Her current book is “100 Tricks to Appear Smart in Meetings.” The next is “How to Be Successful Without Hurting Men’s Feelings.”
On this episode of Recode Decode, hosted by Kara Swisher, comedian Sarah Cooper brings the funny. She talks about how she bombed out as a stand-up comic and went to work in tech as her fallback. Now, her tech background is fueling her comedy career.
You can listen to the entire interview here or in the audio player below. We’ve also provided a lightly edited complete transcript of their conversation.
If you like this, be sure to subscribe to Recode Decode on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.
Kara Swisher: Recode Radio presents Recode Decode, coming to you from the Vox Media podcast network. Hi, I’m Kara Swisher, executive editor of Recode. You may know me as the only person wearing sunglasses on a rainy day, but in my spare time, I talk tech, and you’re listening to Recode Decode, a podcast about tech and media’s big players, key ideas and how they’re changing the world we live in. You can find more episodes of Recode Decode on Apple Podcasts, Spotify, Google Play Music, or wherever you listen to podcasts. Or just visit recode.net/podcasts for more.
Today I’m in San Francisco — where it is a rainy day — with Dick Costolo, the former CEO of Twitter. But Dick has a new role, and he’s joining me for several bonus episodes of Recode Decode this month, talking about comedy and tech.
Dick Costolo: Bonus.
DC: Bonus episodes. It’s not a regular episode, it’s a plus one.
KS: It’s a plus one episode. And so Dick has done stand-up, he almost was a comedian, and he made a mockery of Twitter.
DC: That’s my life, it was almost a bunch of different things.
KS: Almost a thing.
DC: Yeah, it was almost a thing.
KS: Yes, yes. But now we’re entertained by Twitter every day, so it is kind of funny. Twitter’s kind of funny lately.
DC: Constantly setting you up.
KS: In any case, we bring in different people, and we talked to Dick last week about his career. And this week, thank goodness, we have a real guest: Sarah Cooper, who worked at Google for more than three years.
DC: Don’t worry, it just gets harder from here.
Sarah Cooper: Yeah, I know. What will you say about me next week when I’m not here?
KS: No, we like you. I never insult the ladies. Anyway, she worked at Google for more than three years before she decided to quit and become a comedian. She now … Which I’m sure she got plenty of material. She’s now a stand-up comic, the creator of a satirical blog called The Cooper Review, and the author of the book “100 Tricks to Appear Smart in Meetings.” Sarah, welcome to Recode Decode.
Thank you for having me.
KS: So, your background. Google. What did you do there? Talk about how you got to comedy. I mean, assuming you were always funny.
I was always funny. I was born funny.
No, I always loved making people laugh. I was kind of the one who was easing tensions in my family at home and things like that, that was always my role. But I loved acting and I loved performing, and I was at Yahoo for a little bit, and then I turned 30 and kind of had this crisis.
KS: What did you do, what was your role?
I was a user experience designer.
KS: And what does that mean?
You don’t know what user experience …
KS: I do know, but I want you to explain it for the readers.
I made buttons.
I made blue buttons, and I made yellow buttons with text on them that said, “Click here.” No, I actually created … I’m totally doing a disservice to user experience designers now.
DC: And then in later years, they said, “Please click here.”
DC: And then finally, “For god’s sakes, click here.”
You must. This is my job on the line here. No, I designed the interface for Yahoo Travel and then for Flickr. And then at Google, I was a user experience and then manager for Google Docs in New York.
KS: Oh wow.
KS: What was your big claim to fame of clicking here, really? Besides click here. Is there some claim to innovation that you can …
Google Docs. Sheets. Slides. Part of them.
KS: Yeah, they’re good. They’re good.
KS: But is there one part that you love more than any other?
One part of the interface?
KS: The design, yeah.
Just the … I don’t know, it sounds so cheesy, but the toolbar.
KS: The toolbar.
I really enjoyed designing the toolbar and trying to come up with ways to make it seem familiar enough but not too much like Microsoft.
KS: Right, right.
So that was kind of what I was doing.
But I found comedy before that, because I love performing and was just really bad at it. I tried to be an actress and I just was very stiff on camera, and I just wanted to figure out how to be myself more, because good acting is really surprising and interesting and fun to watch. And so I decided, “Hey, if I can get onstage and be myself in front of an audience, maybe that’ll help me be a better actor.” And that made me realize I actually like writing my own material a lot more than reading other people’s.
KS: Which is stronger.
KS: What’s interesting, what I noticed last night at the Golden Globes is, all these actors who are so good at acting are really bad at speeches.
KS: It was really interesting. I was thinking, why can’t they … and then I realized why they can’t.
DC: I love that you were nervous about being stiff as an actor, so you chose … “Well, I’ll do standup comedy!” which is, you know …
Terrifying. Yeah. I was very drunk my first time, very, very drunk.
KS: Well, tell us about that.
I just found an open mic and I had about eight beers. I told a story.
KS: Sounds about right.
DC: It’s about right. That’s about, yeah.
I told a story about a date gone wrong. I was a single girl, and so I was just telling dating stories. That’s kind of what you’re supposed to do. And they couldn’t get me off stage. I was up there for eight minutes. It was supposed to be five. So I really enjoyed it.
KS: Wow, okay. So you just decided to do it, just like, “I’m going to do an open mic.” Where was it, in San Francisco?
No, that was in Atlanta. It was at the Laughing Skull Lounge in Atlanta, and then I decided, “You know what? I’m ready for the big time, I’m moving to New York.” And then I went broke.
DC: Eight minutes. “Eight minutes, I’m in!” Straight to Broadway.
Yeah, Broadway comic! Yeah, no, that’s …
KS: More material.
That’s, yeah. And that’s when I got the job at Google, because I was $ 20,000 in debt and had to.
KS: So you went to New York.
I did go to New York, and that’s where you actually pay to perform. You bring people …
DC: Yeah, take people through that, because people probably don’t understand the supply-demand issue with comedy in New York.
Yeah, yeah, exactly. So they have trouble filling seats in New York, so in order to get people into the audience, they ask the comedians to bring people. And they’re called bringer shows, and if you bring a certain amount of people, then you can get onstage. So for some shows, you had to bring five people. Some you had to bring 15 people to get onstage, so I was bringing …
KS: To drink, and so they pay for drinks.
Pay for drinks and fill the seats, and I was bringing a lot of my Googler co-workers to my shows.
KS: Oh god, the funniest people on Earth.
But they have money, so that worked out well.
KS: Yeah. So you’d bring them, or you would pay if not? Or is that just the people?
No, you just didn’t get onstage if you didn’t have the people.
KS: So unfunny people with a lot of friends could get onstage.
DC: [To Kara] Have you been to any of these things, or ever seen these?
KS: No, no, I’ve gotta do that. I’ve gotta do that now. I miss that part of things. So you did that, and then you went back to Google to make money.
Yeah, exactly. So, yeah, it was kind of ironic that … I kind of felt like I was giving up on my dream. But a lot of other people’s dream is to work at Google, so my fallback career was other people’s main idea of a great career. And it turned out to be a great place to work. I was scared to go back into a 9-to-5 job, but I fit right in and it was really awesome. And there are a lot of really funny people at Google, so I loved working there.
DC: Now you’re going to get Kara staring at you blankly.
KS: Which one? By accident funny? I told you the joke last week, didn’t I, the Larry Page joke?
DC: Yeah, you did.
But I told my husband that joke. I think that’s a really funny joke, but that kind of dry, sarcastic humor, all of the software engineers have it. And I just think that nothing is sacred. They would make fun of anything and everything, so I thought it was great.
KS: Right. He made another one about media that I’m blanking on, but it’s something along the lines of like, “You hear about the future of journalism?” He’s like, “What future of journalism?” And I go, “The future of journalism.” He goes, “Yes, what future?” It was agonizing, the entire encounter was agonizing.
I think your impression of him is pretty good.
KS: Oh, well, I’ve spent enough time around him. I could do a better one.
DC: I still think the Arianna, Larry Page, you’re like right down the middle on both of them, use the same voice for them.
KS: Yes, you can. Yeah, no, I have a good … You’re less easy to do. I’m working on a Jack Dorsey, though.
DC: Oh, okay. All right, can’t wait to hear that one.
You and I were talking about this over email. Why do you think no one really makes fun of thought leaders? Kara and I talked about this last week. There’s sort of a wave of earnestness washing over us. What do you think, as someone who’s also been on both sides of the aisle, if you will, what do you make of that? Why do you think that is?
KS: Are you still at Google? No, you’re not still at Google.
No, I left Google three years ago.
DC: She’s a Xoogler now. Or a X-
Xoogler. I’m a Xoogler. With the hat, yeah.
KS: Were you a Noogler? Were you a Noogler with the hat?
Everyone was a Noogler at one point.
KS: Did you get the hat with the thing?
Of course, yeah, everyone gets the hat.
