Today, Jay reflects on the lessons about love he wishes he had known in his twenties. He examines how movies, media, and cultural narratives have long shaped unrealistic expectations about romance, often equating love with grand gestures, nonstop excitement, and fairy tale endings. Jay challenges these ideas, by showing that true love is not constant fireworks, but a balance of peace, stability, and passion. He explains how the thrill is often mistaken for attraction, and how the calm that comes from trust and consistency is actually the real foundation of a healthy relationship, even if often mistaken for boredom.

Jay also explores the critical role of self-awareness and boundaries in fostering meaningful relationships. He discusses how love without boundaries can cause you to lose yourself, and how repeating familiar emotional patterns from the past can keep you stuck in cycles that feel comfortable but are ultimately harmful. Through relatable examples, Jay highlights the importance of defining emotional non-negotiables, paying attention to how a partner handles boredom and conflict, and understanding the influence of attachment styles. Jay emphasizes that successful relationships are not about finding someone perfect, but about choosing a partner who is willing to heal, grow, and face challenges together.

In this episode, you'll learn:

How to Set Boundaries Without Pushing Love Away

How to Handle Conflict Without Ruining a Relationship

How to Recognize the Difference Between Lust and Love

How to Break Unhealthy Relationship Patterns

How to Choose Patience and Healing in Relationships

Finding real love isn’t an end goal, it’s an ongoing journey you take with intention, compassion, and patience. It’s something you build over time through quiet moments, healthy boundaries, and a commitment to grow, both on your own and together.

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

01:13 Everything You Need to Know About Love

04:12 #1: Chemistry Does Not Equal Compatibility

09:19 #2: Love Without Boundaries is Self Abandonment

12:25 #3: How They Handle Boredom Tells You Everything

14:25 #4: Conflict Doesn't Ruin Relationships, Avoidance Does

16:44 #5: The Thrill is Temporary, Steady Love is Lasting

20:57 #6: How Does Your Partner's Attachment Style Affect You?

23:01 #7: What Feels Familiar Isn’t Always What’s Right

See omnystudio.com/listener for privacy information.

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.

Have you ever thought about starting a business?

What would you do if money wasn’t a problem?

Today, Jay sits down with bestselling author, entrepreneur, and investor Alex Hormozi for a practical and eye-opening conversation about money, business, and what it really takes to succeed. Alex has built and sold multiple companies and now runs Acquisition.com, where he helps scale businesses to over $10 million in revenue.

In this episode, Alex breaks down why so many people feel stuck when trying to grow a business. Alex and Jay dive into the common mistakes that hold people back, like chasing passive income too early, mistaking passion for a plan, or seeking freedom without first building discipline. Alex shares the real steps you need to take to start making money now. He explains how to create active income by offering your time and skills, how to craft offers people can’t refuse, and why direct feedback is the fastest path to growth. Jay and Alex also explore the mindset traps that stop people from moving forward, including fear of judgment, comparison, and the pressure to get it perfect the first time. Together Jay and Alex highlight the importance of showing up consistently, being willing to fail, and choosing long-term growth over short-term comfort.

In this interview, you'll learn:

How to Start a Business with Zero Capital

How to Create an Offer People Can’t Refuse

How to Increase Your Income by Trading Your Time Intentionally

How to Sell Without Feeling Manipulative

How to Get Unstuck from the Passive Income Trap

If you're ready to stop guessing and start building something real, this episode gives you the clarity, structure, and confidence to move forward.

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

00:40 Get Clear on the Exact Actions That Drive Success

02:10 Why Most People Misunderstand How to Build a Business

04:26 Is the ‘Get Rich Quick’ Model Really Possible?

07:41 The Five Emotional Stages Every Entrepreneur Goes Through

10:52 Start Here to Learn the Skills That Actually Make Money

13:36 Should You Follow Your Passion for Income?

23:30 How to Make Your First Dollar from Nothing

27:57 The 10 by 10 Strategy to Build Proof and Confidence

32:27 Your Product Must Solve a Real Problem

35:37 What No One Tells You About the Trade-Offs of Business

39:40 How to Turn Your Job Experience into a Business

52:27 Redefining Success: It’s Not About the Outcome

56:07 Listen to People Who Are Where You Want to Be

01:02:18 Overcoming the Fear of Selling Ourselves

01:04:23 How to Influence Without Manipulating

01:10:17 The Difference Between Criticism and Insults

01:17:28 How to Break Repetitive Negative Behavior

01:26:15 When to Keep Pushing and When to Pivot

01:28:46 The Four Ingredients of an Irresistible Offer

01:37:02 Focus on Who You Want to Become Not Just What You Want

01:38:40 What Would You Do If You Weren’t Afraid?

01:42:46 The Simple Formula Everybody Has But Nobody is Doing

01:45:53 The Most Important Step Is Just Start

01:47:05 Is Work Life Balance Really Achievable?

01:50:35 Be More Productive by Eliminating Everything Unnecessary

01:55:17 Alex on Final Five

Episode Resources:

Alex Hormozi | Website

Alex Hormozi | Instagram

Alex Hormozi | Facebook

Alex Hormozi | YouTube

Alex Hormozi | LinkedIn

Alex Hormozi | X

Alex Hormozi | Books

See omnystudio.com/listener for privacy information.

Have you ever felt like losing meant your life was over?

