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.

Do you ever feel like who you are is holding you back?

Can you really change your personality — or are you stuck with it for life?

Today, Jay sits down with award-winning journalist and author Olga Khazan, whose groundbreaking book Me But Better explores the science of personality change. As a staff writer at The Atlantic, Olga has spent years investigating what shapes who we are — and whether it’s possible to become more confident, resilient, and fulfilled by intentionally shifting our traits.

Jay and Olga explore the surprising research showing that personality isn’t fixed — and that with consistent effort, anyone can become a different version of themselves. Olga shares how she transformed traits like anxiety and self-doubt by applying science-backed tools and testing them in her own life.

They dive deep into how habits shape identity, why a strong “why” is essential for lasting change, and how the traits we envy in others might point us toward who we’re meant to become. They also unpack the difference between being “authentic” and being stuck — and why growth often looks like discomfort before it feels natural.

In this episode, you’ll learn:

How to Change Personality Traits You’ve Had for Years

How to Shift from Anxiety to Emotional Balance

How to Use Habits to Redefine Who You Are

How to Identify the Traits That Align with Your Goals

How to Stop People-Pleasing Without Becoming Cold

How to Make Growth Feel Authentic — Not Fake

True change doesn’t come from pretending to be someone else — it comes from becoming the person you were always capable of being. This episode is a powerful reminder that you’re not stuck. With intention, action, and the right mindset, you can grow into someone new.

With love and gratitude,

Jay Shetty

What We Discuss:

00:00 Introduction

02:08 Key Takeaways From Olga

03:03 Frustration As A Block

05:22 Research Says We Can Change Our Personality Traits

07:30 Why Do We Get So Stuck?

09:46 Is Personality Change Age Exclusive?

11:47 How Can We Change Our Personality?

17:34 Changing Habits Vs Personality Traits

24:31 How Long Does It Take To Change Personality Traits?

35:09 Gender Effects On Personality Traits

37:36 5 Personality Traits That Make Up Personality

41:35 Feeding Motivation For Change

51:46 How Can We Be More Extroverted?

54:04 Exposure Therapy For Introverts

56:56 How Personality Changes Affects The People Around Us

01:01:43 The Social Investment Theory

01:03:15 How Does The SIT Affect Relationships?

01:06:45 From Pessimism To Optimism

01:09:31 How People Pleasers Can Create Healthy Boundaries

01:14:35 Can Introverts Become Extroverts?

01:18:24 Can People With Depression & ADHD Change Their Personality?

01:21:25 Olga On Final Five

Episode Resources

Olga Khazan | Instagram

Olga Khazan | X

Olga Khazan | LinkedIn

Olga Khazan | Facebook

Me, But Better: The Science and Promise of Personality Change

See omnystudio.com/listener for privacy information.

Today, Jay dives into a feeling many of us know well: the sense that nothing in life is going the way we hoped. Whether your career feels stuck, your relationships feel off, or you’re just not where you thought you’d be by now. Jay reminds us that feeling stuck doesn't mean you've failed, but could be life giving you a moment to pause and reset. Jay explains that the way we experience reality depends on what we choose to focus on. When we're fixated on what's going wrong, we often miss the small signs that things are already starting to move forward.

Jay also challenges the idea that success is supposed to be linear or perfect. He reminds us that the people who seem ahead aren’t more talented, they just started sooner. Rather tha comparing ourselves to someone else’s timeline, Jay encourages us to focus on our own path and let go of the pressure to have it all figured out. Instead of trying to achieve something massive all at once, Jay encourages us to “shrink the vision, save the dream,” and take small, consistent steps that compound into real transformation. He reminds us that a plateau isn’t a setback, it’s a season of quiet growth that often comes right before a breakthrough.

In this episode, you'll learn:

How to Break Mental Overload with Movement

How to Take Action Before You Feel Ready

How to Stop Waiting for the Perfect Time to Start

How to Reframe Feeling Stuck

How to Build Momentum with Tiny Steps

No matter where you are in your journey, remember this: you’re not behind, you’re not broken, and you haven’t missed your chance. Feeling stuck doesn’t mean you’re failing, it means you’re in the middle of growth.

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

01:06 Does It Feel Like Nothing's Working?

02:38 What is the Frequency Illusion?

04:39 Step #1: Stop Trying to Feel Motivated

10:04 Step #2: Break the Mental Spiral

12:07 Step #3: There is No ‘Right’ Time to Start

16:14 Step #4: Consistency Outlasts Talent

24:35 Step #5: Shrink the Vision, Save the Dream

See omnystudio.com/listener for privacy information.