Do you feel guilty when you put your needs before others by saying no?

When was the last time you chose yourself—just because you needed it, not because you earned it?

Today, Jay is joined by Meggan Roxanne, writer, entrepreneur, and founder of the globally loved platform The Good Quote. Known for curating some of the internet’s most powerful and inspiring affirmations, Meggan now steps into the spotlight with her own voice, sharing a remarkable personal story of loss, resilience, and transformation.

From growing up in a warm and loving home to experiencing a heart-wrenching moment at just four years old, when a grandparent told her they didn’t love her, Meggan opens up about how early trauma shaped her emotional world. Following her mother’s final wish, Meggan became the caretaker for her estranged grandfather, the very man who once wounded her deeply. Through that act of grace, she discovered the true meaning of forgiveness, empathy, and unconditional love.

Throughout the episode, Meggan and Jay explore the difference between people-pleasing and creating space for authentic connection, how emotional boundaries protect our well-being, and what it takes to stop repeating the pain we’ve inherited. She candidly discusses the challenges of grief, especially after losing her mother, her best friend, her guide, and how that loss forced her to reimagine her identity and rebuild from the ground up.

In this episode, you'll learn:

How to Forgive Someone Who Hurt You Deeply

How to Set Boundaries Without Feeling Guilty

How to Heal After Losing a Parent

How to Reconnect with Your Intuition

How to Break Generational Cycles of Trauma

How to Build Confidence Through Self-Respect

Even in the darkest of seasons, you have the power to find peace, reshape your path, and step into a life guided by intention, healing, and light.

With Love and Gratitude,

Jay Shetty

What We Discuss:

00:00 Intro

00:30 The Pain of Feeling Unloved by Family

04:12 Would You Take Care of Someone Who Doesn't Love You?

10:20 How Do You Enforce Your Boundaries?

16:20 Are You a Chronic People Pleaser?

23:06 How The Good Quote Started

34:59 Do You Trust Your Intuition?

43:49 Your Intuition is Your Best Guide

45:20 How Do You Reconnect with Your Intuition?

50:52 How Meditation Helps Calm Down Your Day

53:10 Dealing with Grief, Depression, & Losing a Loved One

Episode Resources:

Meggan Roxanne | Instagram

Meggan Roxanne | LinkedIn

The Good Quote | Instagram

The Good Quote | Facebook

The Good Quote | Tumblr

How to Stop Breaking Your Own Heart: THE SUNDAY TIMES BESTSELLER. Stop People-Pleasing, Set Boundaries, and Heal from Self-Sabotage

See omnystudio.com/listener for privacy information.

Does anything in your life feel a little “off” right now?

Do you feel like you're settling for less than you deserve?

Today, Jay sits down with Sadia Khan, psychotherapist and relationship expert, for a deep and unfiltered conversation on love, commitment, and emotional healing in the modern age. Known for her bold and counterintuitive insights, Sadia brings clarity to the often murky waters of dating, self-worth, and relationship dynamics.

Sadia shares her powerful perspective on the importance of being able to walk away from disrespect, and how this one shift can transform who you attract and how you're treated. She challenges conventional dating advice by focusing not on what you attract—but what you entertain—highlighting the role of self-esteem in relationship choices. She explains why emotional unavailability feels attractive, how ghosting reflects poor communication habits, and why your dating app rejection might not be what you think it is.

Jay and Sadia dive into the core issues many of her clients face, including infidelity, fear of commitment, and men struggling with masculinity. She unpacks how a lack of male role models, the ability to set boundaries, and people-pleasing behaviors can derail modern masculinity—and how both men and women can break these cycles to build healthier love.

Sadia introduces the "Three A’s" women need to fall in love—Attraction, Admiration, and Adoration—and the "Three L’s" men need—Lust, Labor, and Loyalty—exploring how balance in these elements creates deep, lasting connection. She also breaks down why women might cheat on “nice” men and how misunderstanding emotional needs can lead to betrayal.

In this episode, you’ll learn:

How to Attract and Maintain Healthy Relationships.

Why Self-Worth is the Foundation of Love.

How to Avoid the Trap of Emotional Immaturity.

What Makes Men and Women Truly Commit.

The Real Reasons Behind Infidelity.

How to Build Masculine Strength in a Healthy Way.

Why Peace is Better than Constant Pleasure in Love.

