Meet The Psychology Major Who Became The Highest Paid Female On YouTube (Lilly Singh)

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I just need to be okay with being like, oh, you don't like me? I'm okay with that. And it's terrifying because I've been taught to be likable my whole life. From a psychology student in Canada to.

The Highest paid female YouTuber, Lilly Singh.

Built a $20 million empire before the.

Age of 30 and became the first woman of color to host a network late night show. All while championing authenticity, mental health and representation.

What's going on? It's Lilly Singh. Welcome to the Burnouts.

Could you start by sharing a little bit about your background and the experience that influenced you? Now as a storyteller and leader, I.

Feel like there's a lot of things that happened in my childhood that when in therapy, when you look back, you're like, oh, there it is. That's where it started. Well, yeah, I grew up in Toronto to two immigrant parents that are from Punjab, India. And of course, when I say that everyone's always like, were your parents really strict? That's the first question. Yes and no. I think my parents in some ways can be conservative. Meaning, like, I wasn't allowed to sleep over at people's houses. I wasn't allowed to like, go out whenever I wanted. I definitely was told that girls are supposed to do certain things and you're not allowed to do other things. But they were very liberal in the way of, like, look at my career. I was allowed to be creative. You know, I was allowed to have opinions about things. And so we were kind of living down the middle of sometimes I was allowed to do things, sometimes I wasn't. And I bring that up because I think that's the perfect environment for you to follow your dreams. But have to work really, really, really hard to do them. So every step of my career, I had to convince my parents of what I was doing. I wasn't just allowed to do things. I had to really why I was good at it, why I thought it would work out. And that's kind of what you want, especially if you're going to have a career in the creative field. You really want parents that are like, are you going to be able to pay your bills? Are you going to be able to figure this stuff up? Do you have a plan? Do you have, like, a work ethic? I'm really grateful for all the lessons my. My parents taught me at a young age. But I think the biggest thing that is the driving force, and I'll just keep it 100. I have a giant chip on my shoulder, and it is gender equity. And so a lot of what I've done, though it's like comedy and though it's in entertainment, it's fueled by this idea that I always felt like I couldn't do things because I was a girl. That was my whole childhood. So I was born the second daughter to my mom. And in Indian culture, like a lot of other cultures, that was a huge fail. You know, everyone wanted a son. And so from a really young age, I just remember feeling this feeling of being a disappointment. Like, people wanted me to be a son. They didn't think I would be able to accomplish things. They didn't think I would be worthwhile.

And.

And I'm sure my therapist and a whole bunch of people can tell you that that's a very toxic and unhealthy environment to be raised in, which is fair. But it gave me this fuel of being like, I'm going to prove these people wrong, and I'm going to work really, really hard, and I'm going to show this family, this community, this culture in this world that a daughter and a girl can do whatever it is that she wants to do. And so one of the toughest things in my adult life has been how do I take that? I need to prove people wrong and make it a healthier. I need to prove people right. I will now acquire the skills and create the life to make sure that that never is a question again for the next girl born into this family.

How do you think about your work over time and pushing forward equality when we've had setbacks?

I'm a big believer that storytelling is the intervention. You know, I think a lot of times when we think about rights being rolled back or, like, when we think about things not being funded. We think there's, like, one way to help. It's like, we gotta. All ways of helping are great. You give money to things, that's great. You protest, that's great. You fight for rights in a courtroom, that's great as well. But I think fundamentally for girls and women, the issue is that there is a culture around how we think about girls and women. It's a universal culture. You can go to any corner of the planet, and chances are there's gonna be a family or community that's like, we don't think our daughter should go to school. We don't think she's worthwhile to educate. We don't think she has to be a certain age to get married. They have this idea of what her value is. And I think that's where storytelling is really important. I'm probably not the person in a courtroom that leading this. I could be the person in a TV show, in a movie, in a writer's room, on social media, saying something, telling a story, saying words that maybe someone watching is like, man, this has really changed my opinion about how I think about this. I'll give you the smallest example of this, which is, like, hilarious and kind of embarrassing. I literally, when I tell you Girly Pops played for six minutes in the NBA All Star Game. Six whole minutes. They asked me to play in the All Star Game. I was so nervous. The first year, they asked me, I said no because I was so nervous. Second, second year, I was like, I'm gonna do this. I played for six minutes. I kid you not. Took one shot, missed. I went to India the next year, as I go to visit some of the girls I sent to school, and they had a giant poster that was a screenshot of me in that six minutes, because the girls at that school are on a basketball team, and they're like, you are such an inspir. Like, that's the power of storytelling. Just being able to see someone do something is the intervention they needed because they have the team and. And they have the court, and they have the resources. They just didn't have the example. And so I think that's really important.

And talk to us about the movie you're doing now that's being released. How does that appeal to your broader mission of gender equality in this storytelling?

