So I've been thinking about one of the earliest films I ever did, this movie called Van Wilder with Ryan Reynolds, who is a gem of a man.

But when we went in to do what's called ADR, which is like you basically dub the things that you might have missed when you were actually shooting a scene, and there I am, like early twenties brown dude walking into a big, fancy ADR studio and some of the network execs and the producers who were phenomenal and I really enjoyed working with him.

They basically were trying to give me a compliment and they said, man, you're so good in this movie.

You're so funny, you should go back to India, like you would work all the time if you went back to India.

And I I kind of like tried to laugh it off, and I was like, I mean, I was born and raised in New Jersey, and they're just like, yeah, well, you know what we meant.

I was like, no, I knew exactly what you meant.

That I should fucking go to India if I want to work, because you're giving me the compliment that I'm funny and you kind of brush it off, right, But but you think about that stuff because you're like, oh, are there no other opportunities for me in this industry right now?

And of course there were and doors were opened up thanks to doing movies like that, But it did get me thinking about gatekeepers and then people who have really busted the door down after that.

The system is not actually built to help people like me succeed.

There's a bunch of people that make all the decisions who don't understand how social media works, who don't understand that people like me have a massive audience that want to engage.

And that's why I'm talking with Lily Singh about how the creator economy and Hollywood keep trading places and what that says about who really gets to be heard when a gatekeeping history repeats itself.

Here we go again, again, again again.

Hey I'm Cal Penn and this is here we Go again, a show that takes today's trends and headlines and asks why does history keep repeating itself?

Here we go?

How are you Cal good?

How are you good?

I missed you so much?

I know same here?

How is the vali that everybody's pictures looked?

Incredible?

To talk about where digital creators fit in this insane upside down moment in Hollywood.

I want to introduce you to someone who's always been way ahead of the curve.

What's going on, y'all?

I am Lily, one of Cal's friends, and that's honestly my greatest claim to fame as b being Calpin's friends.

Liar, I'll take it.

But I am an actress, a writer, a producer, got my start on YouTube, and I'm sure me and cal are going.

To get into some issue right now because we're real friends.

Leally Singh basically built the YouTube creator economy as we know it.

She started out filming comedy sketches in her parents' basement and then became a global YouTube icon, and then made history as the first woman of color to host a late night networ work show.

In this fall, she debuted her first feature film, Doing It, which she wrote, produced, and stars in.

I Got to see It at the New York premiere.

She is proving that the future of storytelling belongs to people who just build it themselves.

You don't have to wait for anybody, actor, writer, producer, filmmaker, and my extremely talented friend, Lily sing Welcome.

Of course, I do anything for you, so I've been.

Thinking a lot about technology and I wanted to pick your brain on this for this episode.

Because you started with YouTube, you moved into traditional media NBC movies, and then ironically perhaps now traditional media is moving towards YouTube and streaming.

It feels like there's a gravitational pull to bring you back to the platform that you pioneered, and I'd love to talk to you about this.

Yeah, I mean, the first thing I'll tell you is that nothing makes you feel older than starting off your career in content creation on a digital platform.

Let me just tell you that, because you know, I start I upload my first YouTube video in twenty ten.

Yeah, and so that's like quite a few years ago.

And so when I get questions like what is the landscape?

Like, I'm like, I don't know.

I now too, don't know what the kids are talking about.

I know, true, you know what I'm saying.

So it's actually quite psychologically jarring, to be honest, because just today my assistant was like, Hey, this is podcast coming out and they want to do a collab post with you on YouTube, and I'm like, you can do collab posts on YouTube.

That's where I'm at today.

Okay, this has coming from someone who knew YouTube like the back of her hand.

And so to answer your question, I think it's cool how these platforms are all evolving.

I've always felt from an audience standpoint, there has been this really interesting thing throughout my career where that YouTube audience feels very possessive over me, where when I do things like late night or movies, they're like, come back to YouTube, come back to YouTube.

And I've always felt at a crossroads between this audience.

Really, you know, I've built them on YouTube and that's my community.

But as a creator, I don't want to keep making the same type of con tent for one platform, you know.

I think part of being creative is like experimented with different platforms, different versions of storytelling, long form store from all the things.

So that has been the poll of most of my career, is like me trying to evolve.

Because you have Fanashenka, I grew up with TV and movie stars like you.

You know, I am probably the last generation who grew up without social media.

So for me, it's still really exciting the idea of going to the movies and like watching a TV show on a TV screen.

I think the next generation after me, they don't have that distinction as much.

You know, for them, it's all the same.

But so yeah, it's constantly been a poll in my career.

Do you know from the from the people who have said we want you know, we want you more on YouTube or whatever.

Do you know where that comes from?

And Here's what I'm getting at with that.

I it took me a long time to figure out that when I've never said this before, this is this is where I get in trouble because it's you.

