Too big to laugh: how tech lost its sense of humor

0:05Today we're joined by Alexis Gay, a good friend and brilliant comedian who started her career in the tech industry. She actually just recorded her first solo show about that experience called Unprofessional, which will be coming out later this year. We're going to talk with Alexis about this particular era of tech and why it is so hard to find this humor in this moment. I'm Ashley and Helen and Mack are also here this week. Great Chat is brought to you by Mercury, radically different banking loved by over 300 ,000 entrepreneurs. We use Mercury to run this podcast and love recommending it to other founders and fund managers.

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0:46Alexis Gay:Oh, wait. I'm going to clean my camera though. So you are going to see me use my shirt to clean my camera. I did exactly that before we got on. Don't flash us. So don't stress. Or do. I don't know. Let's see. this is great chat. Anything can happen. What happens in the group chat goes on the internet. So yay. Oh my gosh. Alexis, thank you for joining us. Oh, I'm so honored. Truly so honored. This is fun because I went on your pod back in the day and now - I would say that was a pretty foundational friendship interview. I mean, it was pandemic too. So podcasts were how one expanded one's social circle back in the day.

1:27I made a lot of friends having a podcast. Actually, I feel like you're my only friend from a podcast. Is this a common friendship channel? Should I be expanding my podcast cinematic universe? It's not, but actually you, Helen, and Angela are all my podcast friends and Alexis. Wow. I would say I'm crushing it. You are crushing it. This is how we fix the male loneliness problem. is this why men have so many podcasts yeah so that they can because they just want friends i'm never gonna be mean about a four-hour podcast again like someone to talk to that's just them opening up top of funnel four hours is bottom of funnel like by the end of that you're like joe rogan is officiating your wedding so like i'm really happy for them that's great i i'm so pro this trend.

2:19Guys, I don't know if we have any leg to stand on making fun of male podcasters when we podcast all the time, but I love it. We want all genders to be thriving. So it's great. Podcasts. Wow. Pull that. Pull that quote. We want all genders to be thriving. Yeah. Well said. Not a sponsor of the gender wars. That's right. That's right. I feel like our extra quest for today as we go through what happened in tech and the world over the past week is like, finding the humor in these headlines. Because we have Alexis here and she's a professional.

2:54Alexis Gay:No, no pressure, Alexis. No pressure, I know. Nothing feels better than when someone is like, this is Alexis, she's so funny. Like she's, let me like raise the bar as high as possible. Let's lower the bar. Alexis is actually quite funny, but she's not going to be funny here. So like chill out, guys, please. In protest. Yeah, for sure. That's right. I'm boycotting comedy. She's actually expanding her cinematic universe. she is trying out being capital S serious. So I'm here to announce that. Yeah, I'm going to be I'm pulling like that thing that comedic actors do in their career where they're like, I'm done and I'm only going to take on roles.

3:28This is like when Steve Carell takes on super serious roles and you're like. And I appreciate the comparison to Steve Carell because it feels right.

3:36Alexis Gay:I feel he and I really on the same level. Yeah, this is this is that moment for me. This is my morning show. So nothing funny today. Nothing funny for me. How about we start with something that was genuinely funny without any needed comedian input, which is the Brian Chesky saga. He posted basically a clawed thought swap on tokenization of real world assets. It was like this random Web3 thread, which you can no longer read unless you find someone who screenshot it. And it was funny because I think at the initial wave was a bunch of crypto people, including Brian Armstrong. So you have Coinbase chiming in enthusiastically like, oh, look, crypto is still cool.

4:21And then there was just a massive backlash because it was such obvious AI writing. People were just dunking left and right. And Brian deleted the thread. And the timeline kept having fun with it. And I think he sort of became like the poster boy for let's rein in the AI swap. So that was like the first chapter. And that was fun. And 36 hours later. 36 hours later. When the cycle was dying out. Like it could have just died. There is an article in Fortune about how Brian Chesky's account was hacked. This was not his fault. It was hacked by some crypto person who decided the thing they wanted to do with Brian's huge audience was talk to them about tokenization of real world assets.

