On with Kara Swisher - Lilly Singh on Making It on Social Media — and Hollywood

Episode Date: May 22, 2023

After an update on efforts to rein in TikTok from Montana to Washington DC, we turn to Lilly Singh, a creator who rose to fame in the early generation of YouTube stars and has since made the jump to linear TV. On the agenda: why creators are itching to go from the booming medium of social to a struggling landscape of linear TV, diversity in Hollywood and Kara’s texts with famous people. Questions? Comments? Email us at [e-mail] or find us on Instagram. We’re @karaswisher and @nayeemaraza Learn more about your ad choices. Visit podcastchoices.com/adchoices

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set, grow. Go to ConstantContact.ca and start your free trial today. Go to ConstantContact.ca for your free trial. ConstantContact.ca Hi, everyone. From New York Magazine and the Vox Media Podcast Network. This is Governor Greg Gianforte of Montana, and I would like you to subscribe to my body-slamming ASMR TikTok. Just kidding. This is On with Kara Swisher, and I'm Kara Swisher. And I'm Naima Raza. What was that, Kara? I couldn't quite hear you. You sounded very... What did Elon call you? Shrill. He couldn't hear me. Only dogs can hearaza. What was that, Kara? I couldn't quite hear you. You sounded very, what did Elon call you? Shrill. He couldn't hear me. Only dogs can hear me. What the hell? But does that make him a dog? Because obviously,

Musk is listening to our podcast if he hears you. It's true. It makes him a dog. That's true. I hadn't thought of it that way. He's such a child. I hope you enjoyed it, Elon. We made it for Linda Iaccarino, but you could listen to. Yeah, he clearly heard it at least. I hope she did. She needs to. It was ridiculous. We're talking about Elon tweeted and said, I was so shrill that only dogs could hear me, which is such a lame.

Like, he could do better than shrill. I mean, it's obviously sexist, but, like, there's hysterical. He could just go right to calling me a bitch. I don't know. He could just do right to calling me a bitch. I don't know. He could just do anything. Like it's kind of ridiculous. And he only does things in subtweets. He was responding to a, I'm not going to name a formerly good writer.

A writer formerly known as good. And he had said, you know, don't they realize Arab Spring didn't work? And literally we discussed it in realize Arab Spring didn't work? And literally, we discussed it in detail that it didn't work. So the person didn't even listen before man lecturing us on what we already covered very clearly. Anyway, it was kind of ridiculous. They're children. They're literally badly raised children is what they are. Speaking of free expression, which they are not, I was at the Penn Gala last night where Sheldon Rushdie came. Wow, and? He's got a standing ovation. Pamela Paul was there as well.

Did she yell, free J.K. Rowling? No, she didn't yell that. But I really did appreciate this as a place that has, you know, everyone from Salman Rushdie to Pamela Paul to Jennifer Finney Boylan, Lorne Michael, Robert Caro, Nargis Mohammadi's husband, the Iranian journalist, was there to collect her prize

because obviously she's in prison. And by the way, the CEO of PEN America, Suzanne Nozzle, actually addressed Masha Gessen's concerns about the Russia-Ukraine thing at the very top of it. Oh, okay. Well, that was interesting. Why don't you explain what were Masha Gessen's concerns? Yeah, so PEN America, for people who don't know, it started as poets, essayists, and novelists. And Colin Jost, who hosted last night, said, you got to be worried when novelist is the most financially secure option in the bunch. But it's for free expression. And they really have stood on all sides of this, which is to say that they've spoken out against book bans, but they've also spoken out against the kind of updating of books to avoid cancel culture like Roald Dahl.

And Masha Gessen was upset because of the World Voices Festival, which is the kind of updating of books to avoid cancel culture like Roald Dahl. And Masha Gessen was upset because of the World Voices Festival, which is the kind of flagship event. And I should disclose that I'm actually on the Young Patrons Leadership Board of the organization. But at the World Voices Festival, the organization invited both Russian and Ukrainian speakers to the same program. And Ukrainian speakers said they couldn't appear with the Russians,

to the same program. And Ukrainian speakers said they couldn't appear with the Russians, which put the organization in between a rock and a hard place and maybe kind of false Sophie's choice. And they chose to eliminate the Russian programming as a result. And Masha Gessen, this obviously very acclaimed Russian author, decided that Gessen would step down from the board of trustees. So last night, Susan Nozzle, the organization's head, kicked off with kind of an omission of the mistake that the organization had made, saying there was a better way they could have handled it. And Masha Gessen was the moderator of that panel. They are a very prominent writer on issues around Russia. And I'm a huge fan. And I thought it was handled well. Everyone handled it well, said their piece and talked about it. And it didn't degenerate into something stupid like

they often do. They often do. Yeah. Anyway, speaking of free expression, let's move on to one of the most relevant social media platforms, TikTok, which is crushing it everywhere except maybe Montana. Explain what's happening there. Oh, sure. Montana, led by the governor who likes to body slime reporters, decided that they were banning TikTok. And it's a ridiculous virtue signaling of the right to do this because states have no business dealing with this. This is a national security issue. They have to prove it. The federal government is working on this. But having a state do it just mucks up what they're trying to do in a legal way. And, you know, I was like, why don't you get back to abusing trans people, like the six trans people

that are in Montana? So... Those are our choices, banning abortion, banning trans rights, or banning TikTok. TikTok. And I was like, why don't you get to like governing the state, which has a lot of real issues. And this is just, this was just peacocking and just ridiculous and stupid. And likely unenforceable, right, with VPNs or geofences? Completely, completely unenforceable. Yeah. One thing that's interesting is this idea of finding tech companies rather than finding users, so finding app stores, et cetera. Well, that's because that would be not politically impossible. But the whole thing is just,

states have no business doing this. This is not a state issue. It's a national security issue. It's a federal government issue. And they are working on it in lots of different ways. And it's a free expression issue as well. And the analogy has been used for online gambling. People are saying, well, states can geofence around online gambling.

But obviously, online gambling is less sacrosanct and more regulatable in this country than free speech. Already, the ACLUatable in this country than free speech. Already, the ACLU has said this is unconstitutional. A group of Montana TikTok users sued on First Amendment grounds. Such a waste of legislative time. Literally, why are they paying their salaries there if this is what they spend their time doing? It's completely ridiculous. What do you think the states should do?

