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

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Oct 9, 2025

Lilly Singh, a comedian, creator, and author, transitioned from an immigrant upbringing to becoming a YouTube sensation. She shares how storytelling serves as a tool for gender equity and the inspiration behind her raunchy sex comedy, Doing It, aimed at normalizing female sexuality. Lilly discusses the challenges of authenticity in the age of algorithms, the importance of connection with her audience, and her commitment to supporting South Asian creators through her initiative, Hyphenate. She emphasizes the value of therapy, negotiating pay, and unlearning the need for likability.

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ANECDOTE

Refusing Talent Privilege Excuses

Lilly recalls being told on set 'you're the talent you can be late,' which revealed a culture of excusing misbehavior for celebrities.
She enforces respect on her team and refuses to accept passes that erode professionalism.

ADVICE

Hire For Curiosity And Hustle

Hire based on curiosity and work ethic: geeky enthusiasm and good questions signal great hires.
If someone shows passion and asks smart questions, bet on them and coach skills where needed.

ADVICE

Diversify Income And Invest In Yourself

Build a 360-degree business and diversify income so one shut-off faucet doesn't sink you.
Invest in yourself (therapy, skills, time-saving hires) rather than splurging on status items.

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Comedian, creator, actress, author, and activist Lilly Singh has built a career on breaking barriers and rewriting the rules.

In this episode of The Burnouts, Lilly Singh sits down with Phoebe Gates and Sophia Kianni to share her journey: from growing up as the “disappointing” second daughter in an immigrant household, to becoming YouTube’s breakout superstar with 15M+ subscribers, to launching a late-night show and producing her own films.

She opens up about the chip on her shoulder that fueled her rise, how gender equity shapes everything she does, and why she believes storytelling—not just politics or protests—is the most powerful tool for change. Plus: her new raunchy sex comedy Doing It (why Hollywood called it “too niche”), what she learned about money, gratitude, and negotiating as a woman, and how she built Hyphenate to support South Asian creators.

Lilly also gets real about therapy, unlearning likability, the pressure of “relevancy” on the internet, and why connection—not algorithms—is the only metric that really matters.

Whether you’re dreaming of becoming a creator, breaking into Hollywood, or building a career that actually aligns with your values, this conversation is packed with lessons, raw honesty, and plenty of laughs.

Chapters
00:00 – Growing up in Toronto & immigrant expectations
02:00 – The chip on her shoulder: proving girls can do anything
04:00 – Why storytelling is activism
05:00 – Doing It: sex comedy as cultural intervention
08:00 – Lessons from early YouTube days & feeding the algorithm
10:00 – Losing (and regaining) authenticity & connection
12:00 – Hollywood, “noise,” and drawing boundaries
14:00 – Building her first team & hiring smarter people
18:00 – Hyphenate: supporting South Asian creators
20:00 – Diversifying income & passive revenue
23:00 – Passion projects vs. profit projects
28:00 – Negotiating money & the weaponization of gratitude
31:00 – Unlearning likability & embracing being “unpopular”
34:00 – Hollywood vs. YouTube: who really knows the audience
36:00 – Defining success when relevancy is weaponized
38:00 – Boundaries, therapy, and not being “what you do”
42:00 – Why being a lifelong student is the smartest move
43:00 – Tattoos, spirituality & protection

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