Latest / Success Story with Scott Clary / Lessons - From Secretary to Overstock President | Stormy Simon - Former Overstock.com President

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Lessons - From Secretary to Overstock President | Stormy Simon - Former Overstock.com President · Success Story with Scott Clary

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