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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Rob Dyrdek: ON Dropping Out of School and Becoming an Entrepreneur

Rob Dyrdek: ON Dropping Out of School and Becoming an Entrepreneur

You may know Rob as a former pro skateboarder and the host of MTV’s Ridiculousness, but this conversation is going to show you inside his mind.He’s an incredible strategist, such a planner, someone who is so meticulous - something you don’t see in his persona in his shows.You’re going to see a completely different side of the one and only Rob Dyrdek.See omnystudio.com/listener for privacy information.

1 Apr 20191h 20min

Can You Be Friends with Your Ex? 3 Things to Think About Before You Do

Can You Be Friends with Your Ex? 3 Things to Think About Before You Do

When it comes to relationship questions this is probably the toughest one - can you be friends with your ex?Is it the right decision? Well, it’s complicated.Today’s episode I’m going to share with your some of the studies, insights, and thoughts that are going to help you decide for yourself.See omnystudio.com/listener for privacy information.

29 Mars 201925min

Gisele Bundchen: ON Being Kinder To Yourself

Gisele Bundchen: ON Being Kinder To Yourself

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.Gisele’s wisdom goes deep - from reading the Bhagavad Gita between breaks on the runway to falling in love with discipline in her childhood, you’ll be able to tell immediately there’s much more to her than just being one of the world’s most famous supermodels.See omnystudio.com/listener for privacy information.

25 Mars 201925min

3 Reasons Why Compatibility Is More Important Than Chemistry

3 Reasons Why Compatibility Is More Important Than Chemistry

How do you know when you’ve found the one or if you’re even compatible with someone?Whether you’re messaging someone on a dating app, dating someone right now, or you’ve been with someone for a while, knowing why compatibility is important is key.Today we’ll look at 3 reasons why compatibility is more important than chemistry and how you can apply this knowledge to your next relationship or strengthen your current one.See omnystudio.com/listener for privacy information.

22 Mars 201925min

David Goggins: ON Dealing With Childhood Traumas

David Goggins: ON Dealing With Childhood Traumas

Prepare yourself, today we deliberately get uncomfortable and talk about pain.David fearlessly shares his past with us, how he’s overcome past childhood traumas and why he pushes himself so hard to show what’s possible.This conversation will move you and hopefully help give you the tools to dive deeper in yourself and really question why you feel the way you do about being uncomfortable.See omnystudio.com/listener for privacy information.

18 Mars 20191h 8min

3 Myths About Manifesting Your Dream Job and 3 Ways to Start Doing It Right

3 Myths About Manifesting Your Dream Job and 3 Ways to Start Doing It Right

There’s a lot of misinformation around the concept of manifestation, so today we’re going to dispel some myths.We’ll talk about the importance of intention, why the best intentions are meaningless without action, and a framework you can use to start manifesting your ideal job today.Enjoy!See omnystudio.com/listener for privacy information.

15 Mars 201929min

Daniella Monet: ON Body Image, Eating Disorders and Self Love

Daniella Monet: ON Body Image, Eating Disorders and Self Love

Daniella’s candor in this episode is amazing.She opens up about her personal struggles with family, body image, finding purpose, learning to love herself, and shows us how she’s been able to use the negative experiences in her life to inspire people around the world.We discuss why it’s the day to day grind, and work put into personal relationships that sets us up for success, rather than the social media milestones.See omnystudio.com/listener for privacy information.

11 Mars 201955min

8 Reasons Why People Cheat and 3 Things To Do About It

8 Reasons Why People Cheat and 3 Things To Do About It

All of us know someone who has had the unfortunate experience of being cheated on, maybe it’s even happened to you.Whether cheating has happened to you in the past or are just looking to strengthen your current relationship, this episode is for you.We take a look at the science and statistics behind why people cheat and proactive steps to avoid future cheaters as well as help mend the burns from old flames.See omnystudio.com/listener for privacy information.

8 Mars 201925min

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