Jan. 7, 2026

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

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

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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