Lily Singh Balances Late-Night TV with YouTube Stardom

Sing just got renewed for a second season. So it's great to talk with her today about how she juggles a career in two different mediums. Congratulations Lily, So is this the kind of thing where you were sweating? Is renewal or you knew you had it in the bag? Well, first of all, thank you, I'm so excited to be here chatting about this. Um. Definitely, no, I was sweating. I think if I could summarize season one in any way, or this whole experience in any way, it would be

all of the emotion. I am constantly in the state of nervousness, being excited, being grateful, being honored, feeling like I need to puke a little bit, all of the about Well, don't puke now, but I'll try. What I'm curious about is when when you hear out late night talk show host in their first year, no matter how successful they are, it's a tough road. You're finding your voice, you're learning the ropes. So what was it like for

you in your one? I mean, that's exactly correct. This is the first time I've done anything like you know, I come from the digital world where I am the editor, and I am the writer, and I am the on screen actress, and I do all of the things. I am the standards and practices, and so going into this world, if I'm just being really honest with you, it was challenging.

I did have to learn an entirely new world. Um And just like my first video on YouTube, you know, there were moments and episodes where I was a little uncomfortable, when I was super out of my comfort zone and making mistakes and learning from the mistakes and just constantly trying to level up. UM was my experience. But I think, just like with anything else, it takes practice and it takes experience. And I'm really proud of what we did in season one, but I'm also super pumped to improve

and do we even better in season two. And how hands on are you in terms of producing the show. I mean, as you mentioned from your YouTube days, you were probably a one woman show doing a bit of everything. So is it a big adjustment you have to sort of lose control to some degree? Um, I have all of the hands. Let me just say I tried. I was actually learning her from me, if I'm being honest. When I first started, I thought I'm gonna be involved

in every single script and every monologue. I'm going to have review every single episode. There was a lot I wanted to do, and I managed to do a lot of it, probably admittedly at the cost of sleep and a little bit of sanity, because I interview almost every single episode, which is not typical. I think of most posts. I sat there in the editing room being like cut that with each camera A and will do all that.

It took me a little bit of time to let go of some of that control, But I think that's what comes with a learning process and learning how to delegate, learning that these people are experts at what they do. UM, I'm definitely gonna try to delegate more in season two, but I still think in Jet by Nature, I'm a pretty hands on person. You know, my name is in the show title. It's my point of view that I'm sharing, which I believe is an extremely valuable and unique point

of view in the late night space. And so I want to make sure that things have my personal question that's important to me. And if that means sometimes sleeping a little less, I'm gonna find a balance of doing that sometimes. So how involved was the network was? That's also something that you hear a lot about first year shows. Lots and notes, lots of pointers or do they give you free rank. I'm gonna say, ultimately, I'm pretty grateful

and impressed with NBC in this regard. Of course, some episodes where I'm getting a little too risky and they're gonna be like, all right, write it back a little bit. Every year. Of course, they have stands and practices and that was a word in curve. But for the most part, they let me be who I was. That was my number one concern when I got the Late Night show was am I gonna be, you know, encouraged to be someone else or or fit a mold? And I can

genuinely say that that was not the case. Of course, people shared with me best practices, their point of view, what they thought would work and not work. But at the end of the day, no one made me ever be something I'm not. Was there any particular joke that you remember, or any kind of vein of humor where you had to learn that there were some sensitivities that you might not have otherwise experienced on YouTube? Absolutely, I think, just like you know there's there's you gotta make mistakes.

I mean, the reality is you have to make mistakes when you do things like this or you will never grow. And if I reflect back on back on some episodes, there were things that I didn't work properly or or even the thing mores of the case was there were certain times where I did feel like this this humor, I think, I'm I'm trying to dive into the late night world, and so I'm poking fun at celebrities and trends, and sometimes I felt, is this a little bit in spirited?

