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

EPISODE · Jan 30, 2026 · 1H 22M

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

from The School of Greatness · host Kendra Scott, Lewis Howes

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 Kendra’s book: Born to Shine: Do Good, Find Your Joy, and Build a Life You LoveIn this episode you will:Break through the dangerous myth of balance and perfection that keeps you playing small and burning outUncover the power of making genuine connections before transactions, and why cupcakes and champagne might be your secret weaponDiscover why treating failure as a gift instead of a death sentence unlocks exponential growth in business and lifeTransform your relationship with vulnerability and learn how being authentic attracts the right people, opportunities, and successMaster the art of pivoting when life shakes your snow globe, turning recessions and setbacks into rocket fuel for your next levelFor more information go to https://lewishowes.com/1883For more Greatness text PODCAST to +1 (614) 350-3960More SOG episodes we think you’ll love:Lewis Howes [SOLO]Michelle ObamaSage Robbins Get more from Lewis! Get my New York Times Bestselling book, Make Money Easy!Get The Greatness Mindset audiobook on SpotifyText Lewis AIYouTubeInstagramWebsiteTiktokFacebookX Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

This conversation will transform how you see failure, success, and what it truly means to shine your light in the darkest moments. You'll discover why the recession that nearly destroyed Kendra Scott's jewelry empire became the greatest gift her business ever received.

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

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This episode is 1 hour and 22 minutes long.

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This episode was published on January 30, 2026.

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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...

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