This week on #WorkTrends, to celebrate Halloween, we’re exploring one of the scariest things you can undertake: Making a career move or exploring a brand-new industry.

We talk to Stormy Simon, former president of online shopping site Overstock.com, about her nerve-wracking career leaps and her new passion: the increasingly mainstream cannabis industry. We also hear from Keegan Peterson, whose platform Wurk is adding function to the cannabis industry.

Listen to the full conversation or read the recap below. Subscribe so you never miss an episode.

Making the Leap

Simon took an unconventional path to the upper levels of the technology industry, rising from a 2001 temp position at then-startup Overstock to become vice president of branding three years later, and president in 2014. Overstock expanded dramatically during her time at the company, growing from $18 million in revenue the year she started to $1.9 billion by the time she left.

“The best part about arriving at Overstock in the beginning of an emerging industry was the ability to take a chance,” she says. “There we were, sitting in offices, creating a new way to shop, changing the habits of consumers. In 2001 … I had never placed an online order. People in the office hadn’t really ever done it. We were creating habits that no one had done. That gave us the ability to take a chance because you were first, which also turned out to be a lot of fun.”

Two years into her tenure as company president, Simon decided to leave Overstock to advocate for the legalization of marijuana, with a heavy emphasis on the medical and scientific benefits of the plant. “That was a big deal and it took a long time,” she says of her decision to leave Overstock. “It was one of those multi-year struggling-back-and-forth decisions. It wasn’t something I took lightly.”

Today she serves on the Advisory Board for CannaKids, a California-based brand with a focus on supplying high-quality medical cannabis products to patients of all ages, and she consults for other companies in the industry.

Evolving Industry

Simon says one of the biggest challenges in her transition has been the rapid change within the cannabis industry, particularly when it comes to regulation and taxation.

These types of companies “aren’t treated within their state as an equal business to any other business,” she says. “If you have a grocer that only sells lettuce, they are going to pay less taxes than someone that only sells cannabis. Where do you put your money? There are no banking options or you’re paying outrageously for banking options. Now banks are starting to come up with solutions, but two years ago, it was archaic.

She says that in California, where she resides, the legalization of cannabis that began Jan. 1 has led to more stringent regulation of the industry, which had previously been concentrated in medical marijuana dispensaries. “They were supposed to be medical,” she says. “The lines got pretty blurred and no one was really in control of what was happening here. Well, legalization changes all of that.”

Simon says she expects the rest of the country, and eventually the federal government, to follow in the footsteps of Colorado and California and ease regulations surrounding cannabis. “I think ultimately the federal government is going to approve this plant as a medicine,” she says. “And this is a tricky, controversial thing to say, but I hope that states are brave enough to go recreational before that happens. The reason I say that is there are all sorts of benefits happening in states that are legal, both medicinally and recreationally.”

Learning More

Simon says she loves being an advocate for legalization and that she has her hand in “about five different cookie jars,” including educating people on the medicinal benefits of cannabis.

“I have really enjoyed going around the country, meeting people and starting the conversations that can potentially change their mind or spark their interest enough to get their self-directed education,” she says.

She encourages people who want to learn more about the industry, as well as the ongoing debate over legalization and medicinal benefits, to start with the Marijuana Policy Project, which maintains a library of what states are doing on cannabis policy.

“I encourage the listeners to just start reading,” she says. “This is a big deal in our lifetime. History books will be written and, whether we simply read about it or we jump in, we’re all a part of it. It’s part of our future.”

Resources Mentioned in This Episode

Let’s continue the conversation. Join us on Twitter (#WorkTrends) for our weekly chat on Wednesdays at 1:30 p.m. Eastern, 10:30 a.m. Pacific, or anywhere in the world you are joining from to discuss this topic and more.

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