Jubilee Is Making America Debate Again: How YouTube Hit ‘Surrounded’ Landed Pete Buttigieg and Ben Shapiro — and Why Its CEO Wants to Get In On the 2028 Election
Last week, Pete Buttigieg sat in a studio in Michigan, surrounded by 25 undecided voters who rushed, musical chairs style, to sit across a table from him and debate his positions on Kamala Harris and Donald Trump’s policies. Those on the perimeter raised red flags when they felt each debate had run its course.
It wasn’t a town hall or a cable news panel, and it didn’t air on CNN, Fox or MSNBC. Actually, the encounter didn’t air on television at all. Rather, it was the sixth episode of hit YouTube series “Surrounded,” from Jubilee Media, the independent L.A. production company behind other social experiments like “Middle Ground” and “Swipe or Swap.”
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With episode titles like “Can 1 Woke Teen Survive 20 Trump Supporters?” and “Can 25 Liberal College Students Outsmart 1 Conservative?,” the series has gone viral since its September debut, racking up more than 50 million views on YouTube and dominating social media feeds. Perhaps you saw liberal online debater Destiny “own” skeptics in MAGA hats or, depending on your algorithm, right-wing commentator Charlie Kirk “destroy” leftist teenagers. The fourth episode, with conservative pundit Ben Shapiro in the crosshairs, snared 5.1 million viewers in its first day — roughly the same as a typical episode of “Saturday Night Live.”
The goal of “Surrounded,” whose episodes span two hours and are fact-checked by Straight Arrow News, is to promote open dialogue. While the debates tend to devolve into shouting matches, Jubilee produces shows like “Surrounded” to “provoke understanding and create human connection,” says founder and CEO Jason Y. Lee. With a roster of programs unpacking politics, relationships and stereotypes, Jubilee aims to become “the Disney of empathy.”
“We want to show what discourse can and should look like. Sometimes it can be unproductive but other times it can be quite productive and empathetic,” Lee says.
Jubilee’s shows have chalked up more than 4 billion views since the channel’s inception in 2010. More significantly, the company has grown into a massive media and production house that bypasses the Hollywood studio system. Now it hopes to shape the next era of American political discourse.
Jubilee’s programming shifted toward politics after the 2016 election, which left Lee feeling “discouraged” by America’s extreme political division. He sensed that young people craved content that was nuanced and thought-provoking, but “not in a Mr. Rogers sort of way,” as with feel-good digital media competitors SoulPancake or Upworthy. “I thought to myself, there’s a much larger opportunity here for us to do a lot of good,” he says.
Many of Jubilee’s shows aren’t afraid to tackle hot-button issues. Take “Middle Ground,” a prompt-based conversation series that seeks to bridge gaps between groups like trans and cis people, Republicans and Democrats, and Israelis and Palestinians. Yet Lee insists that the company preserve its neutrality and maintain a diverse team of producers and editors. And while he doesn’t hide that he was once an intern on Barack Obama’s 2008 presidential campaign, nor does he disclose his current political views.
“We try our best to be as unbiased as possible when it comes to the political sphere,” Lee says.
Lee believes the future of political conversation is on YouTube, not traditional media. Leading up to the election, he says, Jubilee was in “deep conversations” with both presidential campaigns about the prospect of Trump or Harris holding court on “Surrounded.”
“By the next election, there should be a presidential debate on YouTube, and Jubilee is the right home for that,” Lee says. Debates on traditional news channels open themselves up to critiques about format and bias, he says, while his company can “strip down a concept as raw as possible so that not even Jubilee can put a thumb on either side.”
That approach applies to all of Jubilee’s content, not just the political videos. “In traditional media, you can feel producers,” Lee says. “You can feel the strings, what they are trying to accomplish. I think there’s an aversion to that.”
While Jubilee has fielded offers from traditional media companies to license or develop its content, Lee sees no advantages in dealing with Hollywood hurdles.
“We’re able to make so much content so much faster, whereas in the traditional television system it might be years before you see a greenlight,” he says. “The real promise is digital. It’s not an afterthought or second tier.”
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