DC: What’s the proper pronunciation of X-oogler? Is it X-oogler or Xoogler?
DC: Or Xog …
KS: And then there’s Noogler.
And there’s Noogler, and then they call the older Googlers Grayglers.
DC: Oh boy.
That’s anyone over 25.
KS: And you know the gay ones. Gayglers.
KS: They have a good name for that.
They had trouble coming up with a name for the black Googlers, though, so they decided to just call them Jake and John. That was easier.
KS: That’s a good one.
DC: That was perfect.
KS: That is so sad and true.
So you left. Why did you leave, then? You were here? Or where were you?
I was in New York and I decided to leave because I …
KS: What prompted that?
I wrote an article called “10 Tricks to Appear Smart in Meetings” and it got a lot of virality in a good way. And I decided to take off and pursue my writing dream.
KS: Right, right, right. And how was Google, was Google supportive of this, they just …
They were supportive. Very supportive. And it’s one of those things where it’s a bigger risk not to do it, because you can always go back to Google. Within a year, a lot of times, if things don’t work out, you can go right back. You can get your same username in their system. So “scooper” was still available.
DC: Scooper, hey, there’s no other scoopers that left! That’s amazing!
KS: I want that one.
DC: I’ve used, I think I’ve used probably more than 50 percent of your tricks to appear smart in meetings.
KS: Yeah, yeah. We’ll talk about that.
DC: My favorite is turn a percentage into a fraction.
A fraction, I love that one.
KS: Yeah, talk about this. So that’s what got you out. You just got a lot of response.
Yeah, that’s the inscription that I wrote on your book, by the way, is that Dick, you probably know a lot of these tricks already.
DC: I do know a lot of them.
KS: So go through a few of those, and then answer Dick’s question about earnestness.
DC: I rotate between …
Yeah, well, the very first one was something I noticed when I was working at Yahoo. A product manager …
KS: Who was the CEO at this time? You don’t remember.
I want to say Brad?
KS: Oh, he was there for a short time.
I think so. This product manager got up and drew a Venn diagram, and this Venn diagram made absolutely no sense. And I thought for sure somebody was going to say, “You know what? You’re wasting time, this has nothing to do with what we’re talking about.” But instead, everybody was like, “No, no, no. Make this circle a little bigger, make this one a little smaller. Let’s change the labels.”
KS: What was the Venn?
I have no idea. I mean, I really have no idea.
DC: Things that are red, things that are white, and the intersection. Things that are pinkish.
Well, I think the middle was the sweet spot or something like that.
DC: Yeah, of course it is. The middle is also the only interesting part of the Venn diagram. “Let’s talk about this intersection.”
So he just handed the marker to someone else to finish drawing, and he sat back down and went back to his laptop. And I was like, my god, that was brilliant. He just contributed nothing but it looked like he did something, and people will remember that he got up to the whiteboard and drew something.
KS: Right, right.
So I wrote that down in my notebook: How to look smart in meetings. Draw a Venn diagram.
The second one was the fractions one.
DC: Yeah, that’s a good one.
Where someone was presenting a statistic and said, “Oh, 25 percent of people clicked on this button,” and another product manager probably said, “Oh, about one in four.” And made a note of it.
DC: So what you’re saying is …
I was blown away by this guy’s quick math skills.
KS: So what you’re saying is 75 percent didn’t. Interesting. I’m advanced!
DC: It doesn’t even have to be correct, and it works.
Yeah. And so I’ve never actually gotten to try that one, but I love it. I love that one.
KS: Yeah. Give me one or two more.
DC: Now my favorite is, and the one I’ve seen most frequently used, is the repeat what the other person just said.
KS: Well, women know that one well.
Well, yeah. Especially if it’s the smartest person in the room.
DC: Of course.
Which is usually the software engineer. If they said something, just repeat it very, very slowly. And then people will remember you as the one who actually said that.
DC: “You know, as Sarah likes to say …” No, yeah.
Another one is just ask if it’s going to scale, no matter what it is.
KS: That happened to me the other day!
Just, “Is this going to scale?”
KS: Yeah. Maybe I asked that question. Maybe it was me. I think it was!
DC: I think I’ll be doing that! Such good idea.
KS: I think it was, I was at a lunch thing with a VC.
You appear smart without even realizing it.
KS: I know that. I did use the word scale. Oh god.
That’s a big one.
KS: Okay, so you leave. You leave and you go and you’re doing … What are you doing, and then I want to get to topics.
I’m doing thecooperreview.com, and I’m writing and I eventually get the book deal.
KS: And explain the book, explain the book.
So the book is a continuation of the original 10 tricks. It’s called “100 Tricks to Appear Smart in Meetings,” and it’s basically everything I’ve observed.
KS: “Let’s take a step back here.”
Yes, that’s another big one. I did that one a lot, that was me. “Guys, what problem are we really trying to solve?”
DC: “Let’s back up and look at this.”
“Let’s just back up, can we back up here? Just for a second.” You’re going to hear it all the time now.
KS: I just did it today, I was in a meeting.
DC: I like to combine them. Do the Venn diagram and it’s like, 25 percent, the intersection is … Or, a quarter of our users …
No, shortly after the article came out, I was in a meeting with a VP at Google, and he was pacing around the room, which is one of them.
KS: Pacing. Yeah.
And he asked the presenter to go back a slide, which is another. He was doing that at the same time, he looked over at me and he winked.
DC: That’s why he got to be vice president, you start combining them.
That’s how you get up there.
DC: Yeah, you use a No. 23 and a No. 14 together. I’ve never seen that before.
KS: Two and three’s a triple axel.
A triple axel!
KS: A couple years ago, Sergey came to Code, and he started pacing around the tent at Code without his shoes on.
DC: I was just going to say, attire is a good one.
KS: Yes, yes. No shoes, pacing around the tent.
No shoes, he got from Steve Jobs.
KS: Yeah, but he was doing it. And mostly he looked crazy, I’ll be honest with you. Everyone was like, “What is he doing?” And then the PR person chased him around the tent and it was my favorite moment.
Wow. Oh, that’s awesome. If you look crazy, you look smart, too. That’s another one. If you look insane …
KS: Yeah, like appearing in weird outfits. That’s a Sergey thing.
Weird outfits, yeah. I think he showed up as Batman once?
KS: Yeah. Yeah. One time … I shouldn’t say this, but I think John Doerr …
DC: Most of your favorite comments start with, “I shouldn’t say this,” so keep going.
KS: I shouldn’t say this.
KS: He showed up to my house in bike pants once, that is just …
KS: Not a good look, I’m sorry. And weird hats. And it was very strange. Sorry, John, but you did it. Yeah.
This is my favorite. Take pictures of ideas at the end of a meeting.
Absolutely. Just spend five minutes taking pictures and it’ll look like you really care about documenting stuff. But don’t worry about sending them out, because nobody cares.
KS: Oh my god, these are so true.
Yeah, they all.
KS: “Draw on a Post-it note,” ideas.
DC: You don’t have to draw the actual idea, you can just draw any thing, yeah.
Grab a pad of sticky notes and just draw something. Yeah. Draw boxes and lines.
DC: And say “hmm.”
Yeah, and say “hmm.”
KS: “Sit on the edge of a table,” yeah? You could do three of these at once. “Put one large word on each slide.”
Yeah, definitely. Like “vision.”
KS: See, the sad part is, this is funny, but it’s really not.
KS: It really happens.
Yeah, it really happens.
KS: Oh my god. So what’s your favorite of these? “Don’t wear a name tag.” I do that.
Yeah, of course.
KS: That’s one of mine.
That’s a networking one, networking trick.
KS: Yeah, I don’t need one.
I like the Kanye.
KS: Which one’s that?
It’s basically, if you … I forget the number, but if you’re going around the room and everyone’s giving an update and somebody’s about to give an update, you can say, “Hey Dick, Dick, I just want to stop you right there. Everyone, Dick is going to give an update that’s really important, so if you could just listen to Dick, that would be great. Okay, Dick, go ahead. Continue.”
DC: And then Sarah gets credit for it.
And I get credit for it.
DC: Whatever happens next, Sarah’s the one who recognized the criticality of it.
KS: Criticality. Did you do these drawings too?
Yes, I did.
KS: They’re great.
The way that I do them is pretty hacky, though. I take pictures and then I trace them. And so that’s my husband and two friends pretending to be in meetings, and I took pictures of them.
KS: I’m not sure I like 88, “Cheer randomly.”
Oh, yeah. You gotta do the woohoo.
KS: Oh, man, really? I don’t like a woohoo. I fire people for woohooing.
Oh. That’s good to know. I should put that in the addendum.
KS: So you did this, this is really great. So the idea is that you were going to make fun of the workplace in general, the idea of what a workplace is like, basically.
Exactly. All of the things that you see people doing a lot of times to make it look like they know what they’re doing when really they have no idea what they’re doing.
