The anatomy of an addictive podcast: How Gimlet Media made a great story out of a bad mistake

Alex Blumberg | Photo Illustration Max Sheridan

Alex Blumberg | Photo Illustration Max Sheridan

I’ve been thinking a lot about podcasts lately. Not about the stories per se, but about the mechanics of podcasts: what makes them different from, say, traditional radio, and what makes them work as a storytelling medium.

If podcasts aren’t your thing, or aren’t even in your vocabulary, check out Gimlet Media’s stripped-down definition. They’re pioneers in podcasts and have spent the last four years thinking about and practicing the art of podcasting.

But if I can just frame podcasts within the context of storytelling, I’d say that what sets podcasts apart from radio is that podcasts offer a more immersive audience experience. With podcasts, you have multiple narrative perspectives, scene changes, music and audio effects. You have chapter breaks, hooks, climaxes, and resolutions.

When a podcast works, in other words, you have fully developed stories that reach you through the most elemental of storytelling channels: your ears.

The Podfather

If you do listen to podcasts, you’ve probably heard of Gimlet Media (mentioned above). Gimlet, a podcasting company, was the brainchild of ex-This American Life producer Alex Blumberg. Blumberg’s vision—his obsession—was to pioneer a digital radio renaissance where podcasts would be the star medium.

Blumberg started Gimlet in 2015 with a podcast that featured him and his quest to set up his podcast company. He called it StartUp. StartUp is good storytelling, and not only if you’re a start-up like we are and take comfort from rubbernecking at the ups and downs of another company trying to get off the ground (#schadenfreude).

StartUp is such good storytelling, in fact, that it’s easy to forget that you’re listening to carefully crafted stories. Which makes sense. Because who wants to know they’re listening to a story while they’re listening to a story?

But this post is all about what makes podcasts work as stories, so I’m going to ask that question. Because diving under the hood of a stand-out podcast can definitely tell you a thing or two about how to write better web content.

So, why is Blumberg’s storytelling so addictive?

StartUp, a podcast by Gimlet Media

StartUp, a podcast by Gimlet Media

You can actually boil that down to three basic elements. I’m going to use one of my favorite episodes of StartUp, episode 9 (We Made a Mistake), to introduce those elements and to see how, when mixed well, they can turn thirty minutes of radio journalism into a brilliant story you’d sit through six minutes of advertising to get to the end of.

Those six minutes of advertising are actually key, because advertising is at the heart of episode 9, which deals with the pitfalls of native advertising, or sponsored ads that are made in the style of any other material a media platform publishes.

This seamlessness is a concern for both listeners and publishers, because unless you draw users’ attention to the fact, they might not even realize the ad they’re experiencing is an ad at all. Consider, for example, this million-dollar native ad the New York Times produced with Airbnb, the tip of a multi-billion-dollar revenue iceberg. The conversation surrounding native advertising is particularly relevant for Gimlet, a company that uses native ads, but that takes its transparency seriously.

Here I should issue a spoiler alert that I’m going to be revealing key plot turns in the following paragraphs, so if you you’re itching to listen to episode 9, now is a good time to do it. For your convenience, here’s StartUp Episode 9.


Element one: the hook

When I said we were rubbernecking at Gimlet’s travails a few paragraphs back, I was actually serious. One of the most potent elements of engaging storytelling is misfortune. And if disasters sell, episode 9 is the equivalent of a five-car collision.

But episode 9 doesn’t start with the car wreck moment when Blumberg realizes he’s unintentionally duped a 9-year-old kid into making a native ad for Squarespace, a hip, NYC-based website building platform that sponsors Gimlet. It begins in the heat of another high-tension moment, minutes before Gimlet is poised to launch the first episode of another new podcast called Reply All.

It’s at precisely this moment when the host of Reply All realizes he’s lost the finished audio file.

Novelist and short story writer Larry Brown once said that his story recipe was simple. He gives his character a problem in the first paragraph. Then he quickly gives him another problem.

The Reply All launch fiasco is just like a Larry Brown story. The Gimlet crew eventually finds the file, publishes it, and then celebrates, but their barely avoided disaster propels them into something much worse. There was a fatal mistake concealed in the podcast no one caught, and it was waiting for them in the jungle of the Twittersphere the very next morning. According to Blumberg, the mistake they made was serious enough to sink the whole company.

This is our first plot turn, a key element in storytelling where the action comes to a head, subsides, and then begins to rise again. Blumberg has engineered this turn behind the scenes. What the listener actually experiences on the surface of the story is simply momentum and suspense. It’s this basic structure that propels most of the stories an audience is likely to invest in.

Breakdown: Weighing in at under 3:45 with the opening ads—i.e. a little under an entire bad Cyndi Lauper video—Blumberg’s hook earns 10 for 10 for pacing.

