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 m...
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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