Career Advice, Executive Feature

From E-Commerce to Cannabis: Stormy Simon Is The Ultimate Maverick

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Stormy Simon joined in the heady days of 2001, when the Internet was new to most consumers and company had fewer than 100 employees. She went from temp to PR chief to branding VP – you may remember her appearance in those “It’s all about the O” commercials – and ultimately rose to become president in 2014.

Two years later, she left it all to embark upon a surprising new career: consulting for companies in the cannabis industry. Simon currently serves on the advisory board at CannaKids, which provides medicinal cannabis oil to pediatric and adult patients with illnesses like cancer, epilepsy, and Alzheimer’s.

Simon explains why she pivoted from e-commerce to cannabis – despite her friends’ proclamation it was “career suicide” – and reveals the one question people should ask themselves before entering this burgeoning industry.

Glassdoor: How did you make the jump from Overstock to the cannabis industry?

Stormy Simon: I left my position as Overstock president in July 2016 and resigned from the board that September. I had a phenomenal story there: I went from temp to president at Overstock and had spent 15 years there including developing the e-commerce business. I was going through something of a mid-life crisis. I had been at Overstock a long time and I didn’t want to do the same thing twice. My mom passed away. I wondered, what does round two look like?

Meanwhile, you can’t ignore that cannabis is going through an incredible transformation. I stuck my foot in the water and decided I would make not only a job change but also a total life change. I moved to Denver for a while and consulted for a company that had dispensaries focused on delivering cannabis to patients. I got schooled: Every day I was learning about state regulatory laws versus federal business laws, how each state operates, packaging rules, the works.

Within six months, my mind was just blown at the amount of entrepreneurialism. This industry is full of free-thinkers. Because it’s so new, there is no traditional path. People are building entire ancillary industries. I’ve met amazing men and women — a lot of women pushing change have children with some kind of disease and they have found success with cannabis treatments along with traditional medicines. Like Tracy Ryan [the founder of CannaKids], whose daughter Sophie had a brain tumor.  I joined the CannaKids advisory board, and I also started working with a magazine in Denver called Sensi Mag, which keeps the community informed and aware of how the laws are changing.

I didn’t make the decision to leave Overstock overnight. And I did turn down lucrative e-commerce offers right after leaving. Some of my friends said, Cannabis, cool! Others said, What a great opportunity. And a few said, You’ve got to be kidding –this is career suicide. I honestly didn’t feel there was any risk jumping into cannabis. I see it as a movement that is not stopping.

Glassdoor: What’s your advice for others who want to get into the cannabis industry? Where are the opportunities?

Stormy Simon: I didn’t realize just how new it all is. I had come from a $2 billion public company in a role as an officer. Walking out of there and into this industry, where big production lines don’t really exist yet and you have to re-learn something you learned last week because the regulations changes…it was a revelation. It’s not big business yet.

So you need to be very flexible. But it also means there’s a ton of opportunity. Everything that a business needs, this industry needs to build. I had to be flexible at Ovetstock, building e-commerce there as the entire industry was developing. I knew I wanted to provide my skillset to these burgeoning businesses—and that’s not in agriculture, as I learned after six months working at a grow [operation]. Instead I can help businesses build executive teams and get organized.  You kind of have to be an intra-preneur: Be confident in what you’re good at and what your passions are, and carve out a place for yourself within this movement.

There are a ton of resources out there to educate yourself. That’s what I did. Check out Marijuana Index or, which have a wealth of information about the various companies out there. There’s also Sensi Magazine, of course, and there are great newsletters from The National Cannabis Industry Association and Marijuana Policy Project.

You can decide if you’re comfortable touching the plant, or you can find lots of jobs that don’t require that. And I do know lots of people who work elsewhere in full-time jobs, and advocate for cannabis in their off time. So there are options.

But the first question you need to ask yourself is whether you’re comfortable with the stigma the plant can bring. Some people are nervous about cannabis in general. And for others, there’s the fact that it’s not federally regulated. There wasn’t a moment I thought it was career suicide. But I reached out to someone I knew to see if he wanted to help a company I was working with. He said a flat no; he had high school kids and wasn’t sure how that would be perceived. That was his view of it, and people should be aware that that’s out there. You’ll have some explaining to do to some people.

Glassdoor: How did you deal with that stigma, and what’s your advice for others?

Stormy Simon: The stigma side of it never really bothered me, because my path is nontraditional every way you slice it. I didn’t go to college, I started at Overstock as a temp and I became president.

The college thing always really bothered me. I don’t know if it was public or personal stigma, but I always thought, I should have gone to college. Even when I quit Overstock I thought about going to college just to say I did. So I guess I always felt like an underdog. I’m used to that environment and it doesn’t bother me.

But I don’t think everyone is comfortable there. So that’s why I say the stigma has to be the first question you ask yourself. You really have to be honest with yourself about whether you feel comfortable personally and whether you’re OK with a friend or acquaintance who doesn’t really understand making comments to you.

Glassdoor: What don’t people understand? What are the misconceptions about working in cannabis?

Stormy Simon: It’s hard to overstate how soulful and hard-working these folks are. They’re honestly not making a ton of money. They get taxed heavily. They have to follow an incredible number of rules, which means more overhead. Regulations can turn on a dime and the people who touch the plant have zero room for error. Make a mistake and you can be shut down. There’s nothing about this industry that’s a joke. Everybody’s working hard – doesn’t matter if they smoke or not.

People might think those who work in cannabis dress a certain way or are a particular type of person. But it attracts all kinds. I mean, Tracy Ryan [the CannaKids founder] was a mom working in marketing. And look at me. I’ve never gambled anything so big in my life. But you know, I’m just super-duper happy. The thing is, I loved Overstock. It wasn’t that I was unhappy. But I figured, you live once, so why not try this?

What’s good to learn—whether it’s through the cannabis industry or something else—is that your identity is just you. It’s easy to get tied up in the idea of, I’m the president of X, I work at this company. That doesn’t define who I am. My identity is just me. And it feels good to know that.


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