Sam Reich was 21 when CollegeHumor hired him as its first Director of Original Content in 2006. In a few short years, the success of in-house webseries such as “Hardly Working” and “Jake and Amir” got Reich and CollegeHumor a sketch comedy show on MTV. While that show didn’t last, Reich helped executive produce, write or direct several others. Among them: Adam Ruins Everything for truTV, Hot Date for POP, and “Rhett and Link’s Buddy System” on YouTube Red. In 2020, Reich acquired CollegeHumor from IAC, where he continues to oversee the making of original comedy videos for the channel’s 14 million subscribers on YouTube. He’s also CEO for Dropout, a subscription-based streaming platform he founded — its shows include Um Actually, Dimension 20, and the game show, Game Changer, which Reich himself hosts. It’s been a long, strange trip making comedy videos, and it’s not over yet for Reich, so let’s get to it!