The day the influence died

Why Facebook’s outage had me on the edge, Dave Chappelle and the "reckless" duty of comedians, tips on asking for more money, and how pro wrestling explains, well, just about everything these days.

📰 This is the Rubesletter from Matt Ruby (comedianwriter, and the creator of Vooza). Sign up to get it in your inbox weekly.

Facebook’s outage

I get my conspiracy theories from WhatsApp group texts, my validation from Instagram Likes, and the outrage that fuels my will to live from Facebook so yesterday was a tough day. In fact, it felt like my very soul crashed.

Alas, there was simply no way to see it coming.

OK, maybe there was an inkling.

Anyway, are you okay? It was like The Day The Music Died for influencers. And personally, I’m nothing if I’m not influencing. I spent the day curled up in the fetal position, drawing self-portraits, and whispering, “Someone would definitely HEART this.” Then I yelled at my neighbors about their political views just to get my blood flowing.

Thank goodness TikTok was still up so I could get my mental health advice from wellness influencers who dance while pointing at text bubbles which tell me to go outside for a walk. It’s true, I should go for a walk.

Or I could just spend hours writing this instead. OK, screw the walk…

Reckless talk

The new Dave Chappelle special is out today and the trailer got people talking.

Well, at least comedy critic Jesse David Fox and I had an exchange about it…


In the teaser for the new Chappelle special he says "Comedians have a responsibility to speak recklessly," which I find to be a pretty radical statement. Both how he uses "responsibility" and "recklessly." For context, he goes on to say essentially that sometimes mean things are funny. Now you might say, sure, but also not mean things can be funny. But again he is arguing comedians are obligated to do jokes that are mean. I find this perspective... unique. Do you agree?

I wrote him back:

Personally, I'd reframe as "The best comedians say things others in society believe but are too afraid to say. We are the tightrope walkers; if we don't do it, who else will? Also, be funny 'cuz otherwise that's just a TED talk. And no prob if you disagree and don't wanna watch."


THIS I get. If he said this, I'd be like sure, fine. But "tightrope walking" is very different than MUST BE RECKLESS. And I'm sure you know that. That's why I find his take so wild. It is like comedians MUST find things to be funny about without consideration of the ramifications


The idea that any artist MUST do anything seems a bit hyperbolic, but perhaps that's the whole point of a rabble-rousing statement like this. There may be differing views of "ramifications" too. I mean, what have been the legit real-world ramifications of his reckless behavior?


Yea, I wanted someone to defend this because I can't figure out what's the idea behind the hyperbole, if it is in DC's case. By ramifications, I meant in how the audience might feel. Like hurt feelings & inspiring people to talk about certain people certain ways. Not punishment


Re: hurt feelings, I think Mike Birbiglia addressed this well in Thank God For Jokes, explaining how every joke has a target and hurt feelings are somewhat inescapable. Imagine one comedy channel that never hurts feelings and another that allows for 'em...which would you rather watch?


I am not saying comedy shouldn't hurt anyone's feelings, but I guess I'd prefer comedians (when they are filming things; live is another convo) (especially when they have a platform and tremendous influence) to consider that they are, opposed to being reckless, ya know

See, I think being reckless is kinda great – especially if the ramifications are merely hurt feelings. I’ll take that over, say, the overly polished answers celebs give at press junkets which are so yawn.

I actually wonder if it’s Dave’s platform/influence that leads to him saying this kinda stuff. People like him and Rogan are two of the few left who can say whatever the hell they please and get away with it. Just conjecture, but I think they purposefully go right up to (and occasionally over) the line because they’re (basically) uncancellable. Considering how few people occupy that position, I could see how it might start to feel like a duty to say the kinda stuff that those who rely on permission from corporate overlords can’t. (Sure, Netflix and Spotify pay them big money, but who’s really in charge of those relationships?)

Plus, comedians like Chappelle, Bill Burr, and Doug Stanhope (three of my faves) thrive on the audience disagreeing with them. They aren’t running for office, they’re gunning for laughs. And they intentionally argue things that are weird, dumb, wrong, and/or mean because there’s an inherent absurdity to saying things like that. IMO, we should appreciate tricksters rather than condemning them for not playing by the rules. The standup stage is one of the last areas where that’s still allowed and it’s part of why it still feels sacred. Let’s not neuter everything.

“That’s what I love about jokes,” Birbiglia says in that special. “They’re just your side of the story.”

Update: Got another response from Jesse after he read this.

not to let you get the last word on this convo ;) i'm not squeamish around what comedians talk about. i just would like them to try harder to write better no matter the area they delve into. and i fear DC has prioritized his responsibility to speak recklessly over everything

Related: Last week, I wrote about idiot compassion vs. wise compassion. Here’s Buddhism expert Barbara O’Brien on the subject; it feels resonant here too.

