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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Lilly Singh: ON Why She Took A Break From YouTube

Lilly Singh: ON Why She Took A Break From YouTube

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.Being a YouTube creator can be difficult for anyone, but Lilly Singh really is superwoman. Despite the success, things haven’t always been easy for Lilly. She opens up about everything: how it feels when being called a role model, her relationships both personal and professional, even her struggles with depression and defining what success looks like in her life. Today’s conversation is a deep dive into what drives her to keep creating at such a prolific level and why she’s determined to keep using her influence for positive social change.See omnystudio.com/listener for privacy information.

4 Maalis 20191h 16min

3 Reasons I Became a Monk for 3 Years

3 Reasons I Became a Monk for 3 Years

In today’s episode I share what led me to becoming a monk and most importantly why I did it, so that it might help you become more clear on your decision making.I’d like to share with you the thought process I learned from my mentors that will help guide you through making the biggest decisions of your life.Are you planting seeds or weeds?See omnystudio.com/listener for privacy information.

1 Maalis 201927min

Mike Posner: ON How Fame Ruined His Life

Mike Posner: ON How Fame Ruined His Life

Mike Posner is the musician behind the hit songs I Took A Pill In Ibiza and Cooler Than Me. But behind the flashing lights and sold-out shows lies a very unique mind, one that has learned to deal with fame and fortune and most recently—the loss of his father. On today’s episode, Mike shares his insights on how to deal with loss, why moments of epiphany must be processed, and what the difference between the mind and intelligence is. Mike even turns the table on Jay—and asks him many profound questions about his own experience unpacking mindfulness.  Tune in to this episode to catch a glimpse of the mechanics behind this singer-songwriter’s brain.See omnystudio.com/listener for privacy information.

25 Helmi 20191h 24min

3 Lessons I Learned From My Ex

3 Lessons I Learned From My Ex

Breakups are hard there’s no doubt about that, but sometimes break-ups lead to break-throughs. Don’t worry, it’s normal to have feelings of bitterness, blame, or even have a breakdown. You are not alone.We cover a lot in today’s episode so whether you’re looking to strengthen your current relationship or need a little help getting through a past one you’re not going to want to miss this.See omnystudio.com/listener for privacy information.

22 Helmi 201927min

Novak Djokovic: ON One of the Greatest Comebacks in History

Novak Djokovic: ON One of the Greatest Comebacks in History

Most people, even non-sports fans are inspired by world class athletes like Novak… but why?To be world class at anything it takes more than natural skill, it takes physical, personal, spiritual development and a healthy relationship with one’s own ego to begin a fulfilling journey to greatness - something we are all capable of, given we know how to use the appropriate tools.In today’s conversation, Novak shares everything.He even takes us back to his childhood where he remembers confiding to his tennis coach instead of his own parents about the growing pains of being a young man.See omnystudio.com/listener for privacy information.

18 Helmi 201959min

Russell Brand: ON How He Nearly Ruined His Career

Russell Brand: ON How He Nearly Ruined His Career

You may think you know Russell Brand - the actor, the comedian, ect... but that’s only a small part of who he truly is.Prepare yourself, today’s conversation gets intimate.Russell opens up about his struggles with addiction, his experience chasing fame, money, sex, and why that’s not something people should aspire to. He shares what has enlightened and led him to a life of sobriety for over 14 years now and the role mentors and spirituality has played in getting him there.He even shares some surprising wisdom from a mutual friend of Puff Daddy, comparing the challenges of life to levels in a video game.See omnystudio.com/listener for privacy information.

15 Helmi 201943min

Jay Shetty Interviews His Wife for the First Time

Jay Shetty Interviews His Wife for the First Time

On the first episode of On Purpose, I have an extremely special guest for you.For the first time ever, and on Valentine’s Day, I’m interviewing my wife, Radhi Shetty.We discuss health, happiness, and the components of a successful relationship. Radhi is a plant-based dietitian, recipe developer, and Ayurvedic medicine enthusiast.Enjoy episode one, and live your life today on purpose.You can follow Jay's wife on Instagram @veggieveganvedaSee omnystudio.com/listener for privacy information.

14 Helmi 20191h 33min

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