The Daily Stoic - Sophia Amoruso on Building Resilience and Defining Success

Episode Date: November 9, 2022

Ryan talks to Sophia Amoruso about how she has navigated the highs and lows of being a successful business woman, how to become great without becoming a monster, the importance of staying grounded while reaching great heights, and more.Sophia Christina Amoruso is an American businesswoman. Amoruso was born in San Diego, California, and moved to Sacramento, California, after High school, soon after relocating to San Francisco. Amoruso founded Nasty Gal, a women's fashion retailer, which went on to be named one of "the fastest growing companies" by Inc. Magazine in 2012. In 2016, she was named one of the richest self-made women in the world by Forbes. However, Nasty Gal filed for bankruptcy. In 2017, Amoruso founded Girlboss Media, a company that creates content for women in the millennial generation to progress as people in their personal and professional life. Her 2014 autobiography #GIRLBOSS was adapted into a television series of the same name for Netflix.✉️  Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hey, prime members, you can listen to the Daily Stoic Podcast early and add free on Amazon music. Download the app today. Welcome to the Daily Stoic Podcast, where each day we bring you a passage of ancient wisdom designed to help you find strength, insight, and wisdom every day life. Each one of these passages is based on the 2000 year old philosophy that has guided some In fact, the fact that we are in the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of

the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of the world of of Wondering's podcast business wars. And in our new season, Walmart must fight off target, the new discounter that's both savvy and fashion forward. Listen to business wars on Amazon Music,

or wherever you get your podcasts. another episode of the Daily Stoic podcast. I am recording this from the Los Angeles Athletic Club, downtown LA, one of my favorite places in the world. On this little bit of a family trip, we were in San Diego, I gave a talk. Then we went to Legoland with the kids. Now we're in downtown LA. I'm recording some podcast interviews to promote discipline. It's destiny that had gotten rescheduled.

I thought I'd bring the family out. That's why we did the Lego Landtrip. We're doing Disney in a couple of days. But when I was picking where I wanted to stay in LA, I wanted to stay in one of my favorite places in the whole world, one of the best swimming pools in the entire world. One of the great swimming pools in the United States

that Robert Green introduced me to. So I swim in laps this morning, riding here at my desk in my hotel room, in the Bruin suite, which is very John Wooden inspired. Anyways, I absolutely love this place, but every time I'm in downtown Los Angeles, I think back to my times at American Apparel, which is right down the street.

I've lived down here, I lived at six in spring, just after I'd left college. And when I think of American Apparel, one of the people that is associated with that time is today's guest on the podcast, Sophia Amarosa. When Sophia was 22 years old, she started an eBay store selling vintage clothing, you know, sometimes literally out of the back of her 87 Volvo, she called it nasty gal. She scaled it into a hundred million dollar a year business. And it blew up. She wrote a book about it actually with the same publisher as I have Portfolio, part of Penguin Random House. If you remember the book, Girl Boss sold a bazillion copies. And she was quite familiar with something I think. Senika would have related to Marx, really, it's what have related to Musoneus, Rufus would have related to, which is you feel like everything's going your

way. And then fortune, Asenika says, behaves as she pleases. She's dumped by her husband of eight months, nasty gal files for bankruptcy. It was a wild ride, you know, and she would she admit she was on the cover of Forbes. There's a Netflix series based on her life. And it all kind of came crashing down. She's come out of the other side of this, a really interesting, thoughtful, resilient entrepreneur. She's building out this business school now, which I spoke to recently, and I said,

I'll do your business school, but you gotta come on the podcast. I wanna talk about this sort of weird period that we both had in the fashion business in the Mid-Auts. And I wanna talk about what she learned rising and falling, crashing and burning, but emerging from that wreckage. And that's what brings us to today's episode.

I gotta go take a shower because I just got out of swimming pool. But I will let you listen to this interview with Sophia Amarosa. You can follow her on Twitter and Instagram. I'll link to it in today's show notes, but it's just her name at Instagram. Sophia Amarosa. And you can pick up her book, Girlboss, Anywhere Books, or Soul, The Girlboss Workbook, as well. And then also her sort of coffee table book, Nasty Galaxy, all really interesting followers on social media. I think you're really going to enjoy this conversation. And if you're ever in LA, check out the Los Angeles Output Club,

one of my places on Earth that if I had a billion dollars, I would buy and live in. I would still share it with everyone, of course, but just one of my absolute favorite places that many of the articles, books, things that you have read for me over the years were written here in these storied hotel rooms and workspaces and anyways, I'll let you listen. Thanks, bye.

All right, so I have a quote from Marcus Aurelius that I think you might relate to or you can tell me if you relate to it. So he says in meditations, he says, the rock gains nothing by being thrown up and it loses nothing by coming back down. I wonder if that jives with your experience. Yeah, I mean, I think it's like a very zen kind of approach to the ups and downs of life. And that's something I'm sure we'll get into and something we all have experience with. And there's, yeah, it's almost like no risk,

no reward, it's like the inverse of that in a weird way. Yes. Well, you had very big ups, right? Like when people go like, how you doing and you're I mean you had very big ups, right like when people go like How you doing and you're like well, I have a company that's made making a hundred million dollars a year And I've been on the cover of Forbes magazine that seems like as good as it can get And it was it was yeah, it was amazing. It was the best I mean, it was, it was, yeah, it was amazing. It was the best.

Was it the best or did it feel like, so it goes up really fast and it comes down somewhat precipitously, not to zero. So I'm not like, you're not like, Elizabeth Holmes or something. I'm not trying to apply this. But I'm just saying, you wrote a very big wave and then that wave came crashing down.

How does that feel to a person? Like, does this Marcus write that it doesn't actually mean anything? It doesn't change you or was your experience different? I think it changes you in that like the rock on its way up doesn't have the level of periphery that the rock on its way down does. And it's really not in the rise that you see what's hiding out that you only see at low tide. And it's that kind of perspective that can inform what happens for the rest of your life.

