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
5 Signs Someone Is Draining Your Energy (And What to Do About It)
Jay explores how draining relationships can quietly take a toll on our bodies, minds, and emotional well-being, leaving us depleted before a conversation even begins and carrying its weight long after it ends. He breaks down five signs of chronic relational stress, from managing ... Show More
34m 23s
Oct 7
Sabrina Zohar: How to Stop Chasing People Who Don’t Want You
Jay sits down with dating and relationship coach Sabrina Zohar to unpack why we chase the familiar over the safe, how childhood attachment shapes adult dating patterns, and the real difference between boundaries and walls. Together they dig into anxious-avoidant dynamics, chemist ... Show More
1h 26m
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
Lilly Singh: The Success Lie She Believed for 10 Years
<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
Oct 2019
Lilly Singh: Becoming Your Own Superhero Bawse
You’ve never seen her on mainstream TV shows, movies, chart-topping singles, or billboard albums. But you probably have seen her videos on YouTube (or a clip on Facebook). Lilly Singh started making YouTube videos after battling severe depression in college. She started to re-con ... Show More
1h 1m