Stormy Simon, Former CEO Of Overstock.com, Launches Her Own New Brand


Stormy Simon is an ecommerce pioneer, business leader, and inspirational speaker. Her direct entry to the workforce and remarkable work ethic helped her climb the ranks in a corporate career, where she eventually became a female leader and president of Overstock.com. Stormy started with the company in 2001, when annual revenue was less than $ 20 million and the company had fewer than 100 employees.

She quickly became a bright star and developed the iconic campaign, “Discover the Secret of the Big O.” This campaign drove sales to upwards of $ 2 billion in revenue and helped Overstock.com become a top 25 e-Tailer by traffic, and was named one of “America’s 100 Most Trustworthy Companies.”

Stormy has now transitioned from her traditional corporate career into life as an entrepreneur as she recently launched Mother Ruggers, a new jacquard rug brand for those seeking to add a lux touch to the floor designs of their homes.

Stormy had this to share during a recent interview with Grit Daily.

Were there any unique challenges that you had to face as a woman working to gain promotion in the workplace, if so what were they?

Stormy Simon: I entered into the workforce in the early 90’s. I worked through the evolution of work equality between men and women. My biggest challenge was staying in a male dominated room, and learning my place while closely considering every work I say in order to be strategic. The second part, which always makes everything more difficult, is being my own worst critic. Because questions often start when a female gets promoted, I had a chip on my shoulder to prove I did this on my own, with my own merit and with my own mind. Learning I didn’t have to fit into the boys club, I just had to know how to play the game.

Tell us more about your career at Overstock.com and what caused the company to appoint you as President of the organization?

Stormy Simon: I started with Overstock in 2001, Overstock was founded in 1999. It literally started for me because I “raised my hand.”

I honestly didn’t think I would be at the company very long, as I was hired as a temp. I think that made me a bit fearless. Within the first 90 days, I was in a room with the CEO and three other department heads. The CEO was talking to my bosses and said “Whose head can I put on the chopping block to make sure this gets done?” Nobody did anything. The other I raised my hand. I said you could put my head on the chopping block.

I felt compelled. It turns out I led the department to $ 20 million… in turn giving me the confidence to ask for the next department, which was PR. Then the next department was music and video in which I helped build up to $ 150 million. I continued to build each department. In 2007 I became CMO – at this point I was fully knowledgeable in almost every department within Overstock. In 2009 we became extremely profitable (12 months of $ 1 billion).

In 2011 I went into operations and built out our partner care program and created the award winning movement – “people care”. I took our vendors from 4k to 10k vendors, so the next natural step was to become president. When I became president I didn’t look at it as losing any of my prior positions. I took all of the experience in all the departments with me. Today I still feel the same way. My experience was like drinking from a firehose. I took it all in, I grew up, the company grew, and now I am ready for my next big step… my own venture, entrepreneurship.

What accomplishments were you most proud of during your time at Overstock?

Stormy Simon: There were so many milestones at Overstock. The accomplishments I was most proud of were; Building out the commercial start to finish for the big O campaign, bringing the company to $ 250 million – $ 500 million in 18 months.

My next biggest accomplishment within the company was bringing customer service from being outsourced to in-house. In structuring out this award-winning customer service department I not only reduced costs but won multiple awards for the company. Two more accomplishments that stick out in my mind are the award we won when I was CMO for the best shopping app, accomplishing 12 months of $ 1 billion. Last, but not least, when I was president Overstock was named one of the top 100 most trustworthy companies in America (chosen by Forbes).

You have now transitioned from the traditional corporate environment to being an entrepreneur? What inspired you to want to be a business owner?

Stormy Simon: In transitioning from the corporate environment into entrepreneurship I find this is my biggest accomplishment and challenge of all. It is now time to do something I personally am passionate about and to bank on myself this time! Banking on yourself is the hardest thing I would ever have to do – I was ready to step outside of my comfort zone. It took me a lot to get me to make the shift – but it all boils down to the perfect “Stormy Storm” the product, the person I get to work with, and all of my expertise and experience up to this point preparing me to build something of my own. What inspires me is the passion, the excitement to work again, to build a business, something to devote my heart to. I never wanted to do something twice. I feel this is a new way women will do business. We consider this to be a family-style business – and we will run it like one – and we will welcome our family employees – and build it to greatness.

Can you tell us more about the type of products in your new rug company and when the brand will launch?

Stormy Simon: Mother Ruggers products will be available in stores by the summer of 2022. We work exclusively with a boutique manufacturer in Turkey creating luxury and affordable rugs. Simon Yildirim is our designer for our luxury line which offers various Jacquard woven collections.

All rugs include incredible warranties of up to 10 years. Our machine washable rugs come in a fashionable tote bag – easy to sell and receive. If you can dream it we can weave it… ..

Orlena USA distributes the Mother Ruggers collections with retail pricing beginning at $ 175 – $ 300 which include:

The Raggaroos Children Collection – Machine Washable, hand-drawn, and printed on velvet and hand finished with a semi nonslip fabric, making it safe for your little ones! Bright fun and colorful designs for newborns to 12 years old. When it gets dirty, just wash it! Two-year defective warranty with proper care.

The Dream Weaver Collection – the option to create your own exclusive designs and textiles MSRP s start at $ 499 – $ 2400. All collections are Machine Washable.

The Rugger Collection – A one-step machine washable anti-slip Jacquard-woven rug with a 3 year warranty.

The Outdoor Pattie-O Collection – Three price points and the best quality outdoor rug available, especially the Jardin. 2 & 3-year warranty with proper care. Great for high traffic areas like the patio – front door, and even outdoors. Imagine an indoor / outdoor rug – that looks indoor but is built for outdoor use.

The Outdoor Ruggaroo Collection- for kids – made on velvet so it stays clean – made for children in mind.

The Shenny Chic Collection – Jacquard woven styles that reflect your personality.

The Simon Leadren Collection – 10-year warranty – 4 different designs – exclusive – by the actually drawn designs.

What advice would you give other women who are looking to transition from their 9-to-5 to becoming an entrepreneur?

Stormy Simon: If you are a woman looking to transition from your 9-5 and become an entrepreneur I would give this advice: Don’t make the move before you are ready. If you are asking how do I know if I am ready? I would say you want to make the move when you can afford to fail at least once.

Remember, you are not starting over. You are only packing your bag and moving forward, taking every skill and accomplishment, and leaving nothing behind. And always remember don’t succeed out of ego, if you have to throw in the towel, start over it’s always a better move, as no success comes from one’s ego.

What’s the greatest fear you’ve had to overcome to get where you are today?

Stormy Simon: The greatest fear I have had to overcome was the fear of failure. I overcame this fear by raising my hand and taking a chance in myself, by leveraging that fear and using it for fuel. I have let go of the fear of failure and the fear to raise my hand… but now instead of for others… It is my turn to raise my hand for me and Mother Ruggers. On to bigger and better fears to fuel my journey of Entrepreneurship.



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