I think success is so fun. I had the best ride, but also, in a lot of ways, success makes you lazy. And everybody gives themselves 100% credit for their successes, and like, you know, blames other people for their failures. Sure. And regardless of who contributed to what happens when you fall, it's important to just take 100% responsibility personally to learn what you can even from the shortcomings of the people who contributed to it. And just assume that even if there's misinformation out there, right, I've had a lot of headlines. There's something to learn from it.

Sure. Because even if it's an echo of a sentiment of an employee that you no longer even work with from years ago that winds up and around up of some pressed thing like years later, it's an opportunity to reflect and be like, how did that happen? And what can I do differently for that not to happen again? Sure. Yeah. Yeah, it's clearly something that the Stokes were thinking a lot about, being that they held a lot of... I think it probably comes from holding elected office, right? You win and you're

powerful and then you lose and all of that goes away. So there's this sense of going up and down probably. Although Zeno, the founder of Stoicism, he loses everything in a shipwreck. He's this dealer in what they call Tyrion Purple, this sort of die that comes from the Mediterranean. And he loses everything in the shipwreck, he washes up an Athens. He would say later, you know, I made a great fortune when I suffered a shipwreck because it sort of changes the course of his life. But it does feel like the Stoics had this, had some sense of the ride that you've been on, which is that you were very celebrated and then the parade stopped. It stopped, but it didn't stop.

Like I think it, you know, I left my first company and I kept going. Like nothing really stopped for me. And I think it's like it does everything even stop or is everything an enzyme for whatever happens next and maybe it's not for everybody but what didn't stop was the fact that on my way up I inspired a generation of people and women and entrepreneurs who probably from the time I wrote my first book, Girl Boss, in 2014, who were like, yay, we're all like going for it, had experienced their own setbacks

by the time I faced public setbacks and it gave them permission to experience those as well, because that's not something that people talk about personally in the same way. And so I feel like my story is just some, you know, pretty common example of things that everybody endures but doesn't necessarily talk about. And those women have followed me. And there was not a blip in their kind of support of me as I experienced the down, whatever from the up. And when I left Nastygout the end of 2016,

I put on a conference and it sold out in two weeks for 500 women and in like March of 2017. Like, I didn't stop. I saw what was happening. It was already happening. I just moved into that space and occupied it with something that I knew people wanted that felt honestly a lot more relevant than

and rewarding than nasty gal at that point. And I had stopped already like when it ended. It's hard to, I know that maybe someone who worked for me could be listening, but personally as an entrepreneur, there was some relief in the end, because unless you're like, bored controls, the business, or which mind didn't, you can't quit and you can't be fired. And that was this kind of purgatory I was in for years, that, you know, the kind of like end of the era of nasty gal

and the changing of the hands and to another owner of the business was really in some ways the only opportunity that I had to move on when I was already ready to move on. Well, I guess it depends on what you identify with as the going up or the going down, right? That may be another way to think about it. So if one's identification of success or being up is the top line revenue or the tenor of the press or whether you're on covers or not, then it's a pretty clear up and down. But instead, if one is identifying with positive change or impact on other people or self-actualization

or any of these things, then actually it's more of a sort of a straight line equilibrium that's not fluctuating wildly, it was successful the whole time. So I guess it comes down to how one defines success, which in the Stokes would say has to be rooted much more in the things that we control or much less about, you know, whether other people think we're a success and more about like what we're trying to do. I mean, I'm not going to say it wasn't hard, right? Yeah.

To be this like millennial, entrepreneurial, outlier, golden child, female, example of what was possible, and this freak story of a community college dropout who built a business that did $100 million in revenue. And was, you know, held up as a hero, and then when things went sideways, was held accountable to, you know, every single thing that could have happened in the business. And I said this on a podcast recently with the morning brew called the crazy ones.

And I said this, it's like one thing nobody knows when you're starting a business is that you probably only know 10% of what's happening in your business. I mean, this is when you've got some scale in people, but you're held accountable to 100% of it. Sure. And like the delta between what you know and what you're held accountable to is really hard, and it's not something you can necessarily even see coming.

And to be then, on the other side, the example of like, she's not a girl boss because I didn't like, pull it off. Like I built like a culture or didn't build a culture, accidentally built a company culture that like, could have been better, but I had never even worked in an office, I had never experienced leadership. I had absolutely no understanding of what people needed to be

successful. You know, it was like the Tower of Babel, hiring 100 people in a year. And that cute, serendipitous story that inspired so many people, you know, kind of like hit its ceiling in terms of my understanding of what it takes to really scale a business. And to this day, it's not like I don't operate from a place where I know what's possible and the eyeballs that are on me and that the next thing better be a hit

and that understand like chasing relevance and you know ego-tistical bullshit like that that comes up. But for the most part everything's the same. I live in the same place. I have the same friends. I'm the same. I'm better. That's why I like the quote.

I think it applies here, right? Is at the end of the day, you're the same person. And so, you know, nothing really changes by going up and changing and changing by coming down. Not the things that really matter anyway. Because there's another version of the quote where he says, because he returns to in a meditation, he says, receive without arrogance, let go with indifference, which to me is sort of the prescription for the formula of a of in a world where one can be extremely successful very quickly

and then extremely controversial or deal with adversity or struggle or reversal in some way just as quickly. I mean, I think the bigger risk in changing as a person is by winning. Like the bigger risk is that you become, I mean, I've seen it with friends. You're like hanging out on yachts with like billionaires. Like who are your friends? Why are they friends with you? Like, if I was worth, you know, if I actually pocketed hundreds of millions of dollars that I

was worth on paper, who would I be? I don reality in ways that had my story, had I pulled it all off, I think I could be a lot more lost than I am. Interesting. Yeah, Tennessee Williams talks about the catastrophe of success. And there is a kind of catastrophe that happens, I think, if you are successful beyond a certain level, like, my books have sold very well, and then I'll meet someone who blows up at a whole other level. And usually the first thing that goes is the marriage, you know, their health stuff. Like, you look at them and you're like, I'm not actually sure. I mean, maybe this is just-

They're like, just pulling me to their wife. It's like every tech bro's, and then they get a divorce and they find someone younger and they're probably still like, you can date me, but I'm just gonna do whatever I want and go to sex part. Like that's it. Like you tap out at like, it's like,

you need like to, your kink has to be edgier like in life, you know You got to eat rare or food and drink rare or wine and you know get like you know get your dick stomped on to like get off or like You know that being the kind of like parallel to what happens in your life when you like have everything like what's left like nothing You don't feel anything anymore. And we can buy anything, because I kind of could for a while. Nothing matters, there's no value to anything. Like it's like what's left?