Okay, well, we're getting ready to strap in here. Okay. So my movie, Doing it, comes out September 19th. It is a sex comedy, which is a big deal for me because I never got the talk growing up. Super Awkward around sex, used to whisper the word sex until literally last year. I was that girl growing up in school that was scared to change in front of people, did not have sex ed, never thought that sex could be enjoyable for women, and never learned about consent. So I'd say for most of my life the subject of sex or sexual health was just really heavy and I felt really awkward. And I grew up and I moved to LA and I was like, everyone knows everything. And I feel so behind and uneducated. And then I start to talk to other women, even grown women, 20s, 30s, 40s, and they're like, we feel the same way. We. Women are just really never taught that they are allowed to enjoy sex or about their bodies, or they're allowed to be verbal about what they like and don't like and so doing it. Yes, it's a raunchy comedic movie. It's very much so in the vein of like 40 year old virgin and those kind of classic movies, but it has commentary. It's about a woman. It's a 30 something year old virgin who finds herself teaching sex ed. So it's a fish out of water story where she's unlearning shame and she's going on this journey of like reclaiming her space in her body. And it's based on a lot of things that have happened in my life. A lot of awkward encounters. And I think it relates to my broader mission because I'm just trying to normalize these conversations. You know, if I had that movie growing up, literally my therapist would not be a millionaire right now. But she is a millionaire because. Because I'm so messed up. You know, when you watch sex comedies, I don't know how many you've seen, but if you watch those movies, it usually features people that all look the same way.

Yep.

And I think what people don't realize about storytelling is it's not just about movies and TV shows and having a good time and laughing. I do think when you don't see yourself on screen, it actually hinders your progress. I think you're not able to see yourself and learn about yourself and learn about others. And that does a disservice to a lot of communities. And this is why I get so irritated with Hollywood execs, because they think it's just about the box office and it's just about numbers and it's just about entertainment. It's not. You're actually hindering the progress of certain communities by not letting them ever see themselves in a story or in different situations. And learn about themselves. So my only goal with doing it is that some young girl, maybe some young brown girl can watch us and be like, I'm allowed to talk about sex. I'm allowed to like my body. I'm like, allowed to ask about consent. That is my own legal.

When I was growing up, I remember I thought you were such a breath of fresh air. Because I was such a YouTube junkie, I would go home, I'd watch YouTube to unwind. And I thought it was so amazing that there was this young, outspoken brown girl on the Internet doing her thing. And it's so interesting to me to hear you talk about this idea of confidence now, because back then I remember thinking, this girl is so confident, so good at smoking. Yeah. And it was so inspiring for me of, okay, it's okay to feel like I can have an opinion and get in front of a camera and talk about things that I care about. And part of what we do on the burnouts is we want people to be honest about kind of how they've built their career, their business. And that's why I wanted to learn from you. What do you think are some of the biggest things you learned early, early on in your career?

I mean, there's so many learnings. I have had so many missteps. I've had wins, I've had losses. I've had all of it. I think when it comes to social media, storytelling or anything that has an audience, it's so easy to start caring about the wrong things. It is so easy. I did it as well. I started making YouTube videos. I found something that really hit, you know, dressing up with my parents, doing these rant style videos. And then I stopped caring about what was fulfilling to me and what was authentic to me. Because I was like, I gotta feel. Feed the algorithm. This is what people expect of me now. It's so crazy that you can be the most confident person and you can say things like, I don't care what other people think and I don't care what people expect from me, and I just want to do what's right for me. All of those things get challenged as soon as you start getting validated. Validation is like a drug. As soon as you start getting validation, suddenly it's like, well, maybe I will just do this thing that people want me to do, or maybe I will be a little bit less of this and a little bit more of this. I'd say the biggest lesson I learned is don't be on a high horse and think that your values and Morals are so high that they will not be challenged because they will be and they'll be challeng challenged very well. And you have to like continuously adjust your moral compass. Now I'm at a spot where more than anything I've adapted flexibility. I think people change for a reason. I had to change as my career has evolved and if I didn't change, I would probably go crazy and I probably would not be where I am. And so I'd say one of the biggest lessons I've learned is adaptability, being willing to throw the old version of yourself away and reinvent yourself over and over again. This is a real one. I'm going to tell you. For anyone that's doing social media and anyone's doing anything with an audience, the reason you started doing it was connection. That is the reason we all do anything is cuz we all crave connection. It's why you guys want to talk to people, it's why I'm sitting here, it's why I came here to be like, I want to meet them, I want to connect with people. Then all these other things get in the way and you convince yourself they're more important than connection. The numbers, the stats, the wardrobe, the fame, the whatever it is. But if we could all just go back to connection, that is actually what we're all missing.

I also wanted to know for you, I mean, you were so young when you first entered the entire Hollywood world. You moved to la. Walk us through the beginning of your career and what do you think has changed since then for the better?

