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The Lilly Singh Empire: #GirlLove, 14 Million Subs, & Toothbrushes

It can be pretty tough to live up to the nickname Superwoman, but Lilly Singh wears the cape well.

Born in the Toronto suburb Scarborough, the 30-year-old Singh is not just one of Canada’s most prominent entertainers, but one of the world’s most recognizable stars in a digital era that is quickly changing the definition as to what “popular” means. With over 14 million subscribers, Singh—who acts, sings, writes, and dances under the Superwoman moniker—is one of YouTube’s fastest-rising stars and a standout breath of fresh air in a competitive digital entertainment world full of tired video game compilations, talk show clips, and music videos.

Singh grew up in Toronto and attended York University, graduating in 2010, but then ended up unsure of what she wanted to do. After shooting some videos and posting them to YouTube, she realized this was something she could get the hang of, and it worked. Singh was the tenth highest-earning YouTuber in 2017, raking in over a reported $10 million USD for the year. She also picked up a number of awards and even penned her own book, How to be a Bawse: A Guide to Conquering Life.

Boss-status is exactly what Singh has achieved over the past few years, extending her entrepreneurial spirit to worthy causes like her #GirlLove campaign, a project designed to empower young girls to spread love, instead of hate, by complimenting other girls rather than insulting them.

After posting the above video about the initiative in 2015, Singh partnered with WE charity, part of the ME to WE organization, and has gone on to raise millions of dollars and empower women all over the world.

Techvibes caught up with Singh at Adobe MAX in Los Angeles last month to chat about the relationship between YouTube and high-level content creators, the evolution of digital entertainment, and how tech has shaped her life on and off the small screen.

Most YouTubers handle both the creative and business sides of their content. What is the right balance between those two worlds?

I have two completely opposite thoughts on this. I’m really grateful for how well-rounded my career has made me. I can write, and if I really had to edit or shoot something, I could. I can play all the roles—if I had to. I don’t have to because I have a phenomenal team.

But having said that, I feel like for the YouTube machine the audience really wants someone who does it all. And sometimes I’m guilted into it, like “Oh you have a team now? That’s not authentic.”

No, that’s not how entrepreneurs grow. They surround themselves with people who can help them grow bigger. I love that I can do everything, but I also love that I don’t have to. I think everyone should aspire to surround themselves with people who allow them to do more, and I don’t think they should feel guilty about that. That doesn’t mean you’re a sellout. Being able to sleep doesn’t make you a sellout.

For the people who don’t yet have a team to surround them and help, is it important to learn a bit about everything?

I think right now, currently, in my career, I might not completely know what my team is doing on an everyday basis, but I can kind of gauge it because I have been in similar roles to them, and to be honest, that makes me a better leader. When you’re starting out it’s important because you should have control of your vision, and that should be the case later on too, but when you’re in the building stages, it’s incredibly important. And that’s hard—it’s a very hard thing to do.

How has your understanding of technology in the digital entertainment space changed since you started eight years ago?

Back then, and even today, I am not a pro editor by any means. Especially when I started out—I have a degree in psychology, so I never edited a video in my life until I started making YouTube videos. Freud could not help me with the video editing.

I remember just wanting to use programs that made it seem like I knew what I was doing. Give me those powerful features where I can tell the story I want to tell. You just want to tell a story when you’re starting out. You don’t want to get super technical.  I started making videos on my webcam, and then I slowly graduated into an SLR. It’s not so much what camera you shoot with, or what the sound equipment is, but it’s the story. But the tech that has impacted me the most is that platform, so YouTube itself—you know, the introduction of annotations, and cards, and new ways to drive people to a playlist.

Do you learn about YouTube updates before they are released?

Yes, I sleep in a tent outside YouTube headquarters, and then I beg them to tell me.

No, but I do sometimes get a bit of a heads up about features. They’re really good at explaining these things to us and how we can use them. Other times, I find out when everyone else does. If they do tell us in advance, it’s so we can play with it and figure out how to best use it. An example would be liking and pinning comments—we got a heads up about that.

Do you get to share your feedback with YouTube and feel like you’re being heard?

Yes. I feel like YouTube is such a massive platform, so it’s really hard when you personally try to implement a change. But one thing they’re good at is listening to creators.

For a recent example, I went straight to the CEO and said I feel like creators should have an option to choose which brands advertise on their videos. Brands have a lot of that functionality themselves—they can request a creator that’s family friendly or things like that.

I want to make sure if a brand advertises on my videos, you know, I want to make sure 50 per cent of their staff is women, or that they don’t invest in horrible things around the world. YouTube really took that into account. I saw Susan [Wojcicki, YouTube CEO] a few days ago, and she told me exactly what I told my partner manager, so they all do really interact with each other.

Diversity has been a key issue in the tech world recently. How do you advance your stance on the issue further and spread it to other partners or creators?

With our social good campaign #GirlLove, every time I travel or I’m on a tour, I try to do some sort of activation where I meet with a bunch of younger female creators, and I basically empower them on a bunch of best practices, like how to convey a message on the internet. Because the best way I’ve learned to do that is not to be preachy, and not to make a video like “This is why women need respect.” It’s through different vehicles like comedy and music and poetry. I try to teach young aspiring creators the best practices in what I’ve done.

I also try to be an advocate to creators in different ways. Recently I did a partnership with YouTube Music. I said, “I’ll do it because I want to, but also I want you to hold a little seminar for creators in Toronto so they can learn from each other.” I want to pay it forward to creators and teach them things because I know what that feels like. I vividly remember what it felt like reaching 1,000 subscribers and how hard that was.

#GirlLove has become very successful. Are you looking to start more initiatives like this in the future?

I am down to partner with any brand that is about creativity, or about inspiring people to be creative and tell their story. Life right now is about storytelling and creative expression, and being able to do that through technology and various platforms. 

Of course, diversity also, because everyone’s going to be a level of beige anyways eventually, so we should just embrace it. Brown people—we’ll get you, and we’ll have babies with you, and everyone will be beige. So you can’t escape us. End quote.

Is there a piece of technology you cannot live without? 

My car. It’s a Tesla (Model S), and I don’t say that as like “ooh I drive a Tesla.” It’s just so smart. I can’t parallel park, so it’s a godsend.

I have my new iPhone XS Max, which I’m really into as well. One of the biggest problems I had—this is so basic—is if I’m wearing a cute outfit like I am today, [Editor’s note: Singh ensured I wrote that her outfit was cute] I can’t take good pictures because we’re always backlit. This camera has solved that, which I love.

Oh, and my dad just gave me an electric toothbrush, and honestly, it’s just the way he sold it to me. He sat down and it was a 30-minute conversation about this toothbrush. He was like, “It comes with a travel case and it charges.” He gave me the stats about how much plaque it destroys, it was a whole thing. So I’m going to say the toothbrush, just because he was so excited.

This interview has been edited for length and clarity.

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