If this sounds like a groaner you’ve heard before, it is. The challenges faced by the online comedy ecosystem in the past decade are intertwined with the rise of social media, which fueled many outlets’ mainstream popularity but also ultimately complicated their existence. “How the hell can you plan for the future when the platforms where your money comes from are completely opaque?” says Adam Frucci, the former director of development for Dropout. “That’s not exclusive to comedy or video. It applies to all online media.”

Websites of all genres saw their ad-driven businesses crater as people stopped consuming content by visiting individual URLs in favor of reading and watching videos on the social web, especially YouTube and Facebook. Journalists lost jobs after their employers crafted strategies around Facebook video, only to discover that the social network had inflated its video metrics. Facebook ultimately paid $40 million to advertisers and apologized for “overstating” its numbers, but the company denies the inflation was intentional. A Facebook spokesperson told WIRED, “Claims that we kept the miscalculation of this metric from advertisers are false. We notified our partners of this issue when we discovered it, and we’ve taken a number of steps since to improve our detection of metrics issues.” But CollegeHumor has had its fortunes explicitly wrapped up with the dynamics of the internet even more than most media outlets. Its founders were instrumental in the mainstreaming of both meme-sharing and streaming video. For two decades, CollegeHumor rode a number of online trends and movements. The company started as the brainchild of literal teenagers, and it outlived many competitors because of this precocity about the social web. Until, all of a sudden, the social web helped render its business model obsolete.

Like the best sketch comedy, it started with a simple premise and progressed unexpectedly from there. The idea: Two 18-year-old best buds just want to make something new on the internet. “We were just trying to start a business online,” CollegeHumor founder Josh Abramson says, sipping an afternoon coffee at a New York café, remembering the beginning of his partnership with his childhood friend Ricky Van Veen. The pair created a parent company called Connected Ventures in 1999, but the pitch for what it actually did was not particularly fine-tuned. “Someone told me I founded a media business many years later, and I was like, ‘What's that?’”

According to Abramson, he had imagined a way to “take all the funny videos and stuff floating around in the dorms and put them on one website,” while Van Veen had envisioned an online platform for “keeping track of what was happening on college campuses.” (Through a spokesperson at Facebook, where he now works, Van Veen declined to comment for this story.) But nothing was definitive. The process of getting the domain was more about “taking two words and putting them together” than articulating a precise vision. Then they found an available option: CollegeHumor.com.

It launched in January 2000. “I like to remind people that this was five years before Facebook,” Abramson says. The 38-year-old entrepreneur is trim and sandy-haired, and has the sort of perpetually boyish face that’d still allow him to sneak into a campus kegger. However, he reminisces about the website with a wistful distance, as though it all happened in another era. In internet years, he’s right. CollegeHumor’s launch came three years before the launch of MySpace and Friendster; the social web simply didn’t exist in a mainstream way.

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“If you wanted to see funny photos, there just weren’t many options,” Jake Lodwick, Abramson and Van Veen’s first hire, says. While all three men grew up in the same Baltimore suburb, Abramson and Van Veen met Lodwick online, and brought him onboard in 2001. (A fourth founder, Zach Klein, joined later.) After the young men graduated from college, they briefly moved to San Diego before deciding the proper place for media upstarts was Manhattan. They rented a 5,000-square-foot Tribeca loft and made it a home office. There was no work-life balance, but there was cash.