Have you changed your position on this? You've kind of been against a ban. I'm not against a ban. I want them to do it legally if they're going to do it. And I don't think that's probably enforceable in general. And I'm always among the earliest people to call attention to the problems with TikTok and the Chinese Communist Party. And that these, you know, he could care less when I wrote about it years ago, this guy, and it's just a political thing. So that drives me crazy. Well, Republicans are always the hardest on China. It's just always interesting when you see Marco Rubio just so concerned for Uyghur rights, but not concerned for the rights of women in his state. Yeah, well, they're full of, aren't they full of ironies? And I just feel like this

is just not their business and they need to move on to the business of Montana, which I don't know, there's lots of things I'm sure the people in Montana want to focus on. And it's not going to work and it's going to make everything a mess and it's not going to get us to the right place on this very important issue. Meanwhile, TikTok's parent company, ByteDance, forges ahead. They have this new app called Lemon 8,

which they launched in March. And last month, they submitted a trademark application for what seems to be this online book publishing business called Eighth Note Press. So they might be building an even bigger content empire, or at least placing themselves to do so. Sure. So let's let our federal officials deal with it. Anyways, one person who's very big on TikTok, Lily Singh. Even though she was late to it, she's our guest today. She is a multi-hyphenate extraordinaire YouTube star, comedian, actress,

writer, and she is all those things. You taped with her live in Toronto at Hot Dogs. Yes, I did. It was great. We had a great time and it was a great interview. And she's a really interesting, she's in a Muppet movie now, Muppet Mayhem. But she talked, she was very forthright about a lot of things and as you'll listen to here. And she's really an interesting person, you know, really was born online in her fame and has been trying to make that transition. Obviously, a lot of people have been trying to do that. But very funny, very talented, pushing very hard for visibility, women of color, and she's bisexual. It's just a really interesting person and so fast on her feet. And I really do love her TikTok. She's got a book club on TikTok, I think it is. Stuff like that. Yeah, she started off on YouTube 15 years ago. I know

a lot of YouTubers who are my age, people in their 30s, who started making these videos when they were 18, 19 in their bedroom. And they've never been able to get out of their age bracket of the supposedly 13 to 18-year-olds on YouTube, which I'm sure are also younger than that since 13 is the minimum. And they've always tried to graduate out of their audiences and had this desire to go to linear when sometimes I would think linear is dying. Why do you want to go to a dying industry? I think she just wants to do content lots of places. She's definitely creative and energetic. I don't have any worries for her. No, and I think that Lilly Singh is one of the ones that has been able to make it to TV. She had a late night show for a couple of years, but I think the world just still wants to slate

social media creators in a different box of celebrity. I'm going to see a Muppet, ma'am. Are you? Yeah, sure. Are you a Muppets fan? I love the Muppets. They're so wonderful. Which Muppet would you be? I like them all. I like them all. There's not a Muppet I don't like. Wow, really? Maybe. I'm trying to think of a Muppet I don't like. I don't know. All the Muppets are great. Okay. You don't want to discriminate against Muppets on this podcast. No, I love the Muppets. I love the Muppets, and it looks like a very funny movie. Okay. While you're thinking of your favorite Muppet, we'll take a quick break, and we'll be back with the conversation with Lilly Singh, taped at the Hot Docs Festival in Toronto.

Think the sweetest chef. That's the Muppet you want to be, Kara. I don't. Fox Creative. This is advertiser content from Zelle. When you picture an online scammer, what do you see? For the longest time, we have these images of somebody sitting, crouched over their computer with a hoodie on, just kind of typing away in the middle of the night. And honestly, that's not what it is anymore. That's Ian Mitchell, a banker turned fraud fighter.

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You need Indeed. I immediately got a gift what what is the gift? What did you bring me? Did you bring me anything? She brought me a gift. You came empty handed? What did you get? Should I open? Are we doing a live opening? Yeah, of course. Oh, yeah?

Okay. All right, here we go. It looks expensive. Looks expensive. Let's see. All right, let's see. What's the bag say? Mubarak Clutches.

Oh, I think I know what this is. This is an amazing brand who makes these amazing clutches. All right, clutches. One love clutch. Wow. I love it. It matches my tattoo. Thank you for being a stalker and being here.

I appreciate you. You're bisexual, right? Right away. Just right away. Just question. Oh, my goodness. No, because... Okay.

Just so you know, lesbians don't use clutches. Okay. Just want to give you a little tip when you're on that side of the island. Anyway, so it's so exciting to be here with a multi-hyphenate. I'm going to call you multi-hyphenate. Many doing many things. But I want to start with social media. You have a million and a half subscribers on TikTok, 13 and a half million on Instagram,

14 and a half million on YouTube, 14 and a half million on YouTube, which was your original platform where you launched your career 15 years ago at age 22. It's hard to master one platform, let alone three. Talk me about how you approach each of them now and how it's changed. Oh, dang. That's a very complex question. There's a science to this, actually. And I love this question because a lot of people assume social media is just social media. But there is actually a strategy per platform. So I started on YouTube where I made short-form content that, like, you do an intro, you relatively quickly get to the point, you are building a community on YouTube. I've always said to build a community, YouTube is the best place to do that.

If I was to take that same video and make it work for multiple platforms, what I would do is I would cut out all intros, I would add subtitles, and I would put it on Facebook. Because on Facebook, people watch it on silent for the most part. They want to get right into act one, know what the content is about. If I was to take that same video and I was to put it on Instagram, I would change the aspect ratio of it, and I would add captions again, and I would make it a singular joke from that video, and I would turn that video into four videos.

And TikTok? And TikTok, I would do pretty much, and I would make it a singular joke from that video, and I would turn that video into four videos. And TikTok? And TikTok, I would do pretty much almost the same thing as Instagram, except I would make sure it's a little snappier, probably make eight videos out of that video. So there is a science to how you caption, to how you format, how you cut, how you execute. So you're on all of them. Which one has changed? What's gone up and down? And you didn't mention Twitter, correct?

Oh, no, we don't speak about Twitter here. Okay, good. Yes, we don't speak about Twitter here. I believe Twitter is the literal depths of hell. Yeah, yeah. It's not good for anyone's mental health. Right. I have had many a therapy session. Right. After scrolling on Twitter. Yeah, yeah, exactly. I unfortunately have to talk too much about Twitter because of Elon Musk, but anyway, let's move on. So talk to me about how they've gone up and down. Up and down, you mean in my experience? Yeah, in your experience. So you're on YouTube, but I suspect you're more on TikTok now, or that's where you get

most of the bang for your buck. I don't know. Are we talking bang for the buck? Well, I'll get to the buck in a second. But what about the bang? Let's talk about the bang first. I'll tell you what my favorite platform is. Right now, my favorite platform is Instagram.

