Do you feel like you need to prove yourself?
Who do you think you’re trying to impress?
Today, Jay sits down with his close friend Lilly Singh for a transformative and deeply honest in-person conversation at the Ellie Caulkins Opera House in Denver. Known for being a trailblazer in digital media and late-night television, Lilly reflects on the hidden chall ... Show More
Yesterday
Alison Wood Brooks: The Science Behind Great Conversations
Jay sits down with Harvard Business School professor Alison Wood Brooks, author of Talk: The Science of Conversation and the Art of Being Ourselves, to explore what makes great conversations actually work and where most of us get it wrong. Together, they unpack how to choose bett ... Show More
1h 42m
Aug 19
Ask Jay: How Do I Let Go?
In the very first episode of Ask Jay, a new series where listeners send in voice notes with their biggest questions, Jay explores what it really means to let go when your heart is still holding on. Through four deeply personal stories, he unpacks the difference between love and t ... Show More
38m 35s
Aug 2025
1227: What a Tumor Taught Her About Speaking Up, Showing Up & Deep Self Trust with Lily Walla
"She's so strong." That's what people say when a woman holds it all together on the outside but what happens when she's quietly suffering inside? In this episode, Heather sits down with entrepreneur and mother Lily Walla, the founder + CEO of Auggie, for a conversation about the ... Show More
37m 50s
Sep 2019
The Only Sustainable Thing is Lack of Judgement for Self and Others | #AskGaryVee Ep. 324 with Lilly Singh
<p>What's up podcast listeners? On this episode the dynamic star and entertainer Lilly Singh stops by the NYC office! Think you're going to love this episode - we talk judgement; of self and others, creating vs being on the sidelines, and lots of tactics and ideas and insights th ... Show More
57m 22s
Apr 2022
How to Change Your Limiting Thoughts & Beliefs Around Success, Self-Love & Happiness w/Lilly Singh EP 1250
<p>Lilly Singh is a Canadian comedian, actress, former talk show host, and YouTuber. Singh has found worldwide fame through her comedic and inspirational content, amassing nearly 40 million followers across her social media channels alongside projects with NBC, Netflix and other ... Show More
1h 12m
Sep 2024
Lisa Bilyeu: How to Master Your Ego and Build Radical Confidence
What if the only thing standing between you and real confidence is your fear of failure? In today’s episode, I’m joined by someone who knows exactly how to turn challenges into confidence. Lisa Bilyeu, co-founder of Quest Nutrition and the host of Women of Impact, shares her powe ... Show More
1h 10m
Apr 2022
Lilly Singh on Investing In Yourself
Lilly Singh is an author, actress + entertainer and started her career on YouTube over a decade ago. She has since gone from a digital superstar, to mainstream media with her own late night talk show, guest staring on Dollface and a new leading role in a Disney+ show. In this epi ... Show More
39m 19s