KS: Right, right. Well, this is kind of down the Dilbert alley, essentially.
It is, yeah.
KS: Yeah, that kind of thing exactly. But he was talking about … But Silicon Valley, Dick, re-ask your question again on this.
DC: Yeah, we were talking about no one making fun of or satirizing thought leaders, and you and I had a discussion about that yesterday. Why do you think that is?
I don’t know. I get anxiety a lot of times listening to these thought leaders who are telling me that I need to be working towards my goal every minute of every hour of every day, and if I’m not then I’m failing. And what am I doing if I don’t love Mondays, there’s something wrong with me, and I think that there’s a lot to be made fun of there, especially with the clones that they create, because a lot of times, it’s not necessarily the thought leader, it’s the people trying to emulate and become that thought leader.
KS: Yes, exactly.
And they’re not emulating the passion, they’re just emulating the pretending of the passion, and so it’s, yeah.
KS: Right, right. That happens quite a bit.
KS: There was a bad, dark period of All Things D and several of the male reporters tried to be Peter Kafka. It was disturbing.
DC: You can’t out-Peter Kafka Peter Kafka.
KS: Well, I was just saying, stop, stop.
DC: As I said earlier, Peter, god bless him, I love him, he’s … By the way, this is something my grandmother would say right before she was about to eviscerate somebody. Peter is the comedy dehumidifier. He sucks the funny out of the room.
KS: Comedy dehumidifier!
DC: Sucked right out of it.
KS: It went on, it went on.
That’s a good name for somebody who does that.
KS: Let me just say, Mike Isaac in particular. Mike is so not like Peter.
DC: Yeah, comedy dehumidifier is not catchy.
Mike Isaac’s not like Peter?
DC: No, he’s not.
KS: He’s so sweet. It was very strange.
So besides that. So you … So why are they so earnest? What is it about tech? Because I think it’s more … Other offices, the show “The Office,” there’s “Office Space,” everything else. There’s something about tech that’s particularly irritating. Do you find that, or not? Or are they like any other workplace?
I feel like a lot of other workplaces said that they see a lot of these same things, so I’m not sure it’s particular to tech, except there does seem to be this Olympics of earnestness, and so the person who can be the most authentic in the most authentic way is somehow better than everyone else. And I don’t know if that’s because we’re all on the internet, we’re all watching people on the internet, we’re pretending to do all these things and show how great we are. And maybe it spreads faster because we’re all on the internet instead of talking to each other in real life as much as other industries.
KS: Right, right. How would you assess tech people, though, as humor?
KS: Not as humor. They are funny and they don’t mean to be. I think they have almost no sense of humor. And I don’t mean to say that they’re grim, it’s that it escapes them.
Oh, I don’t agree at all.
KS: Oh, really?
I think that tech people are hysterical. My experience …
KS: On purpose.
My experience at Google … On purpose. Sometimes not, sometimes they don’t mean to be, but I thought the software engineers there were very dry, very sarcastic. Nothing was sacred. Meme gen, which was just this live updating feed inside Google, making fun of Larry and Sergey as they were talking, so you were watching Larry and Sergey and you were also watching everyone make fun of Larry and Sergey at the same time. It was great.
KS: That was a big thing that they did, the Fridays, the TGIFs.
Yeah, and it went bad sometimes. If there was a big redesign, and they ripped designers apart for doing something like creating white space or anything like that, and they were harsh. So they could be really harsh. But I think that they’re actually really funny.
KS: All right. When we get back, we’re talking to Sarah Cooper. She’s a comedian, she was an ex-Googler, but she’s quit and become a comedian. She’s a stand-up comic, creator of a satirical blog called The Cooper Review, and the author of a book, “100 Tricks to Appear Smart in Meetings.” We’re talking about a range of things when we get back, and we’re here with Dick Costolo, who’s my co-host, discussing comedy and tech.
KS: Co-pilot. We’re going to talk about some of the depictions of tech in comedy, and how they look at Silicon Valley and all kinds of places, when we get back with Sarah Cooper.
We’re here with Sarah Cooper. She is an ex-Googler who became a stand-up comic and a comedian and a blogger, a comedy blogger. Right? Is that what you say?
That sounds good, yeah.
KS: Comedy blogger. And she writes a site called The Cooper Review. I’m also here with Dick Costolo, who’s my co-host this week. We’re talking about comedy and tech. Sarah was just saying Google people are funny. Having been married to one for 15 years, I don’t think so. But …
How did you last?
KS: Just, I would tell jokes and …
KS: It wasn’t lack of … It was lack of humor. It wasn’t grim.
DC: What are you looking at me for? I wasn’t there.
KS: I know, but you know what I mean. When you try to tell jokes to someone, they just don’t get it.
In any case, let’s talk about the depictions of tech people. How do you … “Silicon Valley,” the show. Let’s talk about that, because Dick worked on it and a lot of people in Silicon Valley, when they did it, thought … I think it’s eviscerating, and they think it’s loving, which is kind of interesting, that it’s sort of a loving look at them.
I think it’s more … It’s loving, but then you also get the sense that these characters are nihilistic and a little … They don’t really care about each other as much. They really have a lot of ego and they really want to get ahead. But, I don’t know. You feel like you identify with them.
So the only way that the show could’ve worked, really, is if you create characters where you can really identify with them. And the feedback that I get a lot is that it’s too real. It almost makes people feel a sense of anxiety because it’s so much like their life, and so they’d rather just go to their startup than watch this show about a startup.
KS: Oh, interesting.
That’s kind of what I’ve heard about it.
DC: Yeah, I’ve had numerous tell me, “I can’t watch it. I couldn’t keep watching it because it was too much PTSD for one hour.”
DC: What my real life is like.
KS: Yeah, yeah. I thought the best one was the woman venture capitalist with the bathroom. I thought that was one of my favorite scenes. That she’s located near a bathroom.
DC: They put her across from the men’s room.
KS: But they just don’t say anything, you could just see them in the room. And I thought that was so on point.
Yeah, yeah. I do wish there were more women on the show.
KS: I think that’s realistic too.
It’s very realistic, but it was just kind of … reminds you of this vicious cycle of the fact that there’s so many men in tech, so now there’s a show about tech, and to be realistic, they can only hire male actors. And so it’s like this continuum of, okay, we have to shut women out in order to be realistic about this.
KS: Although the woman … Who’s the one who plays the VC? Not the younger VC, the older VC.
DC: Oh, I’m going to get in trouble. Sarah Cryer.
KS: She’s fantastic. No, no.
DC: Yeah, yeah. The older VC. Her last name is … Suzanne Cryer.
KS: Yeah, Suzanne Cryer. She’s astonishing.
Yeah, I know.
KS: She counts for six people, she’s so funny.
I know. She was on “Seinfeld,” did you know that?
KS: Yeah, yeah. I just found that out.
DC: She’s fantastic, she’s great.
KS: She’s amazing.
Yeah, I love her.
KS: Literally. She’s like six people. You know who I think she’s channeling there? Marissa [Mayer]. She’s doing a Marissa, I’m pretty certain that’s what they told me.
That’s so funny, because I always thought she was just trying to be a female version of the person who played the VC before. Just kind of Aspergery?
DC: Right, right.
KS: Maybe so, maybe so. But I’ve heard Marissa.
DC: Yeah, I think there’s a little bit of … a little bit, the female version of Peter Gregory and that.
KS: Yeah, a little bit.
KS: So anyway, so talk about more depictions of that in tech.
Well, I think that I hear a lot of people say they hate “The Big Bang Theory,” and I completely agree with that. I think there is some depiction that is just too over the top and too nerdy, when the fact of the matter is, a lot of the people in tech are brogrammers now. They’re kind of the other side of that. They’re not cheesy and nerdy, they’re actually trying to be too cool, almost.
I worked on a musical last year called Soma Musical, which was a total parody and send-up of tech. And it was a thinly veiled parody of what’s going on with Uber.
KS: We’ll get to that.
And kind of the CEO gone out of control, with a lot of arrogance and just kind of not really realizing that, hey, there are certain rules that maybe shouldn’t be broken or lines that shouldn’t be crossed. And so I think that is more realistic than a lot of things that we see. Sometimes, in terms of … when it comes to geeks. Being a geek is actually cool now, it’s cool to be a geek.
KS: Right, right.
KS: That depiction doesn’t … They also use it on the negative side. Is that like, when they sexually harass, well, they didn’t go to prom. I’m like … Is that really an excuse?
KS: To grab boobs? I don’t think so.
DC: “Hey, I’ve never been to one of these things before!”
KS: Well, it was interesting, because that Emily Chang piece about the sex parties, whatever, is that, “Well, they never got to go to prom, and therefore they had to have sex parties.” I’m like, whoa. Like, whoa.
That’s a huge leap.
KS: It’s a leap … Even the minor stuff is a leap. “They can’t deal with women.” I’m like, they can.
KS: They actually can.
Women are humans.
You can deal with people.
