NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso

In this new episode Steven sits down with serial entrepreneur Sophia Amouroso. Sophia Amouroso is an American business woman and New York Times best-selling author of ‘#GIRLBOSS’ which later became a Netflix series of the same name. Sophia founded the female fashion retailer, ‘Nasty Gal’ in 2006 when she was 22 years old. 6 years later, Nasty Gal was named the "Fastest Growing Retailer” in America. However, in 2016, the same year that Sophia was named by Forbes as one of the richest self-made women in the world, Nasty Gal filed for bankruptcy. Since Nasty Gal’s bankruptcy Sophia has founded ‘Girlboss Media’, an online community providing mentoring and support for women worldwide. As well as ‘Business Class’, a comprehensive tutorial course that helps founders accelerate and scale their businesses. In this conversation Sophia and Steven discuss topics, such as: How Sophia’s rebellious nature helped her to create an original business How she regards being an outsider as a superpower Why as a CEO you only know 10% of what is happening in your company Why Sophia would never want to be a CEO again You can follow Sophia here: Instagram: instagram.com/sophiaamoruso Twitter: twitter.com/sophiaamoruso Follow me: https://beacons.ai/diaryofaceo Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Steven Bartlett?

  Didn't you get an offer to sell the company for $400 million?

• 0:02Speaker 01

  Yeah, I did.

• 0:03Steven Bartlett?

  Which made you...

• 0:04Speaker 01

  Super rich.

• 0:05Steven Bartlett?

  Why didn't you say yes?

• 0:08Speaker 01

  You're very good at this. Sophia!

• 0:09Speaker 02

  Anna Russo! Founder of Nasty Gal, a bestselling author, and a powerhouse in the entrepreneurial world.

• 0:16Speaker 01

  I was rebellious from a very early age. I was a stripper. I wasn't even 21. I used someone else's ID to work there. Built an online business. The first thing I sold online was stolen. Get a whole shopping cart of stuff, put them on Amazon for 10 cents less than the other resellers. And then gotten arrested for shoplifting. I'm a little dark. I realized I could connect my creativity to something legitimate. Started Nasty Gal, selling vintage.

• 0:42Steven Bartlett?

  Nasty Gal went from $150,000 a year to doing $150,000 over lunch.

• 0:46Speaker 01

  I didn't realize the amount of responsibility I had, being the poster child of entrepreneurship. Then I was this girl boss, but my naivete and lack of experience did send me to the grave. Nasty Gal fell apart after 10 years. My husband of like a year left. The headlines weren't nice. Then Netflix comes out. You just got played.

• 1:05Steven Bartlett?

  What is it like from a mental health perspective?

• 1:07Speaker 01

  It's hard to pull yourself out of a hole when you don't want to get out of bed. It challenged my confidence and I'm still like, I don't belong here. But "I don't belong here" is also a really great motivator. "I don't belong here" means I don't fit in, but that's going to be a superpower. I can do things differently.

• 1:25Steven Bartlett?

  What was the plan in life at that point?

• 1:27Speaker 01

  Oh, gosh.

• 1:39Steven Bartlett?

  Sophia,

• 1:41Steven Bartlett?

  take me back to those suburbs in San Diego and give me your earliest context.

• 1:47Speaker 01

  Wow. I was born in San Diego at Sharp Memorial Hospital. Only child. Eternally an only child. I think wound up having the personality of a probably seven children and the challenge of maybe seven children for my parents.

• 2:06Speaker 01

  We moved a few times. You know, our house was like, it was happy-ish when I was young. I lived in San Diego till I was seven and it's a beautiful place. And I so wish we would have stayed there, but we moved to beautiful Sacramento, California. And that was really the suburban experience where, you know, when you're a... Kid, a little kid, you don't know what a suburb is and chasing the ice cream man is great, but once you get older, living in the suburbs, if you have any amount of curiosity about the world, the homogenous, you know, nature of living in the suburbs is something that totally crushed me. I knew there was more out there and I didn't know what it

• 2:50Speaker 01

  was, but I wanted, I like wanted out from a very early age.

• 2:55Steven Bartlett?

  What, what did you, what did you want at a very early age? When you say you wanted out?

• 2:59Speaker 01

  Oh, yeah.

• 3:00Steven Bartlett?

  What did you want?

• 3:01Speaker 01

  Yeah, I wanted out of my family home. It wasn't happy. My parents didn't get along. I was playing referee, you know?

• 3:09Steven Bartlett?

  Really?

• 3:10Speaker 01

  Yeah.

• 3:11Steven Bartlett?

  What, what age?