If your guts are telling you something needs to be addressed, but you fear doing so because of how other people will react to you, then it’s your ego telling you to stay quiet. If you know something is wrong but have to club your way through an internal wall of conditioning and fear of social censure to speak up, very probably you really need to speak up. And other people need you to speak up, too.

Also (kinda) related: Jesse did a great interview with Martin Short all about how he approaches his Jiminy Glick character. If you’re not familiar, Glick is a great YouTube rabbit hole (and explains a lot about Between Two Ferns). For example: 1) Glick to Mel Brooks: “What’s your big beef with the Nazis?” 2) To Steven Spielberg: “When are you going to do the Big One, the one that connects to the people?”

Getting the freelance bag

When I’m not raking in the big bucks from standup comedy, I do freelance writing gigs for tech clients and others. (Want to hire me? Shoot me an email/learn more here.)

Lately, I’ve been enjoying Freelancing With Tim, a newsletter from Tim Herrera designed to help writers “better navigate the world of journalism — and get paid doing it.” There’s good stuff for any freelancer (including non-journalists) in it.

For example, How to ask for more money — and actually get it gives this golden phrase to use in conversations about your rate:

“As a matter of personal philosophy, I think everyone should always ask for more, so here is me asking: Is there any wiggle room in the budget to increase the rate?”

Love the context there. It’s not just a cash grab, it’s a manifestation of a personal philosophy! Tim also recommends this NYT article on the subject: How to Be an Ace Salary Negotiator (Even if You Hate Conflict).

And recently, the newsletter featured an interview with an anonymous freelancer who made $27,000 in 1 month. Having worked with several startups who need content, I thought this tip was a wise one:

I also use Crunchbase to find startups that might need content. I check out their blog to see if they're publishing already, then I reach out to them. Once I hook them, we talk about rate. If they have tons of seed funding, I don't feel bad asking for more money. (Actually, a good reminder: No journalist should ever feel bad asking for more money.) Also, if I've been working with a pub for a while at the same rate, I ask for an increase after several months of working together. Most editors are respectful enough to consider it, and if they don't or can't, I'll focus on work that pays more.

I'm also at a point in my career where I've come to terms with the reality that, for me, money is more important than prestige. I care more about paying off my loans and building savings than, say, writing for prestigious or "cool" publications that may pay less. (It also helps that I literally never want to write a book, so I don't have to think about bylines or building a platform.) I also care more about building relationships with editors than simply accumulating more work with editors who make me feel horrible. Focusing on these things has helped me earn more and be happier while I do it!

Although I don’t really agree, it’s kinda refreshing to hear someone come on out and admit, “For me, money is more important than prestige.” Made me realize: I must be happy with my heaps of prestige because otherwise I’d be making way more cash, right?

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Speaking of cash grabs, did I mention you can subscribe to the paid plan of this newsletter? As a matter of personal philosophy, I think everyone should always ask for more, so here is me asking: Is there any wiggle room in your budget to go ahead and subscribe? You’ll get bonus content too. And here, I’ll even give you 20% off:

Get 20% off for 1 year


🌀 It's kinda crazy that Elton John wrote "Candle in the Wind" as a tribute to Marilyn Monroe and then years later Princess Di died and he just changed the song to be about her instead and everyone was like "Yeah, whatever, it's another dead blonde lady so sure."

🌀 Re: Latinx, I dislike when it's pronounced like it rhymes with Kleenex, but I like when it rhymes with Malcolm X. It's better to sound like a revolutionary than a tissue.

🌀 These boxing press conferences seem to lead to a lot of unnecessary tension. Maybe it’d be best to do them over Zoom.

🌀 One big mistake media made transitioning to online: Giving opinion pieces and actual reporting the same look/feel. Nothing undermines a pub's brand more than when people think your opinion pieces are your journalism. Instant breach of trust due to lazy design choices.

🌀 Guy announcing launch of new mental health app available via a subscription model: "May it diversify my revenue stream in a way that's deeply beneficial to me in this painful time for you."

🌀 One underrated thing about elites is they save you time; They think things through and sort it all out for you. When you distrust elites, you lose a bunch of your life because you can no longer outsource decision-making and instead need to waste endless hours "doing the research."

🌀 Trivia night is the natural enemy of standup comedy. They're similar except instead of a guy with ideas, it’s a guy with questions.