KS: Yeah, exactly.
Yeah, I think that that has gone kind of the other direction of it. And I think that goes back to, how do we make fun of this? It’s so crazy, that story is so insane, that how would “Silicon Valley” even attack that, because it’s already almost a satire of itself.
KS: Right, right.
It’s so insane.
KS: Right, absolutely.
DC: Yeah, it’s a fair question, I think. There are certainly some things you read nowadays that you think, “Is this real or is this someone having me on.”
Yeah. The raw water thing.
KS: Oh yeah.
That sounds like a “Silicon Valley” episode.
KS: I know.
It just doesn’t make any sense.
KS: Right, and it’s the Juicero guy too.
And it’s the guy who failed miserably, and now he’s telling us to drink something that might kill us. Like, what is going on? I don’t understand it.
KS: Although it’s interesting. It’s so funny, ’cause a lot of things on “Silicon Valley” does then become something, it’s like … In 10 years, it could be that we all are drinking raw water.
You really think so?
KS: Yeah, I do.
KS: Yeah, you don’t.
I do not. I mean, yeah. Did you use Juicero?
KS: No, I did not. You could kill a cat with it if you dropped it. No, no. No, no, no. And before the Bloomberg did the “you squeeze the packet yourself,” a well-known internet person did a video of it and it was going around. It was Kevin Rose who showed that you could squeeze the pack and stuff.
DC: When I was in the writer’s room for “Silicon Valley” in Season Three, all these tech companies would send stuff to the show to try to get basically written into the show.
KS: Right, right.
DC: Constantly. And so the Soylent folks sent a case of Soylent to the room. And the writers kind of looked at this box in the middle of the room like, “Who’s going in? Who’s going in? Are you going to do it first, or will you do it first?”
So anyway, they wrote this bit that ended up getting edited out of the show, unfortunately, but they wrote this bit in which Dinesh and Gilfoyle try Soylent and decide, hey, this is … I could go do this. And so Gilfoyle makes Gilfoylent. There was a good 5-10 minute piece about that.
KS: Oh man.
DC: But it had to be cut for time.
The whole biohacking thing is also hysterical. These people that are just eating pills and fasting. I went to this …
DC: Tons of pills. Like, dozens of pills. Dozens of different kinds of pills.
But I went to a breakfast and this girl was just eating a stick of butter.
She literally had a stick of butter in her hand and was eating it like a lollipop or something.
DC: Did she have a butter mitten that she held it with?
She might as well have. Oh my goodness.
KS: What did you do when she was eating …
DC: Now I know what I’m getting you for your birthday. I’m getting you a butter mitten.
You will not get me a stick of butter. No, but that’s the other thing, is just like everyone is like, “Oh yeah, this is normal. This totally makes sense.”
DC: Don’t you have a butter mitten?
KS: No butter mitten!
What is this butter mitten?
DC: Well, you’ve gotta have something to hold the butter.
KS: He’s always coming up with ideas.
DC: Come on.
Well, that’s patentable for sure.
KS: They were eating a stick of butter.
Eating a stick of butter and …
KS: Did you say something? Did you say, “What the fuck are you doing?”
No. Well, I said, “What’s going on with that?” Oh, you know, “It’s fats and trying to decrease the amount …”
KS: You’re going to get fat.
Something, I don’t know.
DC: Yeah, yeah.
She was very skinny, so I don’t know.
KS: Enjoy the heart attack later. Geez Louise.
So I find that that’s interesting too, is that people are doing these really weird crazy things, but … no.
DC: No one makes, no, no one comments on it.
No one comments on it. It’s just like, “Oh yeah,” because you don’t want to look stupid. You don’t want to look like you don’t know what’s going on.
DC: Oh, don’t you want to live longer? Who isn’t spraying coyote urine all over themselves before they go to bed? What are you, an idiot?
Yeah. What are you, crazy?
DC: You’re going to get fricking’ attacked in the night!
KS: All right. Would you focus on tech in your comedy? Because you could just literally talk about these things.
KS: I mean, like we said, the alibi pony, that’s 10 minutes of gold, comedy gold.
Yeah, I do a lot of tech humor. I tell a joke about how I heard a rumor that the software engineers at Google are so proud of working there that they have sex with their badges on, which is a joke. They do not have sex. So, yeah.
And I talk a lot about my husband, who’s a software engineer, and how if there’s a problem in the relationship, he makes me file a bug for it. I filed a bug, I said we’re not spending enough time together so I filed a bug, and he marked it “working as intended.” And then I said he wasn’t listening to me and I filed a bug for that, and he reassigned it to my therapist.
So I like combining the things that I can understand, because I don’t understand a lot of the things that he talks about, with more of the relationship kind of stuff.
DC: I have a specific tech comedy crossover question, which is: When you’re doing stand-up, you’re onstage doing stand-up, you sort of can say whatever you want. You can be freewheeling with language, you can swear all you want, etc. And before we just got started here, you were asking about cursing and I said, “I haven’t heard the word cursing since the Nixon administration.” But when you’re in a room in a meeting, talk about … So if you’re comfortable swearing onstage and swearing in front of large groups of people, generally that’s sort of verboten in the office. Talk about that a little bit. Were you … just ignored that and swore all you wanted?
I swear a little bit, not a lot. I think that a lot of times, the best thing to do and the funniest thing to do in meetings is just to say exactly what’s going on. If there’s an awkward silence, say, “Wow, that got weird.” Or if somebody says something that could be interpreted in a sexual way, say, “Oh, better call HR.”
KS: There’s a lot of that lately.
There is a lot of that lately. I think that just calling out exactly what’s happening, you can’t really get in trouble for just being honest and just saying exactly what’s going on.
KS: Yeah, yeah. Although it certainly … You can’t say a lot of things, make the jokes you could make.
Yeah, there’s a lot of things you couldn’t say, and I think a lot of times, especially in the climate that we’re in right now, there’s a lot more caution.
KS: Well, let’s talk about that climate. What’s funny about it? How do you make funny sexual harassment jokes? Let’s go through that topic. And we’ll get to Uber. But let’s start with Uber, right? What are the funniest companies, from your perspective, that are comedy gold, essentially? Comedy gold, is that right?
DC: That’s good.
KS: Thank you.
DC: “That’s gold, Jerry.”
Comedy gold? Gosh, I think …
DC: Remember that old “Seinfeld” bit?
DC: Oval. It’s not oval. “That’s gold, Jerry.” All right, it’s an old “Seinfeld” reference for people. Go ahead.
Yeah. I think Uber’s funny, I think. I don’t know. Airbnb.
KS: What’s funny about Uber?
It’s just so ridiculous. It’s just so insanely ridiculous. The situation with losing seats on the board and just the fall from grace, but it’s also not funny in a lot of ways when you think about, seriously, what’s happening and what women have had to go through there. I think it’s just ironic — again, going back to what we were saying before — where so much is going on but no one’s saying anything about it.
And I think that is the biggest problem, a lot of times, in the workplace, is that … It goes back to the Venn diagram. Someone should have said, “What you’re doing is ridiculous,” but no one wants to say those things, and so that’s kind of this …
KS: So how do you make comedy out of that? Like, last night at the Golden Globes, there were so many good sexual harassment jokes, and I was glad to see … They were great, although right on Twitter it was like, “We should not laugh over these things.” I was like, no, we really should, because they were really … The Harvey Weinstein joke, the only person being booed in memorium was a fantastic joke, for example.
Yeah, yeah. Yeah, I agree.
KS: And people were like, whoa. That was the kind of thing. And years ago there was a comic, and I’m blanking on her name, she was really funny. She did a 9/11 comedy show, and she was like …
KS: She felt like it was always too soon, but it was wonderful. It actually was very cathartic, because she also talked about … She was down there at the time. How do you make jokes about these topics, like sexual harassment or gender discrimination or racial discrimination?
A recent statistic came out that 80 percent of people in tech don’t think that there’s a problem with sexism in tech. The rest are women, obviously. It’s just pointing out the obvious of what’s going on. And I did a whole piece about this with diversity, in terms of … It’s very diverse because half of the people wear hoodies on Mondays, and the other half wear them on Fridays. It’s so diverse, some of them went to Stanford, class of ’11, and some of them went to Stanford, class of ’13.
So kind of just pointing out what’s going on in terms of trying to say that we are amazing and we’re the best and we’re so ahead of everything when really, we’re kind of not. And there’s a lot of things that get overlooked.
KS: Right. And you did a whole thing about threatening, non-threatening women, too. I thought that was really terrific. It’s the beginning of all the jokes you’d make about women in tech.
Yeah, exactly. And it just goes back to the way that we change how we speak, and a lot of people took that as real advice, which I think is the best part of any parody, is the people that take it seriously. With the whole gorilla television thing that happened over the weekend.
DC: Yeah, yeah, yeah.
KS: Explain that for people.
DC: Yeah, that was, yeah.