It's like Frent, you talk to friends and you think about shit like this.

Exclusive Okay, when I've when I first started working in comedies, which was really the first few jobs that I had, obviously I wasn't used to getting recognized on the street or anything like that.

And projects do well and this sort of happened slowly.

It was really drawing to me that random people on the street would look at you and laugh, so like, look at you, point and laugh.

The fucked up thing was psychologically I realized that I was uncomfortable by that because that was what bullies used to do, where they would look at you and laugh.

And it took me a while.

It's not rocket science.

But it took me a while to realize that the reason that they feel comfortable laughing and obviously they're showing you love by doing that.

The reason they feel comfortable in my case because of stoner movies or sitcoms or whatever.

You're in their living room every day.

Like Carolyn Komar Go to Whitecastle, almost nobody saw in theaters.

It was very much a DVD and streaming movie.

So people feel like this intimate connection with you because you were in their living rooms, you were in their homes.

They were high half the time, maybe they were on a first date.

Like these core memory for them.

And I'm wondering if you have a sense of what it is about the YouTube audience that they try to pull you in or they try to give you that feedback.

Do you know what it's like what it's about for them?

I do, Yeah, I think.

You know me growing up, when I had like an idol or a celebrity crush or someone I used to look up to, I really felt inspired by that person, and I felt like they're also just so inaccessible and they're like otherworldly.

And what I've heard often.

When people approach from the street is like you were like my big sister, you raised me.

So I get a lot of that where it's like they don't feel like I'm inaccessible.

They feel like this person is my friend.

And it's because the nature of what I did.

Yes, I did two pieces of scripted comedy a week, but I also did daily vlogs, and people come up to me and they go, when you were struggling with this, like I was struggling, Like we went through it together.

I was right there with you.

You were like my sister, And so I think there's this family connection.

Another thing I'll say which kind of speaks to the nature of these platforms and the digital landscape is YouTube is truly global.

You know, when I upload a YouTube video, the whole world sees it at that exact same minute.

And I feel like that's why I have such a global community, like Indians in India bringing Europeans, Canadians, like everyone was able Caribbeans were able to watch at the same time.

Now when I do doing it movies, t shows, it's super segregated, right, It's I have a whole continent over here that's never going to be able to see this thing I did over here, or it's going to come out like six months later, and it's hard to have that community moment when that's the case.

So I think the way that YouTube is just structured globally also really really just gives you this feeling of we're all in it together and we're all part of it now.

The prime example of my last movie, it's only in America, so my fans around the world.

Like they have to wait months.

Yeah, India might never see this, and it's entirely it's entirety.

To be honest, there's a full frontal penis, So I don't know in what way they're going to see this, but it's just that experience is not the same.

Can we we go back to that moment in twenty ten?

I know you've told the story a bunch of times, but the moment you decided to bring out your camera record upload, like, how old were you, how were you paying your bills, where were you living, what were your hopes and dreams?

What made you say I'm gonna I'm gonna do this?

Yeah, it was twenty ten.

I was in my last year of university York University in Toronto, and for most of my life I literally was just following what my sister did.

She went to York University.

I went to York University.

She got a psych degree.

I was like, I'm gonna get a psych degree.

Life is linear like this, We're all going to do this dance.

We're going to get our degrees and get married.

Thought I was going to marry a Matt at that time, and I ra have kids at that time.

Delusions across the board, and someone I remember vividly came up to me one day when my friends, was like, have you heard this website?

YouTube?

People are justly uploading videos?

And I verbatim said it sounds dumb, Like I remember saying those words as why would you do that?

Makes no sense?

For what purpose?

And at that time, I think I was in a really low spot because I was just loving this linear life of life following my sister's what steps.

I didn't feel passionate about what I was doing in school.

I was scared about life.

Honestly, I was like, this can't be what it all it is.

So one day I eventually checked out this YouTube website that everyone was talking about, and I thought.

Huh, this is actually kind of cool.

People are just talking about their thoughts in unfiltered way, and I think there was a level of liberation that really intrigued me as someone who was just following what everyone else was.

Telling her to do.

This idea of being able to speak my mind talk about things I thought were important or funny really intrigued me.

So I remember picking my camera.

I literally cannot express to you that I thought nothing of it.

I have a vivid memory of sitting in my parents' basement.

I was living with my parents at the time, sitting in my parents' basement, and it was like, useer name, and I was like, use her name.

And at the time, my favorite song was a Little Mo featuring fabulous Superwoman, and so I was like, sure, I'm not probably never going to use this again.

We just but it's super Woman here taken.

I was like, Okay, I guess I'll just like make it a design I I Superwoman II success, great, perfect, I'll use this once or twice.

Clearly had no idea would turn into a business, because you know, then the idea of copyright might.

I'm coming to type Brain.

Uploaded this first video and just immediately fell in love with the thought of doing something for myself that I had control over that I was like the final say on and my first video.

