How Ryan Holiday Scaled Podcast Business, Reaches Anti-Ad Gen Zers

Twelve-time author Ryan Holiday’s attention is divided between his books, two podcasts, a YouTube channel, and an email newsletter.

Amid this high-wire act, Holiday has a spotter: Backyard Ventures. The Austin-based media startup does the dirty work for creators like Holiday by finding them relevant brand partnerships.

In turn, Holiday’s YouTube channel and newsletter has grown its revenue 81% from mid-six-figures in 2023 to near the seven-figure mark so far in 2025, according to documentation viewed by Business Insider.

And that doesn’t even include the mid-six-figure sum in podcast ad bookings that Backyard Ventures has landed in July alone, when Holiday expanded his agreement with Backyard Ventures.

Backyard Ventures founder and CEO Matt Cisneros prides himself on helping Holiday’s business, and dozens of others’, grow up.

“We exist so that we can then aid him in monetizing and creating like-minded partnerships that don’t taint his content,” Cisneros said of Holiday in a recent interview.

The author-turned-content creator concurred, telling BI that Backyard Ventures “allowed us to start producing the episodes and to hire a team to do it really well,” which helped “take things to a different level.”

Authentic ads are Gen Z’s jam

Content creators and consumers often treat ads as a necessary evil. Ads feel inescapable and many times are boring, irrelevant, or both.

But even ad-averse Gen Zers can appreciate ad breaks if they’re tailored to their interests and those of the creator, Cisneros said.

Gen Z audiences “want a seamless integration that doesn’t feel like they’re getting served an ad,” Cisneros said. “They’re accustomed to being served well-integrated content.”

Like any good matchmaker, Backyard Ventures vets both parties before recommending a pairing. Cisneros believes authenticity is key to compatibility, so creators should use the products they’re selling, or at least vouch for their quality.

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“If a client has yet to try the product, they’re not endorsing that product,” Cisneros said. “We wouldn’t allow that to happen.”

Value alignment is also crucial. Cisneros works with former ESPN and Fox Sports personality Skip Bayless, who he said doesn’t drink or smoke but is fine with sports betting. So for Bayless’ eponymous podcast, Backyard Ventures responds accordingly. Beer companies might want to reach that audience, but an ad spot would be inauthentic to Bayless and could jeopardize his credibility with fans.

“This is not only about money,” Cisneros said. “It allows the opportunity for your audience to see that you are truly by your content, because we’re only embedding brands that are like-minded.”

Once ad partners are properly paired with podcasters, Cisneros said creators get a say over how ads are presented. Gen Zers are constantly bombarded by ads, so they’re savvy at sniffing out whether creators actually care about the product they’re selling.

“If brands are smart, they say, ‘Here are two or three talking points: please, creator, go do whatever you’re good at,'” Cisneros said.

Backyard Ventures said that most of its clients’ audiences are in that coveted 18- to 34-year-old demographic, and added that 55% of Holiday’s following that they track is 34 or younger.

Gen Z’s view of ads isn’t necessarily night-and-day different from other generations, EMARKETER social-media analyst Minda Smiley told BI.

However, she acknowledged that young people do take issue with creator-advertiser pairings that seem phony, or if they can’t tell if an influencer actually uses the product they’re hawking.

“It’s that gray area where Gen Z gets frustrated,” Smiley said.

Buzz sells, but brand safety still matters

Backyard Ventures doesn’t just put advertisers under the microscope. Cisneros said he’s also choosy about his clients.

While Cisneros said he works with all kinds of content creators, many of his clients have male-skewing audiences. They’re well-positioned to capitalize on the boom in comedy podcasts, including so-called “bro-casts” typified by megastars like Joe Rogan and Theo Von.

“If they have the audience and they can amass views, downloads, and general awareness for brands, that’s who we want to work with,” Cisneros said.

That’s not to say Backyard Ventures has adopted the “anything goes” mantra that some bro-casts live by. The phrase “brand safety” may be taboo now, but Cisneros still has it in mind.

“We’re not going to do anything that might be controversial, in the sense that it gets excessively offensive,” Cisneros said. For example, he wouldn’t be willing to work with Holocaust deniers.

Live-n’ it up

The roughly 200 creators at Backyard Ventures hope to scale their side hustles into full-blown businesses. Cisneros’ firm helps by providing an ad sales team so creators can focus on their strengths.

Backyard charges a few thousand dollars to six- or even seven-figures for brand partnerships, depending on the audience size and other details, Cisneros said. His outfit then takes a 25% to 30% cut, so its incentives are aligned with its clients.

“We are not a retainer-based company,” Cisneros said. “We eat what we kill.”

Podcast ad rates typically range from $20 to $25 per thousand impressions, Cisneros said, though it’s higher for video podcasts. For reference, podcasts on YouTube can rates can range from $20 to $50. Niche podcasts about finance or marketing can command higher rates, he added.

As for Backyard’s next gateway for growth, Cisneros said he’s looking at live events. In-person meetups literally add another dimension to the robust parasocial relationships Gen Zers already have with their favorite content creators.

“It’s like you know somebody, without knowing them,” Cisneros said. “You’re one inch closer to having a friend feel, than the distant download.”