Building Your Career from the Ground Up with Stormy Simon

Stormy Simon is a strategist, executive coach, and the former President of Overstock.com. Stormy joined Overstock in 2001 as a temp worker. Over the next 15 years, she helped the company grow into a top 25 E-tailer in America with nearly $2 billion in revenue and 160 employees.

In 2016, Stormy Simon stepped down from the Presidency at Overstock and entered the budding world of cannabis. She became a medical advocate throughout that journey, spent two years as Strategic Officer for a blockchain payment point-of-sale system, and served on the Advisory Board of CannaKids. In 2017, Stormy joined the board of High Times, one of the leading global brands in cannabis culture.

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

[3:40] Stormy Simon explains how she went from a temp position at Overstock.com to President of the company
[7:35] Stormy discusses the reality of the “glass ceiling” for women in business and how she achieved great things regardless
[13:19] How Stormy raised the number of women executives at Overstock from 7% to 33%
[15:27] When did the shift happen from “I need to survive” to “I want to advocate for others”?
[17:58] Why Stormy left Overstock for the world of CBD
[21:46] The possibilities for cannabis in society and why it’s not more widely known
[31:01] Stormy’s superpower — raising her hand
[35:13] Stormy’s advice to the rising generation of entrepreneurs: listen to your elders
[39:04] The greatest mentors throughout Stormy’s career
[44:20] Opportunities in the cannabis business for ecommerce entrepreneurs
[48:58] Stay flexible during your journey as an entrepreneur

In this episode…

It’s tempting to think that successful people have a straightforward path following steps A, B, and C, to get where they are today. The reality is, the path of success is usually windy with unpredictable turns, drop-offs, and no roadmap. Strategist, storyteller, and executive coach Stormy Simon would agree.

As a divorced mother of two at the age of 21 with no college degree, the outlook on life wasn’t bright for Stormy Simon. But that didn’t stop her from turning a temp job into an executive position at a multi-million dollar company. What’s her superpower? Raising her hand — never being afraid to try even if it meant she might fail.

On this episode of the eCommerce Profits Podcast, Joshua Chin joins Stormy Simon to discuss her path as an entrepreneur. Stormy reveals how she became the President of Overstock.com without a business degree, why she left the company for the cannabis world, and her advice for the rising generation of business leaders.

Resources Mentioned in this episode

Sponsor for this episode

This episode is brought to you by Chronos Agency.

If you are a direct-to-consumer ecommerce brand that wants to unlock the optimum customer lifetime value through email marketing, then look no further than Chronos Agency!

Our team of passionate email marketing experts has helped hundreds of brands generate over $70 million in return from email alone, and our clients receive an average of 3500% ROI from our efforts.

Chronos Agency has worked with a variety of brands, including Truly Beauty, Alya Skin, and many more. Our mission is to help real businesses achieve real results.

If you want to take your revenue to the next level using email marketing, be sure to email our team at sales@chronos.agency or visit chronos.agency to learn more.

Episode Transcript

Intro 0:04

Welcome to the eCommerce Profits Podcast where we feature top founders and experts in the eCommerce industry and take an in depth look at the struggles and successes in growing eCommerce brands profitably.

Joshua Chin 0:21

Alright Josh Chinhere I’m the host of the eCommerce Profits Podcast, where we feature top experts, entrepreneurs and shakers in the eCommerce industry. And we go behind the scenes of the struggles and successes in growing a brand. Now this episode is brought to you by Chronos agency if you run a direct to consumer ecommerce brand that is ready to scale and to double your customer lifetime value. True lifecycle marketing Chronos is your company. We have helped hundreds of brands scale profits with email, SMS and mobile push marketing will getting an average of 30 500% ROI from our efforts. We’ve worked with brands like truly beauty, the UI, Dr. Livengood and many more. Now the next step is to email us at sales at Chronos dot agency or you can go to Chronos dot agency to learn more. Today’s guest is Stormy Simon. Stormy has a really interesting background. She is the former president of Overstock.com. She joined Overstock in 20 2001 2001. During the formative years of eCommerce as attempt, and at the time, revenue was less than 20 million staff was under 100 people in their career she has gone from being an executive assistant to the branding on customer care VP of customer care to cmo and eventually becoming president and board member. over her 15 year career Overstock became a top 25 e tailer in America by traffic and grew to nearly $2 billion dollars in revenue and had approximately 1600 employees. Stormy is an unconventional leader who charged straight into into the workforce, bypassing college and Business School. One of her proudest achievements was growing the ranks of female executives at Overstock from 7% to 33%. We’ll talk a little bit about that during the show as well. In 2016 Stormy staff stepped down from the presidency at Overstock and entered the budding world of cannabis. A mother of two grown sons and three grandchildren. Simon is longtime resident of Tula County. I hope I pronounced that right. She also, she also had the honor, interestingly, of presiding over the first gay marriage to the county in 2011. Stormy, welcome to the show. Thank you so much. You have one of the most interesting stories and backgrounds of any guests have had on the show. Tell that Tell us. Tell us about how, how you ended up in Overstock? And how do you how do you stay in in one company for 15 years? and rice? Basically, from literally the lowest stuff? ranks to literally the highest ranks?