Right. Right? I do think it's possible to build a little bit of a community on Instagram. Not as much as YouTube, but I also just don't have the bandwidth right now to properly execute YouTube. I think YouTube is a great platform if you can be committed to it and you're making content specifically for it, which I have kind of evolved. I love YouTube, but my aspirations lie more in longer form now. And so Instagram, you get more what? Instagram, I get more, honestly, joy right now.

I get more joy. I feel like I can connect with people in a quicker way that kind of takes the amount of time that I'm comfortable spending on it. Right, and so you shot a video at Coachella that got 200,000 views on TikTok with 4.4 million on Instagram. Come on, look at my analytics You're in my analytics over here.

I know, sorry. I love it. Another video, how you're becoming your mom, about how you're becoming your mom. Who is in this audience, I'll try to be careful. By the way, say hi to Lily's parents, everyone. Yes, where's my... Over there.

Yes. So this one, you got 6 million on TikTok, but 3 million on Instagram. So is TikTok becoming a more important platform for you still, or more popular? No, I actually, so this is the truth. I'm going to keep it 100 with you. I actually only started to use TikTok one month ago. Even though I've been posting videos on TikTok for a long time, it was my team syndicating my videos to TikTok because I was scared of it. I was like, this is another thing. I don't want to have to learn another thing. I'm getting older. I can't hang thing I don't want to have to learn another thing I'm getting older I can't hang I don't this gives me anxiety right um recently I had a talk with

myself and I was like can you just chill like not everything needs to be your career you don't need to now become the best tiktoker just like have fun right so over the past month I've just been having fun that video we're talking about that got six million views which is me having fun I don't have like a strategy I'm just just chilling. Do you have any worries about the controversy around TikTok, around the Chinese Communist Party being part of the action there? Yeah, so I have two phones.

TikTok's on the second one. I wrote a column three years ago saying the same question. I have two phones. One does not have any SIM card in it. It just has TikTok on it. Just the TikTok, so for you to post on it.

Correct. When you think about that idea of chilling out, do you need to be everywhere? Is this critically important? Since you started off, would you call yourself an influencer? How would you have characterized yourself? You know what? This has been a challenge of my life

because I think as a content creator, someone that came up in a space where, again, you set your own goals and there's no one there regulating your work, it is definitely psychologically unhealthy in some ways because you feel this pressure to do everything be everywhere and a lot of my peers feel that way where like yeah a new platform comes up and you're like I have to now be on this because I have to the currency that is hung above our heads is relevancy you want to be relevant you have to

do this you have to do this trend you have to be on these platforms I'm kind of unsubscribing to that it's taken many many years but I want to do what brings me joy I mean so much of my life is business but I don't want to live a life where it's all business I have to find the joy where you have to constantly be creating

correct I noticed that among I was at the early makers and they were manic yes being creative on demand constantly is not healthy but that is essentially

what this job is it's for so many years of my life I made a scripted piece of content on YouTube every Monday and Thursday. That's two times a week. Then I daily vlog.

That's nine videos a week. That's a lot. That's not healthy. I don't regret it, but I can't do that again. You can't do that again. And so let's talk about the money you make

on the platform, though. So is it for a thousand views or some brand deals? Talk about each of them and how much do you make at each of the platforms? Okay. Like you want my statements?

Yes, please. That would be good. Okay. Yeah. All right. Well, listen, I'll answer in this way, which is I'm doing pretty good, but I still really like getting free stuff.

Right. Okay. Listen, I'll tell you, the first brand deal I ever did in my life, one of the first ones was a game called, I think it's, what's the Nintendo game? So you think you can dance or dance, the dance general.

What is it? Just Dance. Just Dance, thank you. There it is. Just Dance. Okay. I did it. I was still living in my parents' house.

This was in Toronto. This was like 2011 maybe 2012 and I remember they gave me um something along it was either like three or four thousand dollars and I was like yo I'm rich and I remember my agent at the time saying you shouldn't do this because one day you're gonna get deals that are thirty forty thousand dollars and I laughed in his face I was like you are delusional. That's never going to happen. And now I can say that, yes, I have deals that go into the, well, six figures.

I've sometimes been in conversations that it goes into the seven figures. So between brands and between the TV stuff I do, yes, I'm doing very well. Is there one that does better than the others? Yeah, that's a really good question. It kind of fluctuates. I think previously it used to be brands. It used to be my main bread and butter was me having brand partnerships that were long-term partnerships,

not just one-offs. Now I can say, if I look at my past year or so, because I'm also way pickier with brands, I think for the first time in my life, TV and film are my main bread and butter, which I'm really, really proud about because I never thought that would be the case.

So let's talk about this transition from digital to linear. Yeah. Linear stars always try to make the move to social. Oh, I know. Which shift is easier and why, do you think? They're both difficult. I'm going to have to say that the harder shift is from traditional to digital.

And I only say this because I've helped so many people do this. I announced Dwayne Johnson's YouTube channel at VidCon. I was one of the first YouTube collabs at Will Smith. In fact, the day that he created Instagram, he came to my house to shoot that collab, Subtle Flex. That's right, you heard it here. And so I've really always... I've often been that person that tries to bridge that gap

and tries to teach someone traditional. But they're so used to doing things a certain way. And I think that's harder to unlearn than when you come from the digital space. So the challenge is, well, me coming from the digital space or more traditional is, the first time I went on set,

I remember I started speaking and acting and the director was like, I didn't say action. And I was like, excuse me? I was like, you have to say action. And I think I can learn that, but I'm still really good at telling stories that are super short form and that will

captivate an audience and build a community. I think it's harder for traditional celebrities that have been in that world for so long to unlearn a lot of that organization and a lot of that preparation. Also, entrepreneurism is part of it. Correct. That you're more entrepreneurial in some fashion. So does that suffer when you move from digital to regular? I know when I move to big organizations, I always end up leaving because, again, it's a lot of people. I'm like, Woody, go away. Stop talking to me.

Thus far, my spirit has not been crushed. It's happening slowly, but it's not happened yet. Yes. I'll give you a prime example. I'm part of this new show, which I'm sure we're going to talk about, called The Muppets Mayhem.