Like at my peak when I was, whatever, 27, 28, 29, I was like actually worried that there was nothing more. Really? Really, really naive. But yeah, there were times where I was like, is this like, is this it? Not in a sad way like I wanted more, but like, is there an up from here?

And if you're kind of an adrenaline junkie or a feeling junkie as I think a lot of driven people are. That's probably the most terrifying thing that there is. Yeah, like what, do things just like plateau from here and I'm just like this person because like it doesn't get better. Right. So I've got like a, I've got like the runoff of that and it's great. Life is great. You want to be successful, but you want not to be catastrophically successful. I think it makes people weird. It does. I said this before, I think the harder thing to do is to be very successful or very good at what you do and not become like a monster. or very good at what you do and not become like a monster. Yeah, it's hard. You better get a good executive coach, or therapist, or like wife, or kids, or, you know,

or hobby, or, you know, illness, maybe. Yeah, you have to, you have to, like, the, the, the weight of the power, success, press, attention, responsibilities, stress, et cetera, is so great that if there's not a counterbalance to it, I think you spin off the planet. Also, like, age is you. So if you're just like, I'm like, would I ever want to run a public company and like, fuck, how would that show up for me? I live in Los Angeles. Very stoic. Yes.

But you think about things like that, at least when you're a woman with like hair extensions or whatever. Oh, you mean like who you would have to be superficially to sort of fit into that club? No, just like what are the health effects of dealing with that level of stress? And then also like how much does it show up on your face? Right. Pretty maturely. Just as a vain aside. I've had that consideration. Well, you know what I thought about that earlier today. So I did this little magazine profile,

Austin Monthly, to this little magazine profile of me opening the bookstore, and they had sent a photographer out to take a picture of me. And I saw the picture and I was like, oh, so that's what this is doing to me. Like it was like, it was the first photo I've seen in a long time where I was like, oh, so that's what this is doing to me. Like, it was like, it was the first photo I've seen in a long time where I was like, I look much older than I remember looking. Yeah, no, that's like, at a certain point,

it's like, I'm just gonna like get veneers because I'll just be happier with the photo. Like, it's literally efficient. Like, it's like, I care less about what the photo looks like because I like, I'm happier that like that it doesn't look like I grind my teeth and have like a, my teeth were fine. But stuff like that is like actually practical when you're getting photographed all the time

because you're just like, wanna be like, cool, great. Moving on. Well, but also your peer group changes and your peer group is doing all of those things and then you start to think, well, why do I look different than those people? Do you know what I mean? You're like, you talked about the CEO,

like plastic surgery aside or whatever, but you go, but all my friends have a house that looks like X. All the, you know, you start to get a, it's hard to resist the pull of keeping up with the Joneses even when you're at a certain level. And I think you, you know, Steph just gets normalized. You're like, oh, so and so is flying on a private jet to go on a vacation to here. And then that seems normal to you, even though it's not normal at all.

You want to hear something sad? Yes. I have a friend who's like engaged to a billionaire who has a, she has a startup that's valued it over a billion dollars. And I live in Kauai part-time, and they came and they visited, they didn't like visit me, we were there at the same time, so we hung out,

and I stopped by their rental on the water, and their chef cooked his food. And she, I was like, oh, how is your flight? And she was like, oh, we flew private. And I was like, man, I don't really want more. Like, I don't want more. It's a problem. It's actually a problem.

Like, I don't want more. And I'm kind of lost because I don't want more. But that would be great. Like, that's one thing that just would be so convenient. But again, like whatever. I've diamond medallion. And she was like, yeah, I mean, it's the best. I would live in like a $2 million home

if it meant I could keep flying, right, bit. And I was like, whoa, wow, you're so out of touch. This is scary. And I like made a joke, I'm like good at, like, you know, cajoling people without insulting them. And I don't know if it brought her any level of self-awareness, but it is an example of, you know, the freak show of success.

It is. It's super weird. Flying to, I think, I've flown private a few times and it's definitely much, much, much, much better. I don't know if it's so much better that I would ever pay for it, but I certainly don't mind when other people are paying for it. It is one of the few things that everyone, with the exception of the very, very few people that fly private, it's one of the last places on earth that everyone is equal, like the airport, right?

Like it just fucking sucks for everyone, even if you have status on an airline, even if you can go in the lounges. It just sucks, right? And so like there is probably something to be said about maintaining parts of your life that suck and connect you to the suckiness of life that everyone else is experiencing. Yeah, there was a time where like everyone was doing everything for me and I was like a baby.

Like I had like Tom Cruise's ex assistant and paid her like 130 grand a year and she like showed up and like I didn't even know people did this but this is just like what she was trying to do and what she did. She like packed my suitcase on trips. She like made a whole duplicate of toiletries of stuff that I used at home and she had an inventory of it and she replaced stuff if I ran out of it. Like I we flew together. She I literally just like stared at my phone walking through an airport and she like pulled my idea out of my bag when we got to the counter. She checked us in. She navigated us to the gate and I was just like boo boo boo boo boo. She carried my bag. We got to the crossbee hotel. She gets to, I could go straight to a meeting. She'd have my shit.