Stormy Simon 3:40

Yeah, well, um, a lot of moving a lot a lot of hustling. I mean, you got to, in order to do that, you know, you’ve got to have your eyes open, especially when you think about where ecommerce was at that time. The word ecommerce didn’t even exist, we were calling it etail or online shopping and, you know, our advertisements, that’s what it would say. So it was a very different world. I think timing of walking in there when I did and feeling like, you know, seeing that people didn’t know, you know, we were developing a business as it went. And then being able to share ideas because nobody really knew the right answer. We were just figuring it out. Honestly, just raising my hand throughout that time, and, you know, paying attention to all of the details as things were happening. I mean, it was such a fast moving time that it’s like how do you how did you do it? I just didn’t stop running. I just kept, kept going, kept raising my hand kept doing the stuff, you know, it was going so fast. And you know, fortunately timing plays a piece of every story, the timing of walking through the door, and then I’m just being able to being able to raise my hands and take a project and be able to see it through and, and lucky for me, I had a really good batting average.

Joshua Chin 5:13

Very good batting average. Did you always know you’re going to be you were going to be successful in the business world? Was it an intention?

Stormy Simon 5:22

No, um, I, you know, as a little girl, I would play like, Secretary, is that what, you know, girls were? Um, yes, I’d be like, I’m gonna be a secretary. And I’m going to tie up and we carry a briefcase. And, you know, I always hoped I could wear a business suit for some reason, like in, in like, grade school. And then I was a young mom, at 17. So after that, there really wasn’t like, Oh, I have this big dreams of something, it was more like, Oh, my God, I have to raise these kids. You know, I was divorced at 21. After raise these two boys, and that’s the mission, the mission is to raise the kids and keep them fed and loved and all of the things so that became the mission. And then, you know, the steps within the mission of making that happen. I just made some good moves.

Joshua Chin 6:23

Very interesting, really good moves. And it’s it’s really unusual, because you mentioned that you’re growing up your dream of becoming secretary and that those kind of dosa mindset of I guess, most I

Stormy Simon 6:38

will tell you one thing, I have to tell you one thing when I was in like sixth grade, fifth and sixth grade, I would watch the commercials on television and then rewrite them better. So I did always have a marketing my way. Like, you know what? I’m doing this, and I would always have a different take on what they’ve done.

Joshua Chin 6:58

Okay, interesting. No, I’m not sure. But the landscaping in 2021 and in early 2000s, but obviously, that was the early eight, early stages of the.com. Boom, and eCommerce. But what about the whole? Well, I’m sure there is a glass ceiling at that point in time. And to some degree, I guess, some difficulties in in females rising up the ranks versus their male counterparts. Have you ever experienced anything like of that nature at Overstock?

Stormy Simon 7:35

Well, let’s just say as a female, you experience it everywhere. You know, my children are grown, I have grandchildren I’ve lived through, you know, the thing about it is, you know, and I’m in Utah, it’s a very conservative state, there’s not a lot of women that have a, you know, the opportunity or whatever it is, the timing, talked about timing, to achieve or getting to those positions in the years past, you know, pre 2016 hashtag me to movement those years past. So, absolutely, 100% throughout, I mean, there’s a whole story about the glass ceiling that, you know, where I was actually told by a boss at Overstock in the early days that there was a glass ceiling, and that’s what there would always be. So you know, yes. And then you kind of have to ignore it, or, you know, my younger years, you would have to accept it, because it was just the way the world works. Like that was just the way the world work. Do you know you would be marginalized or it was definitely a boys club, like all of that is real. Now, you know, as a female, you had to navigate through that time you you know, for me, couldn’t can’t speak of anyone else, but you have to navigate it. You have to, you know, you can’t, the world wasn’t ready to be changed. So you have to join it be aware of be aware of it be wise to it. My mom made me wise to it made me why’s that there would be men that put my looks first and that would be the lead every time I spoke with them. Well, she turned it turned out she was right. And so I’d have to take that lead and still be able to prove my value and smart and ability to work harder than because of that, you know, so never been a victim many many stories of where, you know, that was an issue or inappropriate things. You know, and not always sexual either, you know, hashtag me too isn’t all about a sexual movement. It’s about a, you know, the the verbs that we use to The adjectives that we use to describe males versus females, you know, I was referred to as hard headed, most stubborn, tenacious, you know, where my male counterparts were, were, you know, viewed as well spoken, outspoken, confident, you know, and a real aggressive guy in the in the, you know, boardroom or whatever, but they were very, very different. And it was always evident when men spoke of women versus men in the workplace. Even when I was part of the club, because yeah, eventually you get in the club, but you’re not really in the club. Because, you know, I could tell you stories about, you know, why, you know, you’re not in the club, the things that are said, where you just think, Oh, geez, I am a sexual object. And that’s it. So why am I gonna fight, you know, this person on anything else? Not really been fired on, but try to prove yourself on anything else. And a lot of times I,

Joshua Chin 11:02

I’m assuming it’s not, it’s not an explicit aggression of any kind. It’s, it’s kind of like an implicit thing, where you’re sure you’re part of the board. Now you’re proud of the club, but know your place. And it’s 100%. That’s

Stormy Simon 11:20

100 100%. That’s my dog snoring and make him stop. Yeah, it’s 100%. You do you know when to laugh, you know, when to you know? Yeah, you know, I trained myself that way. I mean, as silly as that sounds, and people would say, but I would never say I’m a victim, I was fully aware of what I was doing and what was happening. I had to play my part in order to get

[Continue to Page 2]

Pages: 12