Have you ever failed at something you really wanted?

What did that experience teach you about yourself?

Today, Jay chats with late-night legend Jimmy Kimmel for an unforgettable live conversation at the Greek Theatre in Los Angeles. Jimmy opens the episode playfully roasting Jay, showing off his signature, sharp wit right out of the gate. The laughs quickly give way to a candid, wide-ranging conversation about Jimmy’s life, marked by gutsy decisions, constant reinvention, and moments of surprising vulnerability.

Jimmy reflects on the emotional cost of self-expression, his early struggles with being misunderstood, and how persistence (and a healthy dose of delusion) helped him find his place in the world. Jimmy shares how anxiety has shaped his life, from growing up without much money to now being someone people rely on for support, advice, and even financial help. From outrageous pranks and career missteps to a touching tribute to his prank-loving Aunt Chippy, Jimmy constantly balances humor with disarming honesty. Jimmy also opens up about the challenges of becoming more emotionally available, how therapy has helped him grow, and how being a father, and now a grandfather, has reshaped his priorities and softened his edges.

In this interview, you'll learn:

How to Stay True to Yourself

How to Use Humor as a Tool for Healing

How to Keep a Lifelong Passion Alive

How to Stay Grounded When Success Finds You

How to Cope With Anxiety Through Creative Outlets

How Helping Others is the Key to Healing Yourself

It’s not about being perfect, it’s about being honest, showing up, and continuing to try. Whether through meaningful conversations, creative expression, or simply sharing space with others, healing and connection are always within reach.

With Love and Gratitude,

Jay Shetty

Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here.

What We Discuss:

00:00 Intro

04:44 Why is Putting Yourself Out There So Hard?

08:00 Discovering What Truly Drives You

09:19 The Origins of Jimmy’s Legendary Pranks

11:56 When the Pranks Never Stop

17:02 Failed Firings and Conversations That Went Sideways

18:30 Staying True to Your Creative Voice

21:42 Becoming a Grandfather for the First Time

25:55 Living With Anxiety: How It Shapes Family Life

27:29 Jimmy’s Take on Managing Anxiety

29:56 What It’s Like to Face Financial Pressure

31:17 How Jimmy Met the Love of His Life

32:31 Is Finding Love in LA Really That Hard?

33:17 The Secret to a Strong and Lasting Marriage

38:19 Why Talking About Your Feelings Is So Tough

39:16 What To Do When You’re Feeling Low

43:05 Jimmy on Final Five

Episode Resources:

Jimmy Kimmel | Instagram

Jimmy Kimmel | Facebook

Jimmy Kimmel | YouTube

Jimmy Kimmel | X

Jimmy Kimmel | TikTok

See omnystudio.com/listener for privacy information.

What’s the hardest part of parenting for you?

Do you think kids today are more anxious than before?

Today, Jay sits down with Dr. Becky Kennedy, clinical psychologist, best-selling author, and founder of Good Inside, a global parenting and mental health platform. Named the “Millennial Parent Whisperer” by Time, Dr. Becky is known for her compassionate, practical approach to raising emotionally healthy children while maintaining strong, sturdy leadership as a parent.

In this eye-opening conversation, Jay and Dr. Becky explore why modern parenting often swings between dismissing children’s emotions and letting them call the shots, sharing practical ways to find the balance in between. Dr. Becky shares why parenting is a skill you can actually learn, the surprising power of repairing after conflict, and how boundaries and validation work together to help kids feel safe, understood, and supported.

Dr. Becky shares how to shift your mindset from “my kid is giving me a hard time” to “my kid is having a hard time,” creating a more compassionate approach to conflict and connection. She explains why constantly optimizing for happiness for your kids can actually create anxiety later in life, why letting kids struggle is key to building resilience, and how to release the heavy burden of “mom guilt” by recognizing which emotions are yours to carry and which belong to your child.

In this interview, you’ll learn:

How to Repair After Rupture and Strengthen Connection

How to Set Boundaries Without Power Struggles

How to Validate Feelings Without Over-Coddling

How to Build Capable and Resilient Kids

Why Not All “Mom Guilt” is Actually Guilt

How to Balance Empathy with Leadership as a Parent

Parenting isn’t about getting it perfect. It’s about showing up, repairing when things go wrong, and modeling the emotional skills you want your children to have. As Dr. Becky reminds us, the most powerful thing you can give your kids is the confidence to face life’s challenges knowing they are both safe and valid.

With Love and Gratitude,

Jay Shetty

Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here.

What We Discuss:

00:00 Intro

02:49 Should Kids Dictate Parenting Styles?

06:03 Building Tolerance As A Skill

10:43 How To Overcome Mom Guilt

18:27 Becoming a Mom Shouldn't Be Endured Alone

21:50 What is the Best Parenting Strategy?