My gosh, that was gold.
KS: That was comedy gold.
DC: That was comedy gold.
Basically, someone created a fake excerpt from Michael Wolff’s book, “Fire and Fury,” where they created a gorilla TV channel for Trump, because he loves watching gorilla-based content. That was the quote, gorilla-based content.
DC: Right. He likes to go up close to the TV and talk to the gorillas.
Close to the TV, and he likes to see the gorillas fighting, and so they created this whole channel for him so that he could do that. And a lot of people thought it was real, which is scary.
KS: Yeah, right, right.
Because why would they think that the president would actually do that?
KS: Yeah, well …
So stuff like that. But this goes back to one of my favorite jokes online, was savetoby.com. I don’t know if you guys ever remember savetoby.com.
KS: No, what’s that?
It was this guy who had a rabbit who said he was going to cook and eat the rabbit unless you send him $ 50,000.
KS: This is like the pig thing on Black Mirror.
Was that …
KS: Pig fucking.
Oh yeah, a little bit, yeah. Pig fucking. Yeah, no, it was great. And they actually interviewed GoDaddy and they said, “Why aren’t you taking this down? This is terrible.” And they interviewed the maker of the site in a veil and voice disguiser, and he kept the joke going the whole time even though it was a complete joke. I just love stuff like that. It’s the “Colbert Show” stuff where the person being interviewed clearly didn’t know that this was a complete joke. I love stuff like that.
KS: Yeah, yeah.
And so with non-threatening leadership strategies, people were like, “This is terrible advice.” With my book sometimes, they’re like, “Why don’t you just be smart instead of trying to appear smart?” I’m like, “I know, that’s the point!”
KS: Talk about some of the threatening ones, because those are really, really good.
Yeah, instead of, “Get this to me by Monday,” you say, “Do you think you could get this to me? By Monday?” In emails, instead of saying, “Can I take a look at this?” lots of exclamation points, smiley faces, women are just notorious for this. I do it, I don’t know why, but I just feel like if I put a period, I’m being an asshole for some reason. I don’t know why.
KS: Grammar is at stake.
DC: Whoa, whoa, whoa. What’s with the crazy …
KS: The attitude!
DC: Yeah, what’s with the attitude. It’s funny, the reason I ask …
KS: The semicolon would be better?
The semicolon. Ellipsis.
DC: Ellipsis? Dot dot dot. Yeah. The reason I asked you about swearing in the workplace is, you’ll be in a meeting with a group of people, and the guys can seemingly swear at will, but god forbid, like you just said, god forbid one of the women in the room says “pigs fucking” and they’re like, whoa, whoa, whoa. Just an aggressive communicator.
KS: Right, yeah.
DC: She’s got a very … In fact, in performance reviews, you’ll see that women will more often get the … “very aggressive.”
DC: Abrasive. And “aggressive communication style.”
KS: Yeah, bossy.
DC: And I have zero men who work for me who have an aggressive communication style in their performance reviews.
Well, somebody just called Kirsten Gillibrand transparently opportunistic.
KS: Yeah, right.
“She’s a bitch.” Which is like, okay, so you can be opportunistic, but not transparently … But maybe you can’t even be opportunistic. Opportunities are bad.
KS: Yeah, yeah.
As a woman, I don’t want any opportunities.
KS: I remember, I did an interview a couple years ago, and there was a profile with Sheryl Sandberg. It’s like, she went to Harvard. She’s got children and has shoes.
Oh my god.
KS: And I was like, which of these things is a problem? It’s like, it was an insult, though. She was educated and liked shoes. And it was like, okay. A lot of people would really like to go to Harvard Business School, go to Harvard.
DC: Most of them wore shoes.
KS: And most of them wore shoes. But nice shoes. It was bizarre.
KS: I think I wrote in to Jodi Kantor, who I like very much, actually, about …
Yeah, there was some obituary recently — not recently, but a few years ago — about a female author, and it just spent all this time talking about how she was single and she never married. I was just like, she wrote 50 books, come on!
KS: Yeah, it was interesting. So when you think about … make women … do more non-threatening ones, because this is really the topic du jour, right? The idea of sexual harassment.
DC: Yeah, it is 100 percent. And that threatening versus non-threatening communication style, it’s a whole … We could talk about this for hours. So go ahead.
Somebody steals your idea in a meeting, you say, “Yeah, I just said that.” Instead, say, “Thank you for articulating that so clearly for me.”
KS: Oh no.
That’s the non-threatening version of that. But the way that I end the piece is, basically, I wear a mustache, because if men see you as a man, then whatever you say is fine.
KS: You know what? I think this is true. I think I do a lot better because I’m gay. I do.
KS: I do, yeah. I can send notes that just say, “No.” You know what I mean?
Also because you’re Kara Swisher.
KS: No, no, no. But I just do that. Today, I just got something I didn’t want.
DC: You’re Kara Swisher?
KS: Yes, I am. I am Kara Swisher. But I literally just send a note because I want them to do what I want them to do, and they wanted to endlessly discuss, and I was like, no.
Nice. You’re my hero.
KS: And it was like, a period. There was a period in there.
KS: No semicolon. And they’re like, “Okay.” I’m like, “Thank you.”
I’d have to say “nope.” I’d have to say “maybe not.”
DC: “Nope.” I love nope. That’s good.
I could not say no.
KS: You could use nay. Nay, nay.
I dare say nay, good sir.
DC: Yeah, say it in a foreign language.
Nay works very well. Nah, no. Nyet, yeah.
KS: My new one is, I’m just not going to show up.
No, that was my favorite thing to do at Google, is if I didn’t think I was really needed in a meeting, I would just not show up. And then if they pinged me like, “You need to be here,” then I’d show up.
KS: Oh, nice. Well done.
KS: Yeah, you had that in your thing. “Leaving a meeting for another call.”
Yeah. Yeah, you leave the meeting for a call.
KS: That makes you annoying.
Oh my god, I saw it done so many times.
KS: Is it a power play?
Yeah, because if this call you’re getting is more important than this important meeting you’re in, then you’re a pretty important person.
KS: Yeah, that’s true.
Yeah, a lot of people said, “You’ll get fired if you do something like that.” And I just want to remind everyone, I’m not telling people to do these things. I hate when people do a lot of these things.
KS: Yeah, yeah. So you don’t think women should just get mad. That’s my new advice to women. Just get mad.
Just get mad?
KS: All of a sudden, unnecessarily.
DC: Just start swinging.
KS: Just go, “No!” And then leave.
Just go no and leave? Oh gosh, that’s … Maybe in a few years, Kara. Not now.
DC: Okay, we were talking and, again, we were exchanging emails about some of the differences between Instagram comedians and Twitter comedians. Talk about that.
I think that …
KS: Are you on both, by the way?
I’m on both.
DC: You’re on both?
KS: No, does she use both for her medium, is what I’m saying.
DC: Oh, I see.
KS: Which, does she find more effective.
Well, Twitter is more my thing. I am always thinking in little sentences of things I can describe, whereas I think Instagram is better for visual humor, obviously, and so a lot of cartoonists are in Instagram doing a lot of really funny stuff. My husband built me this little thing that turns my tweets into images that get posted on Instagram.
Yeah. So I’m experimenting with that, just because I’m not a visual person.
DC: You want that? I want that.
KS: I want that. Isn’t that smart?
Yeah, I thought that was smart.
KS: Why don’t you productize it?
I know. If Instagram had an API, I don’t think it has an API, so you can’t …
DC: It’s just that all of the images are crocodiles. It works for the first couple.
DC: No, I’m trying to figure out how he would do that.
KS: No, that was on Dinesh’s thing, remember?
DC: Okay, well, maybe I …
KS: There was an episode of “Silicon Valley,” everything becomes a certain thing.
Oh, the hot dog?
DC: I’m taking somebody else’s idea once again.
KS: Yeah, the hot dog.
The hot dog.
KS: Yeah, yeah, yeah. It’s a hot dog.
It is not a hot dog.
KS: It’s a hot dog. So, go ahead with the Instagram. So Instagram’s better for visuals.
Yeah, Instagram’s better for visuals. But I think there’s a lot of really great cartoonists on there. Sarah Scribbles is one that just love, and she does these little stories. But I’m just more text, and I just think that that was the original dream of Twitter, was that people were just sitting around making these jokes and they were so funny, the non-sequiturs …
KS: Oh, there’s very funny things on Twitter.
But now it’s just laugh, cry, laugh, cry. It’s really not truly fun anymore.
KS: I don’t know, after Sloppy Steve, there were 27 ones that I retweeted that were so funny.
Sloppy Steve feels like it was eight years ago.
It’s … Did it just happen?
DC: Yeah, it literally just happened.
KS: You know who did a good one, was the real sloppy filmmaker, Michael Moore? He called him Sloppy Michael …
KS: And he goes, “I’m the original Sloppy. He’s sloppy seconds.” And he says, “I’m suing Trump because I’m sloppy.”
