What in your day makes you happiest?

Where do you see yourself in five years?

Today, Jay sits down with the iconic rapper, multi-platinum artist, and entrepreneur Wiz Khalifa. The episode explores Wiz’s journey from navigating the challenges of his youth in Pittsburgh to becoming one of the most recognizable names in the music industry. Throughout their conversation, Wiz shares profound insights into his personal growth, family values, and the discipline behind his success.

Wiz reflects on his early days, including the loss of a record deal and the resilience it took to rebuild his career. He discusses his evolution as an artist and individual, emphasizing the importance of gratitude, patience, and staying true to oneself. The conversation also dives into the balance between his professional life and personal responsibilities, particularly as a father. Wiz talks about raising his 11-year-old son, Sebastian, and his new daughter, Cadence, shedding light on how fatherhood has deepened his perspective on life and masculinity.

Jay and Wiz also explore deeper topics like handling grief, cultivating self-discipline, and the nuanced concept of masculinity in today’s world. Wiz’s candid anecdotes, whether about quitting alcohol, building financial literacy, or practicing MMA for mental clarity, inspire listeners to live authentically, embrace personal growth, and focus on what truly matters.

In this interview, you'll learn:

How to Rebuild Confidence After a Setback

How to Balance Personal Life and Career Successfully

How to Find Gratitude in Everyday Moments

How to Stay Calm Under Pressure

How to Teach Discipline and Politeness to Kids

How to Manage Money as a Creative Professional

How to Stay Authentic in the Spotlight

Every setback is an opportunity to rebuild stronger, and every triumph is a chance to inspire others. Prioritize what matters, whether it’s your personal growth, the relationships you cherish, or the values you stand for.

With Love and Gratitude,

Jay Shetty

100% of Proceeds are donated to the National Alliance on Mental Illness. NAMI is the nation’s largest grassroots mental health organization dedicated to building better lives for the millions of Americans affected by mental illness. Visit https://jayshettyshop.com

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What We Discuss:

00:00 Intro

04:15 Navigating Fame As A Star

09:18 The Craziest Fan Interactions

10:07 Family Matters The Most

11:49 Dealing With Grief

13:04 Seeking Family Support

13:54 Finding Balance In Grief

14:50 Life Before Fame And Success

16:47 What's It Like To Lose A Record Deal?

17:15 Confidence In The Face Adversity

18:37 Advice To Younger Self

19:22 Driven Goals And Compulsion

20:50 Being Contented With What You Have

21:30 What's The Hardest Conversation You Have Ever Had?

24:40 Building Connections With Your Audience

25:50 Ever Caught Anything Crazy On Camera?

26:45 Then VS Now Journey With Other Stars

29:13 Advice For Up And Coming Artists

32:11 How Far Do You Plan Your Goals?

32:49 Best Moves In Money Management

35:58 Dumbest Thing I Have Ever Bought

36:35 Best Investment I Have Ever Made

38:20 Relationship With God

40:30 Moving Around In My Childhood

41:58 How My Childhood Experiences Has Impacted Me

44:48 How My Views On Fatherhood Has Changed

50:17 How I Take Control Of My Career As An Artist

54:17 What I Learnt From My Mom

55:31 Something People Should Know About Me

1:00 How Working Out Helped Me

1:02 My Advice For Men Who Want To Get Into Health And Fitness

1:03 My Perspective On Masculinity

1:08 My Take On MMA And Martial Arts

1:12:09 How I View My New Album And Most Viewed Video

1:16:22 My Motivation To Go Sober From Alcohol

1:18:01 First Thing I Do Before I Go To Bed

1:18:32 Wiz on Final Five

Episode Resources:

Wiz Khalifa | Website

Wiz Khalifa | Instagram

Wiz Khalifa | TikTok

Wiz Khalifa | YouTube

Wiz Khalifa | Facebook

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