Episode #459: Sam Reich, Dropout CEO

I spoke to Sam Reich on this podcast back in the fall of 2020, when he was in his first year running Dropout, the subscription-based streaming platform he founded as a follow-up to CollegeHumor where he had worked for much of his adult life. Four years later, Reich and Dropout are ready to graduate to the big leagues, with one of their shows already selling out Madison Square Garden for a live event months in advance, and other shows eligible for the first time for Emmy consideration. Reich talked to me this time about what it’s like seeing his name on an Emmy ballot for the first time — he hosts the game show Game Changer — and why Dropout now is producing and releasing comedy specials. Dropout’s first comedy special from YouTube star and VidCon founder Hank Green debuted in June 2024, with more to come, including two shows Reich saw in 2023 at the Edinburgh Fringe Festival.

Sam sat down with me over Zoom to talk about all of that, and how he successfully runs a streaming platform when the rest of the industry feels upside down and backward.

There’s a lot to get to, so let’s get to it!