My favorite thing today is executive time.
KS: What’s that one? I’m not caught up!
DC: Yeah, yeah, yeah. No, I saw this.
KS: You’re caught up. I was in meetings this morning.
So apparently Trump is requesting less of a regular schedule and more executive time for tweeting, watching television and talking on the phone with friends. But he’s calling it executive time, which is amazing to me. I just had no idea I was doing executive time this whole time. I could be president.
DC: Yeah, right.
KS: But it is, I think it’s funny.
DC: “Listen, if I’m going to run this country, I’m going to need to watch a lot more morning television.”
KS: We’re going to get to Oprah in a minute, but since the Golden Globes last night, President Winfrey. One of the things … Trump isn’t funny, but it has resulted in funny, funny stuff online.
Because he has no shame and he just says anything, and it’s just continuous fodder and you can just continually make fun of it. We gotta get off of this treadmill at some point, right?
KS: Like “stable genius.” I know, you’re right. My 12-year-old was like, I’m like, “What do you think of stable genius?” He goes, “Mom, it’s just a distraction, you need to stop paying attention to it.”
KS: I know, and he goes, “Really, what he’s doing is with the federal courts is …” This is a 12-year-old! And I was like, “You’re right. But stable genius is so funny! Did you see the picture of Mr. Ed?” And he’s like, “Who’s Mr. Ed?” And I’m like …
Oh my god. Oh no, the next generation is telling us that we’re losing focus. That’s not good.
KS: No, I’m good with the next gen, Gen Z, forget the millennials, let’s move them on out. But Gen Z is really smart, they don’t put up with any shit kind of stuff. But I do think Twitter is funny.
But will Gen Z have a good sense of humor?
KS: No, they don’t. They don’t.
They’ll take everything seriously.
KS: They just, they’re on Snapchat, they want ephemeral, they want stuff like that.
So let’s talk a little bit about what you think, go back to the funny companies. Do you find Facebook funny at all?
No, Facebook is terrifying.
Yeah, it’s terrifying.
KS: All right. No jokes?
DC: How so? You just said that like it was a truism, we all …
KS: No, I should not make a joke about Mark Zuckerberg petting livestock. That would be-
So, you know, everyone’s moms … Facebook was cool at one point. It was really exclusive.
KS: Was it?
It was! When nobody could get on it and you were waiting to be able to get on it? That was cool. And now everyone’s on it and I watch my mom scroll through Facebook and she’s just like, “Look at her. Look what she’s wearing. Oh, I guess I’d better like it, ’cause if I don’t like it, she’s going to see that I didn’t like it. And I better like …” And I’m like …
KS: You’re not seeing the shoulder movements.
DC: Yeah, you’re not getting the visual. Everyone’s not getting the mom visual here.
My mom is like, “Oh, better wish her happy birthday, ’cause if I don’t, she’s going to see that I didn’t wish her happy birthday.”
KS: That’s funny!
No, but it’s …
KS: That is a whole bit, that’s …
Okay, that’s funny, that’s funny. That’s funny, but then you think about it, it’s just sad that it’s just …
KS: There’s always a meme in older people using technology. My mom using the iPhone, I could just watch her for hours, doing it.
KS: She’s getting pretty good at it, actually.
But I think that whole privacy thing is just really scary. I don’t know.
KS: Not funny. Facebook, not funny. Come on, Mark Zuckerberg visiting livestock is not funny.
How do you make fun of Mark Zuckerberg?
DC: You’ve got your next book coming out.
Yes. “How to Be Successful Without Hurting Men’s Feelings.”
DC: Let’s get back to that. I want to … This is a gold, this is truly a goldmine.
KS: Gold! Gold! Gold!
DC: Talk about that book again.
Well, yeah. It’s based out of the non-threatening leadership strategies and it’s going to have different chapters on being authentic by hiding yourself.
DC: Being not transparently opportunistic, for example.
Right. Well, yeah.
DC: If you’re going to be opportunistic, for god sakes, don’t let us see it!
Right. How to be ambitious without shoving it in everyone’s faces.
DC: Yeah. That was another … These are all, as you know, real, real things.
DC: “So ambitious.” Like, wait a minute, you like … is that a knife in the back?
KS: Yeah, yeah. Have you done that, Dick Costolo, as a CEO?
KS: Have you said to women, oh, they’re so …
DC: No, no, no.
KS: No? You’re kind of …
DC: What was that?
KS: Kind of a lady.
Kind of a lady!
DC: You once told me I dressed like Ellen.
KS: You do. You do dress like Ellen. Right now, in fact.
DC: Oh, right. Right, yeah.
KS: I know. He dresses like Ellen.
DC: No, you get that. I’m moving. I’m taking it away from me again. You get that, so ambitious. You never hear that said about any of the dudes in the company.
No, no. Right. Well, my favorite is the takes on Trump where it’s like, “Maybe it’s good to have a president who’s a little off-kilter and you don’t really know what he’s going to do or say.” I’m like, “Would you ever say that about a woman who was hysterical, going crazy?” “Maybe it’s good to have a woman that you just don’t know what’s going to happen with her!” You’d never say that.
KS: Oh goodness.
I just say …
KS: What else are you putting in this book?
DC: Yeah, I can’t wait for this book.
Just all kinds of stuff about how to take care of yourself while also stressing out about everything and worrying. It’s all just the impostor syndrome, gaslighting. There’s a whole chapter on gaslighting and how we can do it better. So it’s a whole how-to, gaslighting for beginners.
DC: Gaslighting 101? Good. See, I want to gaslight but I don’t know where to begin.
KS: Yes! Hey, what’s the first step of gaslighting?
There’s a few. One of my favorites … My husband does this to me all the time. I’ll say, “I don’t think this works.” And he’ll be like, “Literally no one has that opinion.” (laughter) I just had that opinion.
DC: Yeah, “I do.”
But if you do that to someone in a meeting, literally no one thinks the thing that you just said you think.
DC: That’s good. That’s gaslighting 101.
It’s gaslighting 101.
DC: You can do it in any situation.
KS: So what’s the response to that, in gaslighting? I mean, it’s anti-gaslighting. You should do anti-gaslighting.
I should do anti-gaslighting, but …
KS: One time, years ago, Bill Gates in a meeting did this. He was at the Washington Post, and the editor of the Washington Post at the time, the Washington Post was super powerful. It is again, but it was really at the height.
DC: At its peak.
KS: And Bill was not, it was pre-Microsoft monopoly trial. So he was sort of up-and-coming. And we had him in, and the whole getting him there was funny, ’cause he arrived in a cab and he wasn’t showered and stuff like that. So we get him in the room, and the editor of the Washington Post, who at the time was Len Downey, said something to him. Asked him a question. And Bill Gates looks at me and he goes, “That is literally the stupidest question I’ve ever heard.” To this guy.
And I’m like, first of all, you just don’t do it at the time. “That is the stupidest question I have ever heard.” So I was like, oh my god, you can’t do that.
DC: Now what’s going to happen?
KS: What’s going to happen? So I go, “The stupidest? The stupidest? Really? Really, come on, it can’t be the stupidest. Really, of all the questions you’ve heard in your life?” And I was trying really hard to do it, but that was gaslighting. I didn’t realize that.
Yeah, that’s a gaslighting one. I asked a question once on UCB, actually. I said something about …
KS: What’s that?
DC: Sorry. Upright Citizens Brigade. We’re doing comedy shorthand now.
KS: Okay, right, sorry. Excuse me.
I said, “I have a dumb question.” “Oh, there are no dumb questions.” Immediately. He was like, “There are no dumb questions.” And I said, “Well, what’s the …” How the herald works, what’s the exact layout of it. And he said, “Have you taken 101 before?” And I’m like, “Yeah.” “Well, maybe you should go back and look at what you learned.” I mean, he made me feel awful.
DC: Yeah, “By the way, totally great question.”
So I was like, “Okay.”
KS: There are no dumb questions.
DC: That probably should be answered a lot in that format.
Yeah, so I felt horrible. So say there are no dumb questions, but then make the person feel like an idiot for asking that question. Yeah.
KS: Can we talk a little bit about last night, the Oprah Winfrey stuff?
KS: What did you think? The internet went crazy on her today.
I mean, it’s Oprah!
KS: I know.
I wasn’t … Everyone seemed so surprised and shocked that she was so amazing.
KS: There was a lull on Oprah for a while, though. There was an Oprah lull for a while.
She’s so … I expected nothing less from her, really.
KS: Right, but I mean the president stuff.
The president stuff, I just want to know, I don’t think we call her President Winfrey, I think we call her President Oprah. Don’t you think?
DC: The first one with the first name. Yeah.
KS: President Oprah.
Maybe we would drop the president, and it would just say Oprah!
DC: Just say Oprah!
We don’t even need the …
DC: It would just be O-TUS.