My job was just to act on that show. But of course, me being who I am, I'm like, let's talk social. Let me pitch you some ideas. I'm not getting paid to do that, but I just know that's important and I want to do that because I want to take my audience and my community on this journey. So my brain still thinks that way. Having said that, it is getting harder and harder and it's getting more tiring and more tiring to keep convincing these corporations that's important. It kind of is like, at some point, that

system has to break. And you're going to have to learn that even though you have years of experience doing that one thing, you don't have any experience doing my thing. And you're going to have to take several seats and just listen to what I'm saying and just take my word on it because I know what I'm doing and I have three billion views to prove it. Yeah, I think it's a really interesting mix is how people make media.

And I think about it a lot because I've shifted quite a bit in my time. And I'm much happier when I have three people versus a whole group of people. At one point I was working for a rather big organization and someone said, someone who I worked with there for, not really for, I don't really work for anybody, but I try not to have bosses. I hate them. I'm obsessed with you.

Are you? Yeah. I just really am. Thank you. I'm really obsessed with you. You should be. Yeah. But I said to one of them,

I said two things. One was, they said, why are you leaving? I said, I don't want to talk to you anymore. I wasn't like interested. And it was more about entrepreneurism.

So talk about the entrepreneurial nature when you're in these linear platforms, because they are big organizations that move at a pace that's very different. Correct. It's not only the pace, but it's also just the rules. I mean, a lot of these corporations are stuck in this, you know, old school system that worked once upon a time and they're so against shifting any of those rigid rules and I'm like you will die you are going you're slowly dying you are slowly bleeding up because you have no ability to be flexible and adjust to the times and I'm trying to educate you and adjust you to the time so

I think it's just about like just because something I often get told is like, but that's the way it's always been done. That doesn't make it right. That does not make it right. You need to be open to change. And I think I, as a person, represent that change. And so I think it's really ridiculous for corporations to not listen to people like me.

The Met Gala was a few weeks ago, for example. And people noted the lack of internet stars. You went in 2019, though. But Anna Wintour reportedly called YouTubers and TikTokers from the guest list after getting complaints for having too many internet stars. What's your reaction? And is there a difference between internet

stars, except that you're probably bigger than others these days? Thank you for saying that. It's true. I know the number. I've seen the numbers. I will respectfully have to call it the hypocrisy of saying I will not have internet stars there, but I will use one to garner views as she interviews people on the red carpet. I think that's an important part of that.

Because if there were truly no internet stars, then Emma Chamberlain wouldn't be there. And previously that was Liza Koshy. So I think there is a little bit of hypocrisy that happens where it's like we will use you for your views and abuse you for your engagement when it's convenient for us, but we're not actually going to value as real value you as real talent that's something i've really had to deal with for a lot of my career and again i'm going to go back to just because i made content for youtube and you made content for tv and film it doesn't make you better than me especially

because again a lot of those people have probably way more views and probably more well known than a lot of those stars so i don't even think it's a competition. I think this whole idea of, like, what is a star, that definition has changed. If you're under the age of, I don't know how many younger people are here, but if you're under the age of, like, 24, can you just raise your hand? Make some noise real quick. Okay, all six of you. Okay. All right, cool, cool, cool.

If you consider internet or digital people stars, just yell out loud. Okay. Like there's no difference to the younger generation. No, not at all. And I think the older generation is just holding on to this idea of gatekeepers. And I'm letting you know it's going to collapse. Yeah. Very, very soon.

Can I add one more thing? Sure. Because now I'm like a little heated. Okay, good. Another thing I will say specifically about the Met Gala. And I'm not taking a crap on the Met Gala. I need to emphasize. I think it's a really cool event and really culturally significant.

But if it's about fashion, which it is, who has revolutionized fashion? It is the younger generations. And Jared Leto, but go ahead. Correct. But I'm saying fashion is about breaking the rules, it's about being revolutionary, it's about showing up as your authentic self,

and no one does that better than some of the people that were X'd off that list, I would say. Right. So it's kind of like you're also halting the revolution of fashion a little bit. Yeah, because Anna Wintour's such a young and vibrant person. You said it, not me. It's okay.

I'm still trying to get invited to the show. All right. I don't want to get invited. I already interviewed her, and that didn't go so well for her. Okay. Anyway, so you're also part of an earlier generation of YouTubers that are trying to make the shift to linear because you do want to get

in that space. Why is that a goal at all? You know, I have spoken about this in therapy so many times. I mean, should it be? Because the reality is like there have been moments when I am sitting in my house and I'm like, okay, you have accomplished so many vision

boards I've met every person I've wanted to meet I've made all the money I've wanted to make I have there's nothing why do I have this obsession with doing more especially being validated by the traditional space and I think it has to do with a lot but I still grew up with tv and movies you know I'm not I'm a millennial that grew up with those traditional stars I think that's going to change with Gen Z I think Gen Z now they didn't necessarily grow up with that and movies. You know, I'm a millennial that grew up with those traditional stars. I think that's going to change with Gen Z. I think Gen Z, now they didn't necessarily grow up with that.

And I think that's why they consider me the same as a lot of these traditional stars. But I still have that itch in me where I'm like, no, I know what it feels like to love a movie star

that was only, you could only see them on the movie. You couldn't interact with them in any other way. And so I still have that desire. And if I'm being truthful as well it's also because I'm so annoying and I want to just prove so many people wrong right I want to

prove people right but I also want to prove people wrong I know that's unhealthy and I should focus more on proving people right but that's me being honest I want to prove people wrong but you're going from a younger audience which is the up and coming, to an older demographic. Correct. Because those are the people I need to be proven wrong. Right. By making them love you? Yes. Okay. Yes.

Or by making them so mad. Right. Right. That they just hate me even more. But really what they're saying is they hate themselves. Okay. Anyone who hates me is just really what they hate is something in their life. I don't think they hate you, perhaps.

That's probably what they're saying. No, they do. They do. Why? Some people, not let me get this straight. A lot of people really have been so supportive to me. Look at this. I showed up on stage and someone gave me free gifts. Right, that's true. It's not lost on me. You got a clutch, yes. Yes. It's not lost on me that so

many people support me and way more people support me than don't. Yeah. But there are, I'm well aware that there are some people that have a visceral reaction to me. To internet, like internet stars or youtube internet stars to women to queer people to specifically me could be to any of those things right and I've had to really unlearn the significance of that because I used to take it really personally I'm actively reminding myself every day that we're all just showing our trauma right we're all just hating people because we're looking at them through a lens that is saying something about our life yeah is it there's the best line in that we're all just showing our trauma. We're all just hating people because we're looking at them through a lens that is saying something about our life.