• 3:13Speaker 01

  Starting at like 10 or something. I mean, yeah, it was just, it wasn't a super happy place and they, yeah, they didn't get along. They didn't always agree on how to raise me. And I think when your parents, you know, everybody's relationship has issues and everybody's, not everybody's, but most people's parents, you know, sometimes don't get along. When you have a sibling, I think you can go be like, mm, that's funny, or they're whatever, let's just go play with Legos or something like that, or let's go ride bikes. But I think being isolated in a house that wasn't super happy as an only child made it worse.

• 3:58Speaker 01

  And I just remember so many drives, silent car drives where I was in the backseat alone and I just remember like the silence and the, the light of the streetlights like washing over the car, just in, in silence with my parents in the two front seat. Um, yeah, they were really like only affectionate after like an argument and even then it was like, I don't know, handholding or something. They were very strict as well. I had to beg to go to a boy's birthday party in sixth grade.

• 4:39Speaker 01

  We weren't super religious, but my mom grew up in the 50s in a Greek Orthodox household, um, just not puritanical because that sounds less cultural than Greek Orthodoxy, but uh, strict, you know?

• 4:56Steven Bartlett?

  What about money? A lot of um, a lot of arguments happened in my household when I was younger because of money.

• 5:03Speaker 01

  Yeah, I mean, my dad sold, my dad did loans and my mom sold houses, but track homes in the suburbs and they were both working with builders and banks and manufactured homes. And so on the weekends, by the time I was, I don't know, maybe 10, my mom was working in the model homes that are all kind of dressed up and you can tour them and pick your manufactured home and change a couple of things. And there was like a fake keyboard in there and just all kinds of funny things to play with. And then, so I was with my dad on weekends and my, and they both worked entirely commission. So I've never seen either of my parents work for a salary and my mom's dad didn't work

• 5:47Speaker 01

  for a salary and my dad's dad owned a motel and they all grew up on a motel. So there's like generations of my family who wouldn't necessarily call themselves entrepreneurs, but they're people who ate what they killed and that's what I witnessed. Money was good, I think, when I was like, you know, when we were in San Diego and I think it got tougher over time. I remember very vividly being in a credit counselor's office. I just can't believe they brought me, but there was no, I don't know where they would have put me, watching them cut up their credit cards, like cut their credit cards in half and put them in a clear jar with like other people's, cut up credit cards and file for chapter 11.

• 6:32Steven Bartlett?

  Bankruptcy.

• 6:33Speaker 01

  Yep.

• 6:35Steven Bartlett?

  Did you know what was going on?

• 6:36Speaker 01

  No. I still don't know what happened. I don't know.

• 6:41Steven Bartlett?

  As an adult, are you able to look back on that? That first sort of chapter of your life and figure out how it had a lasting impact on various elements of who you are today?

• 6:52Speaker 01

  I think it allowed me to, even though it was so challenging younger in life, to learn how to assimilate into different environments. To, I guess, entertain myself independently, to realize that authority was, like, adults were not trained to be parents and weren't any further along with their maturity sometimes than I was at my age. You know, I looked at teachers and thought, wow, you know, you have domain expertise. You know some stuff, but I can tell that, like, you're morally bankrupt and I don't trust you. And why have I been put in your, you know, in your hands?

• 7:36Speaker 01

  I think the thing that had the biggest impact on me is how critical my dad was. So he's half Italian and half Portuguese and his dad was a mean, mean guy. And my dad's very charismatic and I love him and he's super chill now, but when I was young, he had a lot of pressure on him and he didn't really have the best model of what a great parent looked like. And I can't say he was a bad parent, you know, he did his best. I know that both my parents did their best with the materials that they had, the ingredients that they had to be parents. But it instilled in me this unfortunate, but also very fortunate.

• 8:22Speaker 01

  Always peeling back another layer of the onion, examining myself, but also real internalized drive to do better and a self criticism that has worked very well for me. That's been challenging. It's challenged my confidence over time, but it also has been a superpower to, in some ways, I don't know, in some ways, hold myself accountable because I'm always, I almost want to say second guessing myself, but also very.

• 8:56Speaker 01

  In a very, I guess, someone said Jesuit way at one point, but a way where I can see both sides of everything, you know, challenging my doubts and my ego. But the problem with that is sometimes it's hard to differentiate between the two. What is, you know, fiction and what isn't and what of my self critiques are accurate because I want to be, and I think I am a pretty self-aware person. And even with the things that I'm not great at, I'm like, super proud of that because I've got a ton of advantages and things that I'm really great at. But I think it was the criticism I experienced early on in life for so long

• 9:38Speaker 01

  that instilled that in me and I've learned how to turn it into something that's more balanced than what it was when I inherited it.