This conversation is a masterclass in emotional intelligence and healing. If you're navigating heartbreak, struggling with self-worth, or seeking a deep, lasting relationship—this episode is for you.

With Love and Gratitude,

Jay Shetty

What We Discuss:

00:00 Intro

01:17 How to Stop Fearing Conflict and Start Choosing Yourself

02:24 Why We Fall for the Emotionally Unavailable

05:31 The Hidden Dangers of Dating Apps

07:01 Is Wanting Similarity the Same as Settling?

08:40 How to Stop Getting Ghosted in Modern Dating

09:31 The Early Signs of a Healthy Relationship

11:19 The Two Most Common Relationship Struggles: Infidelity and Commitment

12:19 What Happens When Men Lack Masculinity

15:25 Why Men Need Stronger Role Models

18:21 The Unspoken Contract Behind People-Pleasing

19:25 How to Show Love Without Seeking Approval

21:12 The Real Reason Women Cheat on Good Men

24:55 How to Teach Others How to Treat You

26:14 The Three A’s Every Woman Needs to Fall in Love

32:45 The Three L’s Every Man Needs to Stay in Love

36:10 How to Avoid Being Just a Temporary Fling

37:49 Why the Person You Date Isn’t Always the One You Marry

40:42 Sexual Discipline: Why It’s Essential for Self-Respect

42:29 What True Psychological Intimacy Really Looks Like

45:15 Lowering Your Standards May Cost You More Than You Think

46:10 Is Getting Cheated On Ever Partly Your Fault?

48:59 How to Recognize When You’re Being Disrespected

50:13 Are You Loyal to the Marriage or Just the Person?

52:45 The Most Honest Marriage Vow No One Talks About

56:50 Why Some Men Keep Choosing the Wrong Women

59:40 How to Know If You’re Afraid of Commitment

01:04:23 Can a Broken Relationship Be Fixed?

01:06:59 Why Knowing Your Deal Breakers Is Crucial

01:09:03 The Worst Thing to Say to Someone After a Breakup

01:09:56 Why So Many People Stay Stuck in Heartbreak

01:11:43 How to Find Closure Without an Apology

01:15:59 Not Everything You Want Is Good for You

01:66:54 Sadia on Final Five

Episode Resources:

Sadia Khan | Website

Sadia Khan | Instagram

Sadia Khan | TikTok

Sadia Khan | YouTube

See omnystudio.com/listener for privacy information.

What’s been on your mind today?

Do you ever catch yourself spiraling with negative thoughts?

Today, Jay dives into the everyday negative thoughts we all wrestle with—and how we can stop letting them control us. Whether it's replaying awkward moments, spiraling into self-doubt, or feeling stuck in patterns of fear and criticism, negativity can quietly undermine our confidence and cloud our perspective. But what if those thoughts were just noise—and you didn’t have to carry them anymore?

In this episode, Jay shares seven transformative steps to help you build a healthier, more resilient relationship with your mind. Rooted in both spiritual insight and modern science, Jay walks you through powerful shifts—like recognizing your thoughts without letting them define you, challenging your inner critic with evidence, and reframing your day-to-day experiences with intention. With the clarity of a teacher and the care of a friend, Jay helps you see that awareness is not just the first step—it’s your greatest protection.

In this episode, you'll learn:

How to Stop Believing Every Negative Thoughts

How to Challenge Thoughts That Aren’t True

How to Use Mindfulness to Calm Mental Overload

How to Build a Mental Shield Against Criticism and Stress

We can’t always stop negative thoughts from showing up, but we can learn to move through them with clarity, self-kindness, and strength—one thought at a time.

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.

Join Jay for his first ever, On Purpose Live Tour! Tickets are on sale now. Hope to see you there!

What We Discussed:

00:00 Intro

01:06 How Do You Deal With Negative Thoughts?

02:20 #1: Recognize and Acknowledge Your Thoughts

07:30 #2: Challenge Your Negative Thoughts

11:22 #3: Start Reframing Your Thoughts

15:52 #4: Practice Mindfulness and Meditation

18:14 #5: Engage in Joyful Activities

20:12 #6: Look After Your Body

21:28 #7: Limit Your Exposure to Negativity

See omnystudio.com/listener for privacy information.

Have you ever thought about investing before?

What would you do if you could invest without needing experience?

Today, Jay sits down with Vlad Tenev, CEO and Co-Founder of Robinhood, the revolutionary financial platform that brought commission-free investing to millions. Vlad shares his fascinating journey from being a first-generation immigrant from Bulgaria to building a company that redefined access to investing.

