Meet the Superwoman Of the Entrepreneurial World

Lilly Singh discovered YouTube in 2010 — the year she "wasn't in a good place". She says, those 12 months, while finishing college to get a psychology degree, were tough. "I didn't feel creative, which made me sad because I was very creative as a kid. I wasn't sure what I wanted to do after school and I just wasn't excited about life." So she picked up a camera, made a video and posted it on YouTube. It was an attempt to make herself feel happy, and it made her more than happy. Soon she found a community of people who also found happiness in her videos and it snowballed into a successful career.

The Artist in the Making

In the past 10 years, Lilly, known to her fans as Superwoman (inspired by her childhood idea that she had an invisible "S" on her chest), has earned 14.5 million subscribers on YouTube, written a New York Times best-seller (How To Be A Bawse: A Guide to Conquering Life), acted, produced and starred in a live world tour, released a feature film (A Trip to Unicorn Island), earned tenth position in Forbes' 2017 list of the world's highest-paid YouTube stars, and topped its 2017 Top Influencers List in the entertainment category. Initially, she focused on making observational videos that tackled everyday life. But eventually, as her popularity grew, she started attracting celebrities like Dwayne Johnson, Selena Gomez, Seth Rogen, James Franco, Steve Aoki and Madhuri Dixit. Punjabi culture, however, has remained a constant. "My Indian heritage is a big part of me and so it does inspire a lot of my storytelling," says Lilly, who was born and raised in Scarborough, Ontario.

What the World Wants

Lilly credits her Punjabi parents, Malwinder and Sukhwinder Singh, for supporting her throughout the journey. "When I told my parents that I didn't want to go to graduate school and get my master's degree but instead pursue YouTube they didn't say no. Naturally, they were concerned because they didn't know what YouTube was and didn't really understand the Internet. They told me I had a year to try it and if it didn't work in a year I'd have to go to grad school," says the 30-year-old artist. Lilly reacted to their response by hustling "really, really hard" and from that point, she learned how to edit videos, use a camera ("I saved up for a camera"), taught herself comedy, and how to write a script. "I convinced them through hard work and luckily in that year it did go somewhere."

Of course, it hasn't been an easy journey for her. "The biggest (challenge) has been work-life balance. I am in an industry that is 24/7, social media does not turn off, the industry is very demanding so it's challenging to have a personal life," says Lilly, who last year started her production company, Unicorn Island Productions, to create longform premium content to tell some "risky, authentic stories."

Asked about her inspiration, she says. "Finding common threads between all of humanity. I like when people watch my videos and relate to them in a deep sense. You come to realize that, we all go through this experience together even though we feel lonely at times. I want my videos to be positive for someone who is having a bad day and just wants to escape."