• 9:48Steven Bartlett?

  When you inherited it?

• 9:50Speaker 01

  When it was handed to me.

• 9:52Steven Bartlett?

  And the first time?

• 9:52Speaker 01

  The model I had, the level of critique that I had that didn't have the counterpoint that I'm able to provide for myself.

• 9:59Steven Bartlett?

  You're talking about your father here?

• 10:00Speaker 01

  Yeah.

• 10:01Steven Bartlett?

  He, he would critique you?

• 10:02Speaker 01

  Yes.

• 10:04Steven Bartlett?

  When you say critique, do you mean?

• 10:07Steven Bartlett?

  Oh, that's, that's naughty. Don't do that.

• 10:08Speaker 01

  No, no, like that's not how you do something or why, why'd you do it like that? Or can you not? Or, you know, I mean, I love my dad and and he's, you know, as both of my parents have gotten older, they split when I was 17 and I've just watched them both become such better people. I remember congratulating them when they finally split up and was so glad at 17 years old and I was also like, I'm out of here. See ya.

• 10:41Steven Bartlett?

  You seem to become a bit of a rebel. You know, from, from when you moved out of your parents' house for the next couple of years, I, it, the behavior looked really rebellious.

• 10:51Speaker 01

  Oh, yeah. No, I mean, I was rebellious from a very early age. I remember in middle school, a teacher, I was eating an apple in class. I was eating an apple. It was healthy. I was hungry. I've got agency over my body. I didn't know what that word meant. I'm hungry. I'm gonna eat food. I'm human. I'm hungry. I'm gonna eat food in the middle of class.

• 11:13Speaker 01

  But like, who, how could you tell someone not to eat when they're hungry? It's like a simple bodily function and it keeps me healthy and it's gonna make me a better student and it's.

• 11:25Speaker 01

  And I, and the teacher told me to throw the apple away.

• 11:29Speaker 01

  And I just started the apple. And of course, I had the attention of the entire class. And I got up and I sauntered over to the trash can super slowly. And I just like ate the apple all the way to the core, like super fast. Finished the apple and was like, dink in the trash can. Um, so I was like that. If, if someone said not to do something, I did the thing that they didn't say I couldn't do. That was similar. It was peripheral.

• 12:00Steven Bartlett?

  You're pushing the.

• 12:02Speaker 01

  And then by the time I got to high school, I was going to the anarchist book fair in San Francisco. I was sure capitalism was, you know, the worst thing ever. I was very angsty. I thought that adulthood, it's funny, there's a Netflix series about my life. And the first thing that the character says is adulthood is where dreams go to die. And it's so weird to reference your own Netflix series, like who does that? But that's how I, that's how I felt. I wasn't trying to be a child, but I also didn't want to go work in an office. I also wasn't ambitious. So somehow along the way, that lack of desire to live a conventional life became something that turned into ambition.

• 12:44Speaker 01

  Because I didn't even ambition, just curiosity, something that I was good at. And, you know, eventually built a business. But, um, I, uh, in high school, in high school, I remember there being bells. Like right, there's a bell that rings and you go from, from one room to another room all day. A bell rings, you sit at a desk, a bell rings and you stand up and you shuffle over to the other room. And then you sit down and you like memorize some stuff. And then you, like, this is my youth? I was sure I was being trained for something super meat oker, not that, I wanted excellence. I just wanted out.

• 13:27Steven Bartlett?

  Why are you like that? Cause you know, all the other kids were cool.

• 13:30Speaker 01

  I came out like that. I actually came out, I came out like that. Yeah, it is not, I mean, her, I'm, I might have some hereditary, just kind of like Italian, I'm not sure what. Or something, it's not, it wasn't a nurture thing. That was. A nature thing, or I don't know, I just like came out, I actually hatched out of a disco ball. But that's the way, that's how I came out.

• 13:59Steven Bartlett?

  I had Gabor Maté here, who's this like, I think he's just interviewed Prince Harry, actually. In a little like pay-per-view therapy session or whatever, and Gabor Maté said something to me that I've been pondering ever since. He said that as children, we're like narcissists and we are that way because it helped us to survive. So we think that everything is about us when we're like babies and young. So if the parents are arguing, we actually interpret that as there being something that to do with us. And that's the way we view the world as a survival mechanism. And he says, one of the things that happens when we're in a, you were a young child and we're in a house where there's lots of arguing and lots of drama and shouting. Is we learn to avert our attention as a way to help us deal with the emotional distress. And that develops into something they call ADD and ADHD.

• 14:45Speaker 01

  Yeah, I took Adderall this morning.

• 14:49Steven Bartlett?

  Well, they, well, yeah.

