This site has limited support for your browser. We recommend switching to Edge, Chrome, Safari, or Firefox.

A Fun Interview With Stormy Simon Former President & Cannabis Industry Pioneer

stormy simon

Over the course of Stormy Simon’s career at overstock.comshe held a variety of titles including, SVP of Customer Care, Marketing & Branding, and Operations, as well as Director of the Board, and finally President.Today she brings her tenacious entrepreneurial spirit to the cannabis industry, and if all of that isn’t impressive enough, I also discovered she was initially hired by overstock as a temp. I was intrigued as I also worked as a temp early in my career, but unlike Simon, my experience involved a series of self-inflicted mishaps. There was the careless cut and paste incident when I forgot to replace a company name in my cover letter and was asked mid-interview if I was a detail-oriented person to which I responded, “without a doubt” and was then questioned why my cover letter was addressed to their competitor. To add insult to injury, I lied about my GPA and was asked to provide a copy of my college transcript. Let’s just say I wasn’t on track to becoming the President of a company or even hired for that matter.

There’s an interesting statistic that men apply for a job when they meet only 60% of the qualifications, but women apply only if they meet 100% of them (Hewlett Packard). This has often been interpreted as women needing more of that elusive “confidence” that you apparently just wake up with one day, but genuine confidence doesn’t just appear, it’s gained by experience.

In Simon’s case, she was hired by Overstock as a temp in 2001 and climbed her way to the top leaving her mark on every department over the span of 15 years. For Simon, there is no job too big and no task too small, she is not a person that feels the need to parade her credentials for permission to take leadership. Truth be told she has yet to complete her college degree and while that is something she intends to finish, she has never seen it as a limitation.

What I admire most about Simon is her unapologetic honesty. In her Tedx Talk appropriately titled, “Doing it Wrong” she reflects on how her mistakes and shortcomings prepared her to make the difficult and often unpopular decisions that come with leadership. Two years ago, she stepped down as President at and set her sights on the cannabis industry, another difficult and controversial decision. Never-the-less her journey continues.

I had the opportunity to talk with Simon, here’s what she had to say.

MH: As a woman, do you think your leadership is received differently than if you were a man?

SS: Do I think that the same adjectives are used to describe a man in business as they are for a woman in business? No, I don’t. A man can be strong, outspoken, blunt, but a woman is seen as emotional, tenacious, even whiney. We describe them differently. Do I think women and men are perceived differently for doing the same actions in their authentic ways? Absolutely!I am not blaming either side. When I’ve been called “Queen Bee,” I think that’s a negative connotation because given the blood, sweat, and tears that I put into I never felt like a queen bee, I was always a worker. That is my legacy. So, to hear, “Queen Bee” felt so insulting because I really fought for it. I never asked for it, I earned it.

MH: In your Tedx Talk you mentioned a sexual harassment experience when you were younger with an employer prior to You continued to work for that employer, how do you look back on that experience?

SS: Earlier in my career before I was a single mom on welfare with two kids so that dictated my tolerance level. Honestly, and I don’t know how controversial this is, but I learned so much from that job, and that man, and I am grateful for him every day of my life for giving me the opportunities that I had there. I would never have been able to do what I did at had it not been for that experience. It was an amazing education.

This #MeToo movement is important, horrible things are happening to women, yes. And then there are people like me where no, nothing horrible happened to me. I didn’t have a moment where I couldn’t control it, or someone asked for a sexual favor or you can’t work in this building. That never happened to me. But this didn’t start yesterday. Do I expect it to end tomorrow? No, I don’t. It’s an interesting time, it’s an empowering time, but I believe both genders get through it together. There are people who have done horrible things, but I still feel that forgiveness and getting through this as a society and addressing it is the answer. Banishing people and keeping things in the closet is very dangerous. I don’t want men to be afraid to make the right joke in front of me. No, go for the punchline.

MH: What are your self-care habits?

SS: I have been meditating for 30 years. My twenties were about looking for my higher self, my thirties were about my professional self, and my forties were about living my higher self, and answering the question, “What am I looking for?” As far as routine, it’s about keeping in touch with my sacred space. I make sure to have Stormy time each day and say, ‘Today I’m not doing emails.’ Having that freedom has been a blessing and I feel a little bit like a spoiled brat. I know that I have habits that I need to release from working the way I have in my career. I am learning to be a little more laid back, and not so intense. I am allowing the universe to play its part.

stormy simon

MH: Since stepping down as President of in 2016 you have been pursuing the cannabis industry, what has that been like?

Cannabis is still being discovered, so that’s really exciting for me. I was just really curious so I decided I would learn by going to “a grow” in Denver every day, learning the agricultural piece, and the dispensary side. I learned all the regulations on the medicinal side. There’s a lot of passion around cannabis and not just as a civil right but medicinally speaking this is a conversation that has to start, and I love that people are doing it without the government. That’s almost my favorite part. It’s a revolution. These are true leaders that are emerging from this industry because they’re doing things that nobody has done before and they’re fighting relentlessly because their business is being treated differently than any other business and it is not fair.

MH: What do you think the best thing about being a woman is today?

SS: I love what makes us different, and that’s our femininity. I love that today we’re bringing our femininity to leadership. People used to say, “Don’t cry in the boardroom.” Well, that’s a beautiful emotion. It’s passion. Yeah, maybe women cry a little more than men, but who cares? I love authenticity and I think emotion is a form of that. It’s about vulnerability and it’s exposing yourself on a different level. To show any emotion whether it’s anger or sadness, happiness, and I appreciate that in business. We have a unique opportunity to step into leadership without putting on a three-piece suit or cutting our hair or looking a certain way. Wear what you feel good in because appearance and gender have nothing to do with your intelligence.

stormy simon

MH: Define yourself in three words.

Happy. Loyal. Trustworthy.

MH: If you had to get a tattoo what would it be, and if you already have them what’s your favorite?

SS: I started getting tattoos at forty-one, so now I have a whole bunch. I just got one with six other women, it’s just a small tattoo of a moon on my arm. A friend of ours was diagnosed with a really bad disease, so when we left the doctor’s office we all decided to get tattoos.

MH: Who inspires you?

SS: Underdogs

MH: Worst fad you participated in.

SS: I did the whole Joan Jet thing back in high school.

MH: If you were a major league baseball player what would your home field walkout song be?

SS: “Express Yourself” by N.W.A., and “F*ck Tha Police”. Those two songs gave me the power to make decisions. Dre and Ice Cube, you want to talk about inspirations? Who inspires me? Those guys, they inspire me so much.

MH: Screw, marry, kill.

SS: Oh my god, I love this game! Ok, give it to me.

MH: Stephen Tyler, Brett Michaels, Denzel Washington. Go.

SS: Oh my god, I hate you! No! This is so hard!! Haha, Ok, I’d have to marry and screw Stephen and kill both Brett and Denzel. Hahaha!

MH: This was definitely a rule breaker of an answer but I’ll allow it.