I've sid this multiple times.

It only got like sixty seventy views, but I was like, I don't know these sixty or seventy people, so this is exciting.

And from there it just kind of snowballed into the next video, the next And I think very quickly why I became successful is that I was talking about things that specifically other brown girls I don't think they'd ever seen before.

Like there was a brown girl talking about relationships, talking about her period, talking about her parents in a way that was like, oh my god, I thought this was just me.

You were allowed to do this, and so I think that's where that whole you were like my sister, Yeah.

Was there a moment when you realized that the channel Superwoman could become a full time business?

And what was that scalability like?

Because like I obviously had had watched your content before you were on buses in La, right, and I remember feeling such a sense of product.

I may have told you this once is before you and I were friends.

This was probably like twenty eleven, twenty twelve.

I remember had a meeting at YouTube.

I think it was like two years after your channel, you had like these bus billboards in LA and you had you also had huge posters in the waiting room at YouTube, and walking in there and seeing that, I was like, oh shit, like hell yeah.

Usually this is not how it works, like for people listening who don't know if you're a person of color, especially circa twenty eleven, you walk into a waiting room and you usually don't see faces that look like yours.

It's not a particularly diverse environment.

People are perfectly kind, it's not that they're not, but there's something extra about feeling seen.

And I just remember feeling like, Wow, they are investing in this woman, like this makes me feel so proud and so so excited.

I was already a fan.

But was there a jump from making content that was specific to, for example, families that might look like mine and anything broader or is this like your classic case of people underestimate that all people will want to watch brown stories as long as the stories and characters themselves are good.

You know what, I when I started making videos, only made things that I just could mine from my own family, and I did think that, oh, only brown people will be able to relate to this, But almost immediately I would get comments like this is exactly like my Jamaican family, It's exactly like my Korean family, And so I really do believe that if you look at my families, of course there's a lot of brown people, but I think a lot of people watch those family sketches and resonated with them.

And I think it's a.

Classic case of like, no, you can actually see yourself in all types of content, just like I could see myself in Freshman Speller, just like I could see myself in family Matters, you know what I mean.

I think that's something till this day that Hollywood execs do not understand.

But I like that you brought up the YouTube support because it was I think it was like twenty four teenish.

Maybe we're like, yes, there was this campaign where my image is on like Times Square in New York.

And LA and all these places.

And why I was really proud of that is because it wasn't just my face.

It was my parent characters, and my mom character, you know, wears a scarf on her head, and so it was like seeing an Indian family though all played by me on a billboard, you know, in Times, which is really cool.

And I did and This is another safe space, friends, where I don't know if I'm supposed to say this.

I did share through the grape vine that that was a conversation with the powers that be at that time.

If that is going to be something that is received well, But I'm really proud of YouTube for still making that decision because how iconic for little Lily to think, as she's drawing a beard on her face and putting a shallow red that that character will be on Billboard in Times Square, you know what I mean.

The scalability in the business part of it, I'm a little bit in awe of I feel like there's one of the many things that creator economy business model doesn't train folks for, is like you're running a small business without the training of business school.

When you're thrust into a CEO leadership position, how do you learn what you're doing?

And when you start to see revenue come in, how do you know how to manage it and scale up?

Yeah, that's definitely one of the hardest things about being a content creator.

I remember when I started in twenty ten.

You know, also in twenty ten, you couldn't automatically monetize.

You had to like submit your channel for monetization, I had to get approved and you wouldn't get a paycheck until you got one hundred dollars worth of revenue.

So it took me a while to get my first paycheck of one hundred dollars from YouTube.

When did you get your first hundred dollars from YouTube?

It was months into me making YouTube videos, like if I started in twenty ten, probably like eight months, nine months to get that first hundred dollars.

Yeah, but I remember, you know, I never thought when I uploaded my first video that I would need a team or that this would become my job.

But slowly what was happening was I was starting to get inquiries but like will you host this thing?

Will you come be part of this shoe?

We have like a branded deal?

And I was like, oh, I don't know how to do any of this.

And so I joined my first MCN, which is a multichannel network, which was a studio seventy one back in the day, and they helped me kind of with the brand deals and to get revenue.

But then I was like, wait, this is so much work for me.

I think I need an assistant.

How do I hire an assistant?

How do I interview someone to be my assistant?

Leally, what does this even?

And I remember thinking I have no one to ask.

I vivily remember even my accountant, who was my dad's accountant, didn't know how to properly do my taxes, even because we used to get paid through PayPal we had sense and he was like, well, I don't understand this.

He's like this.

I will be fully honest and say I had to pay so many fines from my YouTube money simply because no accountant could understand how to properly file taxes because it was so new at that time, and so in terms of scalability, it was a really steep learning curve, Like my first assistant, how to get a lawyer, how to do a brand deal, how to get paid for that?