5:13There was no pumping of a meme coin or anything like that. And then TVPN did like a little, you know, their little cards that they do. And it was like Brian Chesky's face and it hacked in like all caps. And then Brian Chesky quote tweeted TVPN and was like, sorry, crypto followers. like I was hacked. Ha ha ha. And no one believed him. No one believed him. And so we just got like another round of internet fun. And unfortunately for Brian, ridicule. And so I don't know guys, I think this is pretty funny. I think the funniest possible thing that could happen is that he was actually hacked, but no one believes him.

5:57I don't know, Ashley, like, do you think that the recovery is for Airbnb to post record-breaking earnings and everything is fine and everyone forgets. The recovery is for them to do what they should have done after the first cycle, which is just swallow their pride and let the story die. Instead, they gave it another wave. I get it. That would be a hard pill to swallow. If you were in fact hacked and you were indignant about people attributing this thought leadership, crypto thought leadership to you. I would like to think that in the moment, if I had been who's like crisis comms, that signal call, I would have been like, just let it die.

6:45Alexis Gay:Let it die. Take the L and move on. When the tweet heard around the world came out, was it a real deviation from what kind of the tone that Brian typically posts in? like did it seem odd or did it seem like oh it's funny our last episode helen and i were chatting about how like everyone's engagement maxing even people with like huge reputations and like real legacies are just like going for the going for the likes going for the retweets like him opining on uh like a you know a category of like innovation or opportunity did not actually seem that crazy but the way it was more like the actual writing itself that I think drew everyone's attention and it was funny too because I also saw accusations of like I can't believe your PR team told you to post that I'm like there's no PR team in the world that wakes up and is like let's have like the rental platform CEO make the case for tokenization of real world assets like that's just not not in the playbook but I don't think anyone flinched I don't think that anyone was like, whoa, this is so weird, guys, that Brian is posting.

7:56I mean, because I think to your point, yeah, people are trying all sorts of stuff. I think mostly people were like, okay, that's interesting. I didn't know he was into that. Fine. You know what the 4D chess move would have been? 4D chess would have been - For him to introduce a coin. Yeah, yeah. You get control of the account back. And then you try to pump a coin. And then you say you were hacked. And then everyone would believe you. He's unfortunately, he's still a public company CEO. So like there is some level of decorum. But I think closer what I was thinking when I first saw this happen was what he should have done is get his account control back.

8:33The fortune article is hilarious. The TBPN is even better. And then retweet the TBPN and be like, hey, guys, I heard you loved I heard you loved my content taking a switch in direction and then start a thread on real world tokenization and have it lead to a rickroll. Like just ride it.

8:50Alexis Gay:Just for the millennials. It sort of reads to me, like looking at how he handled it, like somebody who doesn't really care about Twitter that much. And I think that that signals actually great power and influence. If you don't have to care about Twitter, I think of that as you've arrived at a very impressive end state. Yes. It kind of just reads like someone who was like, oh, God. And then just like dealt with it and moved on. because even the way that he posted the quote tweet to the tbpn card was just very like to the person who hacked my account earlier this week thanks for all the new crypto followers to my new crypto followers i'm going to be a very disappointing follow it doesn't have that like oh got him kind of feel that i think someone who was deeply invested in their twitter presence would have like really honed and workshopped that tweet a very good friend of mine like reports to him at Airbnb and I will randomly just send him just random trending Brian Chesky memes or like references to things that happen on Twitter.

9:57And he'll like literally be with him at a Warriors game or, you know, the World Cup or whatever. And he's just like, has no idea. It's never discussed. It's like not, he didn't even know what founder mode was for like a while after founder mode like took off. So Alexis, I think you're right. I do think that there is a separation and that's great, but that supports our sort of boomer strategy that we were talking about last week with the not being so on top of sort of like, you know, what the kids think on X, but. Alexis, is Twitter still like a relevant channel for you as a comedian or not so much?

10:37Alexis Gay:it's an interesting question because twitter is how i started my following how i found you before i met you and that was i'm guessing 2020 mid 2020 the reason i don't spend time on twitter now is that i don't enjoy it like i don't like the experience of being on twitter and so i don't have the dopamine loop of oh i want to open twitter like i don't ever crave it because i'm like, but it's bad. Like, I don't enjoy it. I should be posting jokes on Twitter for sure. I have a big audience there and posting short form jokes like that is a great way to keep building that top of funnel audience, just like it is for any of anyone building a public profile, but especially for comedy, you know, are you using another channel more now?