29:30 The First Step Of Repair

34:18 How to Reconcile with Your Kid

36:54 How to Reconcile with Your Kid

39:17 Your Kid is Just Having a Hard Time

42:04 The Myth Of Always Being Available

44:30 How Do You Set a True Boundary?

48:36 The Communication Skills Every Parent Needs

52:34 What is Your Job As A Parent?

56:48 Your Kid’s Feelings Are Valid

59:12 How Boundaries & Validation Make for Resilient Adults

01:00:40 Should you be Optimizing for Happiness In Childhood?

01:09:45 The Power of Patience & Time

01:12:56 Teaching Kids How To Build Tolerance

01:19:44 Fostering Independence

01:24:36 Teaching Children Self-Reliance

01:30:33 The Value Of Discipline

01:37:56 The Pressure Parents Experience

01:41:52 Independence Vs Dependence

01:50:46 The Fear Of Patterns Repeating

Episode Resources:

Dr. Becky Kennedy | Website

Dr. Becky Kennedy | Instagram

Dr. Becky Kennedy | Facebook

Dr. Becky Kennedy | YouTube

Dr. Becky Kennedy | LinkedIn

Dr. Becky Kennedy | X

Dr. Becky Kennedy | TikTok

See omnystudio.com/listener for privacy information.

Today, Jay sits down with serial entrepreneur, investor, and powerhouse mom of four, Kim Perell. Known for building her first company from her kitchen table and later selling one for $235 million, Kim shares the raw, behind-the-scenes truth of what it takes to turn failure into fortune. The conversation centers around Kim’s latest book, Mistakes That Made Me a Millionaire, and offers a heartfelt blueprint for anyone feeling stuck, unfulfilled, or uncertain about their next move.

Jay and Kim explore why perfectionism can sabotage progress, how fear often masks itself as procrastination, and why waiting to feel “fully qualified” often leads to missed opportunities. Kim introduces her 70% rule: a concept that encourages action over hesitation and reveals how taking small, imperfect steps helped her overcome self-doubt and build extraordinary businesses. The two also dive into the power of mentorship, the emotional toll of toxic relationships, and why surrounding yourself with the right people is crucial not just for professional growth, but for personal evolution.

In this interview, you'll learn:

How to Start a Business Before You Feel Ready

How to Use the 70% Rule to Make Bold Decisions

How to Find the Right Mentor and Build a Real Relationship

How to Stand Out When Pitching Yourself

How to Know When It’s Time to Pivot Your Business

How to Build a Winning Team Without Doing Everything Yourself

How to Audit Your Inner Circle for Growth and Clarity

Making mistakes doesn’t mean you’ve failed, it means you’re showing up, learning, and trying something new. No success story is smooth or simple, but all of them prove that progress is always possible.

With Love and Gratitude,

Jay Shetty

Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here.

What We Discuss:

00:00 Intro

02:57 How to Get Unstuck and Move Forward

04:17 When It’s Time to Pivot Your Career

05:50 Is Regret More Powerful Than Fear?

08:06 You Don’t Need To Be 100% Ready To Start

09:52 Are You Ever Really Ready?

11:29 Dream Big, But Start Where You Are

13:09 The Power of Believing in Your Vision

15:24 Be Delusionally Confident

16:29 How Mistakes Help You Iterate and Improve

18:30 How to Silence the People Who Doubt You

22:15 Teaching Kids to Embrace Failure

23:20 Rejection as Redirection

26:02 The Difference Between Innovating and Iterating

29:14 Build a Support System That Elevates You

31:51 How to Find Mentors Who Truly Guide You

33:55 Why Asking for Help Accelerates Growth

34:44 How Books Can Mentor You Too

38:21 The Four People Every Entrepreneur Needs

39:35 Why You Need the Right Peers Around You

41:58 Should You Start a Business with Family?

44:00 How to Audit Your Inner Circle

46:02 How Toxic People Drain Your Energy and Money

47:17 The Power of Taking Initiative

48:56 Don’t Let Your Past Limit Someone Else’s Future

51:19 How to Lead and Manage People Effectively

53:17 What Actually Gets You Hired Today?

57:51 Going the Extra Mile Sets You Apart

01:00:01 The Biggest Mistake Is Not Asking

01:04:03 Why So Many of Us Feel Unqualified

01:07:07 Pivoting Is the Secret to Success

01:10:13 How to Know When It’s Time to Pivot

01:11:53 Kim on Final Five

Episode Resources:

Kim Perell | Website

Kim Perell | Instagram

Kim Perell | Facebook

Kim Perell | YouTube

Kim Perell | LinkedIn

Kim Perell | X

Kim Perell | TikTok

See omnystudio.com/listener for privacy information.