Well, it kind of relates to what I just said and I'll tell you the exact cycle I went through. When I started on YouTube, I started on a webcam, I didn't have a crew, I wasn't good at editing, I didn't know how to shoot. If you look at my earlier videos, they literally look like they're shot in a potato. They're so bad. But people were connecting to what I was saying, so it didn't matter. And then as I started to gain popularity and I started to progress in my career, I got a crew, I got fancy cameras. Suddenly I had a late night show. I'm on TV now and wardrobe really matters and hair and makeup really matters. And there was a period of time, if you look online on my socials over the past maybe like four years, suddenly it was like really pretty pictures and very. I would hit these talking points and I noticed that my audience, though still there and still supportive, there was something missing. Suddenly missed the Potato. Yes, the potato was missing. Suddenly it was a. Oh, she's not that relatable girl anymore. She's, like, really done up. And I remember having issues with that because I was like, no. But I often do have my hair and makeup done now, and I'm still the same person. And what I've done over the past two years is, yes, I'm still clearly very done up. I'm doing press, I'm doing all this stuff, but I just brought the emphasis to connection back. So now, if you look at my socials, I'm, like, really vulnerable again. I'm really honest. Even in promoting this movie. I think I'm supposed to go out there and be like, I have this big movie and it's in theaters, and I'm so fabulous. But every step of the way, I've been like, this is so hard. I cry every day. This movie has made all of my hair white. I'm just being so honest. And I've noticed that my audience is engaging with me in a way, like 2010 again, because they're, like, seeing this journey, they're seeing this vulnerability. And so I go back to what has changed is me thinking that authenticity and connection is important, unimportant and important. I really have learned unlearned and learned again in that way.

What for? You are like things. When you sit down with your team and you're. You're thinking about content plans, these are just lines we don't cross that we don't do this kind of content.

I'll tell you in terms of content, but I'll also tell you in terms of just behavior, because that's a big thing too. I remember the first couple times I went on set. And you have to understand, I'm like a girl from Toronto. I was not born and raised in la. I did not grow up with, like, Hollywood glitz and glamor. I'm just a girl from Toronto that grew up in, like, a rough neighborhood that has just figured it out, honestly. And so I'm pretty rough around the edges for the most part. Don't let this. Don't let this fool you, okay? I'm usually in the club on a table. Like, this is. You know what I mean? So the first couple times I went on set, I remember I was running a few minutes late, and someone on set literally came up to me in verbatim, said, well, it's okay. You're the talent. You can be late. And I was like, ah, I see what this is going to be. This industry is going to be a bunch of people telling me it's okay to misbehave, and that has been every step of the way. I've been told that I am allowed to be late. I've been told that if everyone else in a room is quiet, I can speak louder. And that is what messes with your mind. That is why celebrities go crazy. It's because everyone is convincing them they're allowed to misbehave and they're allowed to be rude. And it's. It's completely okay because they're the talent. You have to work so hard to counteract that. And I think that's in any. In any business and industry. I think when you have a certain level of success, people start giving you passes. Don't take those passes. That is the path to a nightmare. So my team. I'm very adamant that my team is super respectful to every person on a crew, that I'm super respectful to every person on a crew. And in terms of content, I think there's so much noise out there. Yeah, I think we live in a world full of noise. And I have a very simple rule which is, are we making something to add to the noise, or do we actually have something to say? So very often, my production company will get pitches about, like, a new unscripted dating show that's about, like, these hot people that are gonna go and do this hot stuff. And I'm like, what is it saying? What are we saying here? Because there's so much of that noise, and I'm not against that noise, but someone else can do that noise. I'm trying to say something.

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And I want to go back to your team because I really loved this quote early on when you first got a million followers in what was it, 2016?

And numbers.

Let's 2018, you're at 10 million. And your audience kind of early on was like, hey, you're not doing it solo anymore. You have a team. What does that mean? And you said this is actually something we should all champion. If someone is doing well, we should support them, building the best team around them and having the most incredible people to push things forward. How did you find that first early.

Team is really tough. One thing, one of my first and most meaningful hires was my editor. When I started on YouTube, I shot, edited, wrote, did everything myself. Had a little lamp from IKEA that I shot my videos on. I figured out how to edit. Not very good. If you look at my earlier videos again shot on a potato, don't look very good. Editor was hard because I was so scared to give away that power. I like knew my voice so well. I knew how I wanted the edit to go. I've edited thousands of videos. I could like do it in my sleep of exactly the music's going to go up punchline music's going to cut out like to a T. I could edit it but it was getting to a point where I was like I don't have the time anymore Like, I'm doing events and I'm having all these opportunities and I want to grow. So I need to free up time somehow, some way. Trusting my editor, who is still the same editor I have today.

No way.

Yes, he's still the same. He does everything visual for me. He's edited the trailer for my movie. He edited the key art for the year. He's still editing everything for me was the best decision ever. And I think most people, when they're starting out in their career, they're like. But then I got to sit with my editor and I got to tell them all the things you're doing wrong, and I got to teach them. It is so worth teaching someone your voice. In that way, you'll get to a point where your most valuable resource is time and mine is time. Anything that I can do to get my time back is what I'm absolutely going to do. And I think the smartest thing you can do as a leader is be the dumbest person in the room. I really believe that. So my team, they're all individually better at what they do than I could ever be. So if you are sitting in a room full of people that are your team and you're like, well, I can edit better than that person and I can assist better than that person, and I can graphic design better than that person, that is the wrong team. You have to be the dumbest person in that room. So when I walk into my agency or my manager or whatever it is, I'm like, I need you all to be smarter than me at what you do. And that is makes me a smart leader.

That's. That's honestly exactly what we learned when we were building our companies. It's so important to identify your true weaknesses and to be able to bring in people who are 10 times better at that so that you can focus on what you are actually good at. And that's why I also wanted to know more about how did you actually go about finding your first early team? Was it referrals? Did you reach out to people? What did that look like?