Did you have mentors who helped you?

How did you figure that?

Was it the company that you signed with that helped you navigate.

That kind of But even before that, the closest thing I had was so I was in Toronto at the time, and sure there was creators in LA, but I had no access to them.

I had never even been to LA at that time.

There were a few creators in Toronto and this is gonna be a deep cut out.

I don't know if you're gonna be familiar.

One was called Fluffy Talks.

He was just like a direct to camera kind of talked about the news, kind of spoofed the news him.

And then there's a person called Furious Pete who was like a competitive eater.

Of course, there was just Meat at the time as well, who was just raining.

So there's a few people that were creating, and Fluffy had invited me to his house and I was this is the person young girl in Toronto.

Okay, He's like, I'm inviting a few creators over so we can meet each other.

And of course there's one side of my head that's like this sounds like the beginning of a horror movie, Like this sounds like something I should.

But then there was a side I was like, could this be something?

And I walked into his house I'll never forget, and there was like twenty creators through almost all dudes, twenty creators and it was the first time I met another creator.

And then I vividly remember Fluffy that day was like I bought this house because of YouTube, And I was like, you bought this house because of you?

Too what And that's when I was like, wait, what are you saying to me?

And from that day I locked in to be like two videos a week.

I'm gonna learn how to Edit'm gonna learn how to do all this stuff and take it seriously.

But it took a while.

You know, I'm not a product of a viral video.

I didn't have a viral video that made me a sensation overnight.

Every upload has chipped away, every upload has gotten me subscribers.

And so it really was a tough, tough learning curve, and I made a ton of mistakes.

I probably got screwed over a ton of times, probably lost a ton of money, I probably got taken advantage of a million times.

Because you're right.

As a creative, Even till this day, I manage an entire team of people, and every once in a while, I have to take a step back and be like, I don't know what I'm doing.

I was not trained for this, I'm not prepared for this.

I'm just leading the way I I think I should lead.

I'm being a boss way I think, But it is tough.

I feel like that period of time is when I will spend a lifetime digesting honestly, because so for a young brown girl from Toronto, that five six years was a roller coaster for me to have met every one of my idols, to be like making money that I never thought I would make, for me to be the face of something that I never thought could be the face of it was crazy.

I'll be right back with my conversation with Lily.

Right after this break, I wrote a book that came out a few years ago called You Can't Be Serious, available now in audiobook and soft and hardcovery.

But one of the chapters in my book was about how my partner Josh and I met, and it's not at all what the book is about.

And the book comes out and very naively because I had been living my life relatively openly, personally, professionally for the ten or twelve years before the book came out, with the exception of obviously, I hadn't publicly two strangers said anything about it.

And that's because Josh is a very private person.

He has nothing to do with entertainment anyway.

I was very naive, and the only articles that were out there when the book comes out to me felt like gay.

Galpen decides gay and writes gay book about gay only and that's all the narrative was.

And I felt like, oh, this is because you can't handle a brown man who had to work his ass off for something and decided to share it with the world.

And as I was feeling this, you call me.

I just I look at my phone, and obviously I wasn't answering very many calls, and I see Lily saying and I was like, oh shit, okay, hey, And all you said was like, Hey, I gotta go.

I'm in the middle of something.

I just need you to know.

I'm sure you know this.

You're seeing all of the shit that's out there about these articles.

You're more than that.

Whatever they're distilling your identity and all of your shit too.

I've been through it.

You have to ignore that it's going to pass in a few days, and you're so much more than that.

And you know that, and everybody who loves you that, and most of your fans also know that.

So all of this is noise and you have to like, yes, it's there, but just tune it out.

I can't tell you how much I appreciated that phone call, Lily, so for you to call a friend and just be like, hey, homie.

Here's the deal.

I appreciated that so much.

And you just mentioned the haters and the trolls when you're a public person.

That just reminded me of that.

So I just gotta I gotta give you a big, a big thank you for that.

I appreciate that.

And anytime listen, it is it's tough.

I go back to it's tough.

It's very easy for people not in this industry to be.

Like they don't have problems.

Look, he wrote a book, she got a show, but it's so not true.

And I'll tell you another thing.

You know, as you're talking, I remembered this because you you told me some stories about this.

You know, I've learned so much about you, and I think so for.

Those that are listening.

Cal is one of my friends in the sense like he's been.

To my family's home in Toronto, Like he has had dinner with my parents, like.

You're dad, know what I mean?

Like whiskey it's.

Uh literally right.

And so I've learned so much from you, and I remember that, you know, speaking of giving people their roses, I feel like when we talk about underdog and when you become successful, people also forget people's role in paving the path and it is such a thankless thing in that way, and so I also need to give you your flowers.

And I said it at our Q and A as well, that you literally have paved the path for people like me.