But no, it can't be. It's late night. And when I watched about this episodes, I think, maybe maybe I should have phrased that joke a little differently, And I think I had to go through that process to learn that.

But Um, I think going into season two is something I really want to prioritize is positivity and love and all the things I stand for in real life and kind of feel less of the pressure of Late Night being jabby in some ways because it can be a little bit like that and install thoses that's okay, but by nature that's not necessarily who I am. So that's something I definitely learned. So we'll season to be in any way different than what you were doing in season one.

Any any significant changes, Well, I absolutely hope so, because I feel like, if you know, for our season one, we always said we want to mess with the format and we want to really break the multiple we've seen on Late Night. We did to a certain extent, but at the same time I was learning a whole new world. Like I said, so, there's only so much breaking and redefining you can do when you're learning the ropes, the

very basic ropes of that thing. And so I think now that I have more experience and I know how the game goes, I definitely do really want to just break the rules of the format of Late Night. I want to have people that we otherwise would not see on Late Night in terms of guests, and so I definitely want to change things. I think if the first episode and last episode of season two looks the same, I would consider that not growth and not a great thing,

and I want metually look differently. So what kind of guests might Who's on your dream list? Who do you want to have in season two? Listen, sir, we have the people that I've always want that just the Beyonces.

I also have just learned from. You know, I had the honor of having Lala on my show, and for me personally, that was one of my favorite episodes because I got to really dive deep into her work and just things I've always wanted to ask her about her experiences and turned into this really sweet, genuine and powerful moment. And I think there's other people like that, from the Emma Watsons to the activists that are local to their communities that are doing awesome things. I just want to

have really good conversations with people. I mean, in some instances, yes, it's great to have a shiny celebrity, and other instances, I think there's so much power and value and just amazing this and having people are still a story. I don't really care about their celebrity profile. I just want

good conversation and good stories. Now, from what I understand the way you guys produced in season one, you've already you've wrapped your season back in December, and you shot multiple episodes per day, and those episodes are sometimes months into the future. I would imagine it's meal different this time. Yeah, there's proms and guns to do that. In season one,

we shot nine to six episodes in three months. And when I tell that to people like you, like you just did right now, Yeah, in their face, they're smiling with their eyes are saying, you're a crazy person. And I see that because, um, yeah, it's there's present con It's great because you know, it allows me to fulfill from my other ambitions. It allows you to have a tight knit crew and and production where everyone is committed for a certain amount of times. So there's a lot

prose to doing that. Now we're at a very unprecedented time where I wrapped season one and then unfortunately the world was with the pandemic and where everyone else it's kind of an ironic joke went back to shooting their show at home, something I've done for ten years. I was already wrapped and my shows all have a live audience, So this really timely conversation around quarantine ing UM is so important and everyone else is doing it and I'm not able to because my shows are shot and don't

address the pandemic at all. So it was definitely a learning experien It was definitely interesting. UM. We will make changes for season two. I don't plan to have that schedule for just being topical, my sanity, for sleep, but the clearness of my skin, for the grays on my head, for all of those reasons. We're gonna extend that schedule. But can I just tell you after that, I really feel like I can do anything. I truly believe I can do it anything. You are battle tested, Yes, I

am just ready to go here, ready to go. So the thing is, I can understand, you know, the appeal of actually sort of not having to deal with topicality and you know, providing a certain kind of world where people don't have to be reminded of the issues that are going on. But do you think in this new season, with this new schedule, you'll be able to be a bit more topical at times? And what kind of topics do you think you'll touch on. Well, that's definitely the goal.

UM as much as we can be topical, that is, of course the gole. I don't know if it's gonna always be possible, but we're gonna try to make it possible. In terms of topics, I have never particularly been someone who discusses politics. There's a few reasons for that. I mean, of course I understand the importance of voting and the importance of being informed, but it's a little bit of an interesting situation because I myself cannot vote in the

country I live in. I'm a Canadian. Whether the Late Night show, hav instaid that there are issues I'm very passionate about and that I'm very vocal about. Whether it's gender equity, whether it's about legislation regarding women's bodies, whether it's about um education. There's things that I'm very passionate and I will continue to talk about through comedy because I think comedy is a great vehicle for doing that.