It was a little mix of everything, to be honest. My editor, I found through he was part of a mcn, a multichannel network that I was part of at that time. And then I stole him.

Assistance. I usually everyone else, my team, I think referrals are really important. I'm not opposed to just meeting someone in a cold. In a cold situation, being like, let me get to know you. Another thing that's really important with a team is you got to Find out what their carrot is. Just because I'm Lily and I'm sitting here and I care about my movie and I care about my social media, the people that work with me, it doesn't mean that those are their priorities. They have their own dreams and they have their own carrot that's dangling above their head of what they want to do. I think it's important to learn what that is with people and. And help them get that. I think the best leader is not someone that's like, you're going to be my assistant for 20 years and you're going to be my editor for 20 years. Like, what do you want out of life? How can I help you get the skills and do that kind of stuff, and then you can leave me, and that's okay. I'll be fine with that. I think the best leader is one that's able to let go and make people the best version of themselves.

How do you index on people that are smarter than you being in the room versus betting on young, hungry talent that you think you can ramp up.

To be really good? That's a really good question. And I. I'm gonna be completely honest and tell you that it has gone both ways. I have bet on young people where I'm like, I want you to win so badly. And then I'm like, oh, my goodness, you're so lazy. And I really. You really gotta step it up. But more often than not, that is not the case. More often than not, I've bet on someone and they have really come through and they've showed up. I think if you're meeting someone young and you can't confidently say, like, oh, you're, you know more than me about this thing. Sure. Are they willing to learn that thing? And are they showing you they're willing to learn that thing? And I think work ethic is something you can pick up on if you're a nerd. If you're a nerd, I will hire you. If you are geeking out about what we're doing, I will hire you. If you ask great questions, I will hire you. And I think there's a misconception about that because I've. I've hired some people who think asking questions is a bad thing. And I adore when people ask questions. Asking questions mean you care. I'll be honest, though. To young people, I will say, if someone gives you a chance, you better work your ass off. Because sometimes they don't. They don't always. They don't always.

And I want to Talk about hyphenate. Can you talk about what you're doing there, what you're excited about and creators that you're investing in?

Totally. So one of the things that drives me, let me tell you, when I started on YouTube in 2010, there was not a lot of things for me. There was not anyone that really looks like me doing it. There were a few YouTube networks. There weren't a ton of resources. I had no one to ask when it came to advice or support. I had no one, I had no colleague to be like, hey, this viral video, this million subscribers, this YouTube thing, this licensing music, I had no one to ask. I just figured it out on my own. And so one of my missions has been to leave the place better than you found it. And so I created Hyphen It. I Co founded it, which is a YouTube network dedicated towards South Asian creators. And I say this because I know culturally being a South Asian creator is tough for a bunch of reasons. One, some stereotypes I will say are true. All of our parents want us to be doctors or lawyers. To be a creative in a South Asian household is tough. And I think one of the biggest things that actually young kids or parents come up to me and say is I wasn't allowed to follow my dream and tell your YouTube videos. Parents will also say, I was scared to let my daughter do whatever until I saw your YouTube videos. So I think it's important specifically for there to be a network that supports South Asian creators to show, like, you have resources, you can do this, you can go into a creative field and it will be great, but also just like the knowledge and know how. So what hyphenate does is we're helping them make More Money on AdSense across YouTube so they can have more money to buy their equipment and buy their cameras and, and have this and acquire the skills to kind of make a career out of what they're doing. If we want more people of color on screen, they need to be allowed to go on screen and their parents need to support them going on screen. So it starts right from the. Right from the get go.

I love this note because they also need to learn how to make money from their career.

Exactly.

I want to know what were some of the big things that you learned when you first realized, oh, shit, this actually can be a career? How did you realize you could monetize?

So if you noticed, I did not pull up here in a Lamborghini. And a lot of the people who made YouTube videos in the era of when I made YouTube videos, YouTube videos would be pulling up in a Lamborghini back in the day. I don't know if it's my parents frugal immigrant mentality that is in me, but I never was that person that put all my eggs into one basket and made a bunch of money and then spent a bunch of money. I really believe in having a360 business and I have always believed that. So when I started making YouTube videos, I then had merch, I then went on tours, I then had books. I then also like started a nonprofit and started a production company. I always made sure that if one faucet shut off, there was other things that would keep me going. It's really, really important. Even today in my business, my brain is always like, okay, the movie and then I have this event and then I have to do this brand partnership and then I'm going to do this audition and this shoot. It's we live in a really tough world and a really tough industry and I think if you do put all your eggs in one basket, that is a very scary thing. I think a360 business is super, super important. So if bunch of money I wouldn't go and I wouldn't go and splurge on it like that faucet's going to be on forever.

Yeah, I, I, I hope some YouTube creators are listening to you right now.

But I will say investing in yourself is different from splurging. I am now of the belief that the best investment you can make is in yourself. So if it comes to making myself better, I believe fully in spending money on that.

Like what are some of the things you're happiest about?