The reason I bring that up is I remember, you know, we all get hateful comments, but one of the comments that I've gotten in my life and I'm not supposed to maybe we're not supposed to admit when things bother us, but I'm going to admit this one comment I got.

I was like, ooh, this is actually really hurt my feelings.

The comment was, I can't even believe I'm gonna admit this.

The comment was, remember in twenty ten when we had no representation and so we liked Lily sing what yeah, And it was like it was like years ago.

So I means like it was after like a decade of my work, and that, in a nutshell is the experience of going from like cause, yeah, in twenty ten there was pretty much no representation.

When you're in that situation, there's no representation, it is not easy.

You get asked to do a lot of things.

You're figuring it out, you're making mistakes.

You're getting judged all the things, but you're paving the path for the next generation and for someone to look back and be like, I'm gonna take a shit on that and just say that you were.

Not real for that.

It was like super painful.

And the reason I bring that up is because I remember you talked to me about that too that earlier, on whether it was like what casting directors made you do or like whatever it was, we all had to pave this path, and so any success we have now you have to give flowers to the cowpens of the world because we had to go through some shit.

I appreciate that, and I will I will accept those flowers, but I will over use the phrase standing on other people's shoulders and just give shout outs to There are so many people who are ten twenty thirty years older than me who had been grinding in New York, Young La, New York and LA and London, and I think of them often because you know, we do Q and a's and things like that, right, and a lot of times I get the question.

It's usually phrased in the following way, how much do you regret on a scale of one to ten, stereotypical roles you took in the past, like this movie Van Wilder that I did back in the day with Ryan Reynold, who, for the record, is fantastic, And I'll generally respond with some version of first of all, you're fucking welcome.

That's number one.

You are welcome, Okay.

Number two?

Do I wish that my first role was jumping out of a helicopter with a machine gun to save a bunch of good guys from the bad guys?

Of course, but like that wasn't gonna happen.

It's still probably not gonna happen.

Look at me, right, it just doesn't happen.

And back in the day, you need to get your foot in the door wherever you can.

Had I not done Van Wilder with Ryan, I played a fairly stereotypical Indian exchange student, but Ryan is great at improv and really encouraged me to kind of bring the character to life, and I think there were so many breakout moments from that.

That's one of the big reasons I got Harold Lin Komar Go to Whitecastle, which obviously is not a stereotype, and one of the reasons I got that movie is not that there was a shortage of actors who look like me, But it's because I was the only one who had a studio film credit on his resume, because I had done Van Wilder.

Even the opportunities that I had that a twenty two year old today might look at it through the wrong lens, but that was only possible because there were people who were ten twenty thirty years older than me who kind of helped me navigate all this stuff.

You and I have a couple of things in common, but one of them is that we both had our own NBC shows.

I was canceled after one season of eleven episodes.

They were more gracious with you, But I'm I'm curious about if you remember and if you obviously the last few months there's a lot of attention on the late night space been politicized.

Colbert being pulled off the air for politics, Kim Will obviously getting temporarily pulled off for politics, First Amendment issues.

You're the first in a lot of different ways, but your late night slot was seminal to so many of us who revere that format.

Can you talk about your first meeting at NBC, making your first late night show, like what was that like, because you had ninety six episodes in three months.

Right.

Well, first off, let me start by saying, you know, when I'm looking at the landscape right now of what Late Night is and all the things that these hosts have to go through in all the ways that the administration is attacking them, I wouldn't be lying if I said the bittersweetness of like, thank God I'm not one of those hosts, because I wouldn't stand a goddamn chance right now.

If the Jimmy's and the Sests and the Colberts are then I wouldn't last a day, not a day under.

The hard disagree with that.

What I mean is the attack from the administration.

I'm saying I would probably be the top of the.

List of someone to go out.

That's what I think.

That's what I'm saying is I don't think I would have lasted a chance with all the things I want to talk about, all the things I say.

And just who I am as a person.

My first meeting with MBC, Like listen, I always loved.

Meeting someone who said that they loved Late Night or it's like such a revered space for them.

I growing up in Toronto, admittedly did not grow up with Late Night.

Okay, it was never on in my parents' house.

I don't think they could resonate with it.

We were watching Bollywood movies, you know what I mean.

So when I had my first meeting with NBC, I vividly remember them being like, this is the slot, this is the opportunity, and I just was like, I didn't get into.

This industry to do this.

Like I was just like, I want to act.

I've always had wanted to act, and even in my YouTube videos like meeting sketches, acting storytelling, I was like, this doesn't feel like the thing I wanted to do.

And so I said no.

I've said the story many times.

I said no because I was like, I just it's the time commitment.

I just don't think this is for me.

I think this should be for someone else.

The stars are not a lying.

I said no, and my team was like are you sure?

Okay, Okay, fine, They're very very did not agree with my decision.

About a month later, they called again and they were like, we just want to have a follow up meeting with you.