But yes, I do think to a certain extent, having content that is evergreen and does help people skip is also important because if people are like me, they want to be informed, but they also sometimes want to escape after a long day and I want that option to also exist. You know, there's lots of places you can go to get informant and here drugs about politics. I feel like less and less there are places where you can go where you are not reminded of that. So

I want to find it out. You mentioned being Canadian. That's just one of the ways you're different than pretty much just about everyone in Late night. For starters, you're not a man, Yeah, you're an Indian descent, you're bisexual. There's all these different things than what you see from the standard host. Do you think that's help you cut

through the clutter? Um? Yes and no. You know, it's a really complex thing because obviously my late night show was announced, a lot of headlines said just that, you know, it's that Canadian. The hyphen it's were extreme. Headlines were this one Canadian Indian person with long hair, it's long about it went on and cut and on about who I am. And of course I'm proud of that because

I really truly do believe representation matters. And I think when you see an episode with me and Minty Kaling and we're making references about things from our upbringing that are so unique our culture, that's beautiful and awesome, but at the same time, I don't want to be defined as that, and I'm kind of, from being honest, I'm stuck in a little bit of a loop, right, don't quite know how to handle it because when I'm doing a monologue and I'm talking about my experience, at one hand,

I feel like I'm so much more than all those hychmiths. But at the other hand, my point of view is so influenced by those hype of its. So um, it's kind of this weird pattern of being defined by it and not being defined it. So I'm honestly still trying to figure it out and what it means and how to navigate it. My solution is to truly just be myself. Everything is from my point of view, and my point of view happens to be those hypimiths. So got it?

And of course, you know, in addition to everything that you're doing on NBC, there's that whole YouTube career that is going. How do you how do you balance the two? If you're doing twelve our shoots, you know, from nineties six episodes, how do you have time to keep video coming to your channel? Very poorly, very poorly. Um, it's you know, before season one started, I remember being like, Oh, I'm gonna bank a bunch of YouTube videos. I'm going

to keep uploading during the season one. Then season what happened and I was like, Oh, this is a lot of work and I really want this to be good, and so this YouTube needs to take a back seat. I don't have the answer of how we gonna navigate and this in season two. I just know that YouTube continues to be a huge priority for me. I mean that is where my community is, as what my core fan base is. I believe in the digital space so much.

I'm going to try to figure away. And I think, going back to your question about the schedule, I think expanding the late night schedule will allow me to insert some days where I can do YouTube. But no, definitely, I feel like I have three full time jobs all the time. Um, it's super stressful and exciting, and when I have any other way, absolutely not. I think busy is a blessing and I think I recognize this opportunity.

I recognize what an honor it is. And I think the one thing that will change, if I'm being honest in season she is I don't think I'll feel guilty about it. I think season one I felt really guilty. I was like, oh, I didn't post like YouTube video. I into this. I really want this show to be great. I understand the path that could pay if I understand the opportunity I have. I'm gonna try my best to balance both. But we need to teeter from backseat to

baccine and I'm gonna do that. Okay, Well, did you ever get counsel or advice from I don't know, an agent the network to say like, listen, you gotta just this. This whole YouTube thing's gotta go. You're a TV star now. Um, No one really says that to me. The thing about people counseling, and I'm in such a unique space. You know, other late night closts didn't necessarily come from the digital space. They were on TV and then they now migrated into

the digital space. I am in a very unique position with There's very few people like you ask for in terms of advice, because I have one foot on each ladder. Really, to be honest, there were other people that gave me other sound advice, you know, Trevor know what. I keep referencing this because it was the most beautiful piece of