Absolutely. So I, I mean I always say my job is, is 10% creative and 10 writing and 10 acne. It's 90 mental. And I think this is true for most people. So something that's never a waste of money for me is therapy. Something that's never a waste of money for me is anything that gives me my time back. So a team assistance, an environment that makes me feel safe and comfortable is priceless to me if it means it's an environment I can get work done in and I'm warm in and I feel safe in that is priceless to me. So I think anything that makes you better, any courses, any classes, any new skills you can learn, anyone I can hired to teach me something is never going to be a waste of money for me as well. And an investment beyond myself. Anything to do and this is for anyone with girls and women is always going to be the best investment if.

You don't mind sharing, like breaking it down in terms of how you make revenue through your different businesses. What percentage still comes from YouTube? What comes from brand deals? What comes from movies as you've diversified over time.

I love that you asked this because my upcoming movie, I'm going to lose so much money on. So much money. It's independently financed as I'm literally lose so much money. But that's the goal, to get to a place where you can lose money on things you care about. That is the goal in terms of where I make money from now. So yes, back in the day my number one source of income was definitely YouTube. It's probably not anymore because I don't consistently upload. But the great thing about having a catalog is that still my videos, I have over a thousand videos on YouTube that inevitably are being watched in some capacity. Those same videos are cut down and on Facebook that are inevitably being watched in some capacity. So there will always be some portion of revenue that comes from YouTube. Which is another important lesson, kids. Passive income. We love those two words, passive income. And a YouTube catalog really does that. So I'd say right now maybe like 5 to 10% of my income comes from there where it used to be almost like 90%. Brand partnerships are a pretty big part of my income right now. I'm very selective about brand partnerships because I care about my brand a lot and I don't want to be posting about things I don't care about. And so I generally don't do one off brand partnerships. I'll do like, like a year long or a multi year deal in something I really believe in that feels really authentically me. The biggest source of my income now probably is when I'm doing a shoot like a TV show. If I have a project from a regular on a TV series, if there's a movie, not my movie, just to clarify, not my movie. So if we want to get real honest, we want to talk about passion projects and like getting to a place where you can fund something you care about doing. It is independently financed. Every producing fee that my company, Unicorn island made went back into the movie, which is like in the six figure range went back into the movie. Every single one of my writing fees I put back into the movie as well. I personally put money towards a distribution deal. My manager and my friends personally have invested in the movie as well. So literally it's, this is one where I'm not gonna make money and I'm gonna lose a lot of money. And that is okay because what I'm gaining for that is different. It's my brain, baby, and it's my passion project.

When you invest in a movie, what does that look like? Can you explain to me what is distribution deal? Where is the bulk, some of that money go? Is it the actual shooting and producing it? Is it the distribution part at the end? And then is there a chance, like, let's say it performs super well on the box office that you make it back? Or do you make it back mostly now today with like working with streaming partners?

Right. Well, maybe. Girl, I'm gonna be honest with you. This is my first time doing any of it. So all these things are things I'm learning or just have learned. So it is financed by a financier who gathered a bunch of money from her community. And when I say it's independently financed, I mean she took care of the financing and I've helped contribute to that along the way. Most of the bulk of that money goes to shooting it. It's shooting the actual movie, it's paying the cast and crew, it's paying, it's paying for locations, it's doing all that. Now, in an ideal world, someone then comes in and buys this movie for a boatload of money and you're like, yay, we did it. This one is not the case. And I'll be really honest and tell you that something that has pained me about this movie is it is very much so in the vein of a lot of mainstream movies, bridesmaids, kids, 40 year old virgin, like I mentioned. But the feedback we got, and I can't help but think it's because I am at the lead of this movie, is that it's too niche. And I think that, that people of color get that feedback a lot. That this is too niche and it's now a South Asian movie because like, Lily's at the lead of it. Yes, of course it's through the South Asian perspective, but sex is a universal topic and I really, truly believe anyone can watch it and understand. And I always make the joke that I watch Friends and I was not confused by watching the show Friends. You know what I mean? I fully understood what was happening there.

How could it be too niche if 40 year old version is a huge hit?

Exactly. And also, how could it be niche if one in four people in this planet are South Asian is another question. And any exec that says that to me irks me because I'm like, actually, factually your niche, statistically speaking, I'm not niche. You're actually the biggest insult I've ever heard.

You're niche.

But that word does trigger me because very often in Hollywood, that is the thing we get told like, that's too niche. Which basically means we don't think enough people care about your story because it's too specific. If you look at some of the best pieces of content, they are specific and they are great. One of them days, the Issa Rae movie that just came up did Amazingly Sinners. People would probably call that niche as well. They have proven hits. And so I think this idea of something being niche is garbage and alive. But yes. So we are also now distributing it and in America. And then we'll have to figure out distribution deal for Canada and the UK and every country has their own distribution deal and their own regulations. And it's just a lot, Phoebe. It's a lot. It's a lot to deal with, and it's a lot to figure out. But we're out here. Through God's grace, we're here.

Will you do international distribution deals, too? Because I imagine this movie internationally would be a huge hit.

It probably would be. We're trying to figure it out. It's not in my hands personally. We have a distributor that will go to each territory that has the global rights of the movie and will go to each territory and try to sell them individually. But it is so isolated, which is tough for me coming from YouTube because I post a YouTube video and the world sees it immediately with a film. It's like, I'll give you an example. In Canada, to get the movie scene, you have to get the trailer approved by province, and it has a different rating system than America, and it's a different entire timeline and process just in Canada. So to think about each country and what it is you need to do to get a movie there, it makes me want to break out in hives. Honestly, it's. I just want to say, for anyone listening to this, movies are hard, man. It is hard. Like, I did not think I've been working on this film for seven years. Wow. Seven years of my life. My longest and most toxic relationship has been this movie. And you don't realize that when you go to the theater and spend an hour and a half watching a movie. Blood Sweat into your have got into that for real.

