EP. 1883

01/30/26

Kendra Scott

CONQUER YOUR FEAR OF FAILURE ONCE AND FOR ALL

Why I Cried Myself to Sleep Running a Billion-Dollar Brand

Kendra Scott reveals the shocking truth about 2020: while the world saw a billion-dollar brand thriving, she was sobbing herself to sleep every night, feeling like a complete fraud.

From dropping out of college to build a hat company that failed, to becoming a single mom starting over with $500 worth of jewelry supplies, Kendra’s path to building one of America’s most beloved jewelry brands was anything but glamorous.

She opens up about the moment she closed her first business in the pouring rain, saw a sign that said “Yes, We’re Open,” and realized failure was simply the bridge to her next breakthrough.

Whether you’re struggling to start, scared to pivot, or exhausted from trying to be perfect for everyone else, this conversation will show you how vulnerability becomes your greatest competitive advantage and why your mess is actually your message.

Buy a copy of Kendraโ€™s book: Born to Shine: Do Good, Find Your Joy, and Build a Life You Love

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And now let’s jump into episode 1883 of The School of Greatness!

Some Questions I Ask:

  • But how did you overcome all these obstacles? In the last few years. And how long did that stress or pain last for?
  • What is the thing that most people don’t see? What is the biggest insecurity, shame, or fear that you never share, that people, if they knew you were working on overcoming would see you differently?
  • How long did it take you until you said you’re, to start stepping into being a hundred percent authentic as opposed to controlling an identity or an image that you wanted another to see?
  • If you could go back 20 years ago when you started and been the a hundred percent authentic, you public facing. Where do you think you’d be today? Or do you think it worked out perfectly, the lessons you needed to learn from that journey?
  • What was your biggest fear then? Was it failure or success?
  • Was there ever a time where you didn’t love yourself?
  • If you could go back and tell her to learn three specific skills. It could be personal skills, emotional skills, business skills. What skills do you wish you would’ve been able to learn faster at 20?
  • What would you do if you could go back and speak to 20-year-old Kendra? What would you say to her about love?

In this episode, you will learn:

  • Break through the dangerous myth of balance and perfection that keeps you playing small and burning out
  • Uncover the power of making genuine connections before transactions, and why cupcakes and champagne might be your secret weapon
  • Discover why treating failure as a gift instead of a death sentence unlocks exponential growth in business and life
  • Transform your relationship with vulnerability and learn how being authentic attracts the right people, opportunities, and success
  • Master the art of pivoting when life shakes your snow globe, turning recessions and setbacks into rocket fuel for your next level
  • Plus much more…

Show Notes:

The School of Greatness Podcast
The School of Greatness Podcast

The School of Greatness Show

The School of Greatness shares inspiring interviews from the most successful people on the planetโ€”world-renowned leaders in business, entertainment, sports, science, health, and literatureโ€”to inspire YOU to unlock your inner greatness and live your best life.