She would like unpack me, steam my shit, put my laptop on the desk, plug it in, put my tampons in a cup in the bathroom, everything. And I, she would order room service for me the next morning. She would show up wake me up if I had like an early morning. She'd unlock my room and she'd turn the shower on and be like, okay, and open the curtains and be like, it's time to start your day. Yeah. I had a full-time housekeeper for six years

who like when I had to run, she would like go at like 8 a.m. before I had to drive to work and like gas up my car. I didn't go to gas station for years. And like pre-instacart, like my fridge was always stocked. Like, you know, my bag on the counter, here's what I need, I need this, this, this, this, and if it's scattered, it's what it's not, when I have to leave in the mornings, just like grab the shit and go. Like it was crazy. And I realized when I stopped working without assistant and no longer had a full-time housekeeper, I was like, fuck, like I was like a big baby.

Like I'm a really capable person. And this, I realized like how much pride I have in'm a really capable person. And this, I realized like how much pride I have in being a really capable person and how kind of rewarding and just to stupid shit and solve your own problems, like how to like hack like an airport thing that nobody else knows about or whatever. And that kind of resourceful, when that kind of resourcefulness only

exits in your business, it's like, I don't know, it's kind of boring. Did that go away suddenly or was it gradual? Like was it a reentry or was it a she left and I had another amazing assistant and then nasty gal ended and then I hired my own assistant but it wasn't like a super senior assistant. I didn't have a senior assistant for like a year later when I started my second company Girlboss. But not really. You know, now I drive an electric car and just like charges itself, so whatever. Raising kids can be one of the greatest rewards of a parent's life.

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So if you like to laugh with us as we talk about the hardest job in the world, listen to, I love my kid, but wherever you get your podcasts. you can listen ad-free on the Amazon music or Wondery app. I think about that. I actually have a chapter about this in the discipline book. There's this story about Martin Luther King. He's, his wife, Coretta, is called by the actor Harry Belafonte. And, you know, she's on the phone,

and she's like cooking dinner and answering the door and tending to the children, just all this stuff. And he's like, I have to ask, do you have help? And she was like, no, Martin would never allow it, right? And Martin did have help, it was his wife, right? He just didn't allow her to have help. And Harry Belafonte is like, this ends now. I'm hiring a staff for you,

and I'm gonna pay for it. And it's this breakthrough, because he's like, I want you guys to be focused on the movement, not like, is there milk in the fridge? So I think people have a balance. That's a difficult balance for people to strike. Some people are way too independent,

and they don't outsource and staff and bring people on to make things easier for them. And then certain people have either so much resources or they're so entitled that they have everyone do everything for them. And the middle ground is where you want to be. Like my wife and I, we sometimes we just look at our lives and we're like, we're doing too much and the result is our marriage isn't as good or our we're like, we're doing too much and the result is our marriage isn't as good or we're not spending enough time with our kids because we're not doing it.

And like we have been trying to staff up, but the other thing we've been looking at is like, also, are we just doing too much? Like maybe the thing isn't to have some. Yeah, it's not to have someone travel with you, but maybe just agree to go on fewer business trips. Yeah. I just hired an assistant after a pretty long hiatus. And it's a little risky because business class, which is my entrepreneurship program that

I teach twice a year, you know, businesses down, like people left, you know, it's COVID, they're traveling. So that is what it is across all kind of educational online, online educational businesses. Yeah. And I, but my, I got a brand new roof. It leaked the first time it rained. There's a bucket in my hallway. I think I have to sue these people. My dishwasher broke. This, the faucet, the sprayer broke.

We just had to replace that. We replaced the dishwasher. My curtains were broken. There's like, I have to file like a police report for storage units that got broken into and everything stolen from, trying to transfer my ex filed an insurance claim on a car that like on my insurance, whatever,

or don't put whatever. All this shit happened at once and I was like, holy shit, like this is taking up half my time. Yeah. And I wasn't able to work. And sometimes when you like, in a lot of the time,

when I like cast something out and make a promise, like spend something on someone, this happened with my first employee, it was like, I don't know if I can afford her, or keep her busy full time. And so as soon as that happens, like your life expands to the level that you've committed. Yeah.

And like I just made up like what business class like didn't like make this year. Yeah. In like a two month period. Right. And I've like paid for him, you know, a few times over in a couple months. I tend to find that too. I have never once hired a person and then been like,

I don't have enough work for this person. It's almost always needing another person after. And then I look back and I go, I was abusing the people that I hired before because I was making one person do what is clearly five people's jobs. You know, I almost feel guilty every time I hire someone because they, so it so clearly becomes a full-time person's job to take whatever I hand off to them and then I go, how is I doing this

with no people before or only to do it? But also even worse, like when your team is at scale, like bloat is like a real thing. And you know, like know you're bloated until you like lay people off or fire someone and like the rest of the team absorbs it. And you're like, and and some and that's just like no sweat for them sometimes. Like sometimes they like resent it. But like, you know, this doesn't happen with smaller teams, but with larger teams, it's like, wow, like, what was I doing? How dare I, you know, how dare I have let this happen? But you fire a low performer, you realize, shit, they weren't doing anything. Yes. That's on you. That's on you. I was, I was talking to Gary Vaynerchuk about this recently,

where like, the other thing I struggle with, maybe you do too, on you. I was talking to Gary Vaynerchuk about this recently where the other thing I struggle with, maybe you do too, so you hire staff or whatever. I'm like, okay, I'm doing this now in addition to all my other stuff. Then I'm handing it off to this person and they're struggling with the workload of it. And you're just like, wait, I was doing this two hours a week and doing just fine. And somehow you have 40 hours a week and you're like too busy, you can't take on anything more. And so I go back and forth between like having

very high standards and then empathy going like, hey, maybe I really can do in two hours what it takes someone else 40 hours to week a week. And then other times I get resentful and I just go, what the fuck? Like this can't be that hard. Yeah, no. I mean people join and they're like, I have a career and I'm senior and I'm used to having

a team and I don't execute. I like do strategy. Like I've been at this so long that I'm an expert that I'm just like unwilling to execute and then like they need to hire people to actually execute. And you're like, wait, how did I just build an organization when I needed someone to do one thing? And that's like, it's dangerous to hire someone and then train them. And it's time consuming. If they're like more junior, you hire someone more senior and you have that happen.

