Jay’s Must-Listens: Want to Quit Your 9-5? 5 CEO’s Share the Exact Steps to Start Your Own Successful Business (No Business School Needed!)

Jay’s Must-Listens: Want to Quit Your 9-5? 5 CEO’s Share the Exact Steps to Start Your Own Successful Business (No Business School Needed!)

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.

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Chrissy Metz: On How She Went From Having 81 Cents to Being the Star of This Is Us

Chrissy Metz: On How She Went From Having 81 Cents to Being the Star of This Is Us

Chrissy Metz (This is Us, Breakthrough) is an American Emmy- and Golden Globe-nominated actress, singer, and producer. I sat down with Chrissy to discuss how she went from having 81 cents in her bank account to landing the lead role in NBC’s hit drama series This Is Us. She dives into why she stopped putting pressure on herself to succeed and how she dealt with people constantly telling her “no” in her life. We also got into why you should never be afraid to lose the person you’re with, how to love someone the way they need to be loved and a breakdown of fight languages vs. love languages.See omnystudio.com/listener for privacy information.

24 Juni 20191h 15min

3 Myths About Finding Your Purpose and 3 Ways to Align With It

3 Myths About Finding Your Purpose and 3 Ways to Align With It

Everyone always talks about finding your passion and finding your purpose, but nobody talks about how to actually align with it.The truth is, that regardless of how many experiences we might have: vacations,  relationships, trips, etc. if we don’t align with our purpose, our journeys won’t feel as meaningful.Now, there are so many things that can hold us back like money, practicality or timing but in this episode, I give you 3 concrete steps you can use to look past those reasons and start aligning with your purpose.See omnystudio.com/listener for privacy information.

21 Juni 201931min

Gary Vee ON: How to Stop Caring What Other People Think of You

Gary Vee ON: How to Stop Caring What Other People Think of You

You can order my new book 8 RULES OF LOVE at 8rulesoflove.com or at a retail store near you. You can also get the chance to see me live on my first ever world tour. This is a 90 minute interactive show where I will take you on a journey of finding, keeping and even letting go of love. Head to jayshettytour.com and find out if I'll be in a city near you. Thank you so much for all your support - I hope to see you soon.On this special episode of On Purpose, I got to sit down with my good friend Gary Vee.Gary is an investor, a serial entrepreneur and a 5 time New York Times bestselling author.We got to talk in depth about how to stop caring what people think about you, why you should focus on happiness not hustle and why you need to contextualize advice before you decide to listen to it.There are so many teachable moments in this episode and I know you will learn so much!See omnystudio.com/listener for privacy information.

17 Juni 20191h 9min

The Shocking Ways We Spend Our Time and 9 Ways to Invest it Better

The Shocking Ways We Spend Our Time and 9 Ways to Invest it Better

How many times have you caught yourself being on your phone when you should be doing something else? Or maybe you’re productive for 5 minutes and then take a 2-hour break when you get distracted. We all do it, but there are ways to be more productive and achieve more in your day. In this episode, you’ll learn how to build habits that will stop you from wasting your time and help you start investing it in things that actually matter.See omnystudio.com/listener for privacy information.

14 Juni 201929min

Ray Dalio: ON How to Define Success for Yourself and Set Your Goals

Ray Dalio: ON How to Define Success for Yourself and Set Your Goals

On this episode of On Purpose, I sat down with billionaire investor, Ray Dalio.We talk about why pain is necessary in order to make progress and why we shouldn’t focus on being right all the time. Dalio also reveals what he believes is the greatest tragedy of mankind and gives us 5 steps to achieving success.If you’ve ever wanted insight into how billionaires think, this episode is for you!See omnystudio.com/listener for privacy information.

10 Juni 201949min

6 Healthy Ways to Heal and Move On From Heartbreak

6 Healthy Ways to Heal and Move On From Heartbreak

In this episode of On Purpose, I’m discussing healthy ways to deal with heartbreak. I share how you need to feel before you heal, why you should never define your self worth by how someone treats you and how to stop looking at love as a noun and start treating it as a verb. I know heartbreak is one of the worst pains you can feel so I hope these tips can help you healthily heal.See omnystudio.com/listener for privacy information.

7 Juni 201928min

Charlamagne: ON Being Open About Mental Health

Charlamagne: ON Being Open About Mental Health

In this episode of On Purpose, I sat down with the co-host of the nationally syndicated hip-hop radio program The Breakfast Club, Charlamagne Tha God. We discussed everything from his biggest fears, his struggles with mental health and his unique take on parenting.See omnystudio.com/listener for privacy information.

3 Juni 201957min

3 Things To Do Before Work to Increase Focus and Productivity

3 Things To Do Before Work to Increase Focus and Productivity

“Some people are dreaming of success and others are waking up and making it happen.”You snooze your alarm, scarf down half of your breakfast and run out the door to make it to work on time. Sound familiar? The truth is that when we start our days like this, we are not as productive. But in this week’s episode, I give you practical tips on how to change that. 4 things you’re going to learn from this episode: How to be more productive at work? How to make mornings more purposeful? Why I wake up at 6am every day? What is decision fatigue and how can we fight it?See omnystudio.com/listener for privacy information.

31 Maj 201927min

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