11:27Alexis Gay:I just don't really write those short 280 character jokes. But part of the reason for that is that I spend a lot of time on it. And so I don't just sort of casually throw a thought out there. If I'm like posting a tweet, it has been like run through the mill many times to see how can I make it shorter? What's the right punctuation to use here? Is there a better take? Is this interesting? Does AI, like does Claude help you write jokes? I wouldn't know. I've never tried, but I'll ask Claude or Chachipiti sometimes for grammar help on certain things because if I'm going to break a grammar rule, I want it to be with intent.

12:10Alexis Gay:I don't mind breaking grammatical rules, but, and this is why you guys wanted me on, right? It was talk about grammar. A hundred percent. Great. Okay. I just wanted to make sure this is why you got, you're like, oh, we're going to have a comedian on. We're going to ask her about the semicolon. So I just like to know when I'm breaking grammar rules because I like to do it intentionally. And so sometimes I'll run a written joke or a statement through Chachapiti or Claude to be like, is this grammatically correct? Just to see if I'm right or wrong. And then sometimes it proactively is like, I see this as a joke.

12:37Alexis Gay:If you'd like to do this, you could keep this cheeky tone. And it's always a mess. I've never even been tempted, especially because for the same reason, I don't think that CEOs and entrepreneurs or founders or anyone looking to build a following should be leveraging AI as like the final pass for their own perspective. I do not think anybody in the creative field should be doing it either because ultimately as content becomes easier and easier to produce just writ large, the only thing we're going to have left is perspective. And the only way to learn your perspective is to hone it yourself through repetition.

13:10Did you guys see a merch slop? Did anyone attempt to buy OpenAI merch from the merch store?

13:20Alexis Gay:Man, if I'm ever purchasing OpenAI merch, somebody check in. For sure. But like in contrast, do you remember those thinking hats that Anthropic was giving out at that pop-up coffee shop in the West Village? We talked about this on Great Chat. I happened to be staying at a hotel like right across the street from it and I walked by and I was like, oh, I'll pick up a hat. And I saw the line. It was like wrapped around three blocks. I'm like, absolutely not. So if someone handed me a cool hat or if someone handed me OpenAI merch, I would keep it. I actually love it when companies put time and care and like make it look interesting, make it look cool, whatever.

13:58Alexis Gay:I just the idea of purchasing merch from a tech company is like insane to me. I have really strong opinions about this because I've been thinking about merch for our company for a while now. So I've like started to develop like an actual perspective. Here's the deal. It's especially crazy for us to be getting tech merch from a company that is another fucking white t shirt or like a hoodie or a jacket or even at this point a chore coat because everyone fucking has one. Like I think there's a universe like are you an apparel brand or are you a tech company? What is unique and special to you that like is in a hundred percent your wheelhouse that is a physical good that can remind me of what you do becomes a more interesting question.

14:38So like when you see open AI's like keyboard, that's fucking interesting. Like when Andrel came out with like the Game Boy thing, that was fucking interesting. Like there are things that are cool, but otherwise like unless you're hiring like a really sick designer to work with you, like why bother? What about the all-in guys tequila that sold out immediately?

14:58Alexis Gay:I don't think of that as merch as much as I do the open AI clearly feeling like merch. What's weird about purchasing it from a tech company to me is that I started my tech career in 2013. And the only way you got tech merch was you worked for a company and then they gave it to you. Or you went to a happy hour or a meetup and they gave it to you. And it felt special and insidery. And it felt, in a way, and especially because I was so young, it felt very like belonging. It didn't even feel like merch. It felt like at school, like at school when they give you a t-shirt that says the name of your school and you're like proud to wear it because you're like, I go to this school.