And you're just like, I hate this. I hate it. Yeah. And, and, and I'm just like, I'm also like, I can't burn any more people out. I think that's what, that keeps happening. I keep hiring people and then they make it a few months and then they burn out.

And I'm just like, either I'm a monster, which I don't wanna be or just talking about, or people just can't cut it, you know? And- I think they over-complicate things. Like, just be scrappy. It's not hard. Yes.

It's not, you don't need to push things around that aren't the thing. Just like do the essential things. But again, same, same as I said, like your life will expand, your pants will expand to like you buy bigger pants. Like that. I'm just like a won't buy bigger pants. I'll just figure it out, you know? But like also you hire someone and like they're gonna make enough work to expand to like whatever they're just you know it's like it's not their job to drive efficiencies if

there isn't that much work for them. It's their job to prove to you that they're busy. Right. What if you really... And feel that time. What if you're just walking around an uncomfortable pants all the time and just slightly bigger ones would be a gift to yourself? It's just not something I do. It's expensive to buy new clothes and I'd rather have a camel toe than buy a bigger size. So what was harder for you, some of the professional setbacks or the personal setbacks?

I know you've talked, I'm not just speculating about your personal life, but you've talked about your marriage falling apart basically right around the same time as Nasty Gow. So what hit you harder? Yeah, so, harder. It just felt like it all kind of was part of the same thing. Like it was just so much noise, it was hard to like,

disaggregate anything that was happening at the time. And while like Nastya Gowell had done some layoffs or whatever, like I was still like, you know, and Forbes was like, you know, hey, we estimate your network this, we want to put you in the cover. And it was like, cool. Sounds great. You know, if this company doesn't work out, that's such a big kind of up, like, and this was in earlier in 2016, you know, months before we filed for chapter 11, and I was like, yes, I just say yes to things to like write a story that's going to be entertaining for me. Like, it's totally dangerous. It's really like not strategic, but I'm like, this is super entertaining.

Like, I get to talk about this when I'm old. Like, that happened. And so, in June of 2016, I was on the cover of Forbes as one of America's Riches Self Made Women. And then in July of 2016, my husband of like, which is like, we were together for like five years and you married me like eight months ago, like what do you do and like what?

What? It was so expensive, the wedding was so expensive. The divorce was inexpensive because I had an iron clad pre-napped. And TMZ, like who cares? But like TMZ has an office inside of the courthouse in LA, and they just look for divorce filings, and they were like, nasty gal founder,

files for divorce, pays ex-appitants. It was like, this is funny. Yeah. Okay, this is funny. And then six months later, nasty gal happened, nasty gal kind of fell apart, sold for $20 million in chapter 11, okay. So like, whatever, I didn't make it, but like, still, like such a huge accomplishment. So proud.

Yeah. Like, it was worth that, it's worst. And then, and we filed on the day Trump was elected. So there was all this like women stuff like, oh my god, Hillary could be a thing. And then like my company fell apart, the day Trump was elected. And it was like, oh my god, this guy, ground by the sweat, like, yeah, this is our president, like, and then the whole women's movement happened. And me too, and girl boss was like a very simplistic

view of like my story. It wasn't like an example of all women. I wasn't speaking for all women. I didn't even talk about being a woman in the book. It's just called girl boss. Right. It was just my story and some advice. And then I became like held,

it was just kind of like being a woman was like super politicized. And they were like, speak on behalf of all women. And I was like, I've never worked in an office. I can't talk about like the wage gap, but why? What help? And I started Girlboss, my second company around, and I told you I just kind of went straight into that, like, host of the first conference.

Brands did partnerships with me. You know, we did over a million dollars in brand partnerships four months after my company fell apart. So it wasn't, I wasn't like doomed, but what really snowballed and what was really the noisiest was that in April of 2017 Again four months around the time I held the Girl Boss rally our conference I a Netflix series came out about my life right called Girl Boss in the characters name of Sophia She was starting an eBay store in San Francisco She was starting an eBay store in San Francisco and the company was called Nasty Yow. And I had left Nasty Yow 4 years prior or 4 months prior.

And here's this show that is telling 140 million viewers in 195 countries about this person named Sophia starting a company called Nastyya when after 10 years of being involved, I'm four months out of it and like trying to move on. So and then and then of course there had been press about like, is she a girl boss? Her company fell apart. There was already that up into the show. part, there was already that up into the show, then there's this scripted comedy adaptation of this exaggerated version of who I am out in the world and the amount of, and literally there's, I had been criticized, but TV shows, they're literal critics, it's like their job.

There's, and that's, you know, what happened when a show came up, had so much press, and I've never seen the amount of press that television or entertainment generates. And there were headlines like the worst thing about Netflix's girl boss is its source material. And it was just like, wait, am I the author of GirlBoss, am I a CEO, or am I this character

on Netflix and, you know, what of these things do people think I am? And it all became super conflated. And it was at that point that I was, it was just this kind of like onsslot identity kind of crisis in a way. But I just like kept going. Like I'm a beefed and it's just like what I do. But like personally, I'd say that was the hardest point. Yeah, my first book got optioned to be the reality show. And then it got optioned to be a TV show and then a movie. And I

sometimes think back to that my biggest break was that none of those things got made. Yeah, if you're young and someone's making a show about your life, like it's like, okay, if you're like, whoever, some like, old person. At the end of your life, yes. The end of your life, but telling your story in the middle of it and like marking that place in time when you're still telling your story and you're still building your stories, like really weird and it doesn't really happen a lot, you know? It can't be good for the ego, right?

Like I don't think many people leave that success or failure of the project more well adjusted than when they went into it. Definitely not and I was not unhappy when the show was canceled even though I loved the process. But you know, there are definitely comments that there's so many people love the show, but there are definitely comments on the internet that were like, you know, it was the beginning. The first season was like starting an eBay story. Yay. They were like, can't wait for the next season. They were just like, can't wait for the rest of the story. I never, I don't know.