• 14:50Speaker 01

  Just to prepare for the podcast, just kidding, no, I have major ADD.

• 14:55Steven Bartlett?

  ADD.

• 14:57Speaker 01

  But they diagnosed me as a kid and I was like, no, this is mind control. Forget it. I'm not focused because I thought it was situational. I thought it was my environment. And it maybe was partially because I wasn't interested in what was happening. And distracted because I was curious about other things. But also it's a real thing and it wasn't until a few years ago that I finally realized it was a thing and sought treatment. And it's helped, but it's helped like marginally. It's not.

• 15:28Steven Bartlett?

  How did you realize it was a real thing a couple of years ago?

• 15:32Speaker 01

  I've, I've been, I mean, I go to a psychiatrist and I talk about what's going on with my brain and

• 15:40Speaker 01

  do what I can to help myself holistically. But also I know, I'm also predisposed to depression. I'm not predisposed. I've suffered with depression my whole life.

• 15:53Steven Bartlett?

  Since when?

• 15:55Speaker 01

  My whole life, I don't, I can't remember an age where I wasn't depressed. I, I just, I wasn't always miserable, but I've, I'm kind of a dark, I'm a little dark. And that's not something, you know, it's hard to pull yourself out of a hole when you don't wanna get out of bed. Like that's, you know, to have the willpower to just get over depression and put on a happy face and whatever people do, get in an ice bath and jump in the sauna and meditate and, you know, I'm still struggling to be the well-rounded person, but I'm functional.

• 16:31Steven Bartlett?

  I think we're all struggling to be a well-rounded person.

• 16:33Speaker 01

  I don't know, some people seem to like have these parents that teach them that and they come out and they're like,

• 16:39Steven Bartlett?

  Yeah.

• 16:39Speaker 01

  you know, boop, boop, boop, boop, boop, boop. And it's not, you know, that's almost diminishing to be like, whoa, whoa, whoa. But, but I'm, yeah, there's people who just seem to, you know, and some people come out of the womb like that. I know parents that are creative, chaotic. I know people who are well-rounded, whose parents were addicted to drugs and somehow they just wound up like that. And how to attribute that to your parents, it's, that's a hard correlation to make.

• 17:08Steven Bartlett?

  Did you ever, you said a curious phrase there, which made me ponder, you said, I'm a little dark.

• 17:16Speaker 01

  Uh huh.

• 17:18Steven Bartlett?

  What do you mean by I'm a little dark?

• 17:22Speaker 01

  Hmm.

• 17:31Steven Bartlett?

  Why are you giggling? You're making me think you are a little dark.

• 17:33Speaker 01

  I am. I'm not evil. God. Uh, I'm not a witch. I, I guess I've just, you know, like I said, I've struggled with depression. I'm not a bubbly person. I'm not someone, you know, as a child, my mom has said, you only laughed when something was really funny. You know, I think kids run around like laughing and smiling because they're like children or something, but I had to have a reason. I'm not sure why it's still kinda like that. And maybe it's, I don't know, as an adult, it's become something that requires. It's just being genuine and maybe I'm not, I think maybe I'm not impressed.

• 18:18Speaker 01

  Maybe in general, I'm just skeptical.

• 18:20Steven Bartlett?

  You went to see a psychiatrist when you were sixteen?

• 18:23Speaker 01

  Oh, I went to see a psychiatrist when I was like ten. I mean, I was in, I was in therapy when I was like ten, eleven.

• 18:31Steven Bartlett?

  With what symptoms?

• 18:31Speaker 01

  Trying to be diagnosed, like, what's wrong with her? Why can't she stay on task? Why is she so weird? Why doesn't she get along? Why is she distracted? So I have report cards that say chooses to disturb others. You know, doesn't stay on task. It's stuff like that. It was like, I was always like, you know, not paying attention, curious about something else, engaged with something else. I wasn't always to be rebellious. Sometimes it was very good natured and I would get in trouble for things that I didn't think were bad or intend to be bad. But it was also just very, a very willful, independent thinker. Who didn't fit into a traditional educational environment.

• 19:15Speaker 01

  And, you know, that's something, for whatever reason, seemed to be needed to be diagnosed. But then I was like, no, no, I'm not taking Wellmutrin. And I'm not gonna take, it's like an antidepressant. I didn't take it, I was like, no, I'm not taking any of this.

• 19:34Steven Bartlett?

  When did they, when, what age were you?

• 19:35Speaker 01

  That was by high school.

• 19:36Steven Bartlett?

  So you were sixteenish around that time?

