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Stormy Simon is the former president of She joined in 2001 during the formative years of e-commerce and at the time revenue was less than $20M and with a staff of under 100.  In her career, she has gone from executive assistant to VP of Branding to VP of customer care to CMO to eventually becoming President. During her tenure, Overstock became a top 25 e-tailer by traffic and grew to nearly $2B in revenue and had approximately 1600 employees. 


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Here’s a glimpse of what you’ll learn: 

  • [2:40] Jeremy introduces his guest, Stormy Simon. 
  • [4:40] Stormy shares her career trajectory and how it has changed over the years. 
  • [12:40] A story from Stormy’s Hard Rock Cafe days. 
  • [16:30] What Stormy wanted to do when she was a child. 
  • [20:00] How having a child shifted Stormy’s perspective. 
  • [22:00] Stormy talks about her time at Overstock. 
  • [33:00] What were some of the early products featured on Overstock? 
  • [36:30] Hard decisions Stormy made as the president of Overstock. 
  • [41:20] Why the founder of Overstock has been featured in the news lately. 
  • [44:00] How did Stormy end up working in the Cannabis industry? 
  • [56:20] Why Stormy is passionate about keeping Cannabis away from the FDA.
  • [1:05:15] What is Tribe Talks? 
  • [1:07:30] Closing thoughts from Stormy. 

In this episode…

What does it take to work your way up through the business world to find yourself at the top of one of the nation’s leading ecommerce businesses? Where do you go once you’ve reached that level of success? On this episode of Inspired Insider, you’ll hear from business leader and cannabis advocate, Stormy Simon. In her conversation with Jeremy, Stormy opens up about her career path, how she ended up at Overstock, what it was like navigating work and family life, how she ended up as a cannabis advocate, and much more. You’ll want to pay close attention to Stormy’s power story! 

When was the last time you decided to challenge the status quo? Let’s face it; most people are happy keeping everything the same – it’s not easy embracing change or leading the charge for it. Each person needs to decide for themselves which issues they are willing to take a stand for and which ones they are willing to compromise on. When Stormy witnessed gender discrimination during her tenure at The Hard Rock Cafe – she decided to make a stand and voice her concern. As you can imagine – that didn’t go over too well with her superiors, but Stormy was able to hold her head high, knowing she made a worthwhile stand for her convictions. 

Can you remember what you used to dream about doing as a career when you were a child? Did those dreams ever go anywhere, or did they evolve over time? From an early age, Stormy had a mind for business and more specifically – marketing. She recalls coming up with jingles and advertisements for brands she was exposed to as a child – who does that? Looking back now, you can see how those early thoughts about marketing helped nudge Stormy on the career path she took in her adult life. What can you learn from Stormy’s story? 

When was the last time you reflected on your journey as a business leader? Have you recently celebrated your accomplishments and wins? Most business leaders are quick to analyze and pick apart their failures, but they don’t take the time to look at what they’ve accomplished. Looking back at her tenure as an executive at Overstock, Stormy takes note over several proud moments. At the time, there weren’t many ecommerce businesses advertising on television – Stormy wanted to change that at Overstock. While it took persistence – Stormy was able to move the needle and get the Overstock board to take a chance on her idea for a TV commercial. Stormy’s creative gambit was a success, and the organization enjoyed a surge of traffic! 

How does a seasoned business leader go from a career in the ecommerce industry to become a cannabis advocate? After her tenure at Overstock – Stormy quickly came across an opportunity to work in the cannabis industry. Stormy had been a cannabis enthusiast for a while and was eager to bring her business skillset to the table. Today, Stormy serves on the Advisory Board for CannaKids – a California-based brand with a focus on supplying medical cannabis oil tinctures and products to patients of all ages. She also serves as the Director of the Board for High Times. You can learn more about these organizations that Stormy serves by visiting the resources section at the end of this post. 

Resources Mentioned on this episode

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