Please, no. Yeah, it must be weird too, because you were kind of this symbol, like where everyone was rooting for you. And then culturally, we have, it feels like culturally we have trouble rooting for women on a sustained basis. We can do it in the short term. And then obviously the underdog story

is a perennial one for reason. But it feels like we root for women for a while, just enough making them just big enough that we can really viciously turn on them. Yeah, absolutely. There's fewer of us. So there's fewer of us to hold up as heroes. There's fewer of us to show, you know, be made an example of when things go sideways. You don't see the CEO of a multi-billion dollar company being skewered because he laid

off a bunch of women or whatever. And I was like, not a girl boss. And it's like, guess what? I'm trying to run my company responsibly. There will be, there will be, what's the word, people who are affected by that in negative ways and that's something that's really serious and a responsibility that I take very seriously, but it's also like this is running a business,

like there are ups and downs. I had a bloated business. I had commitments to investors. I owned a lot of the company and I convinced that rest of the employees employees who stuck around I preserved their jobs by cutting heads and you don't see the CEO of whatever company Pinterest, you know if they did, you know Twitter, right? It's not gonna be like Elon Musk is a misogynist it's like you know Elon Musk is a misogynist. It's like, you know, Elon Musk is like a crazy, like, you know, he's a whole bunch of

other things. There are louder things to, you know, call him probably, but you just like don't hear that. And people take female founders down with such glee and it's super misogynistic. I do think that where there is, you know, smoke, there's fire. And as we saw during the Me Too movement, like, people have to be made examples of.

For there to be an archetype that people like don't no longer, that is no longer accepted. And sometimes that is a much larger kind of like fall or criticism than that person even really deserves. And this is coming, you know, whatever, I'm not like a survivor of anything other than my own kind of mind. But so speaking from my perspective,

like, you know, there was a lot that happened during that time that were, you know, unfair exaggerated examples of people who had done stuff that was like, this is just what people did like 30 years ago and it's totally not okay, but like, are they doing it anymore? Like give them a break. And I think that had to happen with, I didn't really have to happen with me, but it did happen with some of these like

women-owned businesses, these startups who, you know, had been, you know, heralded as these kind of heroes in a few years after I had been. And during Black Lives Matter, there was just this whole slate of female founders that were just like taken literally everyone. It was like Glossy's racist, a ways racist, the Museum of Ice Cream's racist, the Reformation's racist. I mean, she, I mean, there's like photos of her like eating fried chicken, like, like, what, like, there's serious shit. And like, you know, employees, you know, with the wing, it was like, they made an Instagram account called Flu the Coo. Like it was like aoo of employees. Yeah.

Glossier had something called Out of the Gloss, because her original blog was called Into the Gloss. And there were some examples made, but I think it was, you know, I think for the most part, they were really extreme examples. And a lot of value was destroyed in those businesses. And I guess you mentioned Elizabeth Holmes at the top of this episode. And I almost stopped you and it was like,

please don't even matter that name. Like stopped. Like stopped. So stop. Like three days ago, the information, this highly respected subscription base, it's like $150 or $200 a year tech news, they have exclusives, they, you know, it's the people who subscribe to it are serious. They had a weekend edition where they did a roundup of Halloween costumes, tech-hull tech-inspired Halloween costumes that you could be for Halloween. And one of them was like

basically like disgraced girlboss. Like I wrote the book eight years ago. I stepped down, out, hated it, as the CEO at NastyGal in 2015. Like I left NastyGal in 2016 and then I built an amazing culture at Girl Boss after that. When we did lay off that time, I got thank you letters, like totally different culture. Nobody knows this.

And this long, this far later, like this is woman-owned publication, I emailed Jess Kalesen, didn't hear back from her. Audrey, from the wing, emailed Jess Kilesh and didn't hear back from her, Jessica. Yeah, the founder. And it's a picture of Audrey who founded, co-founded the wing, wearing wings that were singed

at the ends and it was like, girlboss too close to the sun, which is like a meme. And I actually think it's kind of funny, because was like girlboss too close to the sun, which is like a meme and I actually think it's kind of funny because I did girlboss too close to the sun and inspired people to go like, you know, be way too ambitious and fuck up and that's fine. Better than never having tried. And it says like dress up as your favorite disgraced girlboss

like Audrey Gellman, Sophia Amaruso, or Elizabeth Holmes. And this is like this long after everything. And it's just like to be made a caricature this many years later, having like moved on and done really great things and made a huge impact, continued with women, also with entrepreneurs broadly with business class is just like it's shocking that that's still happening and and to be lumped in with Elizabeth Holmes like I just like I don't even want to say that name again because I feel like I'm doing that by saying her name is just like it's just like super fucked up. No, I'm sorry for even bringing up the name because I was trying to make the exact opposite

point that you made later, which is that you had a business that was successful. And then even when it closed or sold, like even its scrap parts were worth a significant amount of money, which is very different than what it was essentially a multi-billion dollar fraud perpetrated on the public and on investors. And that is bullshit and must be frustrating, but also so out of your control that you've had to just like shake your head and keep moving, I imagine. Yeah, I think what's challenging on an existential level is moving past like who I think I am

and being reminded of like who a few people think I am. Like sure. People, the million people who follow me across social media channels, they don't think of that. My friends, they don't think of it. They've all moved on. But then there's the clickbaity media who, whatever, for whatever reason, does this stuff. So I'm trying to move on. And then most people don't have these outside entities not letting them move on.

If they do, they're friends and you dump them. It's your parents and you're like, I don't want to talk to you or whatever. Yeah. But I am not allowed to do that. And that is, that's a little bit, that's really challenging. Yeah, there's a passage in meditations where Marcus really says that, and this is I think the curse of politics, leadership, success, whatever.

He says, kingship is earning a bad reputation, doing good deeds. So the point is, like, you do what you think is right, you do what you do. And people still dislike you for it or criticize you for it or label you something for it. And it's super disorienting, as you said, when you also have people who really like what you do and you have a good reputation with them, it's like imagine being like, I don't know, in Nickelback or something.