Yeah, there was the best line, and we'll talk about the writer's strike in a little bit, but one of the best signs was, ChatGPT has no childhood trauma. Give it time. Give it time. Give it time. We'll be back in a minute.

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So let's talk about when you bridged the path to Leonard TV a few years ago. Are you going to talk about late night? Yes, I am. Are you going to talk about late night? Just short. Do we have vodka? Yes, okay. I just want to know if there's vodka available. I'm sure we do, but you can handle it.

You became the first and only brown woman and openly LGBTQ person to host her own late show in the U.S. woman and openly LGBTQ person to host her own late show in the U.S. It followed Carson Daly as the 1.30 a.m. slot on NBC, and the show ran for two seasons. Eventually, you stopped doing it after two seasons. Do you think you got a fair shot? No. Okay, good. I don't either. How come, and what could have been done to give it a better shot? Okay. A lot of things. One thing is that factually, late night has been predominantly straight white men. That is correct. That is correct. That is a fact. Majority of those shows took several, several seasons to find their voice. Way more than one, way more than two, way more than three or four.

Right. That is a fact. It takes a certain amount of money to shoot shows. I did 96 episodes in three months, to give people context, of my first season. That's a lot. That's two to three shows a day. For context, some of my peers at that time, they do one a day, and once a week they would do two.

So we're already doing two to three times the amount of time work with half of the writers, factually, as well. So everyone in that situation was set up for failure, because I had less support, less resources, less writing staff. And every critique of the show is so valid, and there's

a reason as to why it is that way, that the average human being will never know because they're not in that industry. Why is the sound quality quality so bad it's because our studio was so small and so poorly poorly you know done sound wise why um during the pandemic were you the only show that had a live audience talking about traveling because we had to bank shoot them because we didn't have the budget to actually shoot them in a timely way right um it was just never set up for success or given a fair shot and it was never considered the biggest thing is it was never never set up for success or given a fair shot and it was never considered, the biggest thing is it was never considered an investment, if you're trying to be

diverse and you're trying to change culture that requires a considerable time and economic investment, it is not an experiment I asked this of Chelsea Handler, of Sam Bee they all have the same thing, is the investments weren't made and they had a shorter runway

and you had a shorter runway. Correct. And you had an even shorter one. Absolutely. And if you're going to experiment something for two seasons, you can't expect it to win. And I said this during my TED Talk. I said, we're fooled to thinking that the remedy to all of this is a seat at the table.

I got a seat at the table, and this table sucked. Like, the table is trash. Because when you're sitting on a wobbly seat, you can't show up to the table your trash because when you're sitting on a wobbly seat you can't show up to the table your best self anyways right because i'm sitting at the table no one's inviting me into the dinner conversation no meal is in front of me but i'm at this stupid table so i really think we need to rethink about how we talk about just women getting chances not the chance you've talked about that you need a new table this idea Yes. What does that table look like from your perspective?

Okay, well, I'm going to be honest and tell you I know what it looks like. I'm not 100% certain how to get there because there's so many obstacles to get there. For sure there has to be more women, more diverse women, more BIPOC women at that table, for sure. And I think one of the things that has to happen is there needs to be a cultural revolution

and it's exactly what you just spoke about, which is the fact that white men are held against this standard of potential. When women of color, or people of color, are in those exact same scenarios, they're held against a standard of

proof. You have to prove to us you deserve a seat at this table. We don't believe in your potential because we've never seen it before, so you're going to have to prove it over and over and over again. Every day you will have to prove you belong at that table. That needs to change. That culture of potential over proof has to change. So how does that happen from your perspective?

Because you get things like a couple of years ago, Black Panther, huge worldwide hit. Well, look at that. There needs to be more people that look like me in leadership because that's just how it has to be. If you look at... And I actually look to the black community a lot for this. I'm so inspired by the black community

because I feel like they are just making waves in entertainment and I love to see it. And it is because when you analyse it, it is the Kenya Barris, it is the Lena Weiss, it is the Tyler Perrys. They're making it happen, and they've kind of said, oh, you're not going to do it for us. We're going to do it for ourself,

and I think that is a little bit, the sad and beautiful reality of the situation is that we need to get those leaders up there, and then they need to make it happen for us, and so I'm hoping to be one of those people for the South Asian community. So when you're, you're now hosting two Canadian TV shows, Canada's Got Talent.

Eight. Eight, what? I was just saying eight. Eight, okay. And the game show called Battle of the Generations. Eight. Okay. Do you have hopes of coming back to the U.S.?

Or are you like, fuck those guys? You know what? When I lived in Toronto, ain't nobody was knocking on my door to shoot anything here. And now that I live in LA, I get to do two Canadian shows, which is the joy of my life. Listen, I'm going to keep it real with you. Out of the things that I do,

do Canadian shows pay the same amount? A fraction, a fraction of the amount as something like the Muppets would pay. But again, I've earned the privilege of sitting here and saying, I don't care. I love Canada. And I'm going to do those shows.

So you mentioned the Muppets series. Talk about this. It looks great. Why did you do that? What were you thinking when you were doing that? I know you have a Netflix comedy series you're working on. Yeah, I have a bunch of things. I have a production company called Unicorn Island Productions.

We have a slate of a bunch of things. And the Muppets was not on that. Obviously, The Muppets is not my original production. But I had aspirations to act and get into the traditional space. Probably because I have a little bit of a chip on my shoulder not being taken seriously as a digital creator. And I thought, I want people to take me seriously. That's a whole conversation we just had. But I actually did not get offered.

I got an audition to be in the Muppets, which makes me really happy because it makes it that much more meaningful that I got it. I auditioned three times. I did an audition, I did a callback, and I did a chemistry read. And I did it via Zoom.

And my number one question was, am I going to log onto the Zoom and there's going to be Muppets? There was not. There was humans voicing the Muppets. That's a disappointment. I know. I was like, I low-key hoped that the Muppet,

that I'd be like, hey, you're on mute, and they'd be like, oh, sorry. I really was hoping that would be the case. Yeah. But I want to be vulnerable and say, I did not think I was going to get the role. Because? Because the character, whose name is Nora,

has a younger sister named Hannah. And I was like, okay. Real white. So they're going to have to not only cast me, but they will have to find another brown girl to play my younger sister. And that is going to definitely work against me. I knew that. It can't be two. No, not only, yes, a lot of people think it can't be two.

