Modern Entrepreneurs: LILLY SINGH

Naomi Robinson
7 min readOct 3, 2020
tubefilter.com

Influencers Reign as Modern Entrepreneurs

In the midst of a social media and technological boom, ordinary people have turned their attention to professional online autonomy. Many have taken advantage of online platforms and created digital brands as internet celebrities with millions of followers. This in turn, has resulted in these influencers having increasingly viable modes of generating income and building a business (Abidin 2018).

The statement in the title above is riddled with subtext, but it is one rooted in truth. The internet has enabled people to gain global entrepreneurial success through carefully navigating the thin line of positioning themselves as brands while creating authentic, accessible and entertaining content online.

This case study will specifically look at the life of Lilly Singh. Rising to notoriety through a YouTube channel under the screen name ‘Superwoman’, Singh who hails from Canada, went from making videos online to crossing entertainment industry boundaries and becoming a late-night talk show host for mainstream media.

YouTube/Lilly Singh

The Rise of a Superwoman

In 2010, when she was 22 and in her final year of a psychology degree, Singh posted her first video on YouTube from her family home in Canada (Leskin 2020). It started with original and relatable content that produced a following of 15 million subscribers by 2020 (Singh 2020).

In 2016, Singh went on a live world tour that was transformed into a YouTube Originals documentary called, A Trip to Unicorn Island. The following year, she published a self-help book that became a New York Times bestseller, How to Be a Bawse: A Guide to Conquering Life (2017). This year was also when she cemented her growing popularity, earning the number one position on Forbes Magazine’s Top Influencers List in the entertainment category (A&E Television Networks 2020).

Openly bisexual after coming out on Twitter in 2019 (Lilly 2019), Singh continues as she always has, using her platform to leave a positive mark on the world. She is open about her struggles with mental health and focused on helping people through entertainment (A&E Television Networks 2020).

2019 was not only a big year personally for Singh, but huge on the career front. It was announced that Singh would be taking over Carson Daly’s late-night slot on NBC with the show, A Little Late with Lilly Singh (Schomer 2019). Singh, as an Indian-Canadian, became the first woman of colour person to host a late-night talk show and first openly queer host (Noah 2019; Leskin 2020). Singh was also the first YouTuber to land such a mainstream position. As such, she helped set new heights from non-traditional online celebrities to enter the traditional landscape of broadcasting television and celebrity.

Mindy Kaling on A Little Late with Lilly Singh

The Road to Entrepreneurial Success

On an individual level, there are potentially four factors linked with entrepreneurial success: intrinsic motives (passion, self-fulfilment, flexibility, independence, and self-determination); commercial motives (need for fiscal independence, growth, sustainability and career viability); entrepreneurial motives (proactive, innovative, and risk-taking decisions); and human capital (knowledge and skill) (Höllen, Lengfeld, and Konrad 2020). If we assume that focusing on the market and customers are key factors in entrepreneurial success, Lilly Singh certainly fits the bill. Even more so, when we pair this alongside a person’s willingness to actively search for profitable assignments and stretch in order to develop a competitive edge on others as the above study suggests.

When asked how she got her first career break, Singh’s answer was simple: by working incredibly hard and essentially not hoping for a viral video as a big break (Noah 2019).

Breaking it down, Singh had immense passion for her YouTube channels and the community she was building. More than this, she was determined to take her own path to success. Pushing herself to stretch beyond the beloved skits and relevant videos and not always look toward the horizon helped her land where she is today. Many of the decisions Singh made along the way were risky, some of them paid off, some did not. Always, her motives and ability to use everything she had at her disposal, and continue learning and reaching, resulted in Singh being one of the top entrepreneurial success stories from the YouTube sphere.

How to be a Bawse book cover

Interestingly, it would seem that Singh’s entrepreneurial success is one where creative outputs are embedded within her own identity and representation as a human brand. Therefore, from a marketing perspective, success comes with time and effort while building an ongoing relationship with an audience. Much like other influencers, Singh’s career trajectory is one dependent on how well she can nurture an audience while creatively staying authentic. After all, the brand is fundamentally linked with her public identity. This has been discussed in more detail elsewhere (Robinson 2019).

Singh has always kept her YouTube channel active, even after starting the talk show because she is very aware that an important part of her career is this relationship with her audience (Alexander 2019). Ultimately, fans and followers are consumers who need to be entertained and validated. For Singh, 15 million subscribers and 3.3 billion views on her main channel alone (Social Blade 2020), equates to impressive fiscal and social capital can then be harnessed to take steps outside the box. A common narrative in the entertainment industry is that it is very rare for YouTubers to make it in mainstream media, and when they do, they face criticism. This includes Singh, who faced backlash for not shaking up the late-night format enough or not catering to the new audience more explicitly (Dodgson 2019).