You have these like fans who love you, and then you have these like, what we would call elites who hate you, and you exist in a world where both those things are simultaneously being bombarded at you at all times. I mean, it's also why Marcus Relays is just like, don't be a king. Yeah, sure, right.

You don't want to be a king. Yes, you don't want this. No. So having gone through what you've gone through, how has it changed your definition of what success is? I imagine you've experienced a lot of different lives, right? What is the life that you're like, that's what I want my life to be, that's what success is?

Because you've started other businesses you have one now. I'm no idea. Like I wanted to have kids for like eight years and I tried with two different guys and now I'm like, I have a boyfriend, but I'm like, shit, I'm 38, like do I want that? Like they seem like, that seems like really challenging. Or like, you know, I'm just like,

I like took the ride from there to here. And I don't want to take a ride. I want to be really deliberate with what happens next. And my ride is great. Like I could just like fart and manifest shit. Like it's crazy, but it's dangerous. And I don't want to be like opportunistic without being strategic, which has served me, but also not added up

to something, to what I, to something is meaningful as I think it could have been. And my next question is like, what's gonna be meaningful? Not like, how much money am I going to make? But like, 38 to 48 is really different. Like you're pushing 50 and then you're like, fuck. Yeah. Right?

Yeah. Like, 28 to 38 is like, okay, cute. You like did all this stuff and none of it was cute. But it's just, I feel like it gets more serious. And I've like taken my Expect not expectations of my life, but what I want in my life like I'll like personally some of that like hasn't really Like manifested like having a family being one of them and now I'm not saying like I'm not sure if I want one just to like De-flect and be like well, I didn't get what I want. I think people make excuses

and just instead of sounding disappointed, they say, I'm not sure if I want that, but I literally, I don't want my future to be a hangover of what I used to want. Sure. Or chasing things that you used to want, but you're not actually sure. Just because I didn't get them.

Yeah, sure. So I'm like, I've really kind of put myself in a place where I don't know. And if I do want those things, I want it. And this is what I'm really good at this. But it's also peeling back layers of the onion. Do I want this? Am I influenced by this?

Am I, do I want this to live up to something culturally or because I want to chase relevance or how did this enter my mind and why is it still here? Is this something I'm attached to because I used to be attached to it? And I've just kind of leveled everything for myself and I don't have an answer to your question. And I'm kind of at the beginning of like, OK, how I've settled everything for myself, and I don't have an answer to your question. And I'm kind of at the beginning of like,

okay, how do I build real resilience, not the kind of resilience people think I have because I just like keep showing up on podcasts or whatever. Like how can I build like emotional resilience and how can I build something greater than myself that isn't just some like flywheel of content or like, you know, people, like a business

or whatever, there's like more than that. Yeah, you know, it's funny you were describing your life earlier, the traveling around, the assistant, you know, snow plow in front of you, making sure you never have to struggle with things going from meeting the meeting city to city. And I've had that life, and I've met a lot of people who have had that life. And one of the things that I always feel when I'm getting close to it or when I meet people

who have it is I go this person is very successful, but not very free. Like this person is is in a very nice, gilded cage. They are not in control of their schedule. You know when you meet someone and you're like, okay, yeah, we can get on the phone. You can call me tomorrow at 207 PM and we can talk until 2.13 PM or whatever. And you're just like, what world do you live in? You're scheduling in six minute increments or whatever. That sounds like it sucks.

And I have come to think of freedom or autonomy as the ultimate form of success. And I've come to pity people who are very rich and powerful, but have no autonomy. Yeah, there's like, there's a balance there, you know, like I went from, in some ways, being that person and being super busy and building a company with Girlboss and then started business class, which is, you know, an online course that we do twice a year. And so I was like, the next thing I want, I don't want to be this undertow of entrepreneurship where I have a team and I have to feed the beast all the time. I'm trying to bring in revenue. I'm shipping goods all year round or I'm trying to close like projects. So I started a business, but I made it feel like a project.

And the outcome of the business is outsized to the footprint of the business from a human perspective, from an investment perspective, from an effort perspective. And there's a playbook for that with online courses. And I was like, I'm not gonna reinvent the wheel. So I'm gonna launch this in the spring

and enroll students in the spring. I'm gonna enroll students in the fall. And I like wanna break for a second. And it was fall of 2020 that I launched business class. It brought in a million dollars in revenue and a few months after I started putting the content together. The next year it did, you it did several times more of that, bought a house in Kauai, and I just like,

did nothing all summer. And it was amazing, but then I went through a breakup, and now I'm like, all right, like what am I gonna go hang out by myself for months on end in like a beautiful place? Or am I gonna like, you know, use my talents, fill my time and get busy again, and like not just a fill time, but also,

like I wanna use my brain, I wanna be curious, I wanna build things, and also maybe I'm ready to like regain the confidence it'll take for me to do something bigger and a, that's a bigger commitment than like an online course that happens twice a year. Like that fit the thesis of what I want to then and I have room to do more now and I'm not sure what that looks like

and it's gonna take more than a strategy. It's gonna take some personal work as well, not to do it like living in fear and like it's piece of Swiss cheese that, like, the, like, the wind blows through when, like, you know, something happens, or like a room by looking for, like, some shit, like, just thinking, like, this might fulfill me, like, it's, it's like, you want to be busy, but not too busy. You want to have power, but not too much power. You want to have money, but not too much money.

It all comes down to what the Stokes would call temperance, the right amount. And not of some things, no amount is the right amount. There's not just the right amount of doing heroin or being a creep, like we were talking about earlier. But you want to be like, you wanna be like in the league, but I don't know if you wanna be LeBron James. Do you know what I mean?