But the difficulty to finding that person, I knew that they would be like, oh, it's going to be so hard to find another brown young girl. And I truly in my heart felt like I wasn't going to get the role. Right. And then I got it. And it meant that much more because I was like, ooh, not just one of us. Now there's two, baby. I made it so there's two of us. I actually manifested that role like a true millennial.

Thank you. I photoshopped my name as the character into the credits. And I looked at it every day. Wow. Until I got the call. That is super Oprah Winfrey of you. That's right. She has the vision boards. You get a manifestation. You get a manifestation.

We all get manifestations. She likes the vision boards. My vision board is in my shower. Is it? It is. Wow. I made the giant error of when she said, talked about vision boards in a group I was at, and I was like, what's that? What's that? I said that to Oprah.

Oh, yeah. Oh, no, no, no, no, no. Well, that's how it ended up. Let me just say. I'm lucky to be here today. I like your subtle flexes when I was chilling with Oprah. No, no. I was in a group.

No, we get it. We get it. Okay. I love it. I just want to share this. when I was chilling with Oprah. No, no, I was in a group. No, we get it, we get it. Okay. I love it. I just want to share this. I left my phone back there. No one steal it, please, now that I've revealed that. But I said, Kara, are you going to take your phone?

And she said, oh, I have to take my phone. I have so many famous people's numbers. And showed me some of them. And I was like, oh, I believe you. Yes. I believe you're very famous. Yes. I believe you're very, very famous.

I'm not famous. They're famous. You're famous, though. Anyway, we're not going to go into that. You also have a book club. I do. I was like, what the fuck doesn't this person do? Why do you do all these things?

So I've just felt like, so I, as a, you know, when I was in university, I would read a lot because I had to. And then in my adult life, I stopped reading because I was like, who had time for that? Yeah. And then I got back into reading because I discovered that representation in books is actually years beyond what's on screen. All the things I've always wanted to see on screen exist in the pages of so many books. So Lily's Library is a book club dedicated to championing South Asian authors.

And I will say, this might sound like common sense, but a lot of people ask me this, the stories in books are ones everyone can enjoy because, spoiler alert, you can enjoy stories from other cultures. Yes. Yes. I know a lot of people don't think that, but like, you can enjoy stories from other cultures. Yes. Yes. I know a lot of people don't think that, but like, I watched Friends.

I understand it. I enjoyed it. I wasn't like, hmm, I don't really get what other Chandlers say. Like, I was A-okay. So one of the things,

a lot of this talk, it's like how to remain relevant is what I talked about, the idea of, so how do you, if you're not going to be this talk, it's like how to remain relevant is what I talked about, the idea of, so how do you, if you're not going to be constantly making, if you're trying to think of being more, not rare, but just concentrating, I did ask this to Jon Stewart on The Daily Show.

Famous, we get it, famous. No, he was in my podcast. He was on my podcast. I asked him how you maintain relevancy in this fast media age. There is a pace that is changed rather significantly. What do you think the best way to do that? Or is it just like...

So I'm a big believer. I'm a businesswoman. Clearly, look at my suit. Yeah, I see that. But I'm also a very spiritual person. So I always try to combine business and spirituality. And my answer to that is I would argue that every single person is relevant and irrelevant at the same time

because of how we consume information. Like social media is an echo chamber. I, this is a prime example. How many of you have been obsessed with someone or watch a show and you're like, this is the best thing. You go to someone, they're like, I've never heard of that in my life.

Yeah, a lot. All the time. It's because relevancy is so subjective. Right. You know, people will come up to me and oh, calm, a user of 6479 will comment on my post and be like, oh my God relevancy is so subjective. People will come up to me and, oh calm, a user of 6479 will comment on my post and be like, oh my god, you're so irrelevant. And I'm like,

I'm literally on a red carpet because I have three shows. Who are you? Why are you? It's just so subjective. And I think because of social media we've lost this idea of things even being subjective. We think everything is a fact. We think opinions are facts. They're not the same thing. Except that it does move faster.

A hundred percent. It does move faster. And it's very hard for people to maintain one thing we all share together or something that everybody knows. So it's split over and over again, which makes it more difficult to be impactful. So maybe it's something we should stop chasing. Fair point. One of the things, we were just talking about diversity. I did interview Gina Davis.

She pointed out that often male executives think there's only space for one woman in a movie or film. After Thelma and Louise, she was excited about other films, and executives kind of told her, oh, we've already done that. How do you, what do you think has happened? This is something, this is 20 years ago she was talking about. Yeah, it's freaking stupid. It's so stupid. This idea that there, honestly what it is is a fragile system that's scared. I think people are scared of women and they

should be scared of women because we're awesome. And we're going to crush things once we get there. A woman has worked like a million times harder to accomplish things. So imagine if you gave multiple women a shot. You know what I'm saying? So for a lot of my career I kind of subscribed to accomplish things. So imagine if you gave multiple women a shot. You know what I'm saying? So for a lot of my career, I kind of subscribed to this idea. You know, I was like, oh my God,

I can't support another brown woman because like then I won't get the brand deal. Then I won't get the spotlight. And I've had to actively unsubscribe from that idea because that's what they want. They want me to sit there and be like, oh, there's only space for me. But the second we all are like, no, forget that, I'm actually

going to bring every woman to this table, that's when change is going to happen. Do you feel at, in competition with like a Mindy Kaling or whatever, one of the hardest parts of being a minority, looking like how I look, and I'll speak, but I won't even say minority, let me speak from my own experience. One of the hardest parts

about being South Asian is that you see yourself so little on screen so you you feel this need to be represented by the one or two things that are on screen right and no human being can accomplish that mindy kaling cannot represent two billion people she can write from her experience and she can create art from her experience and so that is a challenge of being a minority creator is that you have the pressure like i kid you not someone came up to me when my late night show was announced and literally said to me, 2 billion people are counting on you. There is no way I will make 2 billion people feel seen and heard and talk about their experience because we're all different. But when you have so little

show, so Mindy's been crushing it for us, but people will give her flack for being like, you didn't do this and you didn't do that. She is not the problem. The system is the problem. Because if there was a hundred shows featuring people that looked like us, you would not be giving her that flack. And so really give the criticism where it is due. It is not due at the minorities that are trying their best to make this happen. That's absolutely true. It's the same thing with gay people for many years.