Reply All, a podcast by Gimlet Media

Reply All, a podcast by Gimlet Media

Element two: plot turns

So what kind of a blunder can threaten an entire company’s existence? If you’re a US company, it would be a mistake that involves a perceived ethical trespass, an enraged third party, and the spectacle of remorse. While Larry Brown’s recipe might work for short stories, this is the recipe that feeds the voracious US news cycle.

In Gimlet’s case, the ethical trespass was putting a kid in a native ad without his knowledge or consent. The enraged third party was the kid’s mom. The spectacle of remorse was supplied by Gimlet’s founder, Alex Blumberg, and his assistant producer, who failed to adequately explain why Gimlet had reached out to the boy or how they would be using the interview they eventually recorded.

At this point in the story, as Gimlet’s mistake simmers on the internet, Blumberg tweets his de rigueur apology. In the podcast narrative, Blumberg’s staged mea culpa is a pretext for weaving his nascent ruminations on corporate responsibility into the story arc. Blumberg, the storyteller, ties this very public story about a personal lapse of judgement into a broader discussion on the nature of native advertising itself.

This detour is a clever way of extending and enriching the narrative, giving Blumberg’s stake in the story even more weight. It’s also an effective way of prolonging the suspense, which has been slowly brewing like a darkening thunderclap of angry tweets for five minutes now.

But tension can only build so far before it breaks. In our story, this happens when the online news company BuzzFeed decides to write a piece about Gimlet’s handling of the Squarespace debacle, and then for some reason decides to kill it.

Is this an anticlimax? Well, maybe, but only if you wanted to see Alex Blumberg and his start-up thrown under the wheels of a train. And besides, an angry mother is still waiting for us after the commercial break.

Breakdown: The second act is about twelve minutes long with plenty of drama, shame and ethical brooding. But the excruciating journey we’ve taken feels like it’s passed in a flash. This isn’t an accident. This is what good pacing should feel like. This also brings us to the third act, which, minus the four minutes of ads at the end, gives Blumberg about eight minutes to resolve his story, and ease his worried mind.

Icons courtesy of the Noun Project

Icons courtesy of the Noun Project

Element three: resolution

In countries ravaged by civil war, when the strife has passed, sometimes mediators within communities stage truth and reconciliation tribunals. The tribunals give aggressors the opportunity to “own” their crimes and victims the relief that the crimes against them have been officially and personally acknowledged.

In the third act, Blumberg stages a truth and reconciliation tribunal of his own. He sets up that interview we’ve all been waiting for but are still dreading. Blumberg talks to the angry mom, who turns out to be a freelance writer from Eugene, Oregon, named Linda Sharps who was “super mad” but now just wants to be “super clear” about her side of the story. Blumberg, in turn, leads us step by step through his dark hour of the soul, acknowledging the mistake honestly and wholly.

And it works. Here’s why.

Blumberg is aware that showing us a resolution makes for much better storytelling than just narrating his emotions and capping that off with a moral learned. And, again, this isn’t a surprise. It’s a basic storytelling principle. If there’s a storm in your story, don’t describe it, show us what it does. If someone’s afraid, don’t tell us they’re afraid, show us what they’re thinking or feeling or how their environment reflects that fear.

What’s even more satisfying for listeners is that Blumberg’s resolution leads him not only to think about what happened, but to take action. Episode 9 ends with a promise from Blumberg to articulate a company policy on native ads so that the Squarespace debacle never happens again. In a media landscape where we sense that most apologies are lip service or worse, Blumberg’s promise feels radically authentic.

The breakdown: While many stories end too abruptly or without a sense of closure or reflection, Blumberg gives his audience eight minutes to transition from the climax to the final ad spot. Those eight minutes aren’t without their own drama and suspense—the drama of an impending confrontation—and they close with an authentic discussion about corporate responsibility. If there was a storytelling equivalent to executing a triple Lutz, this resolution would be it.


Putting it all together

If the best stories are experiences, what we feel as an audience is still practically always an engineered effect. This doesn’t cheapen the experience or a story’s message. It’s just the nature of storytelling.

Engineering stories doesn’t necessarily mean, and shouldn’t mean, manipulating them beyond the contexts in which they occurred. What happened to Alex Blumberg and his company Gimlet Media actually happened. It does mean, however, that when retelling stories, what you choose to give weight to and when will make or break a narrative. The same is true for story arc. If you don’t mimic motion with your plot turns, building the tension up and then resolving it, your story will flatline, and your users will very literally click on something else.

StartUp Episode 9 isn’t a story I’d tell my grandkids, but it’s a story I told my wife over dinner. And if you think of how much narrative gets pumped into our ears on any given day, and how little of it is memorable or repeatable, I’d say that that alone earns Blumberg a 10 for 10 as a storyteller.   


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