• 19:38Speaker 01

  Yeah, fifteen, sixteen. And I was like, this is, it's, I don't feel like myself. Feel wired and weird and I got, like, I think I got Ritalin. Someone tried to buy it off me in like high school and I was like, what are you, what? I don't even get it. And I was like, I'm just throwing this stuff in the trash. I didn't.

• 20:00Steven Bartlett?

  And then so you so you get diagnosed and prescribed antidepressant at sixteen ish. Your parents break up at seventeen ish. You leave.

• 20:08Speaker 01

  I move out.

• 20:08Steven Bartlett?

  You move out.

• 20:09Speaker 01

  I move out at seventeen before I graduate high school. I was homeschooling, so I got my diploma in the mail. I thought the like most embarrassing thing would to be would be to wear the cap and gown. I was like, what is that? I don't understand. What's the tassel? Why do you have to wear a robe? What is this robe? I I wouldn't have been proud standing in a group doing some group thing. I'm not a group person. Even though I've built a lot of really powerful communities, I'm not. I don't assimilate well into groups. And I think groups are responsible for the most heinous things in like human history. So.

• 20:46Speaker 01

  So I moved into a closet.

• 20:48Steven Bartlett?

  You moved into a closet.

• 20:49Speaker 01

  Under the stairs for sixty dollars a month.

• 20:52Speaker 01

  With a sleeping bag. These guys that were like in bands and artists who had met going to shows. Because I was really into music and went downtown in Sacramento and saw music and.

• 21:06Steven Bartlett?

  What was the plan in life at that point? Was there a plan? You know, you're like seventeen, eighteen.

• 21:09Speaker 01

  No, he told me there was a plan. I wanted to go to, I first wanted to go to Reed College, but that was expensive.

• 21:18Speaker 01

  But then I wanted to go to the Evergreen College. So by the time I was eighteen, I had moved to Olympia, Washington to get residency to go to the state school called the Evergreen State College, which is a super duper hippie state school that's interdisciplinary and there's no majors. To the point of it not really being worth going. But if I was gonna go to college, I was gonna go to a place like that. But even state tuition was expensive. So I lived in Washington State for a year to get state, to get residency. So I could go to that school. And by the time I got residency, I was like, this school's not gonna do anything for me.

• 22:00Steven Bartlett?

  You described this chapter of your life as being very lost.

• 22:03Speaker 01

  Super lost, super lost. I was looking for my, I kind of hate this word, tribe. I was looking for people like me. I thought I would find people like me and then all would be well. Like, you know, some Disney character, the, you know, ugly duckling or someone who loses, you know, they're lost from the wolf pack. I don't know what these movies are. And then they find their family and people understand them. And so from the time I was seventeen, I moved from downtown Sacramento to Olympia, Washington, lived in two places there. Seattle, lived in two places there. San Francisco, lived in one or two places there.

• 22:44Speaker 01

  Oakland with my alcoholic fry cook boyfriend. I had met in Olympia. We couldn't get jobs and my parents were like, yeah, we can't help you with college stuff. So then we moved to Portland. I was a stripper. I was lost. I was lost.

• 23:04Steven Bartlett?

  That's an interesting turn of events.

• 23:06Speaker 01

  Yeah, that was an interesting turn of events. And

• 23:11Steven Bartlett?

  That chapter of your life in some ways mirrors the transience of the start of your life. You said you moved to like eight, eight or 10 different schools when you were young. And then when you leave the nest, you end up bouncing around as in your own words, like looking for your family.

• 23:26Speaker 01

  I was, yeah, I was looking for some place to belong and I never found it and I kind of love that. Cause it's forced me to make my own and forced me to stay a creative thinker. And also, I don't know, this isn't fair, but the people in some of those communities like peaked and never left. It's like, you know, I listened to pop punk in high school. Can you imagine? I'm sorry if anybody listening is like never graduated from listening to pop punk. But if you don't graduate to metal or some other, it's not even more sophisticated, but like less juvenile varieties of rock, it's the same as finding, you know, some comfortable community when you're 20 and then never leaving.

• 24:11Speaker 01

  Like that sounds, that sounds awful to me. So I'm, I'm glad I didn't find a comfy place.

• 24:20Speaker 01

  And it's been uncomfortable since then.

• 24:22Steven Bartlett?

  How long did you try the stripping thing?

• 24:25Speaker 01

  I don't know. I mean, when you're in your late teens, early twenties, time just feels like it felt like a decade that I was, you know, bouncing around to these places. Probably three or five months. It was fun. I loved it. Nobody pulled anything. I never got messed with. I drank my White Russians and ate the Subway sandwich from next door and played photo hunt. And I wasn't even 21. I used someone else's ID to work there. And I got to dance to music that I liked. I made money. I didn't really have to engage with anybody. And I got really comfortable with my body in a way that I hadn't before, and that was cool.

