Tech CEO Rhymes 'AI' With 'So Fly' in Deeply Cringe-Inducing Freestyle

The San Francisco-based tech CEO quickly drew comparisons to Kendall Roy and Marnie Michaels.

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For today’s heavy dose of cringe, we have a San Francisco-based tech CEO who’s making headlines thanks to a viral freestyle clip.

The CEO in question, Thunkable co-founder Arun Saigal, is seen in a @farouk.ramzan-shared clip rapping for attendees at a recent Tech Week party. At one point, he opts to rhyme “AI” with “so fly,” thus pairing two things that couldn’t be further from congruous.

When the footage first started making the rounds around the Thanksgiving holiday, the surely-should-have-been-expected mockery was swift. Appropriately, many were quick to compare the moment to the misguided tendencies of one Kendall Roy, the would-be heir to fictional Waystar RoyCo boss Logan Roy on HBO’s Succession series.

The oft-memed character, played by Jeremy Strong, once performed a rap in honor of his father, complete with copious amounts of cringe. Fervent comparisons to Marnie, Allison Williams’s character from another HBO classic, Girls, were also drawn for similar reasons.

Here’s a sampling of other mockery-minded reactions, all pulled from Instagram and TikTok comments: “I heard everyone in the video jumped off the building after he finished,” “My cringe just had a cringe,” “The quarter-zips have mutated to something none of us could have imagined,” “The Notorious GPT,” “The tech bros have ruined everything,” “I hate what my city has become,” and the list goes on.

Mercifully, there is some self-awareness here. In a recent interview with Max Harrison-Caldwell for The San Francisco Standard, Saigal provided some context to the moment while conceding he sounded “pretty terrible” in the video.

“It’s no fun to have people on the internet who don’t know you hating on you. Does it sting? Totally,” Saigal said, as seen here. “But if I watched that and had no context and thought it was a serious tech CEO who’s forcing everyone to listen to him, I’d be like, yeah, that guy’s terrible. And I’d probably blame him too.”

Anyway, now’s as good a time as any to fire up a front-to-back Succession rewatch.

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