KS: Would she be good for tech? That’s my think piece. Would Oprah be good for tech? How is this going to affect me personally?
DC: Well, yeah. I mean, god. Yeah.
KS: She would be good for tech. She likes Sheryl. Sheryl Sandberg would be …
DC: She was good. Her speech was great. I mean, come on, it was even when you have high expectations, she really delivered. It was solid.
KS: Don’t you think she would hire a lot of internet people? Because Sheryl would be secretary of treasury, Bezos would be secretary of commerce, Michelle Obama would be the attorney general.
Oh, say no more then.
KS: Say no more, right?
Say no more.
KS: Come on, free delivery for everybody.
DC: Gayle [King] would be chief of staff.
KS: Chief of staff or communications, like the Sean Spicer job.
DC: Oh, there we go. That’s good, I like that.
KS: I’ve just already thought it out.
DC: I’m liking this idea.
KS: I’ll be tweeting this later.
I would just hate for all the Trump supporters to have to move and leave the country. That would be the saddest part about it.
KS: All right, we’re going to talk a little bit more. What else do you think is funny about tech? I mean, we’re going to be focused on tech. I’m sorry, this is a tech show.
Yeah, yeah. Tech show. Wow, putting me on the spot here. This is funny.
KS: What other companies do you find funny?
I don’t know.
KS: Or the whole Russia thing. Do you find any humor, is there any comedy to be made about Russia or people hating on tech now? Because that’s the new thing, is to hate on tech.
Yeah, I mean the … just the whole fake news things and just things being so crazy that they could be believable but they’re not real, and there’s really no … No one knows what’s true anymore, and I think Trump is just taking advantage of that. And that’s because you can’t believe your eyes. Pictures can be manipulated, video can now be manipulated. And so I don’t know if that’s funny, but it’s just kind of scary.
KS: Well, what is funny to you? What could be, of the topics?
I do love “Black Mirror,” I do love the kind of more sinister stuff that’s kind of dark.
KS: I can’t watch “Black Mirror.”
KS: No, it’s just the lesbian one I liked. The one in …
Okay, I haven’t gotten that far yet. I’ve only watched Season One.
KS: Yeah. Season Three. San [Junipero] or something.
But I think there’s a lot of different types of humor. There’s crazy characters that are kind of zany and all over the place, but I just tend to like the more realistic stuff that’s just so … I don’t know, sinister and real, and just, I don’t know. It just creates a whole other world, and that’s kind of the stuff that I think, to me, is just funny.
KS: Do you consume comedy stuff on the web, like The Onion and stuff like that?
Yeah, I love The Onion. I love it to death. They had an article recently that was like, it was business advice from Jeff Bezos. “No matter what you do, I will crush you.”
KS: It’s true, that’s funny.
So it was just this whole article where it was like, “You could diversify and do this, but I will crush you. You could try this industry, but I will crush you.” It was the whole thing.
KS: Bill Gates used to be that character.
KS: Yeah, oh yeah. No, he actually said that day … I only know this because it was the opening of a book I wrote, where he said, “You could either sell to me or go out of business, because I’ll crush you.”
Yeah, yeah, no, The Onion is great. And I think College Humor’s also really good, there’s a lot of good video content that they do.
KS: Is there any money to be made for comics like you online?
I’m still trying to figure that out.
KS: Yeah. No. That’s a hard no.
DC: That’s a hard no. Just the books and the musical and the stand-up and the …
KS: [To Dick] Why didn’t Twitter do anything around this, given your almost-comedy career?
DC: I mean, as you mentioned earlier, it’s a perfect platform for comedians to use material.
KS: Helping them create businesses. Why did you not do this, Dick?
DC: I don’t know, I don’t know.
So many Twitter comedians are now asking for donations through other platforms …
DC: Yeah, like Patreon and things like that.
… so why doesn’t Twitter do something?
DC: Why are you asking me? I don’t work on that, I’m basically unemployed right now.
KS: I don’t know, you were running it for a while, did it ever occur to you to help people create their businesses?
DC: Of course.
I think Medium’s new model is going to work, actually.
KS: They have a new one? It’s their seventh one, right?
They have a paywall. Maybe, maybe their seventh one. But they have a paywall system where if you write something that’s for members only, you get paid for it, depending on how much attention it attracts. And so I think that might be another way for people to create content online and make money.
But it’s still a lot of … The big get is traditional media, the HBO special, the Netflix special, the book.
KS: So you’re putting your stuff out there for free.
I’m putting my stuff out there for free, and I recommend everyone do it, because you need an audience. In order to get anywhere, you need an audience. So I don’t mind putting things out there. This has been stolen a million times, and it’s just going to happen.
KS: Right. Does it help with your stand-up, getting gigs and things like that?
Yeah, it does. I mean, if people know that I have a platform and that I can help promote any show that I’m on and things like that, it definitely works. And I’m also doing speaking engagements and doing panel discussions and things like that, and for any conference that needs some humor or some levity, yeah.
KS: Yeah, they’re a laugh riot, our conferences.
Yeah, I mean, conferences are just … So a lot of them can be really stale.
The same stuff over and over again.
DC: We were talking about this before, last week or so, but one of the advantages now of technology for comedians is you have so many more ways of getting your material in front of people.
DC: Twitter, podcasting of course is really taking off again, it’s had this amazing resurgence.
KS: In comedy especially.
DC: In comedy especially. And what was the name of the place you performed in in Atlanta?
Laughing Skull Lounge.
DC: The Laughing Skull Lounge. These places all have the best …
DC: All have the most amazing names.
KS: It’s like gay bars.
DC: I mean, it was what you had to do, right? You drive from …
KS: Moby Dick in my neighborhood. The Spike.
DC: The Laughing Skull Lounge, also.
KS: Swinging Richard’s, where’s that?
That’s in Atlanta, sorry.
KS: Oh, really?
DC: No, see, I mean, you used … That would be what you had to do, right? And now you’ve got vehicles like podcasts and Twitter and all these other platforms, so I think that’s certainly enabling this new generation of comics.
Do you think — I know I’ve got to wrap up soon — but do you think there is a generational difference in the way people think about being funny now and maybe because of, or through the new technology and what they like?
KS: Yeah, and let me add to that. My kids watch a lot of slapstick. Like, a lot. Like, a ton. They love when doors bang in people’s faces.
It’s like sort of the old …
DC: I still like that. It’s the old Three Stooges stuff.
KS: They’re like, “Look at this, Mom.” I’m like, “That’s the Three Stooges.”
DC: Physical comedy’s coming back. Yeah.
KS: They’re like, “What?” I’m like …
DC: Who? Yeah.
KS: But it’s interesting, that’s what they watch.
KS: Or memes, memes are funny to them. But not the traditional thing.
Yeah. I find that there’s a lot more extremes, things that are funny to a lot of millennials are kind of scary to me.
KS: Like that Paul guy.
Yeah, that stuff.
KS: Not the dead stuff, but the stuff he did right before it.
The stuff he did right before in Japan where he’s taking down his pants and he’s being completely disrespectful.
KS: And putting fish on cars.
Yeah, and just wearing the hat and the whole garb and stuff, and walking through the city and being really, really loud. And I just, that’s not funny to me, but it’s very in your face, quick editing, kind of crazy stuff. And I think there’s some millennials that like that kind of stuff.
KS: Yeah. Gen X doesn’t like it.
So I think it’s just more extreme. But then at the same time … Yeah, Gen X doesn’t like that.
KS: They don’t. My son was like, “He’s a douche, Mom. Everyone knows.” I’m like, “Oh, thanks.”
But then there’s this other strain of millennials that gets offended by a lot of different things, and so even saying “hey guys” would be offensive to a millennial, maybe, in an office workspace, because they’re not … not everyone is a guy.
KS: Yeah, yeah.
And so little things like that, where that would’ve just rolled off my shoulder, I didn’t care about stuff like that in the workplace, they get offended by. So it’s kind of weird.
It’s like these two extremes of super offensive but hysterical, but then, “Oh, you can’t say this, because that’s not … correct enough.”
KS: Do you like any of those, any comics that do that sort of shock? It’s almost like shock jocks.
Yeah. I mean, not really. I did see the Gilbert Gottfried documentary recently and I thought it was very good. And I actually didn’t appreciate him when he was bigger and he was doing more stand-up.
KS: Or Andy, what’s his name, was another one who did that.
DC: Andy Kaufman.
Andy Kaufman, yeah. It’s so funny how a lot of those things, it’s funny when you sort of look back on it, but when you’re in it in the moment, it’s not funny.
DC: It’s not funny. Yeah.
DC: It’s true. Some of the Andy Kaufman stuff is great in hindsight, but when you see the story of it being put together, but in the moment it’s kind of like, what’s going on? This is just weird and not hilarious.
Yeah, remember when he did the … Yeah. When he did the wrestling.
DC: Yeah. Yeah, yeah, yeah, that, for example.
KS: Yeah, real ugly.