15:38Alexis Gay:That's how I felt when I would get shirts and stuff, American Apparel tri-blends from the companies that I worked for. And the idea that it then becomes something to purchase, instead of being on the team, it makes, it's a, you're a fan. And I think that's a weird, different, it's like a different kind of relationship to introduce into the equation where when I was working in tech and I'd get a shirt, it's like, oh yeah, this is my team, the team that I play on. Here's my shirt. And then now it's like what you can just buy like a fan. I don't know how I feel about that being the trajectory of how tech companies are going to start showing up.

16:13Alexis Gay:Like we're, then we're going to, are we, we're rooting for them? It's almost like a flex if you don't work there though. Like, oh, I have a friend who got me this or. That's what I mean. That's what it used to be though. I would feel super cool. If my friends who work at OpenAI gave me a shirt, I'd feel cool. That would make me feel cool. I'd be like, ooh. But the second you buy it, it changes the equation. It really does. To me, it really does. Am I alone? What do you guys say? No, you're not. But I also think what you're speaking to also speaks a little bit to with this change in new media versus traditional media and how tech companies are showing up.

16:47I think more and more companies are following in the Cluelly example of like actually like marketing now is just pure entertainment. Like there's this piece of like the only way that you can compete on earned media and on owned media even is by competing with entertainers in that universe where like Sam Altman is a person that millions and millions of people follow and who people are like hanging on his every word. It is a team that you're rooting for in a way. I'd say it's more like the Super Bowl than like than an actual team itself. But I do think that there is that piece of it you know those t-shirts that people can make where it's like you can buy them for like your mom or whatever where it's like the face and it's like the holographic sort of face and you're sure sure we should just take it to the nth level and just start making like ai ceo versions of those shirts wait does great chat have merch i would wear great chat merch we do i will send you i shouldn't i shouldn't we have merch yeah yeah yeah matt I have, Alexis, I have a sweatshirt with your name on it.

17:53Alexis Gay:Okay, but this is a great example. I'm going to feel so cool whenever I wear that because then people are going to be like, what's great chat? And I'll be like, oh, it's my friend's podcast. And that's going to feel amazing. Okay. I did see merch that I would actually buy, but it wasn't technically, it wasn't technically merch because it was like, it was like robe merch. The fan fiction of merch. someone had made ceramic mugs that had excerpts of the sam altman and mira marati text exchange around the sam ouster and so it's like this mug and it has like the right like text coloring and sam's like how's it going in there and mira is like very bad or whatever and i was like directionally very bad directionally but i was like i would i would i would i would drink my morning latte from this like i need a link i need a link immediately and double double so what i really want is the sunny balwani and elizabeth holm this is our year tiger are you doing tiger this is our year i want that so badly can we do like a round table what is your tech quote tech tech lawsuit quote.

19:03I would really like

19:04Alexis Gay:Directionally Very Bad please on something. Alexis, that's what this mug was. Alexis, I will make you a sweater. I really need it. That's a good podcast name. Directionally Very Bad. It's just... That's what Thinking Machine's podcast should be. You guys, this is a whole category of merch that is perfect for great chat because this is a pod based on a grid chat. Yes. And so like future merch... That's such a good idea. And then we just show these like incredibly cringe conversations that have come up in legal discovery from like a variety of, oh my God, it's perfect. One of the things I've been thinking about lately, and then I like bounce off Alexis, is tech is kind of in a weird mode from a humor perspective.

19:51And especially like tech's own sense of humor about itself. but then of course Alexis brings the perspective of someone who has made a lot of comedy and content about tech and and this era is like a little bit trickier so basically like I feel like every week there are like funny things that happen but when you go online and especially on Twitter but even on like Reds is earnest, Blue Sky is angry, people are upset, people are self-righteous, people are victims. There's like very little self-deprecation, very little self-awareness, et cetera. And so anyways, we thought Alexis would be like the perfect person to come in and talk about how humor has shifted both within and about tech through the ages.

20:36And Alexis, you are like the perfect person because you began your career in tech. That's right. Your content that you mentioned from 2020 was like your early, at least as far as I know, like your early content that really like took off and put you on the map was poking fun at like crazy things people tech people say and we all loved it so maybe just to start like it's it's it's not just me right like tech used to be used to be funnier than it is totally totally i feel that way helen and mac do you agree with that that it used to feel funnier i mean like for christ's sakes we used to have a tv show documenting how funny we were are we talking about Silicon Valley.