blatant and blunt advice. And you know, he said, everyone's gonna tell you that you'll be able to do other things during the show, and you'll have balanced during the show, and you should know that's a lie. You should know that you're gonna go to the show and it's going to consume your entire life and it will take up every moment of your day. And I was like, huh, but he was not wrong, and that's exactly what I

needed to hear. Um. I think anyone that says to me that don't worry about YouTube on TV now is night. I think digital space is such it can't be more. We're not in living in the time anymore where you can just say YouTube, YouTube, and it's just no. That's how a lot of people consume content. And it's um the line between traditional digital and definitely blurring. You know, there's been a lot of Internet stars that have tried to make this resition transition and have not made it work.

What do you think has enabled you to dodge something? You know, there's been others that have really stumbled with this. I mean, listen, I can only speak to my experience. I what I can say, and this has just been being like looking straight into my webcams super candid. It's

really hard. It is super super hard to do. There's been countless times where I have been pretty close to giving up, if I'm being honest, because you come from a world where you are your own boss, where you have these rigid schedules uploading things, and that's really tiring. I know people think about ten minute YouTube video, how

long can that take? But those are that's just a lot of energy and social media seven job, and so you already have that, and then to try to transition into something else on top of keeping up with their socials and doing brand partnerships and doing events and doing

all of these things. It is a lot. And then when you go to late night, especially for me, I had all of these ideas that I wanted to do, which there's so many reasons you can't do them a late night because of because of unions and because of rules, because of standard of practice. That's not't a bad thing,

it's just a different machine. And so I really did feel like the dumbest person in the room a lot of times where I thought, wow, I have to learn a whole new set of everything, and I could see in that moment how people would be like, why am I doing this? Let me just be my own boss again on YouTube? And it's really hard. It's really really hard, if I'm being honest. There's some days on season one where I left feeling that was a great episode, this

is amazing, I'm so proud. Is exactly what I wanted to do. But just like anything else, there's some days where I literally cried for hours in my green room being like, I don't know what to do and I don't know how to deal with this. I don't know how to navigate this, and actually just give up. So I have nothing besides positive energy towards anyone who has ever stumbled in this process, because it's a doozy for sure.

Well what did you think it is in terms of is there something about the nature of the appeal of YouTube stars or stars and other platforms that possibly doesn't

translate to TV that maybe you figured out how to navigate? Um? Yes, and no, I feel like the style and the way in which we do things doesn't necessarily translate to TV because now you have a crew of so many people, and the more people you have, the more complex processes get I think it's easier to do a jug kind of video and execute something when it's you want a smaller prove in some ways, to be honest when it's mean my YouTube prow I do feel like we move

at a different pace, but the quality of our product doesn't compare to the quality of a TV show at the same time, So there's definitely pros and cons. I think what it is is that, more than anything, it's, like I said, learning a new set of rules. I don't think that the talent doesn't translate. I don't think that the energy doesn't Hansley. I think it's learning a new world. That is what you know, hurdles people to be honest. Well, let me ask you this is is

YouTube Lily and NBC Lily the same? Because when I watch both I see some differences. No, definitely, I wish the answer to this question was yes. I want to sit here and tell you, yeah, let's same. But I know that they are not um or Season one NBC Lily and first YouTube video Lily the same. Yes, they're both trying their best. There you can see glimpses of like,

oh that's when we go. It's really funny, but you can tell they're still learning being done, which is why my main sentiment going into season two is like, again, like I said, I'm so proud ninety six episode three months, the things we did, I'm really proud. But for people that have been like you know, I feel like your monologues are not kind of like you on YouTube, You're right because I'm sitting there learning in front of three cameras, in front of a live audience, with notes from a studio.