A post shared by Matt Ruby (@rubymatt)


1️⃣ Naturalist Rachel Carson evoking beginner’s mind in "The Sense of Wonder" from 1965:

A child's world is fresh and new and beautiful, full of wonder and excitement. It is our misfortune that for most of us that clear-eyed vision, that true instinct for what is beautiful and awe-inspiring, is dimmed and even lost before we reach adulthood. If I had influence with the good fairy who is supposed to preside over the christening of all children I should ask that her gift to each child in the world be a sense of wonder so indestructible that it would last throughout life, as an unfailing antidote against the boredom and disenchantments of later years, the sterile preoccupation with things that are artificial, the alienation from the sources of our strength.  

2️⃣ Been arguing for a while that everything is pro wrestling these days so I was excited to find this old piece from Judd Legum that uses French philosopher Roland Barthes’ thoughts on professional wrestling to explain Donald Trump.

This public knows very well the distinction between wrestling and boxing; it knows that boxing is a Jansenist sport, based on a demonstration of excellence. One can bet on the outcome of a boxing-match: with wrestling, it would make no sense. A boxing- match is a story which is constructed before the eyes of the spectator; in wrestling, on the contrary, it is each moment which is intelligible, not the passage of time… The logical conclusion of the contest does not interest the wrestling-fan, while on the contrary a boxing-match always implies a science of the future. In other words, wrestling is a sum of spectacles, of which no single one is a function: each moment imposes the total knowledge of a passion which rises erect and alone, without ever extending to the crowning moment of a result.

Everyone else showed up for a boxing match and Trump was the only one who realized America had become Wrestlemania. As Legum writes, “As the rest of the field measures up their next jab, Trump decks them over the head with a metal chair.”

3️⃣ Wrestling, the Spectacle, Politics, and the Desire for Justice dives deeper on Barthes’ wrestling thoughts and the “grandiloquence of gesture.”

The passion and immediacy, notes Barthes, comes out of what Charles Baudelaire calls the “grandiloquence of gesture.” The focus is not on narrative and not on intellectual content; it is on the body. Barthes points out that the body of the wrestler signifies immediately…What is displayed for the public is the great spectacle of Suffering, Defeat, and Justice. Wrestling presents man’s suffering with all the amplification of tragic masks. The wrestler who suffers in a hold which is reputedly cruel (an arm-lock, a twisted leg) offers an excessive portrayal of suffering. 

4️⃣ Al Pacino on going to the Oscars high:

I was at the Oscars once, for Serpico. That was the second time I was nominated. I was sitting in the third or fourth row with Diane Keaton. Jeff Bridges was there with his girl. No one expected me to come. I was a little high. Somebody had done something to my hair, blew it or something, and I looked like I had a bird’s nest on my head, a real mess. I sat there and tried to look indifferent because I was so nervous. Any time I’m nervous, I try to put on an indifferent or a cold look. At one point, I turned to Jeff Bridges and said, “Hey, looks like there won’t be time to get to the Best Actor awards.” He gave me a stange look. He said, “Oh, really?” I said, “It’s over, the hour is up.” He said, “It’s three hours long.” I thought it was an hour TV show, can you imagine that? And I had to pee—bad. So I popped a valium. Actually, I was eating valium like they were candy. Chewed on them. Finally came the Best Actor. Can you imagine the shape I was in? I couldn’t have made it to the stage. I was praying, “Please don’t let it be me. Please.” And I hear…”Jack Lemmon.” I was just so happy I didn’t have to get up, because I never would have made it.

5️⃣ Dan Savage Revolutionized Sex. Then the Revolution Came for Him. A good profile on Savage from someone who has complicated feelings about him.

He obviously hasn’t always succeeded. He’s driven off readers with his carelessness and callousness and tendency to dig in his heels. He’s used bigoted language. He’s been dead wrong. He’s been slow to understand the way superficially gender-neutral prescriptions can affect men and women differently, and he may never be done issuing clarifications and updates to his code of conduct.

But there is genuine compassion and insight and, three decades later, real earned righteousness beneath the sarcasm and diatribes and acronyms. I was struck a few times when we spoke by moments when Savage articulated psychological and interpersonal dynamics I’d experienced with a specificity I’d never heard from anyone before. It felt like Savage was looking right through me. There may not be any truly universal sex principles that empower everyone in every circumstance, but Savage’s worldview has expanded.

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About the Rubesletter: Weekly musings from a standup comedian and startup veteran. If you like my comedy or writing, if you dig tech, politics, art, wellness, & pop culture, if you enjoy smart/nuanced takes & hate BS, if you’d like me to turn you on to other people making cool stuff, then subscribe.

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My latest standup special is free on YouTube. And you can stream my standup albums “Feels Like Matt Ruby” and “Hot Flashes” too.