Trapital - profit vs. morals

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profit vs. morals

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Hey! It’s bittersweet to watch Kanye West’s partnerships end with both adidas and Gap. I’m not surprised. He has hated corporations for years. It’s even harder when they ignore his requests and insights. This all felt inevitable.

Ye’s a creative savant. But if that creativity had been paired with a long-time business partner who can scale businesses, has Ye’s trust, and can push back when needed, I bet Yeezy would be multiple times bigger than it already is. I’ll do a deep dive on Yeezy sometime soon, so stay tuned for that.

Today’s memo is about the business of comedy and entertainment. I had a great chat about this with the comedian and actor, Roy Wood Jr, who came back on the Trapital’s podcast. We talked about returning to comedy clubs, pros and cons of streaming, and the state of the “cult classic.” He shared a bunch of insights in this one. Here are the highlights!

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Roy Wood Jr on the business of comedy

Roy and I last spoke on the podcast in mid-2020 when lockdowns had curbed his usual comedy performance routine. On the outside, it might not seem Roy has changed much since our first convo — he’s still a regular on The Daily Show with Trevor Noah — but internally, Roy is ready for that next step.

Roy made a successful comedic career, three specials on Comedy Central over a five-year span, out of finding unique angles to discuss external events such as news and politics. But now, Roy wants to talk about himself.

How and where he delivers this refined message hasn’t been decided yet. For now, he’s taking time for himself to think through how he’s changed, and so has comedy and the entertainment industry at-large.

In our discussion, Roy hinted at some of those major changes:

a detour from comedy clubs

Between 1998 and 2020, Roy never went more than 10 days without performing a live stand-up show. The pandemic snapped his streak, but even as comedy clubs re-opened in 2022, Roy has mostly stayed away from what was the backbone of his career for 23 years.

The distance stems from the heavier topics Roy wants to discuss — his deceased father, raising a six-year-old son, and more introspective themes. Those topics won’t go over as well at the typical comedy club, where fans go for late-night laughs as they hit their two-drink minimum. A venue can influence how his material is received by an audience, and the club isn’t the platform he’s looking for right now.

profit vs. morals

Comedy has changed a lot in the social media era. More comics have faced backlash for their material, both old and new. Lately, every Dave Chappelle Netflix special is bound to spark controversy due to its transphobic jokes. Comedy has indeed changed, Roy said, but not the actual comics themselves.

But despite the outrage from the public, it’s the corporations that make the final call. The way Roy sees it, corporations must pick between profit and morals — one or the other, not both. That tug-of-war is usually won by profits. That’s why Chapelle’s Netflix deal is unaffected (and still gets nominated for Emmys) and why Louis C.K. is performing again. The controversy often draws more attention to their material.

the death of “cult” shows

Outside of his live show acts and role on The Daily Show, Roy also writes scripted series, some of which have sold as pilots.

But the streaming giants are now the main show in town for scripted content. They make fast decisions on whether to cancel a series or re-up a new season based on internal metrics — that are largely hidden from the show’s creators and the public. This makes it harder for “cult” shows to cultivate an audience and become a hit over time.

There are outliers, sure, like the hilarious show South Side. Its first season reached a smaller audience on Comedy Central. But when its second season got picked up by HBO Max, it reached a bigger audience. That also comes with bigger expectations though. As a South Side fan, I hope HBO Max doesn’t give it the Batgirl treatment!

My chat with Roy was full of even more insights on the business of comedy, his influential meeting with Dick Gregory, and Roy’s appearance in the new movie, Confess, Fletch, which is now out in theaters.

Listen to our full conversation here:

money moves

• How Wall Street stormed the music business​
• BaseNote now lets fans invest in artists​
• ​Arpeggi Labs raised $5.1M from a16z, Steve Aoki, 3LAU, and Wyclef Jean
• Why Kanye West terminated his deal with Gap​
• Warner CEO Steve Cooper says the record label is “less dependent on superstars”​
• ​YouTube paid $6B to music industry in 12 months

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coming soon from Trapital

Essay: How do expensive concert ticket impact an artist’s relationship with fans? Coming on Monday!