Over the years, Singh has not faltered in the type of content she wants to produce gaining trust with her audience as a reliable source of entertainment. This means that her social media presence was likely a selling point to network executives because they now had access to bodies of people who might not normally watch late-night talk shows, and in turn, Singh could have gained YouTube subscribers from fans television broadcasts. Singh’s foundation as someone with an existing fan base and her will to collaborate with countless celebrities, influencers and professionals has helped her craft a hybrid where fans exist across platforms and mediums.

The Future Is Never Set In Stone

To conclude, the fact that technology and the internet have made it possible for people to take the plunge in entrepreneurial tendencies is simultaneously an exciting prospect for the screen industry and in an increasingly saturated landscape.

At 31, Lilly Singh has done what many have tried and failed. A huge step forward for diversity, yes, but also a great testament to dedication, talent and luck. As such, Singh embodies several notions that could be applied across entrepreneurial enterprises.

The first, that Singh is a perfect example of having multiple avenues for revenue. Once fiscally viable, Singh started broadening her outputs. However, she was also selective in her choices. Second, you only get out as much as you are willing to put in. Motivations are important, and if someone is expecting instant fame from posting a few entertaining videos they are sorely mistaken. Although a viral video star might burn bright for a moment, it most likely will not last. Finally, for YouTubers specifically, building a foundation from passion for creating will result in a more meaningful endeavour and a solid place to land if one of the selective risks does not pan out.

Singh was not the first influencer to publish a book, or even be involved with network television, however, she was able to establish herself well on the other side. There has long been a distinction between mainstream media and the internet where the validity of internet royalty in the ‘real world’ is consistently questioned. Singh has helped bridge this gap in ways few people have, thanks, in part it would seem, to networking, being genuine, and hard work.

*Originally written for CNE400 at SAE Institute in AUGUST 2020.*

Find me on Twitter: naomieir

Find Lilly Singh on Twitter: Lilly

Sources

A&E Television Networks. (2020). Lilly Singh Biography. Biography. Retrieved 6 August 2020 from https://www.biography.com/personality/lilly-singh.

Abidin, C. (2018). Internet Celebrity: Understanding Fame Online. Bingley: Emerald Publishing.

Alexander, J. (2019). Lilly Singh’s NBC series debut proves late night TV and YouTube need each other. The Verge. Retrieved 6 August from https://www.theverge.com/2019/9/17/20847627/lilly-singh-late-night-youtube-jimmy-fallon-jimmy-kimmel-seth-meyers-nbc.

Dodgson, L. (2019). YouTube stars rarely break into mainstream entertainment despite being worshipped by millions of fans. Here’s why they might be better off online. Insider. Retrieved 6 August from https://www.insider.com/why-youtubers-struggle-to-break-into-mainstream-entertainment-2019-12.

Höllen, M., Lengfeld, C., & Konrad, E. D. (2020). Business success for creative and cultural entrepreneurs: Influences of individual-and firm-related factors on revenue and satisfaction. International Journal of Arts Management, 22(2), 52–65.

Interview Magazine. (2020). “Lilly Singh Answers 16 Questions”. [Video]. YouTube. Retrieved 6 August 2020 from https://www.youtube.com/watch?v=qgoNljjS0hA.

Leskin, P. (2020). The life and rise of Lilly Singh, the YouTube star who now hosts her own late night show and is now worth over $10 million. Business Insider. Retrieved 6 August 2020 from https://www.businessinsider.com/lilly-singh-youtube-net-worth-life-career-late-night-show-2019-11?r=AU&IR=T.

Lilly. (2019). Female. Coloured. Bisexual. [Tweet]. Retrieved 6 August 2020 from https://twitter.com/Lilly/status/1099837949951111168.

Noah, T. (2019). Lilly Singh Tells Trevor Noah How She Plans To Change Late Night. Interview Magazine. Retrieved 6 August 2020 from https://www.interviewmagazine.com/culture/lilly-singh-tells-trevor-noah-how-she-plans-to-change-late-night.

Robinson, N. (2019). Performances and publics while watching and live-streaming video games on Twitch.tv. MPhil Thesis — University of Melbourne. Retrieved 6 August 2020 from https://minerva-access.unimelb.edu.au/handle/11343/227046.

Schomer, S. (2019). Lilly Singh Conquered YouTube — Now She’s Taking On Hollywood. Entrepreneur. Retrieved 6 August 2020 from https://www.entrepreneur.com/article/328067.

Singh. L. (2020). “Home”. YouTube Channel. Retrieved 6 August 2020 from https://www.youtube.com/user/IISuperwomanII.

Social Blade. (2020). Lilly Singh. Social Blade. Retrieved 6 August 2020 from https://socialblade.com/youtube/user/iisuperwomanii.

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