100%. You came out as bisexual in 2019. You said it was one of the scariest experiences of your life. Does that add on to it? 100%. Did you see the headlines? Which ones? Every possible bisexual woman from India, openly this, dog mom.

I was like, how many more things are you going to specify about me? Right. It was so scary. It was so much pressure. I literally, I mean, it was the most unhealthy time of my life but I remember after

one of my tapings I literally went back to my green room and I made a list being like how many times did I mention being a woman how many times

did I mention being South Asian did I do that enough did I mention being queer enough did I do it too much did I do it too little like who wants to live like that that's not a fair position for everyone to be in

and we shouldn't expect that of people at the same time there isn't enough representation there isn't but there's people mad on both sides because I didn't say it enough and because

I said it too much. So what's the solution in that regard? The solution is to say, F both of you. I'm doing what's right to me. Okay, just doing my story. Yes. And that's the, and I've learned, and I don't even mean to be, like, rude. It's just the truth. I cannot please both parties. I can just do what I can do. And going back

to Mindy, because this is how we all came from it, every single time I've ever needed guidance or help or mentorship, she has immediately picked up the phone, texted me back, and helped me. Okay. Let me, I want to end on two things. Because I'm famous and I have her number.

I understand that. She has turned me down ten times for an interview. She's turned me down. She's turned you down. That's interesting. That's really interesting. I literally love, I'm like a huge College Girl fan. I like everything she does. I'll tell you what. You's interesting. That's really interesting. I literally love, I'm like a huge Calla Girl fan.

I'll tell you what. I'll put in a good word. She tweeted back at me saying I don't like answering questions. I assure you she's a wonderful great person. I agree. I'd love to talk to her. I think she's one of the most entrepreneurial. I genuinely will text her. Alright, thank you. You text Bob, I text her.

We're talking about Muppets. Doing a great interview with Lilly Singh. You're welcome. Because it's on the Disney Channel, Disney Plus. He wrote back, she is so talented with three exclamation points. Really? There you go. Really?

Wow. I want to end on news of the big strike. You're a member of the Writers Guild of America. Of course. Talk about the fight. The last strike in 2008 was hugely consequential for the industry. It arguably led to a rise of reality TV. What do you think what's happening

right now? Listen, I think it is an extremely tough situation. I will be honest, in 2007, 2008 I was not even remotely in the entertainment industry. So this is my first experience actually seeing people strike and I just think it's honestly kind of awesome. I mean, like I said, I worked on my late night show.

My writers worked so hard and were overworked so hard. And what is this industry if not for the writers? They are the backbone of the art we make. So I absolutely think the writers are fighting for something that's totally worthy. Is there any big issue? Is it AI? Are you worried AI is going to replace you? Am I worried AI is going to specifically replace me?

AI, I don't know enough about it, but I will say at first glance, it's a little scary. It's a little scary. I will conclude by saying I think everything is a double-edged sword. I think that technology can do great things. I'm a product of technology doing great things, but I also really like humans. I don't want us to ever lose the magic of humans, of human interaction, of connecting with people.

I don't think that's replaceable. And I don't think we should try to replace that. What if it is replaceable and cheaper? Because that's really the problem. But I think I just don't believe it is replaceable. I don't in my heart believe it's replaceable. Do you have a prediction for when the writers strike us again? Because right on the heels of it will be the actors and the directors. Of course it'll be SAG, it is replaceable. I don't in my heart believe it's replaceable. Do you have a prediction for when the writers strike us again? Because right on the heels of it will be the actors and the directors. Of course it will be SAG, it will be DGA. And I'm part of all of those unions. I'm WGA, I'm SAG, and I'm DGA.

I have no predictions whatsoever because, like I'm saying, I'm experiencing this for the first time. I hope it's as long as it needs for change to be made. And if that means studios are going to be put in a situation where they're going to have to face consequences then that's what it's going to be um there's a lot of data around teens social media and mental health i mean there's all kinds of data around especially girls um how do you think about that when you were making those things that people just immediately scroll now yours was healthy, but compared to other things people are watching, it's not. Yeah. Again, double-edged sword. It has been something I think about a lot because pros of

social media. And I do a lot of social impact work around gender inequality. And even when you look at gender inequality, technology really helps. Access to internet, access to a cellular device helps in a lot of places actually makes women safer it helps them progress it helps them get opportunity so it is really good it is you know like all things also really bad and I think what needs to happen is there needs to be more regulation around it I think it needs to be taught in schools I think literally we need to teach kids about mental health in schools for this reason people need to know the distinction between online and real life because they're not the same thing yes things that happen online are real and they have real impact, but it's not real life. 100%. Do you worry as being such a part of online and

doing so much online, do you think about your impact on girls, for example? I am always thinking about my impact on girls. It literally keeps me up at night. It truly does. And so the way I reconcile that is that if technology is the solution and often the problem, I'm really trying to hone in on the idea that it's a solution. So I'm trying to, you know, bring eyes to all those community-based organizations, particularly in India, that are doing great work so that they might not be able to tell the stories online, but I can tell it for them. And so I think about every waking moment is how I can have an impact on girls. Last question, what's your greatest worry then for people who live, especially young people that live online quite a lot, besides the addiction element and the self-esteem element?

My biggest worry is that, and we joked about it previously, but to be serious, is that people will believe the only true validation comes from strangers that have never met them. When in fact, there is people that are right beside them that love them, that will happily validate them, but we're choosing to ignore them that's my biggest story because i catch myself doing that sometimes in fact i find myself when a comment really drives me crazy the first person i call is my mom because she tells me it's fine then i'm like forget this

person forget them you're stupid my mom thinks you're dumb bro you're an idiot you don't even what you're talking about my mom says i'm the best. But I do think we need to continue to value that, that the people in our lives that know us. You know what, T.I., the rapper, said this in an interview. T.I. said, yes, I'm quoting the great T.I. right now, said, you cannot give people with the least information the most consideration. And I fear that we do that as a result of social media.

I would agree. I just say, fuck you to people. That's excellent as well. Yeah, it works. And the last thing I'm going to say, and I don't know if this will be edited out. It's fine. I have to say you are amazing.

