$20M YouTuber Lilly Singh: How to Tell a Story That People Remember, and The #1 Top Confidence Trick

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.Chapters00:00 – Growing up in Toronto & immigrant expectations02:00 – The chip on her shoulder: proving girls can do anything04:00 – Why storytelling is activism05:00 – Doing It: sex comedy as cultural intervention08:00 – Lessons from early YouTube days & feeding the algorithm10:00 – Losing (and regaining) authenticity & connection12:00 – Hollywood, “noise,” and drawing boundaries14:00 – Building her first team & hiring smarter people18:00 – Hyphenate: supporting South Asian creators20:00 – Diversifying income & passive revenue23:00 – Passion projects vs. profit projects28:00 – Negotiating money & the weaponization of gratitude31:00 – Unlearning likability & embracing being “unpopular”34:00 – Hollywood vs. YouTube: who really knows the audience36:00 – Defining success when relevancy is weaponized38:00 – Boundaries, therapy, and not being “what you do”42:00 – Why being a lifelong student is the smartest move43:00 – Tattoos, spirituality & protection🔗 FOLLOW USPhoebe GatesSophia KianniLilly Singh🔥 FOLLOW THE BURNOUTSInstagramTikTokLinkedIn📲 Support What We’re BuildingPhoebe and Sophia aren’t just your hosts—they’re the founders of Phia, a fashion-tech app helping shoppers find the best prices across retail and resale. Download the app, try it out, and help us grow this communityAbout The BurnoutsThe Burnouts brings you raw, unfiltered conversations with today’s top founders, creators, and culture-shaping entrepreneurs. Hosted by Stanford roommates turned startup co-founders, Phoebe Gates and Sophia Kianni, the show goes beyond the headlines to share the real stories, lessons, and mindsets that define your 20s.Past guests include Paris Hilton, Chelsea Handler, Kris Jenner, Karlie Kloss, and Tommy Hilfiger.🛎️ Subscribe for the insider playbook to build your dream career.