Lessons - From Secretary to Overstock President | Stormy Simon - Former Overstock.com President

In this lessons episode, explore what it truly means to bet on oneself and redefine success beyond money or titles. Discover how necessity and responsibility build self-trust encourage to take uncomfortable risks, understand why curiosity and growth matter more than external validation or status, and uncover how staying grounded through success requires clarity around freedom, purpose, and personal values. When did you understand that you could bet on yourself? Because that is something that I think is a very important point. I think that's the reason why people don't leave jobs, and people don't push themselves into things that are slightly uncomfortable. When did you realize that? Was it because you had figured everything out and you were just again repeatedly successful, like what was the thing that allowed you to feel comfortable jumping into that new thing that you didn't know? I knew I had to. After I had the kids and decided I was going to do it as a single parent, there was no one else to bet on. There just wasn't anyone where I could go, oh, I'm going to, you know, I need you to do this for me, or there just wasn't anyone to bet on. It was me or nobody, and it's not a sad story because I had support of my parents, but you know, they weren't wealthy, they were blue-collar, and so I had their support, their love, their undying, like they thought it was awesome. But when it came down to making it happen, that was just me, and I think I've always felt like that to some degree, you know, you have that feeling of, I don't know if the whole world does, but kind of being alone, but knowing that you're amongst this amazing universe, but yeah, you got to pull your own weight. That's the thing. And you can pull as much or as little as you want, and there's no judgment or measure of success, right? Like, people measure success by money, and that's a pretty shallow measure. What pushed you to move? What was the thing that you saw in the new job that made you say, I want to prove out myself there? This is like the next step. Um, you know, there could be a piece of, often it was, I would look at what my next step would be at that job. Like, I completely loved being the assistant to the president. That was my favorite thing because I would learn something every single day. And I think as I've got chronic auto-diadact, I just the knowledge and curiosity of what I don't know, like, and we get one life. So how much can you learn or experience in one day every day and not have too much on repeat? You know, it's the repeat that would scare me. So once I hit a repeat of, oh god, I don't want to do this today, I couldn't do it. I just couldn't. It's like, I don't want to do this today. That's it. And then you get up and do it again and again, and how I, I don't want to wake up like that. You know, many people do that their entire life. Two money. I know. I, you know, that's where money is money, the success, you know, the measure of success. You, for me, you know, and I always think it's easier. Oh, yeah, once you get a little bit of money, you can say all the things you're going to do to change the world and how to live. And, you know, I'll always identify as the welfare mom. I know what it's like to be totally afraid to have your light shut off with children. It's terrifying. And so many people live like that every day. We have to find a new measure of success that doesn't include, you know, just money, more money, putting yourself up against someone with a jet or, you know, the Kardashians or anything like that. Like, it's just life. You've been, you're obviously super, super grounded. And I think that's important. But I think the interesting thing that I want to try and eventually figure out, maybe, maybe you're cognizant of it. You've had extreme success. Like, you've had, you've operated at a level like far beyond what most people have ever operated at with the companies that you've run. How did you stay grounded through all this where now you have been successful. And now you still know that what's happiness and success for you. And it's freedom. It's living in a trailer in the middle of the desert. Like, that's not obviously not always where you are. But still you enjoy it. You enjoy this part of your life. And when people start to get success, I feel like everybody starts off a little bit grounded. And a little bit, I don't feel like money's everything. But then you start to get it. And then people change. Or maybe they don't change. Maybe just, it just brings out what was always in them. But how did you stay grounded as you grew through as you can, as you got more and more successful over your career? Well, I wouldn't say I stayed grounded the whole time. I'm more grounded now. You know, I walked in pretty grounded with a lot of just this spiritual way that I lead my life when I first came to Overstock, you know, which was the big one, right? Everything I did let up to these skill sets that I was able to apply at Overstock and just had amazing, you know, success in the ideas I had or things we executed. But the groundedness, because that was, I went through 10 careers there, like legitimate PNLs, building a business to 100 million, doing crazy things like that. And then I mean, just an apartment to 100 million, we grew the business to 2 billion and along the way, holding so many different responsibilities, building them and taking them with me along the way, there were moments I wasn't grounded. Like we, there weren't these mentors that I could go to and be like, you know, what should I do next? The founder and CEO was very, was a mentor of course, but I would say he had a very aggressive, like his mentorship, very successful, great, but probably something, you know, when I look back now, I wouldn't adopt now, I wouldn't be in the cycle. But as a female and in Utah and, you know, me and the CEO and founder of