• 25:09Steven Bartlett?

  You know, they say, I read in your book where you said that you believe you hold the world record for having the most shitty jobs, like back to back throughout that period of your life. They say, you know, I've learned this from this podcast, that every job teaches you something.

• 25:24Speaker 01

  Mm hmm.

• 25:24Steven Bartlett?

  And that thing can be applied to business. There's always a sort of a transferable skill or whatever learned. What was the transferable skill?

• 25:31Speaker 01

  Hmm.

• 25:32Steven Bartlett?

  But you learned from stripping that you think has probably stayed with you today?

• 25:39Speaker 01

  I think that even though I wasn't, didn't have the upper body strength to be the traditional one upside down, swinging around. What I could do, I mean, it was like shuffle around and whatever was enough and still charismatic enough and still great enough to entertain other people. And then being comfortable with my body. It's like exposure therapy. You know, I was the girl at

• 26:08Speaker 01

  18, would like make out with someone. And then if I was like naked or something, I'd like. Put on my clothes to go to the bathroom or something. I was like not, I didn't sleep with anybody till I was 19. So I was just, I was kind of late. By 20, I was stripping in Portland.

• 26:29Steven Bartlett?

  That escalated quickly.

• 26:29Speaker 01

  I'll tell you the crescendo of that experience. So dating with, dating Wade, the alcoholic fry cook, who was 10 years older than me. I like, I was on birth control. I went off birth control for like one day. And there was almost, we were hardly even, you know, engaging in the way that someone might like get pregnant, like so briefly, like that day. And then no other day.

• 27:02Steven Bartlett?

  You're describing sex.

• 27:03Speaker 01

  Yeah, I'm like, I don't know. I don't know who's watching. And, and I wound up, I wound up pregnant. So I'm like 20, maybe 19. And I went to the sliding scale women's clinic. And, but, but, and it was the only day I could get in. But it also happened to be the day of my court date because I had gotten arrested for shoplifting. So I had to have the women's clinic write an excuse to the court, telling them why this poor girl couldn't make it to her court date. And the whole thing got there. Just, I kept following up to be

• 27:47Speaker 01

  like, when is it rescheduled? And I think they all just felt so bad for me. It kind of vanished. But that was, that was like, okay, no more shortcuts. It wasn't like, I'm gonna go be a CEO. But it also just taught me that breaking some rules puts you in other people's hands. And I was, you know, being arrested. I'm not as autonomous as I would have liked to have been. And, you know, even with stripping, to a certain extent, it was a shortcut. I was trying to evade, like, working hard. But it was also a lot of fun. But that was really, that was a low point. I've had lots of low points. But at least

• 28:31Speaker 01

  it's like this, right? It's been like this.

• 28:37Speaker 01

  You know, doesn't, it doesn't ever go that low.

• 28:42Steven Bartlett?

  There's clearly a slight issue here with authority. And it feels to me like the ultimate authority, which is the law, eventually was like, you can't fuck with us. We're not the teacher.

• 28:50Speaker 01

  Yeah, it was like, okay, like, maybe just figure out how to get along, you know? It wasn't like, wow, I'm gonna go have a career and do everything. I'm, I'm gonna just do everything differently, but also I just didn't want to cut corners. I didn't want to end up not in control of my environment or stuck in jail or something stupid.

• 29:14Steven Bartlett?

  Shoplifting.

• 29:16Speaker 01

  Mm hmm.

• 29:17Steven Bartlett?

  Why'd you make that sound?

• 29:18Speaker 01

  I don't know. It was fun.

• 29:21Steven Bartlett?

  What was your favorite thing to steal?

• 29:26Speaker 01

  I don't endorse shoplifting.

• 29:27Steven Bartlett?

  Neither do I.

• 29:28Speaker 01

  My rationale for shoplifting was that there was so much excess in, you know, our culture that it would never make a dent to steal organic tampons from Fred Meyer, which is like Target in Portland or whatever. So I, when I did get caught, and this was my favorite thing, was just walking out with stuff. So I would get a whole shopping cart of stuff. I had a little teeny tiny little razor thingy. So I knew where the sensors were and I would cut them off. They were there and pile a shopping cart high and just walk out with no bags or anything.

• 30:11Speaker 01

  I did it at grocery stores. I furnished apartments. I walked out of places with like literal rugs this high, just walked out because nobody expects you to be that like obvious about it. They're looking for somebody who's like putting stuff in their pockets. And when I did get caught, I had like a George Foreman grill, I think a basketball, organic tampons, some food, really nice shower curtain rings. They were metal and then they had like ceramic, they were heavy and they had like a ceramic thing that said hot. And then the other one said cold.