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I want to ask like a more general question just for other young women of color specifically. I'm sure in the beginning it was really hard for you to ask for money and to know what exactly your worth was. What is your advice? Especially for young women who are negotiating who are asking for their first paycheck? How do you go about those conversations?

Okay, I have like three to four things to say to this because I love this topic. One is I think one of the most tragic and evil weapons used against women is gratitude. I have spoken about this a lot, I think very often because women fight to be in spaces that were otherwise not in. And the best example I can give is when I had a late night show and I was the only female host, I was very often told or kept in check by gratitude. Like you should be really grateful to be here. Even from my own agents sometimes, honestly, hey, like I don't have the resources to do the show well, I'm like not being paid as much as all the other late night hosts. I don't have the number of writers they have. The sound in the studio is so bad because we don't have the right equipment. Like, okay, we should be really grateful. Like not a lot of people get this opportunity. You should be really grateful. Watch out for gratitude being used as a weapon because they use gratitude as a way to basically say don't ask for what you deserve, deserve. And so you can be grateful and also ask for what you deserve. Those two are not mutually exclusive. The second thing I'll say is, it is so important for all people, but especially women, to talk about money. I think so often when we're on a. I'm on a set or when I'm doing a brand deal, I have a friend or colleague that's on the same set or has the same brand deal, and we never talk about the economics of the situation. And then later on, you realize, like, wait, I didn't get that thing in my deal that they said it was impossible what you got, and vice versa. So now I literally just pick up the phone and I normalize calling other women to be like. Like, how much did you get paid for this? Did you get this deal point? Did they agree to this exclusivity? And I have found that not a single woman I've ever asked has been secretive about it. She's always been like, I'm so happy to tell you, and we should absolutely make sure we get the best deal. And I have found every single time that I was lied to about what I could get, that they got something more, that they got something less, and that we all just win if we talk about money. And there's a reason they encourage us to not talk about money. And it is exactly that. It is to. To keep us at a certain level. And the third thing I'll say is, and this doesn't keep it real, you will always be painted out to be a villain if you're a woman and talk about money. And you just have to be okay with that. Speaking of the Forbes thing, when I was on that Forbes list, I had just tweeted about being the only woman on the list. And when I tell you the wrath of the Internet came for me. Oh, they came for me.

Why?

Why are you making this about gender? What is YouTube supposed to do if people want to watch men and not women? I was simply pointing out that the year before, there was multiple women on the list. And on that year, I was the only woman on the list. And I was painting the picture about how YouTube is supposed to be this place without gatekeepers. And that's why it's different from Hollywood. It's like, anyone can have a voice. And it concerned me that it was following the same pattern of Hollywood being like, now, only a certain type of person, but men. I tell you, the boys on the Internet came for me. Oh, did they come for me? And so I think you kind of have to be okay with that. People don't love a woman talking about money. We just gotta keep doing it. We just gotta keep pointing it out. And the boys will be mean, and that's okay.

I'm so glad that you have that attitude because I think that will make other women feel okay with. At the end of the day, it is gonna be uncomfortable to have that conversation, especially in the beginning. And they should go into it with that expectation that over time it does get easier.

I will say one of the hardest things I've learned and I still struggle with it today. And I talk about in therapy all the time. It was such a. A painful thing for me to be like, those people don't like me because I talk like, like this. I spoke about money. Now these people don't like me. In the back of my head, I was like, what can I do to make them like me? What can I do to make the late night people like me, the audience like me? I think my whole life has always been a. I want people to like me because we're taught we need to be likable. Being likable as a woman is a survival mechanism, right? It's like we. If we're likable, we'll be safe. If we're likable, we'll get the job and we'll get the opportunity. At a certain point, I'm realiz that you have to unlearn being likable because you have to be in situations sometimes where you're like, I need to stand up for myself. And if the result is you not liking me, I have to be okay with that. Like, I just have to be okay with that. Going back to the movie. Oh, I've learned that over the past years, business situations where certain jokes in the movie that were so culturally specific. I was told to cut, and I was like, no, I'm not going to cut them. And if you don't like me, that's okay. When this movie comes out, I'll also tell you there'll be so many. I already know this women and men, but particularly I know this men that are not going to like this movie because it's about a. A sexually empowered woman who is fully owning her body, fully enjoying sex, fully talking about sex. I have two masturbation scenes in this movie. I have multiple sex scenes in this movie. And there's gonna be some men that watch it and are like, this is shameful. How dare you. And I just need to be okay with being like, oh, you don't like me? I'm okay with that because this movie is more important than you liking me. And it's terrifying because I've been taught to be likable my whole life.