Vlad shares candid reflections on his childhood, marked by resilience and an acute financial awareness. He recounts pivotal moments, from immigrating to the U.S. during Bulgaria's economic turmoil to his early fascination with math and finance. Vlad also shares how he manages stress and stays grounded while navigating the demands of leading a high-impact, rapidly evolving company.

Jay and Vlad dive deep into the origins of Robinhood, exploring how the platform sought to democratize investing by eliminating barriers like account minimums and trading fees. Vlad highlights the company’s commitment to innovation and its mission to empower everyday investors. He also shares lessons learned from Robinhood's challenges, including the high-profile GameStop incident, and reflects on the importance of transparency, authenticity, and adapting to evolving market conditions.

In this interview, you'll learn:

How to Build Financial Knowledge Early

How to Balance Work and Wellness Daily

How to Innovate in a Crowded Market

How to Use Feedback to Improve Products

How to Overcome Fear of Investing Mistakes

How to Scale a Business for Long-Term Success

How to Prioritize Customers' Needs in Business

Change can be a powerful and uplifting journey when approached with self-compassion and intention. The power to transform is already within you—let it shine.

With Love and Gratitude,

Jay Shetty

What We Discuss:

00:00 Intro

01:19 Learning the Value of Money at a Young Age

05:50 Reuniting with Parents After Years Apart

09:13 Challenges Faced by Young Immigrants in School

13:57 How Math Became a Gateway to Academic Success

19:00 The Inspiration Behind the Name Robinhood

21:29 A Look Back at the First-Ever Investment

24:32 The Benefits of Starting Young in Business

25:26 The Role of IQ in Early Achievement

29:27 Witnessing the Collapse of the Financial World

34:42 Investing in Crypto Before the Hype

36:58 Starting an Investment Journey with Just $10

39:40 Common Mistakes New Investors Should Avoid

43:45 Choosing Companies That Build Everyday Products

47:52 How AI Is Reshaping Financial Services

50:49 Renting vs Buying in Today’s Economy

55:06 The $72 Trillion Wealth Transfer Explained

57:09 Breaking Barriers to Financial Access

58:25 Rethinking Retirement and Long-Term Planning

01:01:17 Offering a Smarter Approach to Retirement Savings

01:02:36 Robinhood in the Media: What They Got Right (and Wrong)

01:05:15 Representing a Company in the Public Eye

01:09:31 Transforming the Customer Experience from the Inside Out

01:12:46 How Mistakes Shape Company Growth

01:13:46 The Pitfalls of Premature Optimization

01:14:59 Inflation, Interest Rates, and the 2022 Reset

01:20:21 Enhancing the Experience for Active Traders

01:24:46 Making Professional-Grade Trading More Accessible

01:27:00 Prioritizing Customer Needs to Solve Core Issues

01:28:16 Managing the Pressure of Negative Publicity

01:31:38 Balancing Leadership with Personal Life

01:35:19 Navigating Marriage and Work as a Founder

01:36:26 Rethinking the Traditional Credit Card Model

01:40:52 Vlad on Final Five

Episode Resources:

Vlad Tenev | LinkedIn

Robinhood

See omnystudio.com/listener for privacy information.

When was the last time you looked back and thought, “If only I knew this earlier”?

In this episode, Jay shares the seven life-changing lessons he wishes he’d learned in his teens and twenties—insights that could have reshaped his relationships, career, peace of mind, and sense of purpose. These aren’t just reflections; they’re powerful revelations most of us only discover through struggle, heartbreak, or burnout.

Jay dives into what it truly means to speak with intention, to know when it’s time to let go, and to stop outsourcing your self-worth. From learning to stay quiet in a world that rewards noise to realizing that boundaries are an act of self-love—each lesson is a powerful reminder that growth isn’t always about adding more, but about releasing what no longer serves you.

In this episode, you’ll learn:

Why Saying Less Makes Your Words Matter More.

Knowing When It’s Time to Walk Away

Why You Should Talk To People, Not About Them.

What Stress Reveals About a Person’s True Nature.

How to Raise Your Standards Without Guilt.

Why Some People Miss the Old You (for the Wrong Reasons).

How to Stop Absorbing Others' Emotions and Expectations.

This episode is for anyone feeling stuck, overlooked, or overwhelmed. Jay reminds you that you don’t get what you deserve — you get what you accept. And that sometimes the most powerful transformation happens when you choose peace over performance, presence over perfection, and truth over approval.