Or you don't wanna be Tom Brady probably, right? Like you don't wanna actually be the greatest, best person with the most. You wanna have access to all those things and be personally fulfilled without being consumed by it at this catastrophic level. It's just like leading from behind. It's not leading from the front, it's leading your life from behind. It's building a bottom-up plan instead of a top-down. And the same with your business, it's not just like, of course, you want to shoot for the stars, and there's your top-down plan, but you have to temper it with reality.

I imagine that's a little weird with business class too, because you've learned how to have a successful business, and you've learned all these things about the actual realities of running and succeeding in business. You have this deeper philosophical and personal understanding where you probably questioned some of it, where you put it in perspective, et cetera. It must be when you're talking to someone who's 23 and they've got their first business, it must be interesting for you to decide

like which of your hats are you gonna instruct them with? The one about like, here's how does grow and scale this, and then here's the one about like questioning it, and where does it fit in your life and all the sort the larger philosophical. No, not when you're 23. Just go. When you're 23, just go be messy, but also kill your darlings quickly.

Go have multiple businesses. Don't be attached to what it is that you start messy, iterate, start with a skateboard, put some handlebars on it, then build a seat, and then you have a bicycle, but don't start with a bicycle. I feel bad for rich kids, it's hard for them to do that. Yeah, I just took my kids to Disneyland, like this is the day before yesterday,

and we had to make this decision about you can hire a guide at Disneyland that takes you around and you don't have to wait in any of the lines. And it was like, do we do that or not? And it was like, cause I don't wanna wait in the line, right? And, but they should probably wait in line. I've waited in the Disneyland line

saying I know it out my whole life. And so we didn't, and then we flew home on Southwest. So I feel like it was character built. You did it. We did not do it. We And so we didn't, and then we flew home on Southwest. So I feel like it was character building. You did it. We did not do it. We did. We didn't pay for the guide. I probably bought them more toys than my parents would have ever bought me at Disneyland.

There was a fast pass thing on the app now. You can like buy your way into, and here's the trick, because you have multiple tickets on there. You can book like three people on one ride, and be on the wait list for that for like a few hours later, and then book one other person for a different ride. Or two and two. It's easier with two people to be like, I'm booked on this, you're booked on that,

and then you go to the one that's like the earlier one, and you're like, boop, scan the barcode, and then you boop the other person's one, and you're like, boop, scan the barcode, and then you boop the other person's one and you're like, what happened? Like, why, oh my God, I thought we both signed up for this one and they're like, whatever, just go through. Well, that's very genius.

Like, we did. We did. We did. We did. We did. We did. We paid for the app. So we got like some fast passes.

But the guide thing, you can just do any ride in a time, no thing. Oh, it's so expensive. I did that on New Year's one day. Well, my friends all stayed over. We were super hungover. I had the kind of assistant that could literally just call Disneyland be hours later.

We show up, and there's a guide, and we just went on everything. But that was many years ago. We kept it small, but then we ordered room service in the hotel, which my parents would have never done. Can you stay at the Grand Californian? No, it was booked up, so we were in a Hilton Garden in down the street. Again, all character building on purpose. Good job.

Yeah, you try. on purpose. Good job. Yeah, you know, you try, you try. But, but I think the, the, the one I struggle with more is like, they're like, can I have that? And I'm like, I don't give a shit. You can have a churro, you know, like, uh, or you can have this Lego set. I think, I think I probably buy them too much stuff. And that's probably not the best lesson. I think that's wasteful.

I think it matters less like about whatever, but just like don't make too much, don't make too much garbage. No, that bigger lesson for your children is like, this is also it's like you're the guy who's like would know it would understand like dead weight more than anyone. You know, like meaningless stuff like in your life, you're not Marie Kondo, but also like, it's just a funny contrast, that's all. No, it is, it is. I've talked about this, we just speaking of hiring people, we had to like hire an organizer to like just come

and organize our stuff because one, we buy too much stuff for the kids, but also like, I don't know about if you've experienced this is a very first world, but people just mail me shit and then I feel bad throwing it away, but it just, it fills up my life, you know what I mean? Like, not just books, I mean, I get thousands of books

that I didn't ask for, but people just mail me stuff and I'm like, feel bad throwing it away or even giving it away and then it's just there and I had to bring someone throwing it away or even giving it away. And then it's just there. And I had to bring someone in to clear it all out. You're like, donate stuff. Yes, that's what I do, but it's still weird. Well, there's a weird note to end on, but we should call it.

Yeah, don't fight shit. I mean, that's like, that's the moral of story, temperance. It is. But it takes discipline because when you can afford to, and it's a rounding error, it feels inconsequential to buy it, but it's not inconsequential. Mm-hmm. It does all that up. It does.

It both in your house, in the landfill, and everywhere else. Well, this is amazing. I hope we can meet some time. I know. Let me know next time you're at Disneyland. I will. I will. Well, if you get enough people, it starts to make sense to get the guide. I know. You need like 10.

Yes, exactly. All right. So you all put you down for the next time and go to Disneyland. All right. To me, discipline is the most important trait a person can have, right? It's not knowing what you should do, it's being able to do it, right? To have the force of will and character to stick to the right path, and even, as Seneca says, when those around you are hopelessly lost. There's no one truly great that we truly admire, who hasn't been defined by their self-control

and their discipline. So I can't wait for you to check out the new book discipline is destination the power of self-control. The second in my four virtues series on the Cardinal Virtues of Stoicism, Courage, Discipline, Justice, Wisdom. The new book is out now. We're still honoring some of the preorder bonuses which you can grab at dailystoke.com slash preorder. You can pick up discipline, it's destiny, the power of self control, anywhere books are sold.

Grab it on Audible, you can grab it on Kindle, you can pick it up at your local indie bookstore. If you want me to sign your copy, you can also do that at dailysteoic.com slash pre-order and we even have some signed manuscript pages for people who order five copies, plus you get a bunch of other bonuses which I'd love to give you. So sign up at dailysteoic early and ad-free on Amazon Music, download the Amazon Music app today, or you can listen early and ad-free on Amazon Music, download the Amazon Music app today, or you can listen early and ad-free with Wondery Plus in Apple podcasts.