• 30:50Speaker 01

  And I was like, yes, this is, this is luxury.

• 30:53Steven Bartlett?

  Worth jail time.

• 30:54Speaker 01

  So that was, yeah, and.

• 30:58Speaker 01

  You know, I built an online business. And the first thing I sold online was stolen. So another thing, and I learned this from people who were professionally trying to like avoid getting jobs and participating in capitalistic culture, which is a privilege. It's lazy. It's, it was, it was, I was really young and I just didn't want to work. You know, it was some kind of quasi-political lazy excuse for just not working hard. Anyway, I learned from some of the best. I had a friend who had written a book called evasion, literally.

• 31:37Speaker 01

  And I would go into Barnes and Noble and they had a no chase policy. Like I knew what the policies were at these places. Because if their employees chased someone shoplifting, it's going to cost them way much more if they get like knifed or something than it would for them to lose a few books. And so I would go on Amazon and I would look at the bestselling books. This is in 2002, 2003. It's like, and even look at the ratio of most expensive book to leased pages. So I could stack them, as many of them as high as possible. And I would just walk to the front, like the front of the store would have all the

• 32:21Speaker 01

  bestsellers in huge stacks. And I would just like pile them high. I looked like an employee, like who's carrying a huge stack of books. I was right in the front of the store and I just like walked to my car. And I'd put them on Amazon for 10 cents less than all the other resellers. I'd sell them overnight. I'd ship them media mail and I'd pay my $350 a month rent.

• 32:43Steven Bartlett?

  Why weren't you scared?

• 32:46Speaker 01

  I think I was. But it's when you get scared that you get caught. And it's when you hesitate, you fail. It's the same thing. If you're snowboarding and you're like, oh, oh, it's kind of icy. Let me look down. You're just like, catch an edge. If you're surfing and you look at the nose of the board. Right?

• 33:05Steven Bartlett?

  So even that taught you a life lesson.

• 33:07Speaker 01

  I guess, I guess.

• 33:08Steven Bartlett?

  Also.

• 33:09Speaker 01

  I'm not proud of this. I was really young and I was finding my way. I never stole from individuals. That was like not on thesis for me.

• 33:20Steven Bartlett?

  Who can justify it?

• 33:21Speaker 01

  It's not. No, I couldn't justify it. I would never have felt comfortable doing it.

• 33:26Speaker 01

  But big box retailers, I was like, hmm.

• 33:29Steven Bartlett?

  So by this time, you're getting a little bit acquainted with the internet and selling things on the internet, clearly because you're selling stolen stuff.

• 33:35Speaker 01

  Yeah.

• 33:36Steven Bartlett?

  Vintage.

• 33:37Speaker 01

  Mm hmm.

• 33:39Steven Bartlett?

  Why, why vintage? Why did you start to sell vintage clothes?

• 33:43Speaker 01

  Yeah, so by two thousand six, I had gotten some real jobs. Now, after, after I'd worked in shoe stores and record stores and photo labs and Subway again. I dry cleaners, I.

• 34:02Steven Bartlett?

  How did you get on with those jobs?

• 34:06Speaker 01

  It didn't last very long. I liked jobs where you alphabetized things, though. So record stores, photo labs, bookstores, like paper, makes me feel important for some reason. Mailing things, I don't know, it worked out with my eBay store. And the last job I had was in the lobby of an art school in San Francisco. At seventy nine New Montgomery Street called the Academy of Art University. And it was a job I got because I needed to get health insurance. And at the time, you couldn't get health insurance with a pre-existing condition. You.

• 34:40Steven Bartlett?

  Is this your hernia?

• 34:42Speaker 01

  Yeah, the hern.

• 34:44Steven Bartlett?

  The hern.

• 34:45Speaker 01

  Yeah, so a hernia, if you don't know what it is, is a place, it's a hole in your muscle wall that your guts poke out of and it makes a little bump. And I had one kind of in my groin area called an inguinal hernia. And it didn't hurt, but they're kind of dangerous because they can, like, if your muscle tenses up or something, they can get strangulated and necrotic, which is a disgusting word. So I had to get it fixed, but before I got it fixed, it was kind of fun. I shaved everything but the hernia. My poor boyfriend, my poor boyfriend. And yeah, it was, it was entertaining. It was kind of funny to have like a small lump in my pants for. A few weeks or something.