We really really want you to seriously consider doing the show.

And I thought, Okay, those opportunity is coming around for the second time.

And that's when my team at that time, who was not my team now, but they sat me down and they were like, let me explain.

To the historicness of this format.

You would be making history.

You would be breaking saying all the right things for me to be like, hmm, that sounds really good, but also to be honest, like it felt like a lot of pressure when you explain it to someone like, Hey, if you do this, you could be making history.

You could be paving the path for people that look like you.

You could be breaking.

What am I gonna say no for the second time to that?

I mean mental health would argue, yes, you say no, but any other part of me is like no, So then I said yes, no.

Idea what I was getting myself into, Like, I cannot emphasize enough how unprepared I was for that entire situation.

I had my first meeting and it was like verbatim, it was said to me, Lily, you can be as much or as little of a host as you want to be.

If you want to just.

Show up and read the teleproduct or we can make that happen.

If you want to be involved, we can make that happen and me be who I am.

Obviously, I was like, absolutely not.

When I do things cal you know me, When I do things, I do them one hundred percent.

So I'm like involved now with hiring the writers, involved with all the staffing, involved with the market, involved in every other part of it.

It is a machine that no human mind is able to tolerate.

It was me going on to set and there were a hundred people there.

Okay, I came from making YouTube videos in my house, so like, I don't know what any of you people do, but okay, what was jarring to me was that I was hired because of what I had built on YouTube, because of the way I am on YouTube.

But then I was tasked with like be yourself, but also like you're after.

Jimmy and Sasol, Like we need to keep their audience, so like, be yourself, but make sure it's palatable for that audience.

Don't over index on the cell Asian stuff.

Now, as a South Asian person who's very proudly South Asian, I don't know how to take that note because I don't know what that means.

If we don't over index on myself, you know what I mean?

The first season, I was in the worst physical, spiritual, mental shape of my life.

And so it was really really tough.

There were some shows that I was like, this one was okay, But for the most part, as a creative it really really was so crushing for me because there were days when I'll be walking to the monologue spot and blessed my writers who were so overworked because we had half of the writers room of any other show.

We're all just like, this is not our best work, and I'm gonna have to go out there and I'm gonna have to sell it as if it is my best work.

And then when it released, there was a global pandemic.

And so when you bank a late night show, you lose the timeliness of the show.

And so my late night show was talking about traveling and relationships and making out with people, and I've got a live audience.

And it airs those episodes aired during lockdown, right.

Correct, So then I'm bombarded by things, how dare you have a live audience?

How dare you not follow porticos?

And I'm you know what I mean.

So I was like, Okay, that was really really hard, But now I've learned and I'm going to really stick to my guns for season two.

Season two did feel more like me.

It was more my style of comedy.

But people had already made up their mind based on season one.

Yeah, all the press had made up their mind.

Everyone had made up their mind.

I had no opportunity to ever find a voice on that show.

My writers never had an opportunity to find a voice.

They expected in one season for to be a hit late night show.

You look at Jimmy and Seth and any of them, They've taken quite a few seasons, Yeah, to figure out to this, right.

But what I learned from that is NBC did really.

Try to do something different.

I really believe in my heart they were like, we want to give.

This person a platform.

We want to try something different.

It's the system is not actually built to help people like me succeed.

It's not.

How so, what do you mean by that?

What I mean by that is if you are investing in change someone that looks different, and you're telling me yourself, I'm after Jimmy and Seth and I got to help build an audience while maintaining that audien and change takes time.

Billion audience takes time, You know what I mean?

It's not after one season that suddenly everyone's gonna be like, we know Lily now, and we know her brand, we love what she has to say.

You got to make an investment, like a longer term investment into talent.

I think you need at least like four seasons to figure out the voice of a late night show.

At least it's not scripted, it's late night.

Four seasons for guests to even feel like it's worthy to come on the show.

And so that was a long rant of saying I learned so much from the Late Night Show spiritually and professionally.

I feel like I can tolerate any schedule for better or for worse after a late night show.

But it was definitely the hardest two years probably of my entire life.

If you want to talk about pressure, the human mind should not be tolerating that amount of pressure.

For people to come up to me and say a billion people are counting on you.

You represent all Indians, all women, all queer people.

But then NBC's like, don't know her in next on this all thing, and I'm just like, literally.

In my green room.

I remember one day I had a mental break down in my green room.

I literally after the monologue and everyone had left the studio and I went into my green room and I had a donut in my hand, I Vivily remember, and I was like, how many times did I mention being a woman, being queer and being brown?

And I made a list just to be like, how much is enough?

How much is not enough?

Who's gonna yell at me?

Who's not gonna yell at me?

It was just an inhumane yeah situation, All right, don't go anywhere or convo with Lily continues after this break.

You made a video a few months ago where you talk directly to your Superwoman channel audience.