I'm I'm gonna have to learn and make mistakes. And so if you ask me this question four seasons from now, I'm confident my answer will be yes, that YouTube really who is the real Lily? And NBC Lily was also the really? But learning, that's my goal. When you say something like four seasons from now, I'm curious, are you looking that far ahead? And you know, the thing about late night TV is it is not uncommon to have careers at last decades. Are you in it for the

long haul? I'm in it to win it, baby, I really want. I really believe that I can mold this show into something that consistently excites me and other people and means a lot to myself and other people more so than it already does. Um. I always know, it's just they never say never. You don't know what the future holds. I think right now in this time, we know that, know that more than any other time. But no, I really am grateful to NBC and my fan base

for this opportunity. I know it's bigger than myself. I know that, you know. I remember there's one episode with me and cal Penn and we're Indian restaurants. Remember so many comments under that episode being like I have never watched the show where two people are making Hindi or Bollywood references talking about this, and I remember reading that like this is why and it's not just because of that. I don't want to say that it's just for Indian people, but it's the fact that it's a point of view

that we don't see. And I think that's bigger than me, and I'm in it to win it. I am gonna if I have to cry in my green room for a couple more seasons to figure it out, then I'm gonna do that. You know, you mentioned ethnic jokes, and the thing is there's criticism that comes with that when you do that kind of humor. People are going to get annoyed. Even if you think it's brilliant and hilarious, and you've gotten your share of criticism, both on YouTube

and on NBC. Do you have a thick skin that you've grown as a result of this or do you feel it again? I want my answer to say, yes, I have thanks care, But I being honest, of course it gets to me. If you care about something, when someone criticizes it, it's gonna get to you. You know. It's why people are very protective over their children. This show is my child, and so of course I get affected by it. Um Am. I used to it in terms of it's not my first rodeo, of course, and

make YouTube's for ten years about all the comments. But I think for me is what I'm learning is I'm gonna I'm gonna try my best to make sure I have an inclusive, positive, wonderful show. Is it gonna be everyone's cup of tea? Absolutely not. That's impossible. That's truly impossible.

I've learned that. Um there's times when I make jokes about my ethnicity where people don't like it, and then there's times if I don't make jokes about my ethnicity, people think I'm not representing, So it truly is you can't please everyone. I just want to be myself, be true to who I um. And that's literally the only

solution because you will not please everyone. And I can tell you truthfully on any situation or any issue, there is a loose, loose scenario and in some way, so to stop paying attention to it, be who I am. If people like a great if not, Luckily, there's so many other things that you can watch, so it's great. It's a great time of content. So, as you mentioned, you wrapped back in December. Uh, what have you been up to in I know right now, like everyone else,

you're probably homebound. Uh. You know everyone's lives have been sort of disrupted by the pandemic. But you've actually done some interesting things online, some interesting charitable efforts. Talk about what you've been up to. Yeah, I mean I've done a game of things online, from supporting causes in India

to supporting the Global Citizens Cause Stronger Together. There's there's been many things online I've done, and I think it's so important just because it's crucial to remember this pandemic does not affect people equally. And I've always been the person to at least try to check my privilege. You know that the thing about privileges, it's so hard to check because it seems like it doesn't exist, but it does exist. And I'm constantly the process of checking my privilege.

And this pandemic has been just that. Knowing that in India people some parts of it. In other parts of the world, people can't socially distance, knowing that a small business is going to suffer more than a bigger, mega company. You know, it's moments like this where I really try to focus on the silver lining, which is, yes, people are suffering, the world is struggling. But for me, the silver lining is the world is also coming together in a way which really really makes me restore my faith

in humanity. I think people are there for each other, people are willing to support each other, and I want to be a part of that through and through and through because at the essence, that's what I love about humanity, like I love people, and this right now is what I love about people, is that we innately do care about each other, even though sometimes when we're not in the pandemic, we like to pretend that we don't and

we get distracted by things. But when moments like this, you really see at the core that people can be there for each other. I saw on your YouTube channel you actually interviewed Dr Fauci about a month or so ago. What was that like? Super cool? I mean, it's a huge honor to to be interviewing someone going straight to the source because and that was really important for me