the company were such great friends and apologetically and on a shame, shamefully is that a word? It is no, let's go with it. Love that word. But that is, you know, with that brings a lot of baggage as a woman. You know, there was a lot of accusations or rumors and it becomes a really hard place to know what's worth fighting and what's not. I was never a victim, but it would be crazy at my age to say, oh no, I just skated through everything as a female with none of that on my hands. Nobody ever hashtagged me, too, or of course, we all went through it. But, you know, there's a lot that you navigate to do that as a female. And there are people that root against you at least at the time. And I think that, you know, it's easier sometimes for people to say for a woman for some reason that maybe, you know, she must have slept with the boss. It's got something else to do with it. And, you know, you step out of it and look back at your life and all the amazing things, you know, there's not just one place that that happens. That, you know, as a female, when you get success and hard work works, people still want to put that on them. I don't get it, but they do. And as I've stepped out of the whole arena, right, where it's just like, the truth is it would have been way easier to sleep your weight at the top. I mean, honestly, what's that 15 minutes a day? I was spending 15 hours a day as a female. I mean, and these are the things we have to talk about because there was never a moment in my career where I was a victim. Because any time there was that type of situation, I got through it, not as a conqueror or a confrontor, but as a navigator, because it wasn't worth my time to, it wasn't worth my time to fight certain fights, you know, at work with something like overstocks, especially, there was so much greatness to be done, so many things that were exciting and every turn that anything that was not about that company and the functions of it to me was a distraction. And so my focus, I don't remember what your question was. No, well, I didn't even go into this. I think you just took it into a direction that I probably would have asked you about, but you're a great storyteller, so I don't need to ask all the questions, because I think that the whole point of what I want to pull out, I want to pull out obviously, like, you've done incredible things at overstock. And if like the numbers, it was like from like 20 million to 2 billion or something incredible, but I think the actual, the actual things that you've done, you've, I know that you increased the female seats or women that were at the executive table to 33%. Like, there was a lot of, and even when we first started speaking, I was saying, oh, there's so much talent of Utah, and you're like, oh, interesting, like, have you spoken to women out of, you know, other women business leaders? And yes, a lot, because I think that you did things at overstock based on, unfortunately, probably your own negative experience that allowed you to understand that like stuff has to be done with how we empower women in the workplace, how we help them support them in the workplace, and how we get them into, get them to where they should be without all the other shit that you dealt with. And I think that you probably experienced that because overstock was like pretty, I'm pretty sure that's pretty me too, that's pretty all of this, right? That's pretty much everything. I left overstock in July of, well, I left like officially, right? I was there a long time. It was a big position. You got to sign papers, but I left officially September 30. But when I literally, you know, quit, quit, that's such a harsh word, but quit resigned, I guess is something. You resigned. You, you were like, I'm leaving now. Yes, and by the time that was July, I'm thinking of the official day, sometime in July, I know it was right before my birthday, and then I was on the board another three months, right after that, like within weeks, the whole Fox story on me too broke out and I thought, how brave, how brave of her, how brave, very immensely brave. And that was just a moment for me. It was a moment and there was a wave happening. The only way I can describe it because I, you know, when I left overstock, it was for many reasons we talked about them whenever I woke up and went, I have to go do this. I'm not doing that in my life. I don't want to wake up and ever be like, oh, I got to do this today. I want to wake up and be like, do in the day, no matter what it takes to get to where I'm doing the day, that's the path I want. And so when I left, you know, I wasn't thinking, well, nobody was thinking, hashtag me too. But when you're allowed to tell your story, when you're allowed, when you feel like it's empowerment and not a weapon and not a grudge and not anything, but just your story, that's the movement we need to get to. That's the movement. And, you know, we were talking about mentors and throughout my leadership, I have some horrific stories. I acted horrible at times. You know, there's articles about leaders becoming sociopaths or psychopaths. A good executive or something is sociopathic, I can't remember which one, but I read the article and I thought, yes, it makes it, there are some emotions you simply have to turn off. You have to because you're not, you know, managing people, your responsibilities are, you know, columns on a cell sheet and all the people equaling a column. So I had to do horrific things in my time that I would never don't, I don't even feel like fit me as a human or a spirit. But I did, I'm, I did them well and I was able to execute and succeed, but you don't see it when you're in it, you see it when you're out of it. Thanks for tuning in. If you found this valuable, don't forget to hit that subscribe button so you never miss an episode. And if you want to dive deeper into this conversation, check out the links in the description to watch the full episode. See you in the next one.