When did you realize it’s okay to fail?

Today, Jay sits down with four-time Grand Slam champion Naomi Osaka to explore her journey beyond the tennis court. Naomi, known for her powerful game and quiet resilience, opens up about the challenges of fame, the weight of expectations, and how motherhood has reshaped her outlook on life.

Jay and Naomi discuss the pressure of being a high-performance athlete, the loneliness that can accompany success, and the struggles of maintaining a sense of self in an industry that often reduces people to their achievements. Naomi candidly describes how, for years, her self-worth was tied to her ranking and performance, but becoming a mother has given her a new perspective—one that prioritizes joy, presence, and growth over perfection.

The conversation also dives into Naomi’s evolving relationship with competition. While she once measured her success by titles and trophies, she now finds fulfillment in self-discovery and personal progress.

In this interview, you'll learn:

How to Detach Your Self-Worth from Achievements

How to Cope with External Expectations and Criticism

How to Use Journaling for Self-Reflection and Growth

How to Prioritize Mental Health in High-Pressure Situations

How to Learn from Setbacks Without Letting Them Define You

Success is not just about winning; it’s about growing, learning, and showing up for yourself every day.

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

01:47 Open Discussions About Mental Health

03:10 Impulsiveness as an Athlete

05:28 Moving From Japan to USA

08:02 Lifelong Training and Career

10:13 Incorporating Culture in Fashion

12:38 Discipline and Diet

13:53 Indulging in Guilty Pleasures

16:48 Passing Time While Having Impulsive Tendencies

18:46 Winning the First Grand Slam

21:09 Dealing with Public Hate

22:39 A Long-Time Serena Williams Fan

25:16 Experiencing Motherhood

27:39 The Different Facets of Life

29:07 The Power of Journaling

31:55 Loving the Life You're Living

34:57 The Habit of Comparing Yourself to Others

36:27 Stop Chasing Your Old Self

38:21 Motherhood Realizations

39:46 Rigorous Training After Giving Birth

41:18 Setting Boundaries During PressCon

43:01 No One Can Predict Someone's Path

45:21 Finding Calmness Through Meditation

47:44 Setting New Goals

50:25 Shamed for Taking a Break

54:17 Getting Support from Fellow Athletes

55:52 Friendships and Camaraderie

57:08 Mentored by Kobe Bryant

59:31 The Haitian Way of Giving

01:00:58 Who Are You Spending Your Time With the Most?

01:04:29 Loving Yourself and How You Look

01:05:29 Game Day Routine

01:07:33 You're Never Alone

01:09:04 Fear of Being Forgotten

01:12:40 Naomi on Final Five

Episode Resources:

Naomi Osaka | Instagram

See omnystudio.com/listener for privacy information.

Have you ever thought about being your own boss?

What kind of business would you start if you could?

In this special compilation episode of On Purpose, Jay Shetty curates powerful insights from five extraordinary entrepreneurs: Emma Grede, Michael Rubin, Codie Sanchez, Brian Chesky, and Suneera Madhani, offering a dynamic, behind-the-scenes look at what it truly takes to build something meaningful from scratch. Each guest brings a unique lens to the entrepreneurial journey: Emma Grede reminds us that the most powerful companies are born by solving real problems for underserved communities; Codie Sanchez breaks down how grit, financial fluency, and deal-making are more crucial than a flashy idea; while Brian Chesky reveals that building a world-changing company like Airbnb starts with seeing your business as a reflection of your inner world.

Jay weaves these stories into a powerful masterclass on purpose-driven entrepreneurship, showing that success doesn’t come from confidence, funding, or perfection. It comes from grit, learning through failure, and showing up again and again. Michael Rubin drives home the power of obsession and adaptability, while Suneera Madhani brings it back to reality, reminding us that the biggest risk isn’t failing, it’s never starting. It’s a powerful reminder that stepping out of comfort and into aligned action is where true transformation begins.

In this episode, you'll learn:

How to Build a Purpose-Driven Brand from Scratch

How to Master Deal-Making and Speak the Language of Money

How to Stay Innovative When Success Hits

How to Start a Business Without Industry Expertise

How to Scale a Company Without Losing Your Values

How to Take Risks Without Letting Fear Lead the Way

The most meaningful work often comes from solving problems close to your heart, staying curious, and showing up even when it’s hard. You are not too late, underqualified, or behind.

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

03:06 Start With the Problem Only You Can See

06:40 The Power of Who’s in the Room

08:10 Believe in Your Vision Before Anyone Else Does

10:44 What Really Motivates You Every Day?

13:26 Three Essential Skills for Building a Business

18:33 How to Master the Art of Deal Making

28:03 Redefining What Success Means to You

31:10 Life’s Greatest Lessons Start Within

34:17 Surround Yourself With the Right People

38:54 Can Hustle and Drive Be Taught?

40:46 Learn by Observing Others’ Mistakes

41:30 What is at the Heart of Entrepreneurship?

42:52 Bringing Innovation to What You Love

47:14 Avoid These Common Mistakes when Building a Business

49:44 Pattern Recognition Is a Business Superpower

52:05 Why Hard Conversations Build Stronger Foundations

55:34 Courage Is the First Step Toward Risk

59:46 Start by Solving a Real, Specific Problem

01:03:49 What Got You Here Won’t Get You There

See omnystudio.com/listener for privacy information.