Last September, CollegeHumor rebranded as Dropout. The 25-year old comedy platform made the move after a surge in subscriptions to the company's streaming platform, Dropout TV. After decades of struggling to find profitability, this became the centerpiece of its business model.

“Truthfully, as a high school dropout, I never really connected with the brand name CollegeHumor,” said Dropout CEO Sam Reich. "We promised ourselves we would only do away with the name when we felt that Dropout was popular enough to eclipse it, and we feel that time is now.”

Since purchasing the company for a whopping $0 in 2020, Reich has prioritized producing long-form improv content, keeping costs low and driving brand awareness through vertical videos on social media networks like TikTok. Dropout currently has 11 active series including its two most popular properties Game Changer and Dimension 20, a series where comedians actually play a live game of Dungeons & Dragons. By the end of this year, they are set to have 15 series including a live comedy special series called Dropout Presents that will launch this summer with a stand-up special from YouTuber Hank Green. The company has also ventured into live event programming for Dimension 20 in partnership with Live Nation, starting with a four-show tour of the U.K. this spring and, most impressively, leading up to a show at Madison Square Garden in January of 2025.

How Dropout competes in a cutthroat, subscription-streaming market 01:05:35 Share

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How Dropout competes in a cutthroat, subscription-streaming market