According to Jack O’Brien Thrives on Lists and Honesty went from the online version of a rebooted humor magazine to a successful outlet in its own right by formulating an iconic and successful user-focused strategy. It’s one that is based on honesty as much as funny.

Jack O’Brien has guided the Cracked ship since the 2006 relaunch. On episode 74 of The Wolf Den podcast, he explains to host Adam Sachs the secrets to the site’s “funny but true” sensibility.

“We don’t target anyone in particular, just people who like interesting articles. We make it a point to say that no subject is off-limits. We can write a funny article about feminism and the men’s rights movement. We manage to always keep the audience engaged, sandwiching in jokes every few sentences. The comedy is a candy-coating.”

This list article is a tried-and-true format for Cracked, from “4 Real Brainwashing Techniques Every IKEA Is Using on You“ to “6 Easter Eggs In Popular TV Shows That Change Everything.” Jack says they rely on lists so heavily because ”it’s what people want to read."

He notes that the list format is nothing new, even if it’s found new life on the internet. “If you look at Comso magazine in the 70s, there’s lists,” Jack observes. People like them because “It tells you exactly what’s going to be there–there’s no bullshit there–unless you lie. It’s going to be this many (items) of this very specific thing. We try to have some substance and some takeaway.”

Jack first guested on The Wolf Den in 2011, where he floated the idea of having a podcast. Since then the Cracked Podcast launched on Earwolf, bringing the “funny but true” approach to the audio medium.

He started out thinking it would be a highly edited and polished show. “If you listen to the first one,” he recalls, “it’s a lot of edits. Five conversations. It took us a month and a half to make it.”

Realizing that tact wasn’t sustainable, the podcast quickly evolved. It now features a conversation between staff members, sometimes including a guest expert, focused on a single Cracked-worthy topic, like “Insane Internet Fan Theories” or “How the PG–13 Rating Took Over the World.”

A key to pulling off the show is to “have your five facts together”–there’s that list strategy again–“then the subject sorts itself out. We (the hosts) don’t talk about it before we get in the room.”

To click with the audience, Jack says “it has to be based on some relationship where the people know each other and like each other. That’s true of our team.” This applies equally well to the website as it does the podcast.

Listen to the whole episode to learn how Cracked plunged into video, and why the site is moving away from display advertising.

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