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This Podcast Company was Dad on Arrival

Even before Terry O’Reilly convinced his wife and kids to join him in launching the Apostrophe Podcast Company, he had a track record of being persuasive.

Under the Influence, perhaps his most well-known podcast, is a narrated show about the world of marketing, and it started as a syndicated program for the Canadian Broadcasting Corporation, even though, by Terry’s assessment, it didn’t have the best shot of getting picked up. “I didn’t think they would buy a show on advertising on an advertising-free network,” he laughs. But he made it happen.

Terry’s productive pitching, whether to his family or to the CBC, is certainly due in part to his own background in marketing. Before Apostrophe, he co-founded the commercial firm Pirate Radio and Television in Toronto and, before that, wrote scripts for ads; he graduated to directing them after starting Pirate. Though he’s long experimented with the art of persuasion, it’s hard to say if his now-full-blown podcasting company came to be purely because of his convincing nature, or if it’s also because he’s just a nice guy, one who’d be pleasant to work with. It’s likely a mixture, just as there are multiple reasons why his own family members are his best-suited partners for this new storytelling business: They, too, come from marketing backgrounds. And they, too, are pretty pleasant to work with. In fact, they’re so aligned professionally and socially that they’ve actually done this before: Until recently, Terry’s daughter Callie was one of Pirate’s directors.

Terry and Debbie O’Reilly have three kids, two of whom, Callie and Sidney, now work for Apostrophe. Mother Debbie comes from a career in advertising; daughter Sidney studied journalism. All four had a hand in making the flagship Apostrophe show Under the Influence before Apostrophe was even an idea, with Debbie line-producing, Sidney pushing out social media content, and Callie coordinating the music when the program was still strictly for radio. Having extra O’Reilly hands on the project made sense, considering the four have worked in varied-enough roles within the communications field that they all bring something unique, says Terry. They’re “not one homogenous group,” he says, “and that collision and those sparks are pretty wonderful.” At the same time, they’re still able to approach projects with an aligned understanding of what works for a given audience, he notes. Callie agrees: “It’s so easy to share work and hand things off to each other because we have complete trust with what that person is going to do with it.”

While one might assume that such synchronized standards are a product of similar careers, it goes back much further than that. “We grew up in a pop culture house,” says Callie, and she and her siblings were shown how to analyze media, whether they knew it or not, because of their dad’s ever-present interest in entertainment and the art of the ad. This undoubtedly planted the seeds for future jobs in media, but it also established a more fundamental synergy in how the family interacts. “We have a shared taste and a shared trust in each other’s instincts,” Callie notes, not from work alone but “in a way that can only come if you’ve grown up together.”

It works particularly well that at the heart of Under the Influence, the first production that the O’Reillys collectively left their mark on, are the movies and commercials they’ve spent so much time consuming and discussing as a family. I personally felt drawn to listen as if I was part of the family myself, since a good amount of the show’s subjects are familiar to me, too, having come up of age around the same time as Callie and Sidney, albeit in Massachusetts. Who doesn’t love a “10 commercials you forgot about”-style roundup? (I’m currently 18 minutes deep in this one.) Under the Influence, though, goes one step further by explaining how things like commercials came to be and the effect that certain elements were intended to have.

“We developed that language early on,” Callie says, recalling that watching the Oscars together, for example, was a household tradition. “It’s kind of in our blood.” These days, brainstorming sessions often reference those early, formative memories, which makes it possible to cut out small talk or roundabout discussions, thus speeding up the editorial process. “Shorthand is critical,” Terry says. “One of us will say, ‘Hey, remember that moment in that movie where someone says that thing about that thing?’ and we all just say, ‘Yeah, yeah yeah!’”

Being exposed to entertainment so early and often gave the O’Reillys a sort of double education on the world of media — one informal, in the home, and one supported by academic institutions and real-world jobs. Such comprehensive schooling doesn’t hurt, considering that the best marketing references other media, or else it depends on complex and compelling characters, framing, and hooks. It’s a “fascinating field,” Terry says, because it’s “study of human nature,” playing into and revealing what drives people to feel and act certain ways. And the O’Reillys seem to have it down.

Speaking personally as a fan, Under the Influence hits many of the right notes. When the show itself isn’t reminding me of the cereals I used to eat as a kid, its theme music, an energetic, jazzy tune overlaid with crackly recordings of vintage commercials, achieves a setup akin to the THX intro — it sets the tone, and it gets you excited. I once described it as a great show to listen to while roller skating. Because of that energy, it’s very nearly a show that I can’t listen to at 1.5x speed, for fear of not being able to keep up with all the action. But fear not: Each episode ends by recapping the stories’ lessons and throughline. Even if you don’t need a summary, you might listen through anyway, if only to hear how Terry will lead up to the last line, which always ends with “… when you’re under the influence.” When I learned that the O’Reillys call their shows “driveway podcasts,” meaning that you’d gladly sit in your now-parked car to finish listening to an episode you started on the way home, I agreed.

The O’Reillys’ marketing know-how yields a polished product that’s jam-packed with stories, a widely applicable skillset that’s allowed them to branch out from a show strictly about the marketing world to other narrative series, such as Alone Together and We Regret to Inform You. They also just launched an interview show that breaks from their trademark style of a solo narrator guiding you through a curated list of stories.

Indeed, the company appears to have various marketing tones that they can dial up or down. When showcased through its official website, on which the origin of the company’s name is front and center, Apostrophe (referring to the punctuation in “O’Reilly”) is a family business. But if you come to one of the company’s shows purely by way of that show, you might have no idea, and instead all you get is a sharp, highly produced audio product, able to duke it out with something from a much larger or more established media company. (Though it built on collective decades of work, Apostrophe itself only launched in January 2020.)

I found Under the Influence through the CBC’s podcast directory, took a liking to it, and one day just happened to listen all the way through the credits and notice that the host and one of the producers had the same last name. I Googled and Googled and was able to find only one thing suggesting that the two were married (Terry’s Wikipedia page, because, for some reason, maybe having to do with international borders, the Canadian company’s “.ca” site never came up). I boldly emailed Terry to ask if I was right, and I was. And thank goodness, because “O’Reilly” isn’t exactly a rare last name: According to 2014 data on the site Forebears, every 1 in 8,462 people in Canada has it — that’s compared to the 601,093 you’d have to sort through to find a Bracci in the U.S.

Perhaps the O’Reillys will more aggressively market the family angle in the future if it becomes useful or relevant; after all, that’s exactly what they did with the Airstream-trailer-turned-podcast-studio they use: Though they’ve been recording in it for years behind the scenes, as soon as a listener jokingly referred to it eponymously as the “Terstream” studio, the team adopted it as part of their brand and messaging.

Until then, the O’Reillys’ family dynamic shines in how it sets a foundation for the business, rather than how it operates as a facade. It does occasionally make itself known, though. For one, you can’t ignore it when you get two of them on the phone together and pose a question to them both, and Terry, in such a dad-like way that it could’ve been ripped straight from the script of The Parent Trap, volleys the inquiry to his director — and daughter — with a “go ahead, Cal.”