21:16I also feel like people took themselves less seriously. Do you guys think that this is true in real life? Or do you think that this is just like the nature of the discourse online? Well, now it's so performative that it's harder for things to be like accidentally funny unless they're like true like fuck ups, right? Like the Brian Chesky thing being funny is like, well, that was a fuck up, right? Nobody's like, I don't know, it's just different. And I think that that comes from a little bit of tech previously having been like a really small cottage industry almost. And now tech being like Mag7 crushing, you know, like being a main AI being main part of the discourse.

21:54It's just harder to be self-deprecating, kind of like non-serious and just sort of like this casual funny when you're like the star. Right. And I think that that's probably one of the biggest shifts since that earlier era that we've been mentioning. I agree.

22:10Alexis Gay:I think it's a multi-pronged situation that leads to this sort of, I would say, pervasive feeling that tech feels less funny than it used to. And I would say part of that definitely comes from the fact that where people are gathering to enjoy humor and connect with each other feels less funny. I think we could say Twitter feels less funny, the primary tech watering hole. But tech as an industry, for me, it feels harder to make fun of now. I started my tech career in 2013. I worked in tech full-time for seven years. So 2013 all the way to 2020. Worked at startups, worked at a big public company.

22:49Alexis Gay:And my last job was at Patreon, midsize at the time. And I've been doing comedy full-time since then. So I've been doing comedy for about five and a half years full-time. Granted, I'm still pretty close to the tech industry. In a lot of the work I do, I perform stand-up at corporate events. I have a lot of good friends like Ashley that are in the industry. I stay somewhat on top of what's going on. And I have a long-term partnership with a tech company called Vanta, where I make comedy videos specifically for them, for their accounts. So it feels like I'm still in tech. I also have a comedy sketch show on YouTube called Paradise, which is sort of a dystopian tech vibe as well with my good friends at Krizam.

23:27Alexis Gay:So even though I haven't worked full-time in the tech industry, I've still been pretty close to it and What's been interesting to me is that The videos ashley mentioned when I first started doing comedy were about tech people but They were really about me All of them were about me all of them It was just me making fun of myself me making fun of myself for doing this me making fun of myself for saying that And a lot of my comedy and I I I this is something I try to do is it should all still feel like kind of loving in a way I my humor is very much like I make jokes in the way I would like make fun of my friends And helen you mentioned silicon valley or maybe mac mentioned silicon valley Um, mike judge said the same thing in an interview about that show like oh well We make fun of these characters the creator mike judge we make fun of these characters the way you make fun of your friends And that's a huge foundational pillar of my work because it is just like the tone that I think brings the most joy.

24:22Alexis Gay:To me, that is like maximal joy. If we are bringing joy to the most amount of people and not hurting the most amount of people, then that is like maximum joy. Because if you have to piss people off and make people sad in order to make other people happy, to me, that's not like net joy. Okay. It's like neutral. So I don't like that so much. Yeah. I mean, I think there are a lot of Anon accounts that are trying to find laughs, cheap laughs taking shots dunks I'd say most of the time when I'm like on it and I just close it and I say like okay no more today is like that stuff right like I that's just it doesn't feel good it's not funny and the people who find it funny are the worst and so it's just sort of like I I don't want anything to do with this and so I think all of this just speaks to a larger societal shift like I think this is the same culture I think this is the same like culture discussion that we have just like with a different focus on like with a different focal point of like All of us, generally culture has shifted to a place where people feel less comfortable being vulnerable and comedy inherently requires a decent amount of vulnerability and honesty that is really, really hard to allow when you are feeling a level of almost surveillance.

25:36And also when we're now decades into an attention economy where like we're really mining anger and fear more than almost any other emotion because comedy is you laugh, you move on. But anger, you think about it and you ruminate for the rest of the day. Same with fear. And so I think like it's a bit of this is sort of and I think tech is even harder because if we're looking at ourselves with honesty, like we have a large amount of the culpability for that shift in the general in the general cultural sphere. So I think like I mean, this is the industry that makes the algorithms that have led to that.