DC: The telling of it is amazing and genius, and while it’s happening, you’re thinking, “Wow, this is just a train wreck.” I guess maybe that’s the point of it, but it takes a while.
DC: He’s long gone by the time everyone realizes the genius behind it.
KS: Yeah, which is interesting. All right, I want to end up talking about anybody in tech that you think is funny.
Anybody in tech?
KS: Yeah. All right, we’ll go through some names. You can say, “I don’t know.”
DC: True or false, go.
I thought Larry and Sergey were hilarious.
They were like a two-man show every Friday, TGIF.
KS: And again, often not on purpose. You think they did it on purpose. They do have a sense of humor.
They 100 percent did it on purpose. They made some very subtle, very subtle jokes that even someone had to explain to me. So, yeah.
DC: On the back channel?
No, the engineers were making those jokes.
KS: Is it a joke when it has to be explained? “It was so intensely brilliant!”
It was so intense. Maybe, I don’t know, maybe I have some kind of Munchausen syndrome or something. I don’t know. What?
KS: Okay, let’s go …
Stockholm syndrome, I think that’s what I meant to say.
KS: Stockholm syndrome. Munchausen is when you make things up, pretend to be sick.
Yeah, yeah, yeah. You think you’re sick. No, I think I’m sick.
KS: No, that’s another one, I think. I think … I don’t know. Anyway, it’s a syndrome. You have a Google syndrome.
I have a Google syndrome.
KS: Yeah, everything’s funny in the Plex.
KS: Food is so delicious! Mark Zuckerberg, you think is not funny.
I don’t think he’s funny at all. I think he’s very robotic. I think if there was a character on television that was a robot, then someone could play like Mark Zuckerberg and it would be a believable robot. And I think that’s going to happen soon. There’s going to be a robot character on television.
KS: Well, he’s trying.
DC: Sarah was starting toward me when she said that. And just realized, well, I can’t say that about him. He’s in the room.
KS: Right, exactly. Well, Jack Dorsey. Is he funny?
DC: Jack’s very … I’ve told you this before. Jack is extremely funny.
KS: He’s not, but go ahead.
DC: He is.
I just don’t know as many people as you do. I don’t know any big names.
KS: Who in tech do you think is funny? Bill Gates.
No, not funny.
KS: Not funny? Steve Jobs was funny.
Steve Jobs was probably funny.
KS: Tim Cook is not funny.
Tim Cook doesn’t seem that funny.
KS: Yeah, no, not at all. Marc Benioff is funny.
KS: Marc Benioff is very funny.
Yeah, he’s very funny.
KS: But there aren’t that many. Sheryl Sandberg’s not funny.
DC: There’s a 90 percent chance Marc Benioff is in Hawaii right now.
KS: Or in his tower. In the top of his tower.
DC: Or, there’s also a 9/10 chance Marc Benioff is in Hawaii right now.
KS: The author of “Disrupted,” what was his name?
DC: I don’t know, I don’t read books.
KS: Dan Lyons.
DC: Oh, Dan Lyons.
KS: That was a really funny book.
That book was hysterical!
KS: That was hysterical, that book.
No holds barred in that book.
KS: Right. Well, he was Fake Steve Jobs, if you recall.
I know, that’s another one of my favorite books.
KS: Yeah, yeah. Fake Steve Jobs.
Yeah, that stuff is hysterical.
KS: I’m trying to think who else in tech is funny.
KS: Yes, she’s great.
Who opened up for the Crunchies, she’s one of my favorite comedians, and I think she did some awesome jokes.
DC: Chelsea’s hilarious, she’s really, really good. Yeah.
KS: Crunchies are still going on, right?
No! It’s over.
KS: No? Oh, it is?
DC: It’s done.
KS: Is it done? Did what’s-his-name ruin it?
DC: Chelsea burned it down after she hosted it and said no one will ever host this show again after me.
KS: But I think it was TJ, I think it was TJ that really burned it down when he was making fun of …
I think it goes back to people just taking it a little bit too seriously. I think when they first started, it was kind of this funny thing, like, ha ha, we’re going to give each other these silly awards. And now people gave real speeches and they really took it seriously, and I was like, do you know where you are? This isn’t for real.
DC: Do you see the statuettes got a gorilla, a plastic gorilla on it?
KS: I think we should just … It’s interesting, because I do think people don’t like to laugh at themselves here as much.
Yeah, no, I get through with that.
KS: It’s super like, “Oh, that hurt my feelings.” It’s more … They’re not mad at you, they’re like, “You hurt my feelings.” And I don’t need to make jokes about them. I just flatout insult them.
DC: I like that the answer to who’s funny in tech is Chelsea Peretti, whose brother is in tech. Who’s funny who has a relative?
It’s Benioff. It’s just Benioff. Benioff is funny.
KS: Anyway, Sarah, where can we find you? Sarah, you have your book?
KS: “100 Tricks to Appear Smart in Meetings. “We’ve got your website, The Cooper Review. How do you get to that?
DC: How do you get to that? Say I wanted to type into a browser.
KS: An url, an url.
You just type into Google, “How do I get to The Cooper Review dot com?” and it’ll take you there. And I’m performing this Saturday at the Setup, which is a comedy show that goes on in San Francisco.
DC: Where is that? Hyde Street, somewhere on Hyde Street.
Yeah, it’s on Hyde Street, and yeah. You can just check out sarahcpr.com to see my upcoming events and things like that.
KS: I have to go to a sexual harassment panel with Katie Couric on Saturday, but I’ll bring her.
That sounds hysterical.
KS: It is. She’s a funny girl. She’s a funny woman, not a girl. She’s a woman. Not a gal. A gal, I’m saying gal.
I’m so offended.
KS: I know, gal. But I’d love to come to see that. And then your book comes out when?
My next book comes out in October.
KS: All right. And we will … And it’s called, say it again?
“How to Be Successful Without Hurting Men’s Feelings.”
KS: And your Twitter handle?
My Twitter handle is @sarahcpr.
KS: And the same thing on Instagram.
KS: All right. Dick Costolo, thank you so much.
KS: This has been totally enjoyable. We’re going to be coming back with more shows on comedy and tech, and we’re not going to reveal who we have. We have some great people coming up. Next two shows, we have two more shows to go with Dick Costolo, who’s very good, who probably should have a show of his own.
Yes, I agree.
KS: And he might.
DC: Oh, please.
KS: No, seriously.
DC: Oh, stop.
KS: Vox asked me about this. “Does Dick Costolo want a show of his own?” I’m like, “There’ll be no living with him!” That was the case.
DC: Your impersonation of him also sounds like your impersonation of …
KS: No, what I actually said, what I did say is, “Then he’d have to work.”
DC: Yeah, that’s right. Good point.
Kara Swisher is funny.
KS: No, Kara Swisher’s mean. We at one point were going to do a show where we just made fun of tech people the whole time, but I think only we would find it hysterical.
DC: Yeah, no, we were just going to …
KS: We just crack each other up.
DC: Can we do something else?
I just have one impression.
KS: All right, okay.
I just have one impression, and this a CEO who just got back from Africa. A tech CEO who just got back from Africa.
Oh my gosh. I just got back from Africa, and did you know that there’s poor people in the world? I had no idea. If I was going to start a country, I would call it North Africa, ’cause there’s a South Africa, but there’s no North Africa.
KS: Thank you, I just had that conversation.
And they wear beautiful clothing when they’re there. They’re so beautiful, such beautiful clothing. So warm.
KS: If we could take their products.
I’m going to write a Medium article about this, and I’m going to tell people that I’m going to start giving back to the community.
KS: That is no joke, just so you know. Anyway, Sarah, it was great talking to you. Thanks for coming on the show, and thanks again to Dick Costolo. Is it Cos-to-lo, people ask me that.
KS: Costolo. I like Cust-olo. For co-hosting.
DC: You can call me what I like, well, then by all means, exchange the pronunciation of it.
KS: Oh, we didn’t get to the name “Dick.” You wrote a note saying we should make fun of the name Dick.
KS: There’s not any Dicks anymore.
I just …
KS: There’s plenty of dicks, but not enough Dicks.
I just feel bad that every photo of you is a Dick pic. That’s gotta be hard.
DC: It never ends. 54 years old. 54 years old and still getting this. Since I was four.
KS: Don’t you remember the greatest lead I’ve ever written about the Twitter board?
KS: “Three Peters and a Dick.”
KS: It was about sexism on the board of Twitter. Thank you. He called me up, he goes, “Kara,” and then he goes, “But that was funny.”
“I’m very offended but also amused.”
KS: “Well done.”
DC: It never ends.
KS: It never ends.
Hey, my name is Sarah Cooper. They call me “Pooper Scooper” all the time.
We all have our little crosses to bear, Dick.
KS: Yours more than others.
DC: Yeah, a little bit more. A little bit more.
KS: Pretty much, the name just brings it right home for us all.
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