For some, success is elusive while for others, it’s years of hard work and dedication.

But how can one truly and effectively achieve success?

How can we be as successful as the leaders we look up to?

Today, in the On Purpose podcast, Jay sits down with New York Times Bestselling Author, Alli Webb. After spending 15 years as a professional hairstylist, in 2010, she pioneered the Drybar concept, a chain of hair salons known for blowout services that quickly expanded nationwide. Jay and Alli go in depth about what the journey was behind creating a business to eventually selling the company for $225 million! Alli’s remarkable journey has landed her on the cover of Inc. Magazine, Fast Company's "100 Most Creative People in Business" list, Fortune magazine's "40 Under 40," and more.

Alli and Jay explored the messy truth about starting something new– whether it’s a business or a relationship. They also talked about the importance of intuition and paying attention to red flags in entrepreneurship and the role of passion and love for what you do.

You will also learn about how Alli balances her personal and professional life and the difficulty of navigating and ending a marriage. Remember that sometimes, we won’t always have the ‘perfect ending’ in our stories, and that’s okay.

In this interview, you'll learn:

The messy truths of entrepreneurship

The importance of acknowledging imposter syndrome and using it as a source of motivation and growth

The challenges and risks associated with starting and running a business

How to take feedback as a gift

How to cope with life changes and challenges

Remember that the most beautiful masterpieces are often created from the messiest of beginnings.

With Love and Gratitude,

Jay Shetty

What We Discuss:

00:00 Intro

02:50 Success Is Messy

03:55 The Truth About Starting A Business

05:55 Anyone Can Be An Entrepreneur

07:40 ‘I never thought I would be successful’

10:30 From Hobby To Business

13:20 DON’T Think About The Money

14:26 The 2 Secrets To Success

15:56 Being Right Or Being Delusional?

20:05 How To Find Your Passion

22:04 Finding The Right Business Partners

25:31 Making Your Idea Work

27:21 Dealing With Potential Failure

29:22 Feeling Like An Imposter

33:00 The One Piece Of Advice For Success

37:00 How To Accept Criticism

40:50 Can You Be Successful AND Happy?

45:10 Finding Love During Chaos

48:25 Navigating Challenges In A Relationship

51:15 How To Balance Your Life

54:01 Finding Closure Within Yourself

57:30 How To Cope With Uncertainty

1:00:29 Hardest Part Of Divorce

1:04:58 What Do You Need To Change About Yourself?

1:07:33 Dealing With Trauma

1:11:41 Alli’s Best Advice

1:19:00 Alli On Final Five

Episode Resources:

Alli Webb | Website

Alli Webb | Instagram

Alli Webb | TikTok

Alli Webb | Book

See omnystudio.com/listener for privacy information.

Episode 264 - Jesus teaches the Parable of the Good Samaritan - Sunday July 13, 2025 - Lk 10:25-37