Perplexity Will Advertise on Theo Von’s Podcast To Answer Questions in Real Time

AI search company Perplexity has signed on as a sponsor of comedian Theo Von’s popular podcast This Past Weekend.

The sponsorship is part of a deal with podcast network The Roost that runs through the end of the year. Perplexity’s AI technology will be woven into Von’s unscripted interviews, answering questions in real-time during the episodes that appear on the video version of Von’s podcast. Perplexity has been advertising on Von’s show over the past couple of months, signaling the start of the new partnership.

Perplexity’s messages won’t carry a “sponsored” label, though Dmitry Shevelenko, the company’s chief business officer, described the arrangement to ADWEEK as a commercial deal, with Perplexity sponsoring the podcast. The messages will replace the standard 60-second ad breaks in Von’s show.

Von, 45, is known for his inquisitive, slightly oddball style. His episodes can be compassionate—covering topics like drug use and addiction—or frivolous, as when he asked comedian Bobby Lee if he “feels Asian” when he wakes up. 

“Theo asks the most original, out-of-the-box questions out of podcast hosts,” Shevelenko said. “That kind of extreme curiosity can be extremely funny. He asked questions during our Comet demo that I would have never thought to ask—it was a big part of the appeal.” 

The Past Weekend releases every Wednesday, and each episode is up to two hours long. Von often pauses mid-conversation to ask his guests for clarification or looks at the camera to prompt his producer to pull up relevant information—a habit that makes Perplexity’s real-time answers a natural fit into the program.

“This partnership with Perplexity solves those questions,” said Catherine Brown, vp of revenue and partnerships at Root Podcast Network. “And because Perplexity is model agnostic—that gives trustworthy answers.”

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The deal follows Perplexity’s partnership in March with the Ben Shapiro Show.  Since then, Shevelenko said the campaign had exceeded expectations, seeing a 50% increase in lifts and recalls, though he declined to share further specifics.

Perplexity reportedly had $850 million in the bank at the end of December, leading the company to recently make a bid to buy Google’s Chrome for $34.5 billion.

This Past Weekend began in 2016, steadily climbing the charts to land at the fourth spot on Spotify’s 2024 year-end ranking. The show claims to reach nearly 54,000 monthly listeners. Meanwhile, Von’s YouTube channel boasts 4.15 million subscribers, with some episodes attracting more than a million views.

Given The Past Weekend’s free-flowing, sometimes far reaching interview topics, Shevelenko said: “Unlike ChatGPT, which can be sycophantic, Perplexity gives you facts, and doesn’t encourage you to go with your idea, even if it’s not grounded in anything.”

“The meta strategy for us to be part of where culture is happening,” Shevelenko added. 

Von is increasingly associated with the so-called “manosphere,” a cluster of right-leaning, hypermasculine influencers including Joe Rogan. While his political views are relatively monolithic, Von often balances episodes with diverse voices—like interviewing Donald Trump ahead of 2024 election or talking to guests about the Israel-Hamas war, as he did the episode with Aziz Rahman, an American intensive care specialist who traveled to Gaza on a medical mission. OpenAI CEO Sam Altman was a guest on Von’s podcast in July.