Success Story with Scott D. Clary

Episode: Lessons - From Secretary to Overstock President | Stormy Simon - Former Overstock.com President
Date: January 7, 2026

Episode Overview

In this candid, insightful episode, host Scott D. Clary sits down with Stormy Simon, the former president of Overstock.com, to unearth what it means to truly bet on oneself and redefine success beyond traditional markers like money or title. Together, they explore Stormy’s unique journey from single mom and secretary to corporate president, and the personal philosophies she developed along the way: courage through necessity, prioritizing self-growth, and staying grounded in the face of growing responsibility and external pressures, especially as a pioneering female executive.

Key Discussion Points & Insights

1. Betting on Yourself and Self-Reliance

• Life circumstances fueled necessity:
  • Stormy shares that as a single mom, betting on herself wasn’t a choice as much as a necessity. There was no one else to count on, which built a unique type of self-trust and determination.
    • “As a single parent, there was no one else to bet on. It was me or nobody… making it happen, that was just me.” (03:11)
  • Family support was there emotionally, but not financially:
    • “They thought I was awesome. But when it came down to making it happen, that was just me.” (03:22)
• No single definition of success for everyone:
  • Stormy challenges society’s shallow tendency to equate success strictly to earnings.
    • “People measure success by money, and that's a pretty shallow measure.” (03:53)

2. Pursuing Growth Over Comfort

• Avoiding life on repeat:
  • For Stormy, personal curiosity and continual learning were always more powerful drivers than stability or prestige.
    • “Once I hit a repeat of, ‘Oh God, I don't want to do this today,’ I couldn't do it... You get up and do it again and again. How—I don't want to wake up.” (04:42)
• Value of new experiences:
  • She emphasizes deriving meaning and avoiding stagnation by seeking diverse challenges rather than getting fixated on external rewards.

3. Redefining Success and Maintaining Groundedness

• Honesty about financial realities:
  • Stormy is open about her struggle as a young, single mom, recalling the fear of not being able to keep the lights on for her kids, and highlights that many live this reality. She keeps those memories close to retain perspective even as she attained traditional “success.”
    • “I'll always identify as the welfare mom. I know what it's like to be totally afraid to have your lights shut off with children. It's terrifying.” (05:57)
• Grounding through adversity:
  • Success never removed her connection to her roots.
    • “How did you stay grounded through all this… now you still know that what’s happiness and success for you? And it’s freedom.” (06:35)
  • Stormy admits she wasn’t always grounded, but grew to be by remembering her core values:
    • “I wouldn't say I stayed grounded the whole time. I’m more grounded now… I walked in pretty grounded with a lot of—just the spiritual way that I lead my life.” (07:34)
• Responsibilities and shifting perspectives as a leader:
  • She reflects on leading through ten career phases at Overstock, handling growth from “an apartment to 100 million. We grew the business to 2 billion,” and acknowledges that leadership sometimes demanded emotional suppression she later recognized as detrimental (“There are some emotions you simply have to turn off… You don’t see it when you’re in it, you see it when you’re out of it.” 17:04–17:38)

4. Navigating Corporate America as a Woman

• Facing stereotypes and adversity:
  • Stormy is forthright about the unique prejudices and rumors women in leadership face, particularly regarding their relationships with powerful male colleagues:
    • “It’s easier sometimes for people to say for a woman… ‘she must have slept with the boss’… The truth is, it would have been way easier to sleep your way to the top. I was spending 15 hours a day as a female.” (10:14)
  • She never allowed herself to be a victim, focusing instead on the company mission and “navigating” rather than “conquering” adversity:
    • “Any time there was that type of situation, I got through it. Not as a conqueror… but as a navigator.” (10:43)
• Empowering other women:
  • Inspired in part by her own negative experiences, Stormy took action to create systemic change at Overstock, increasing female representation in leadership to 33%:
    • “…you increased the female seats… or women that were at the executive table to 33%. Like, there was a lot of [change].” (13:16)

5. The Era Before the #MeToo Movement

• On leaving Overstock and reflecting on shifting awareness:
  • Stormy discusses how her departure came right as the #MeToo movement broke, and how it was a pivotal social moment:
    • “…when I left Overstock, it was for many reasons… But when you’re allowed to tell your story… that’s the movement we need to get to.” (16:09)
  • She notes that true empowerment comes when sharing a story isn’t seen as holding a grudge or weaponizing experience, but as honest self-expression.

Notable Quotes & Memorable Moments

• Self-Reliance:
  “As a single parent, there was no one else to bet on… making it happen, that was just me.” - Stormy Simon (03:11)

• Redefining Success:
  “People measure success by money, and that's a pretty shallow measure.” - Stormy Simon (03:53)

• Learning and Growth:
  “The knowledge and curiosity of what I don’t know… we get one life. So how much can you learn or experience in one day, every day, and not have too much on repeat?” - Stormy Simon (04:51)

• On Staying Grounded:
  “I wouldn’t say I stayed grounded the whole time. I’m more grounded now… I walked in pretty grounded with a lot of—just the spiritual way that I lead my life.” - Stormy Simon (07:34)

• Navigating Sexism:
  “The truth is, it would have been way easier to sleep your way to the top… I was spending 15 hours a day as a female… because there was so much greatness to be done.” - Stormy Simon (10:11, 10:21)

• Leadership and Hard Choices:
  “There are some emotions you simply have to turn off… You don’t see it when you’re in it, you see it when you’re out of it.” - Stormy Simon (17:04–17:38)

Important Timestamps

• 03:01 – Stormy describes when and why she "bet on herself."
• 04:35 – The danger of living life on repeat; importance of curiosity.
• 07:32 – How her grounding and perspective changed through her career.
• 10:11 – Confronting and navigating gender-based adversity in leadership.
• 13:16 – Structural change at Overstock: increasing women in executive roles.
• 15:56 – The cultural moment on leaving Overstock as the #MeToo movement broke.
• 17:04–17:38 – Leader’s self-reflection on difficult decisions and personal change during a high-powered career.

Conclusion

Stormy Simon’s story, as told in this episode, is more than a blueprint for professional ascent—it’s a lesson in trusting oneself amid necessity, redefining personal success, and confronting systemic challenges with determination, empathy, and candor. Her path, marked by both practical learning and deeply personal growth, is a compelling guide for anyone looking to build a purposeful and resilient career.