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.

Join Jay for his first ever, On Purpose Live Tour! Tickets are on sale now. Hope to see you there!

What We Discussed:

00:00 Intro

01:37 Things I Wish I Knew

03:27 Lesson #1: Speak Less, Say More

11:57 Lesson #2: Let Go Before It Drags You Down

17:34 Lesson #3: Talk to Your Partner, Not About Them

21:43 Lesson #4: Understand the Whole Person, Not Just the Parts You Like

28:05 Lesson #5: You Get What You Tolerate, Not What You Deserve

32:52 Lesson #6: People Cling to the Old You Because It Was Easier to Control

36:22 Lesson #7: “Bad at Texting” Often Means You're Not a Priority

See omnystudio.com/listener for privacy information.

Do you ever feel like you need to be funny to be liked?

How do you handle pressure to always “perform” for others?

In this candid, hilarious, and unexpectedly moving episode of On Purpose, Jay sits down with comedian, actor, and podcast superstar Bert Kreischer—famously known for his shirtless stand-up and his ability to keep audiences laughing nonstop. This conversation goes way beyond the jokes as Jay and Bert dive deep into the real stories behind the spotlight, revealing the layers of vulnerability, self-doubt, and emotional growth that make Bert more than just a party-loving comic.

Bert shares what it was like growing up with a tough, old-school dad who believed in powering through pain and never showing weakness. That mentality helped shape Bert’s work ethic but also left him carrying emotional weight for years. In one of the most touching moments of the episode, Bert shares how a simple, unexpected conversation with his dad, while they were both high on edibles, changed everything, helping them finally see each other clearly and connect on a deeper level.

With Jay’s thoughtful guidance, they unpack Bert’s real-life struggles with anxiety, chasing approval, and feeling like you’re never enough, things so many of us can relate to. Bert is refreshingly honest about his mental health, his parenting ups and downs, and what it's like trying to stay grounded while raising two sharp, hilarious daughters who aren’t afraid to call him out.

In this interview, you'll learn:

How to Stay Humble While Chasing Big Dreams

How to Raise Kids Who Keep You Grounded

How to Keep Showing Up Even When It's Hard

How to Use Vulnerability as a Superpower

How to Manage Anxiety Without Shame

How to Turn Criticism into Growth

How to Stay Grateful Through Every Stage of Success

This episode is full of laughs, a few tear-jerking moments, and plenty of insight into what it really means to show up, be yourself, and keep going, even when it’s hard.

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.

Join Jay for his first ever, On Purpose Live Tour! Tickets are on sale now. Hope to see you there!

What We Discuss:

00:00 Intro

02:45 The Wildest Plane Stories You’ve Ever Heard

04:25 Why a Marriage Built on Laughter Works

06:01 When Your Family Becomes Your Funniest Critics

07:16 Were You Always the Funny One?

09:08 How Bert Mastered the Art of Storytelling

14:35 Growing Up with a Tough-Love Dad

17:56 What It’s Like Seeing Your Parent Cry for the First Time

20:40 Realizing Your Parents Are Human Too

23:36 When Your Dad Realizes He Can Use Your Fame

24:35 What It’s Like to Share Your Success with Your Parents

29:05 The Lifelong Quest for a Parent’s Approval

35:08 How a 6-Figure Deal with Will Smith Changed Everything

37:20 The Moment You Know You Have to Chase Your Talent

42:50 Embracing the Power of Pressure

44:09 Is There a Pain You Can’t Laugh Through?

47:06 Letting Your Kids See You Cry

49:56 Why the Way You Tell a Joke Matters

51:43 How Your Kids Really See You

54:05 The Challenge of Uninterrupted Family Time

56:51 Just Show Up and Do the Work

01:01:33 Success Was Never a Straight Line

01:07:24 Don’t Let Greatness Become Familiar

01:11:12 Living with Anxiety When Life Doesn’t Slow Down

01:17:26 Building a Healthier Relationship with Alcohol

01:19:29 How Tracking Your Fitness Can Change You

01:22:00 Bert on Final Five

Episode Resources:

Bert Kreischer | Website

Bert Kreischer | Instagram

Bert Kreischer | X

Bert Kreischer | YouTube

Bert Kreischer | TikTok

Bert Kreischer | Facebook

See omnystudio.com/listener for privacy information.