked Media contributor. He pointed out that the company merely attempted to create a carbon copy of rightwing radio. “Air America was lefty Limbaugh,” he told The New York Times. “Rather than trying to replicate what’s worked on the right, [Crooked Media isn’t] taking the same tropes you see on Fox or hear on conservative talk radio and applying them to the left.” Limbaugh himself, monster though he may be, made a similar point when critiquing his new competitor right after its debut. “First, you have to entertain people,” he said. “You have to make it interesting to listen. I don't hear any of that."

Pod Save America doesn’t feel like a left-wing facsimile of conservative talk radio. It eschewed the single host format and instead adopted the roundtable approach common to most non-narrative podcasts. Even better, it dispelled with the imaginary line between punditry and activism and embraced political organization. Many of its segments are action-oriented with specific calls-to-action. It partnered with already-existing organizations (MoveOn, Swing Left) to raise money and designed its own website landing pages aimed at mobilizing voters.

It also expanded into other mediums. It produced a series for HBO, launched a YouTube channel that has 200,000+ subscribers, and hired away an editor from The New Republic to write for and edit its website content. While it’s difficult to make an apples to apples audience comparison to right wing radio, it’s clear that it punches far above its weight in terms of exerting influence over the political narrative.

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Of course it’s worth pointing out that Air America, though it struggled to remain afloat throughout its entire existence, finally collapsed during the Obama era. One could argue that its final bankruptcy was triggered, in part, by liberal complacency. We’ve yet to see if Crooked Media can thrive in a post-Trump era. If the polls are any indication, we’ll soon find out.

But with its lean infrastructure and rabid fan base, it’s safe to say it’s not going away anytime soon. Crooked Media may never reach the power or influence of a Fox News, but it’s proved that there’s an audience for unapologetic liberal opinion and, more importantly, there’s a business model to fund it.

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Simon Owens is a tech and media journalist living in Washington, DC. Follow him on Twitter, Facebook, or LinkedIn. Email him at simonowens@gmail.com. For a full bio, go here.

Image via Wikimedia Commons