Lessons - From Secretary to Overstock President | Stormy Simon - Former Overstock.com President

Success Story with Scott D. Clary

Lessons - From Secretary to Overstock President | Stormy Simon - Former Overstock.com President

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Published on Jan 7, 2026, 6:06:36 PM
Total time: 00:14:20

Episode Description

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In this "Lessons" episode, Stormy Simon, former President of Overstock.com, reflects on her journey from secretary to executive leadership and what it truly means to bet on yourself. She shares how necessity, responsibility, and self-trust pushed her to take uncomfortable risks, while redefining success beyond money, titles, or external validation. Stormy explains why curiosity and continuous growth matter more than status, and how recognizing patterns of stagnation became a signal to move forward. She also opens up about staying grounded through massive success, finding freedom on her own terms, and aligning life decisions with personal values rather than societal expectations.

 

➡️ Show Links

https://successstorypodcast.com  

YouTube: https://youtu.be/zA6FnGKhPT0 

Apple: https://podcasts.apple.com/us/podcast/stormy-simon-entrepreneur-equity-advocate-breaking/id1484783544 

Spotify: https://open.spotify.com/episode/0YHm9qv1avurZTABkf1t09 

 

➡️ Watch the Podcast on YouTube

https://www.youtube.com/c/scottdclary 

 

More about Success Story with Scott D. Clary

Welcome to the Success Story Podcast, hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary (@scottdclary). On this podcast, you'll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups and entrepreneurship. Scott will discuss some of the lessons he's learned over his own career, as well as have candid interviews with execs, celebrities, notable figures and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas and insights. He sits down with leaders and mentors and unpacks their story to help pass those lessons onto others through both experiences and tactical strategy for business professionals, entrepreneurs and everyone in between. To get more of the Success Story podcast, go to www.successstorypodcast.com.