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!

Hank and John Green began influencing online viewing long before we tied the word influencer to social media, launching their Vlogbrothers YouTube channel on Jan. 1, 2007, 17 years, 3.77 million subscribers and almost a billion views ago. Three years later, the brothers founded VidCon, the first and largest global gathering of YouTubers, growing since 2010 to include video pioneers, stars and would-be stars on YouTube, Vine, Facebook, Twitch, Instagram, TikTok and whatever comes next.

Hank Green also co-created The Lizzie Bennet Diaries, a YouTube adaptation of Pride and Prejudice that in 2013 became the first webseries to win an Emmy (for Outstanding Creative Achievement in Interactive Media – Original Interactive Program). Hank, who majored in biochemistry in college, then earned his master’s degree in environmental studies from the University of Montana. Hank has mega millions of viewers these days — watching him host the educational Crash Course series or SciShow on YouTube, or following his exploits on TikTok, Instagram and X/Twitter.

Although you may have laughed more than once at his videos, Hank Green never toured as a comedian until he decided to present his diagnosis and recovery from Hodgkin lymphoma as stand-up. His debut special, Pissing Out Cancer, came out in June 2024 as the first of six comedy specials for Dropout, the subscription streaming platform that rose out of the ashes of CollegeHumor. Green joined me over Zoom to talk about making his debut comedy special, making it for Dropout, how he can still enjoy making videos for any brand of social media in 2024, and what he expects to see when he attends his first VidCon in four years at the end of June in Anaheim.

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

At the age of 49 — three decades removed from an FBI drug bust that sent him to prison, and 24 years into his career as an ex-con turned stand-up comedian — Ali Siddiq was still seeking his big break in show business. His debut special, It’s Bigger Than These Bars, found him back in a Texas jail performing for inmates, but it came and went on Comedy Central after a few airings in 2018. The following summer, NBC put him in primetime where he competed against a similarly then-unknown Matt Rife on Bring The Funny (Siddiq won that round). But come 2022, Siddiq, just like Rife, found himself on his own, producing and releasing his next stand-up special straight to his YouTube channel. And just like Rife, Siddiq’s career and fame have skyrocketed since. The Domino Effect: Part 1 has earned more than 15 million views in just over two years, and landed Siddiq on multiple year-end best of 2022 comedy lists. But unlike Rife, Siddiq’s viral fame has yet to lead to a lucrative Netflix deal, even while he continues to rack up massive viewership on YouTube. The subsequent two chapters of The Domino Effect (with some 20 million combined views and counting) have followed Siddiq as he tells the rest of the story of how he grew up in the Houston projects, wound up selling drugs, and eventually getting busted at 19. The fourth and final chapter, The Domino Effect: Pins & Needles, premiered last month on the subscription platform Moment (making him Emmy-eligible), and drops for free on his YouTube channel just in time for Father’s Day.

Siddiq sat down with me to talk about how far he has come without taking a Netflix deal or leaving his hometown of Houston, and how Father’s Day hits different for him now that he finds himself as a successful comedian trying to raise both an adult son and a teenager who will never truly understand the struggle he endured. There’s a lot to get to, so let’s get to it!