Today, Jay sits down with serial entrepreneur, investor, and powerhouse mom of four, Kim Perell. Known for building her first company from her kitchen table and later selling one for $235 million, Kim shares the raw, behind-the-scenes truth of what it takes to turn failure into fortune. The conversation centers around Kim’s latest book, Mistakes That Made Me a Millionaire, and offers a heartfelt blueprint for anyone feeling stuck, unfulfilled, or uncertain about their next move.

Jay and Kim explore why perfectionism can sabotage progress, how fear often masks itself as procrastination, and why waiting to feel “fully qualified” often leads to missed opportunities. Kim introduces her 70% rule: a concept that encourages action over hesitation and reveals how taking small, imperfect steps helped her overcome self-doubt and build extraordinary businesses. The two also dive into the power of mentorship, the emotional toll of toxic relationships, and why surrounding yourself with the right people is crucial not just for professional growth, but for personal evolution.

In this interview, you'll learn:

How to Start a Business Before You Feel Ready

How to Use the 70% Rule to Make Bold Decisions

How to Find the Right Mentor and Build a Real Relationship

How to Stand Out When Pitching Yourself

How to Know When It’s Time to Pivot Your Business

How to Build a Winning Team Without Doing Everything Yourself

How to Audit Your Inner Circle for Growth and Clarity

Making mistakes doesn’t mean you’ve failed, it means you’re showing up, learning, and trying something new. No success story is smooth or simple, but all of them prove that progress is always possible.

With Love and Gratitude,

Jay Shetty

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What We Discuss:

00:00 Intro

02:57 How to Get Unstuck and Move Forward

04:17 When It’s Time to Pivot Your Career

05:50 Is Regret More Powerful Than Fear?

08:06 You Don’t Need To Be 100% Ready To Start

09:52 Are You Ever Really Ready?

11:29 Dream Big, But Start Where You Are

13:09 The Power of Believing in Your Vision

15:24 Be Delusionally Confident

16:29 How Mistakes Help You Iterate and Improve

18:30 How to Silence the People Who Doubt You

22:15 Teaching Kids to Embrace Failure

23:20 Rejection as Redirection

26:02 The Difference Between Innovating and Iterating

29:14 Build a Support System That Elevates You

31:51 How to Find Mentors Who Truly Guide You

33:55 Why Asking for Help Accelerates Growth

34:44 How Books Can Mentor You Too

38:21 The Four People Every Entrepreneur Needs

39:35 Why You Need the Right Peers Around You

41:58 Should You Start a Business with Family?

44:00 How to Audit Your Inner Circle

46:02 How Toxic People Drain Your Energy and Money

47:17 The Power of Taking Initiative

48:56 Don’t Let Your Past Limit Someone Else’s Future

51:19 How to Lead and Manage People Effectively

53:17 What Actually Gets You Hired Today?

57:51 Going the Extra Mile Sets You Apart

01:00:01 The Biggest Mistake Is Not Asking

01:04:03 Why So Many of Us Feel Unqualified

01:07:07 Pivoting Is the Secret to Success

01:10:13 How to Know When It’s Time to Pivot

01:11:53 Kim on Final Five

Episode Resources:

Kim Perell | Website

Kim Perell | Instagram

Kim Perell | Facebook

Kim Perell | YouTube

Kim Perell | LinkedIn

Kim Perell | X

Kim Perell | TikTok

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