If I remember correctly, in the video, you said you're not going to be doing sketches in the same way that you've moved on.

You got board of feeding the algorithm.

You want to be challenged.

Do you view your next steps as a reinvention?

Do you view it as an evolution?

Is there a plan on how you think about how you're creating content?

You've got books, movies.

What does the future look like for you?

You know, that's a really good question, And I'll tell you why.

When I was doing it, so for those that don't know doing it is my first feature film, and it's an independently financed film, and it's so good and so thank you so much, bab It was independently financed, which is extremely extremely difficult, you know, no real marketing budget.

Blood, sweat and tears into this project.

And one of the things that turned all of my hair gray was I did, at moments feel how I felt on Late Night, which is I creatively know the answers, I creatively know how to make this a success, but there are so many bureaucratic layers that are preventing me from doing that.

With this movie was the same thing, even though it's independently finance, we still had a distributors still like films still have to go through distributors and stuff to go through all these people to get into theaters.

And every step of the way, I had a creative idea to get my fans involved, a creative way to release this thing, a creative launch moment, and every step of the way, traditional media is like, we don't get it, we don't do it.

There still seems to be this lack of cohesion between traditional and digital, which.

Is just blow blows mind.

Because it's twenty twenty five, now fifteen years isn't I mean my first YouTube video, and there's still certain things that I'm just like, really, we're still struggling with this.

This system which we currently operate in to release content is broken.

It is archaic and is broken.

The fact that a film distribution team like cannot figure out certain things around how to engage my audience, about how to involve the digital it just makes no sense.

So I definitely will have to break the system in some capacity for my next releases.

Whether that's like taking a more of approach as like a combination of digital traditional, I don't know, but something it reminds me a lot of publishing.

You know this because you've written a book cal publishing, and I love books.

We love publishers and no shade, but I have to say, in my experience, is one of the most archaic industries I've ever operated in.

The first book I wrote, I got handwritten notes mailed to me in my mailbox physically to review any idea I had.

About like a digital component.

It was just so archaic.

I thought movies would be further along, but they're really not.

It's the same type of thing.

Behind the scenes.

There's a bunch of people that make all the decisions, who don't understand how social media works, who don't understand.

That people like me have a massive audience that want to engage.

I'm begging people to have the movie come out in the UK, begging people for the movie to come on in and I'm just like, because you do not understand what the statistics and analytics and demographics of my YouTube and my career.

You just don't understand.

So there's still a major disconnect.

And so to answer your question, the short version is I will have to break this system, and when I figure out how to do that, cal you'll be the first.

And what I mean I would love to know.

But why do you think people are still in these old habits?

Is it is it?

Is it?

Is it cultural habits?

Or is it business habits?

Do you I know?

My honest answer, my absolute honest answer.

Yeah, it's because people don't.

Care, that's honestly, people meaning audiences or executives.

No, I think it's the same reason and why the investment wasn't there in my late night show Why Sunnyside?

And again, this is not a drag, this is not che I'm just being honest.

If all the decision makers look a certain way, they don't have the same pull you and I have cal when we make things like this or your show.

Of course, we're doing it because it's our passion, projects, our baby, but we understand something like this is bigger than us.

It is for the culture.

It is paving the path.

It is trying to do something different for our community.

People that do not look like this, they do not care about that mission.

They simply do not care about that mission.

You know, I wanted this movie in theaters, not to make a bunch of money at the box office, so small Indy.

There's no way this is gonna compete with him, which is the Jordan Peele movie that came out the same day.

There's no way it's competing with Taylor Swift's documentary that came out the next week.

I know that, But I see value in a poster like this being in an AMC.

I see value in kids getting, you know, young brown girls going and being like I could watch this in theaters.

Do I think any other person on the distribution team cares about that the way I gar apps.

They're just looking at the numbers and they're looking at the box office, and so this is where I'm like, maybe my heart is too weak for this industry because I do care what things like that.

Well, that's what's crazy to me is that you you are the queen of having monetized this space on your own.

So it's just so ludicrous that you have to deal with the same shit that a lot of other people are Because sure, I assume that executives, even if they were brown, I don't assume that you went and got your MBA because you care about representation.

I hope that you also care about representation.

And the folks I've talked to are like, yeah, representation is great when we can either monetize it or add it as a nice plus.

Like great, Fine, It's not going to change how I write and sell content because I know what's funny to me, I know the characters that I like to write or create.

What's bonkers to me in hearing you say that is you've already proven something in terms of revenue that you generate that I have not been able to prove without that relationship.

You've been able to prove it independent of that relationship.

So whatever these growing pains are that are happening in our business.

It makes me excited to hear you say this, because while it might suck right now, especially to get eyeballs on an incredible movie, I feel like whatever that next step is, as the industry figures it out, like you're just gonna crush that.