Thank you. It's truly been a pleasure speaking to you. No, I really mean that. Thank you. I do a lot of these things, as I'm sure you do, but this has been such an insightful conversation, and I really appreciate you just taking the time to chat with me. Thank you.

And your outfit is fantastic. Thank you. Thank you so much, everybody. She's got that Mark Benioff live interview swagger, I think. She does. She was great. She's charming you. She was, trying. Saying, yeah, saying she's obsessed with me. I doubt think. She does. She was great. She's charming you. She was trying.

Saying, yeah, saying she's obsessed with me. I doubt it. We had a really good time. She's such a smart content maker. I don't know how to call her. She's so many things. She does so many things. Contrepreneur. Contrepreneur. Contrepreneur. I really enjoyed that. But when I say Mark Benioff interview swagger, because she's like kind of giving you compliments, drawing you in, and then giving you grief for your phone numbers of famous people. Yes, I do. I don't know what to tell you. We get it. You're famous, Kara. I'm not famous. I have phone numbers of famous people. I do. Doesn't that make you famous by association? I have a certain kind of, I'm like famous in Pittsburgh. Oh, wow. Not actual Pittsburgh. It's an expression. Among a certain group, I am.

Among a certain group. You're very famous. But how do you think about that when someone is very good at playing the crowd and you're doing a live interview? I love it. Right? Because I think it creates a tension, which is interesting. Not a tension between you and her, but a tension to getting to the answer. Yeah, and she did give answers. That was the thing.

If you do that and then don't give answers, it also says a lot about you. They come to play. I like when interviewees come to play and really want to have a discussion. And actually, she's a performer. She wants to perform for the audience. And I'm similar. And so I like it. I love it.

I love live events, period. I'm good at them. And I think people do better in them, especially performers like her, you know, do better in them. But some CEOs do better. I thought Mark was superb in that setting. Well, Trump is a performer. And we saw how he did in an interview the other day. He's a toxic performer, but he's good at it. He really is. It was interesting to see, she's actually quite honest about her quest for validation. I mean, she was joking and being self-effacing about it, but it was interesting to hear her say that. And

of course, someone who's grown up on social media, you would be, right? You grew up in this fishbowl and, you know, she says she wants to unsubscribe from the idea of relevancy, but I think it's going to be very hard for her. Yeah, it's got to be a worry if you're like looking at your numbers every day. What's really interesting about this writer's strike, too, is there's all these creators everywhere sort of doing writing right now. And they're used to the rigor of constant creation and constant content making. And it's a very different metabolism. And she has that metabolism, which I think will serve her well in the future as moving forward.

She knows how to make and keep making. And her stuff is quite strong. I was really quite charmed and entertained by a lot of her stuff. You know, and she's trying different things, like her book club focusing on South Asian authors, which I thought was cool. And I don't know, her clothes thing. I'm South Asian authors, which I thought was cool. And I don't know. I like her clothes thing. I'm not into clothes, but I think it's very amusing. I could tell from the clothes.

Yeah. She was wearing a bright pink outfit, and I was wearing black, because I know black matches with everything. That is right. So, Kira, you say you're not a fashionista, but you know the tricks. Yeah, that's it. Is this black? It matches black. Good.

Let's go. But apparently black does not match black. Depends on the blacks. Do you know what French Navy is? No. I don't It matches black. Good. Let's go. But apparently black does not match black. Depends on the blacks. Do you know what French Navy is? No, I don't want to stop right now. Dark navy blue, Kara. Let's close out. Okay.

Getting into fashion. Let's move along. She said something very interesting, that quote from T.I., you cannot give people with the least information the most consideration. But should you give them some consideration? I think she was talking about people who slag her, right? I get that. I mean, I just got slagged by one of the richest people in the world. But should I give him consideration? I think I will. Because I think it signals to his whole group, his bunch of toddler army, that I'm not going to back down from this bullshit.

I think, yeah, sometimes you do. Other times it really does mentally fuck you up, I think. She probably gets much more super negative stuff than I do. Vitriol. Yeah, she certainly does. People are very wary to really go at me, but they do from time to time. Have you felt that by blocking, because you block comments on Twitter, do you think that you're also blocking out noise that might be useful or instructive to you? No, not now. It was. I used to keep them on forever until recently, but I'm getting a lot of, I'll be honest, on Twitter, for example,

I'm getting a lot of porn. It just doesn't happen on any other of the social media sites I use. Porn. I'm getting a lot of porn. I'm getting a lot of people calling me the C word. Oh, was it Tucker Carlson? No. Not yet. Not yet. It's just, I don't want to listen to it. You have to scroll through a lot of dumb people. And I don't feel like I don't talk to dumb people in real life. So I don't know why I should talk to them online or give them two seconds of my life. I only have so many seconds of my life and I don't have time for them. But she's right.

It doesn't mentally affect me. I don't feel like, oh, no, people don't like me. But I suspect in her group of people, being liked is, you know, it's part of the constant pressure. Yeah, the fandom is important. I think that other sites do a better job of letting you kind of restrict comments from people who haven't followed you for Instagram. You can restrict new followers. Or I think Twitter, it's kind of binary, which is, when it's binary, it's really hard because you do squeeze out the people who want to maybe give you instructive feedback or maybe are really engaged with your content. Sure.

No, she doesn't at all. You know, not everybody deserves access to me or her or anybody else, right? They just don't. Why should they deserve access? Just because they can type with their little fat fingers and say mean things. I'm sorry. One of the things that people come at her for is that they're, you know, people want to be stands of one thing. And I really like that conversation about Mindy Kaling. Yeah, she has to represent all South Asian women. It's ridiculous. And also all gay women, et cetera. Yeah. And that point about, oh, am I saying it too much? Am I saying it not enough? Am I, you know, I totally understand that. She just doesn't get to be the person she is. Everything has to signal. And I think that's true. I think it's a real burden for especially

women that they have to signal something all the time. And so I think she was right. That was a very sophisticated point she made. Yeah, that was great. And she said she's going to help us with Mindy Kaling. Yeah, Mindy, see how well that went with Lily? Come on on, Mindy. Let's see if Mindy shows up. Until then, Cara, will you read us out, please?

Yes. Today's show was produced by Naeem Araza, Blake Neshek, Christian Castro-Rossell, and Megan Burney. Special thanks to Kate Gallagher. Our engineers are Fernando Arruda and Rick Kwan. Our theme music is by Trackademics.

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