Well, it's kind of like that saying, a friend to all is a friend to none. If you're trying to appeal to everyone, then you're going to alienate that niche core audience that really believes in you. And that's what I was really curious about is you were Talking about how YouTube is so different than Hollywood. Because ultimately, in Hollywood, there are certain structures, there are certain power brokers that really determine whether or not someone gets watched. What has been your biggest learnings, kind of transitioning your career into something where you are interfacing with those people? What have you learned in the process? And what advice would you give to other people who want to break into Hollywood?

Okay, so I grew up with TV and movie stars. I grew up not in the era of social media. And so the idea of being on TV and in Hollywood is still very intriguing to me. I think it's a little different now. I think kids growing up now think social media is the same. They think. And I know I've said. People have said this to me growing up. You were my idol. I was like, me. I was like. My idol was like, Dwayne Johnson. Yeah. You know what I mean? Tv, movie stars. And so I think if you want to break into Hollywood, the first question is why? Why is it that you actually want to do that? Because not to take a crap on my own movie that's gonna hit theaters. The most watched streamer is YouTube. Even in living rooms on TV, that is still YouTube. So if it's to tell a story, if it's to reach audience, the question is, why do you want to break into Hollywood? Is it your ego? Is it your pride? Is it? And if it is, that's okay. Those are not wrong answers for me. I tell you, it is my ego and pride. I grew up being like, I idolize these people, and I want to step into their arena. I remember when I went into late night, there was all these notes I was given about what people would want to watch. And there was these execs being like, well, we think this is funny, and this is what people are watching. I'm like, Respectfully, I have 3 billion views on YouTube, and that is more than this show will ever get. And I know what people want to watch. And so the really tough learning lesson for me was when you go from YouTube or digital space or something where you have control to something where now there's all of these people that have an opinion. Everyone in that situation just has a job they're trying to hold onto. It doesn't mean you're going to get the best product. It doesn't mean it's the best story. It's just you're in a system now that has other priorities that, that are more important than actually telling the story. And that's really, really tough. And so I really would question why? Why do you want to get into Hollywood? And different stories and different projects deserve different distributions. Like, there's some things that I just wouldn't make a movie about, and there's some things I wouldn't make a YouTube video about. And so you have to think, what is the best platform for me to tell this story? The answer is not always going to be the same. It's going to be different.

What advice would you give to someone who wants to be a creator Again?

Go back to why. When I started making YouTube videos, it's because I was lonely and sad and I wanted to connect with people. And so I was driven by something really real. I have a bunch of people that come up to me and say, I say, I want to do this as a content creator. What do I do? And I always say, what is your goal? Just be really honest with what your goal is. If it's money, say it's money and act in accordance to it being money. If it's to further representation, act in accordance to that. Because those things will not always align. I just told you about doing it. I'm going to lose money on that. The goal is not money, it's representation. You need to be really clear with what your goals are. Intentions are not from a place of judgment. Don't judge your why, just know your why.

Honestly, I think honesty in this space is super important because I remember I have two different friends and they both have pretty equal followings, and one of them is making a ton of money and the other one is not. But it's because their goals are different. The other one is making very specific, like tech business content where she knows she can partner and get a ton of money for it. And the other one is like, this isn't my main goal. Like, I'm just sharing my story. I just want people to have this information. I don't care about monetizing and those goals will change.

One of the tough things for me is that I, you know, was kind of YouTube's like, poster child for a second there. In 2010-2015. I was like, the YouTube girl. And I had the viral videos and I had the tour and I had all that stuff. And then I stopped creating content in that way and my desires moved to more long form. So I was like, I want a production company. I want to do TV and film, I want to audition. That's why I did the late night show. Now I'm in TV and movies. Sometimes the Internet also weaponizes relevancy against me, me. So every once in a while there'll be someone that says, oh, you posted something, didn't even go viral anymore. Or like you, you did this thing. It didn't even sell out like it used to sell out. And I had to learn a hard lesson from you, which was growth is not accomplishing the same goals over and over again. You know, I think we get stuck in this idea that success means I did it before and I did that goal and I accomplished and I got those numbers and I have to do that for the rest of my life. That's not success, that's being stagnant. I don't need to keep repeating the same successes and the same goals. I give myself permission to grow. And when you talk about your two friends, the one that makes a lot of money and the one that maybe is doing it for different reasons, I think the Internet is really bad at weaponizing relevancy. Or you're irrelevant, or you didn't get these views or you didn't make this money. It doesn't matter. If that's not my goal, you're projecting a different goal onto me. And that's not what I'm trying to do. And so that's why I just say the why has to be really clear. And the why can change and the goals can change. And that's okay.

How now it sounds like you're on the go doing everything between your media company, between your movie. Do you have boundaries in your day to day? And how do you avoid boundary?

What boundary? Call your therapist.

We're getting therapist on the podcast next to do a tell all.

