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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Payal Kadakia Pujji: ON the Self Discipline Needed to Become an Entrepreneur

Payal Kadakia Pujji: ON the Self Discipline Needed to Become an Entrepreneur

If you want to feel motivated and encouraged to be a little more self-disciplined, you will love this weeks episode with Payal Kadakia.She is the founder and chairman of ClassPass as well as the artistic director for the Sadance company.In this conversation, she shares how she achieved her entrepreneurial success at such a young age with her incredible work ethic and unparalleled self-discipline.See omnystudio.com/listener for privacy information.

29 Apr 20191h 13min

3 Ways to Know How Long it Takes to Fall in Love

3 Ways to Know How Long it Takes to Fall in Love

How long should it take to fall in love?Is what you’re experiencing the real thing or is it just infatuation?Whether you have just started dating someone and felt love immediately or if you’ve been in a relationship for a long time and still aren’t sure where it’s going, here are 3 ways to find out how long it might take for you to truly fall in love with someone.See omnystudio.com/listener for privacy information.

26 Apr 201922min

Zachary Levi: ON Growing from Depression, Anxiety, and Mental Health

Zachary Levi: ON Growing from Depression, Anxiety, and Mental Health

On this week's episode, Shazam’s Zachary Levi opens up like never before.He shares his personal struggles with depression, anxiety and mental health as well as how meditation, prayer, and therapy have helped him grow from it all.If you are going through a tough time, this episode will help you shift your mindset and trust that, as cliche, as it sounds, everything happens for a reason.See omnystudio.com/listener for privacy information.

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3 Ways to Grow Your Passion Even With a Full Time Job

3 Ways to Grow Your Passion Even With a Full Time Job

How many of us are scared of leaving our current jobs even though we know we're not living up to our full potential?Maybe because of the money, security, or prestige?In this episode, I'll give you step by step tips on how you can grow your passion even with a full-time job.See omnystudio.com/listener for privacy information.

19 Apr 201930min

Humble The Poet ON: Quitting His Job to Become an Artist

Humble The Poet ON: Quitting His Job to Become an Artist

It’s so easy in the world that we live in where everyone sees quotes on Instagram, motivational sayings everywhere, to think you’re deep...without being deep.So today we’re going to do some unlearning with our wordsmith of a guest - Humble the Poet.We talk about becoming conscious of and taking ownership over your unconscious biases, unlearning old habits and ideas that may no longer serve you, and how to not only survive but thrive.See omnystudio.com/listener for privacy information.

15 Apr 20191h 18min

7 Things to Do This Weekend to Boost Your Mental Health

7 Things to Do This Weekend to Boost Your Mental Health

You don’t have to be struggling with anxiety, or stress, or pressure to focus on boosting your mental health.So if your mind is telling you right now, “I don’t need to hear this, I feel great.” Then please give this episode a listen.Just like you don’t need a physical challenge to go to the gym, you don’t need a mental challenge to go to the mind gym.See omnystudio.com/listener for privacy information.

12 Apr 201925min

Chelsea Handler: ON How Therapy Changed Her Life

Chelsea Handler: ON How Therapy Changed Her Life

If you’re on the fence about whether or not you can learn anything from therapy you’ll be interested to hear Chelsea open up about how it completely changed her life.She gets candid about losing her brother at such a young age and how she’s using tools she learned in therapy to cope with it now. Her vulnerability in this episode is inspiring for anyone who has had to deal with loss in their life. Just remember, I AM. Identification, Awareness, Modification.See omnystudio.com/listener for privacy information.

8 Apr 201942min

4 Types of Negative People & 3 Ways to Deal With Them

4 Types of Negative People & 3 Ways to Deal With Them

We all have friends that we love but are absolutely draining to talk to. Every time they call you, you know exactly what you’re in for.  No matter how hard we try to optimize for the optimistic, negative people will always be a part of each of our lives and that’s okay.  In this episode, we take a look at the 4 different types of negative people and 3 ways to proactively deal with them.See omnystudio.com/listener for privacy information.

5 Apr 201925min

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