From your lips to God's ears, man Be's and I appreciate it, and I know I just also want to say, I know when I talk about stuff like this, I'm well aware that I can come across a little bit like.

She's frustrated, and she is.

I care so deeply about what I do, and I have come to terms with the fact that what you said is correct that from twenty ten to twenty fifteen to twenty twenty to forty years from now, there's still going to be challenges in this way.

I am in this for the long, long run.

I know that this is not going away anytime soon, and we're just in it.

We're in it to change the culture.

One of the last questions I wanted to ask you, this is a this is a teen sex comedy that you've written and started and released.

Can you walk me through what it was like sitting next to your parents at the premiere when there's all this sex stuff going on.

Yes, to give people context, I have some intimate scenes.

I have two masturbation scenes in the movie.

And for the screening in La my parents flew into watch and so it was me and beside me was my mom, and beside my mom was my dad.

And so this masturbation scene comes.

Up, and I'm just no words will describe to you what's happening in my body at that moment.

It was like literally hyperventling.

I just look to the left to look at my dad and he just has you know, the uncle just blank stare, just and I am literally dying in my seat, and I'm just like, oh my god, Oh my god, oh my god.

I was so nervous, genuinely quite nervous, because I genuinely thought my dad was gonna be mad.

I thought he's going to be like, this premiere is done and he's going to like go back home and he's be like what in the actual And so the second week and the uber, I'm like, okay, just give it to me, like what what are the thoughts?

And one of the most healing moments of my entire life is my dad going, you know what, I actually really liked it, him being like, of course there were scenes that made me feel awkward as a father, But I thought the messages.

I thought the message was so good and I actually think all parents should go see it.

I think it's actually made for you're calling it a teen movie.

My dad said, verbatim, I think it's actually made for parents.

Oh yeah, awesome, And I.

Was like, hell yeah.

And then you know what's crazy, cal is I did a video of my parents reacting to my sex comedy.

Obviously promo and obviously my parents are going to watch the movie.

And obviously in every interview I do, people are gonna be like, what did your parents think?

So I was like, we're just gonna show the world what my parents saw.

And I did this reaction.

Video when I tell you the amount of.

Indians that dragged my ass from here to the moon because I showed my dad this masturbation scene.

I have so many followup questions.

One is, did you think my parents are not gonna watch my movie?

You know what I mean?

What the comments were.

It's one thing to show your mom, but how dare you talk about this with your dad?

What?

And that's where I was like, what this is?

Why?

We need this movie that you think.

A daughter shouldn't be able to talk to a man or her father about this is crazy.

These people are projecting their shit on you.

Literally.

I was like, y'all need took me the first in line to watch this.

Bring your parents to this movie?

Yeah, exactly, really that's great.

My mine was way more straightforward.

I brought my parents.

Uh.

They they had seen Van Wilder, and since I shot Van Wilder, I had my rule as always, I'm gonna I'm gonna give them a copy of the script to read if there's anything that's kind of racy or that's you know, that's out of the norm of what they might usually watch.

And so they came to the haroldin com My premiere and they loved it, and their note was My mom had two notes.

So the opening scene, I'm basically tripping my pubes and you see my ass and it's shot from the back, and she said, what did you why did you think I would have an issue with that?

You know, I've seen that a million times.

I used to bathe you like typical, like typical, wonderful, loving response.

And then I heard her talking to my aunt on the phone.

A couple days later and she was clearly asking about the movie, and my mom goes, it's much better than that Van Wilder because Gulpin has a lead role in this one, and I was like, oh, hell yeah, you also get the Nummers.

There are things that do trump awkwardness and ratchetness to Indian parents and its success.

I will tell you that, see, kids never give up.

Exactly.

If you become successful enough, you can do all types of weird shit on screen.

Lily, thank you so much for joining.

Us, of course my pleasure.

You can watch Lily's first feature film doing it on Amazon, Apple, Fandango, YouTube, all the places highly recommend.

It's very funny.

You can also find Lily on all the socials at Lily l I l Y.

Here we Go Again as a production of iHeart Podcasts and Snafu Media in association with New Metric Media.

Our executive producers are me Calpen Ed Helms, Mike Falbo, Alissa Martino, Andy Kim, pat Kelly, Chris Kelly, and Dylan Fagan.

Meghan tan is our producer and writer.

Dave Shumka is our producer and editor.

Our consulting producer is rom And Borsolino.

Tory Smith is our associate producer.

Theme music by Chris Kelly, logo by Matt Gosson, Legal review from Daniel Welsh, Caroline Johnson and Meghan Halson.

Special thanks to Glenn Bassner, Isaac Dunham, Adam Horn, Lane Klein, and everyone at iHeart Podcasts, but especially Will Pearson, Carrie Lieberman and Nikki Etour.

Thanks for listening.

Everybody, tell your friends write a review.

All of this helps.

I appreciate you listening, and until we go again, I'm Calpen