because maybe you can relate. I was in so many groups with so many people who were what's that doctors who were sending articles and sending facts, and it was creating fear, and I thought, you know, I had this opportunity to interview Dr Faucci. There's so many different directions I could go. Of course, I could get politically do all these things, but I'm like, I think it's really important to just get the facts about this virus and let people know to try to alleviate some fear and

try to alleviate some misinformation. We I do think this information is really as just so much more pain into the world right now, And so that was really cool to do with myself and two other creators. I got to do it, and I thought it was a huge honor. He was very cool and very willing to talk to me, even though I, you know, I don't know any terminology or anything about science or anything about anything he does. But he spoke to me like a real person. That

was great. Well, but I think what's great about you doing that kind of interview is particularly on YouTube or your your fan base is probably young and not necessarily attuned to the news. You in effect becomes sort of something of a news person. It's you're reaching an audience with serious information. Do you feel that kind of responsibility in that instance? I definitely did, you know, because we're, like I said, in an extraordinary time where information is

so valuable. So yes, um, otherwise and other times in my life yes and no. You know, it's an interesting balance you have to play when you have a platform, because of course you want to have a sense of responsibility where you are spreading positivity, information, education, knowledge. But you can't do any of that well if you yourself are not a happy, productive, healthy person. And that's where we go over here, and to be happy, healthy, productive

you have to be true to yourself. So and you can't do that if you always feel like you're responsible for the masses. You always feel like you are living for other people and delivering to other people. Now, it is crucial, and I think people really need to understand that all these people that have a platform, their platform is gonna mean nothing if they're not doing well for themselves. And so I think it's important to find the balance

of doing stuff for themselves and for the masses. You know. Also, we're you know, certainly when you're talking about NBC, you're talking about an American audience, but YouTube it's a very global audience that you've got there. Um, how do you sort of cultivate audiences outside the US US and resonate with them? Uh? Is there is there sort of a difference in your appeal and say India or the UK or wherever, uh, compared to what you're resonating with here

in the US. Yeah, that's a great question. I think that's also why I'm pretty keen on making sure that some of my material is evergreen and it's not topical, because we do need to remember that a lot of these topical episodes are topical to Americans. You know. It is a very catered to cater to an American audience, which is why in season two I want to prioritize motivation, positivity,

evergreen comedy because those are universal languages. And I think that's why my YouTube channel is so appealing to people worldwide, because you don't need to live in America to be down one day, watch a video and film motivated. That's a universal concept. Um, if a joke is funny, universal concept. So again, it's about directing that balance. And I do think that is a little unique to my position because I did come from a world where I have a

good blocks. I had a huge audience in India, and it's very important to me when I do my late night show that I'm not excluding them. I want them to be part of that conversation, especially because the show gets screamed. It gets streamed in India, you know, and the clips go on YouTube, which is for the world, and I want my show to be for the world. Like I said, I'm Canadian. I know what it feels like to be raised. I moved to l A five years ago. I know what it feels like to feel

like everything is scared to an audience. Um. Of course the audience is huge and has a lot of power. Doesn't mean that the rest of the world doesn't deserve to see content that they can well literally, congratulations again on the second season. Uh, you're keeping busy now on YouTube? Until when does the new season start? By the way, I have no idea what productions it will look like

because everything is currently shut down and pause. But what I can say, just as a final thought, is, in case it didn't come through, my effort is going into this show. Extremely grateful to NBC and everyone who's supported me. Um. I can't wait to learn more, come back stronger, come back from more experience, and tell well that supported me. Please keep at it because it means a lot. Folly, I'm here right now. We're here right now, So thank you,

thanks for your time, really, thank you. Bye. This has been another episode of Strictly Business. Tune in next week for another helping of scintillating conversation with media movers and shakers, and please make sure you subscribe to the podcast to hear future episodes. Also leave a review in Apple podcast let us know how we're doing.