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Caught in the Midroll

Studies in unskippable podcast advertising.

Before I tell people why I love podcasts, I’m always surprised by how often I have to explain what podcasts are. The conversation usually goes like this:

What is it? Like a radio?

Kind of, but it’s on your phone.

And it’s just two guys talking?

Well, some are. Others are more structured.

What are they mostly about?

Literally anything.

And people listen to these?

Maybe not as many as watch TV, but the people who listen to them, like them a lot.

That last part is important. Because most podcasts are free, the primary method of financial support comes from advertisers. Since I’m still routinely explaining what podcasts are, the opportunity for brands to reach new audiences is not about volume, but about passion

Podcasting is unique because there are no consistent quality standards and there is almost no barrier to entry. To illustrate this, I decided to see how long it would take me to create and publish my own podcast. I recorded myself on my phone and then uploaded it to SoundCloud. I titled it the first thing that came to my mind and used my most recent picture as a profile image (it was a receipt for snacks I bought on the Amtrak from Oceanside to Santa Barbara).

It took me just under four minutes.

Since anyone can be a podcaster, it means not every podcast is going to be an effective platform to market your business. Some brands understand this and are partnering with specific podcasts to build a message that seamlessly aligns with content. Here are three different ways podcast ads are successfully connecting to their target customers. 

Case 1:

Hollywood Handbook & Square Cash

The Podcast

Hollywood Handbook is a weekly hour-long satirical podcast that lampoons Los Angeles entertainment culture. Comedy writers and hosts Sean Clements and Hayes Davenport describe the show’s mission as “trying to replicate the worst conversations you overhear in Hollywood coffee shops.”

The Brand

Squarecash is an app that allows users to instantly send money between friends or accept card payments for your business.

The Ad

Taking what would normally be an easily forgettable 30 second pre, mid, and post-roll ad, Davenport and Clements read the provided copy and then continue to improv an increasingly elaborate scenario. The result is a truly bizarre story of how Sean and Hayes use Squarecash to pay their teacher to tell their dads they have girlfriends. 

Why It Works

On Hollywood Handbook, the characters adopted by the hosts are over-the-top caricatures of entertainment industry blowhards. By remaining in character for the ads, the Squarecash brand becomes braided into the show’s sprawling mythology that fans cultishly fawn over. The ad isn’t just part of the episode. It’s part of the world Sean and Hayes are building. 

Case 2:
Dirty John & Hunt a Killer

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The Podcast

Dirty John is a limited series true crime podcast about one family’s harrowing experience with a sociopathic conman. It strikes the perfect balance between pulpy radio play and clear-eyed journalism.

The Brand

Hunt a Killer is a subscription box service, but instead of trinkets you’ll throw away when you move next, it delivers a monthly mystery to investigate and solve. 

The Ad

Each episode of Dirty John ends with a maddening cliffhanger and wildly suggestive clips from the next chapter. Just when a listener is trying to connect the dots and predict what’s going to happen, the post-roll ad for Hunt A Killer comes on. In addition to the cleverness of the concept, the ad makes special mention of how there’s an application process to join. It’s exclusive. 

Why It Works

Dirty John is the kind of podcast that drives audiences to preemptively sleuth out the story’s end. The show is peppered with feints, hints, and red herrings to rile up the amateur detective in even the most casual listener. Thanks to the success of shows like Serial, there is a whole new generation of true crime fanatics to collect clues and develop theories. Simply put, the kind of person that obsesses over Dirty John is exactly the kind of person that Hunt A Killer was made for. 

Case 3:
Revisionist History & ZipRecruiter

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The Podcast

Revisionist History is a podcast by Malcolm Gladwell—author of Tipping Point, Outliers, and other great books to read on airplanes. Over the course of a 10-episode season, the podcast explores a central theme and examines how our preconceived notions can be misleading, misinformed, and sometimes flat-out wrong. 

The Brand

ZipRecruiter, an online job posters and seekers directory. 

The Ad

At the end of each show, Malcolm interviews a different member of his staff about how they came to work at Revisionist History. Because you can’t major in podcasting (yet), everyone has disparate backgrounds ranging from journalism to finance. Each story has a familiar arc—a talented, yet out-of-work person, through a few twists of fate, finds happy employment at Panoply Media. While Malcolm Gladwell appears to have been lucky with quality candidates, the ad implies that other businesses should use ZipRecruiter and not leave it up to chance.

Why it Works

Post-roll ads are the easiest to avoid, but these short vignettes fold in nicely to the inquisitive tone of Revisionist History. The ad leads a listener to reflect on how much of finding a job is dumb luck and how ZipRecruiter simplifies the process. It gives the audience a behind the scenes look at a group of diverse content creators while distinguishing ZipRecruiter from a crowded marketplace. 

As people require more of their content on demand, podcasts will continue to become more relevant. Don’t assume you can just copy-and-paste a radio spot for a podcast ad. 

"Don’t assume you can just copy-and-paste a radio spot for a podcast ad." 

There is an entire generation of storytellers shaping the future of audio content. If Hollywood Handbook, Dirty John, and Revisionist History have anything to teach us, it’s that there’s no one way to take advantage of this opportunity. While the format is different, effective podcast marketing is not unlike all great ads—fearless, clever, and authentic. 

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