I do. My mental health, I won't lie, has ebbs and flows. I'm in a very good place right now and that's because I take my mental health very, very seriously. But through the course of my life, I've definitely have ebbs and flows and that's because I have all of the trauma that is the worst for being in the spotlight. You know, when you have issues around proving yourself or validation or not feeling like enough, the worst job you can have is being in the spotlight. Because it just really emphasizes all that stuff like. Like growing up, the number one thing I had to unlearn was what will people think? I think every Indian kid has heard, what will people think? I'm sure you might be. Really, a lot of cultures are, how could you wear that? How could you do that? How could you say that? What would people think? You spend a lifetime trying to unlearn that. And then I get a job on social media and I get a job in Hollywood and my whole career is based off what people think. My success is based off what people think. It's. It's whether they like me or whether they don't, whether they go to the theaters, whether they don't, whether they watch me or they don't. I don't. So that's been really, really tough to deal with. And so all that to say my mental health has had ebbs and flows. Now, I do have boundaries. I have a few things. Unless it's extenuating circumstances, not a single work thing is allowed to be scheduled on my calendar before 10am So I refuse to do any work before 10am and that's because I learned that for years and years of me waking up and within minutes going into work, you don't give your brain any chance to do anything besides work. And then what that does is it makes you define yourself solely by your work because you're starting your day like that, you're ending your day like that. So I now wake up at seven. I have at least a two to three hour morning routine where I just be a human, that is Lily, before I do any work whatsoever, which is my tea in the morning, my journaling in the morning, cuddling my dogs, stretching, working out, having breakfast, shower and getting ready for my day. So the 10 o' clock thing is a very big deal for me. I also have worked really actively on how I define myself. So. So for a decade of my life, if someone asked me about myself, I would be like, well, I have this many subscribers, I have this many views, and this is the late night show I did. And then I was on the Muppets, ma'. Am. And then I have a movie coming out. And I think we all define ourselves solely by what we do. And I remember when my therapist explained to me, she said, you are not what you do. And I actually had a mental breakdown. I was like, what do you mean I'm not what I do? I don't even understand what that sentence means. And she's like, you're so much more than the Things you do. What she's saying is that we're so used to defining our worth by what we're able to provide for people and. And the things we accomplish, but actually there's this whole other side of us, of who we are, that has nothing to do with that. And I don't know how what people's feelings are about ChatGPT, but I'm going to be mildly controversial and bring it up for a second. Post therapy, I was like to chat GPT. My therapist said, I'm not what I do. I do not understand what she's saying. And ChatGPT was also like, I agree, you're not what you do. And I got so frustrated, and I was like, well, I've asked you a bunch of questions over the past several months. You tell me who I am without listing a single accomplishment. And then it did. And then it did. And it said things like, you asked me this thing about your friend because you're a really good friend and you're a really good listener, and you asked me this thing about your dog because you really care. And then also you asked me this question because you're so dedicated to growth. All of these things have nothing to do with my job. Wasn't a single movie role, wasn't a single audition. It wasn't nothing. And so I think when it comes to boundaries, that's the biggest one I've learned, is that I'm so proud of my career. I'm so grateful I have this career. I'm so proud of my accomplishments, but they are not who I am. I am a whole individual that just happens to do these other things as well. And I think that's the best boundary you can make for yourself.

For women who have so many ideas about what they want to do with their career, they're just the beginning. They're in doubt about themselves. What's your message to that young woman today?

I remember being at a place where I was like, I want to do this, I want to do this, I want to do this. And I don't know what I want to do. I would say try it all. I have. So one of my newest tattoos, it says student. And I believe in being a student for life. The most detrimental thing you can ever be in life is someone who thinks they've figured it all out. I think, be open to trying things. Be open to learning everything. Take the class, ask that person out for lunch, and pick their brain about this random thing that you're interested in, and you will figure out what it is you want to do and be a nerd. Honestly, I cannot encourage people to be nerds enough. I love learning. I love learning about random things. I love learning about people. I love asking people about topics I know nothing about. Just the other day, I invited a bunch of friends over because I want to do this thing where I hire an expert about something random, and they come and teach us a bunch of things, like, I'm a nerd through and through, and being a nerd is the coolest, hottest, smartest thing you can do. And so really put yourself out there and learn. Learn as much things as you can learn. Be a student for life is my best advice. Spice.

I mean, I've learned so much from you, from here and also from the deep research. And actually, we. We did this with Anine Bing. I'm curious, what do your tattoos mean?

Oh, well, I'm. I have a little bit of tattoo fever right now. I'm not gonna lie. In the past month and a half, I've gotten, like, eight tattoos. Eight small tattoos. Yeah. One of them is student. My most recent one I got, it's under here. It says 1313 and 1313, because in Punjabi, the word 13 is theta, and so tera, theta means yours, yours, yours. And it's a reminder of, like, spiritually, all these things that we care so much about. Podcasts, movies, they're not even ours to begin with. Everything is just the universe, as we're just here borrowing all this energy, all this. These skills are not yours. These skills are not mine. We've just borrowed all of this in this lifetime. And it's a little bit of, like, alleviating control that has happened. And then I also got the evil eye, because haters, gone.

Hey, type, pretend your middle finger.

You're coming after me. Look at this. We got protected. We're protected up here.

Well, Lily Singh, thank you so much.

For coming on the Burnouts.

I personally have learned so much from this episode about personal identity work, and how you build an incredible team, and I can't thank you enough for taking the shot.

Appreciate it.

And can I give you one quick summary? This is gonna sound so cliche, and I know it's just a quote, but I. For the past 15 years of my life, there's still this one quote that I still live and die by. The number one key to success is work hard and be nice to people. That's literally just all that. If I could tell you two things I've done, it is those two things. Work hard and be nice to people. There's no other shortcut at Truly.

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