• 35:29Speaker 01

  But at the time, you could not get health insurance with a pre-existing condition, even with depression. If you had medical records that said you had depression and your insurance lapsed, insurance companies would decline you now. That's not the case. You can have a pre-existing condition, apply for health insurance. You'll be given health insurance. You could only get health insurance with a pre-existing condition, like a hernia,

• 35:54Speaker 01

  with group health insurance, with a job.

• 35:58Speaker 01

  So I had to go find a job that had health insurance. And I got this job in the lobby of the art school as a campus safety host, which was a different way of saying you're cheaper than a unionized security guard. And I wore a starchy white shirt. It was like a men's clothing. I had to wear this awful uniform with like a magnetic thing here that had my name and the school's logo on it. And check students in and say, hi, you need to sign in. Can I see your ID? That was

• 36:29Steven Bartlett?

  Were you doing anything sort of criminal at this point?

• 36:32Speaker 01

  My job, no.

• 36:33Steven Bartlett?

  So all of your money came from that job and?

• 36:36Speaker 01

  Yeah. And so there was a three-month waiting period for health insurance.

• 36:42Speaker 01

  And while I was there, I had time to, I had some downtime in this lobby and there was a computer. And there was no Facebook or Instagram at the time. This is 2006. And I was starting to get friend requests from these eBay sellers on MySpace. I wore only vintage. I was like, you know, rootin', tootin', scootin' to like oldies and rock and roll and dive bars and subsisting on burritos. I loved vintage. I wore vintage. I wasn't necessarily into fashion and I didn't want to be in fashion. But I loved style and I loved vintage and I loved thrifting. And I saw what they were doing. And their auction prices were crazy.

• 37:26Speaker 01

  Like I thought Haight Street was expensive because I had shopped at thrift stores and found great stuff. And saw what their auctions were going for, and these were actual prices that the customer was determining. They would start the auction price at nine ninety-nine, and these things were going for like two hundred, three hundred dollars. And they were just making it look like something that Sienna Miller, some boho, at the time it was like boho Olsen Twins, Sienna Miller kind of vibes. And they would do that, put this stuff online, and the customer determined the price. And it was so much money. And so I thought, okay, so I waited my three months for my health insurance, because there was a three-month waiting period. Got the hern fixed.

• 38:10Speaker 01

  And I started an eBay store, and I wasn't trying to be an entrepreneur. I was trying to legitimately not work for anybody. And that's when I realized that I could connect my curiosity and independence and creativity and resourcefulness to something legitimate that made money, that I learned from every step I was taking, and started Nasty Gal, selling vintage out of my boyfriend's apartment.

• 38:43Steven Bartlett?

  Before that point, would people have called you lazy or unmotivated?

• 38:49Speaker 01

  I didn't know any people who would have said something like that, because my friends were just like me, so.

• 38:56Steven Bartlett?

  Objectively, then.

• 38:57Speaker 01

  Objectively. I think just lost.

• 39:00Steven Bartlett?

  Lost.

• 39:01Speaker 01

  I think it would be a judgment to say I was lazy.

• 39:05Steven Bartlett?

  I can relate to so much of what you've said, especially all the stuff about authority. Like, I just decided to stop going to school. And I was polite about it, but I've always had a challenge with authority. Every job I had through that period of my life lasted for three months. I was just call center hopping, get to the bonus threshold, quit, gives me two months where I don't have to get a job, call up another call center.

• 39:22Speaker 01

  Employed those people.

• 39:24Steven Bartlett?

  Yeah, I'm one of them. And it's funny, because I think people would have looked at me in school and stuff and said, like, written me off, oh, he's lazy. Well, like, my thesis is that everyone, most people are lazy, and you should be lazy for things that you absolutely hate doing. Like, you should be, so.

• 39:39Speaker 01

  Yeah, I'm only motivated by things I'm curious about. If someone assigns me something, like, I've tried to write a second book. I published two books after Girlboss, which was a thing. I can't, I cannot be assigned something. I, it either comes out, or it's not there.

• 39:58Steven Bartlett?

  That's the, do you think that's the rebel in you?

• 40:01Speaker 01

  It is, but it's why everything I do is so inspired and honest and I don't wanna be like, I'm unique, but.

• 40:07Steven Bartlett?

  Cause you never accepted or learnt compliance.

• 40:09Speaker 01

  It's an actual representation of who I am and what I think and how I feel and my perspective, instead of a manufactured version because somebody has given me an assignment.

• 40:19Steven Bartlett?

  Like you didn't even want the bell in school to tell you what to do?

• 40:22Speaker 01

  No.

• 40:24Steven Bartlett?

  It's a gift and a curse though, right?

• 40:26Speaker 01

  I mean, it's pretty logical that you would question what a bell ringing and someone moving from one room, the same room to the next room every single day.

• 40:36Steven Bartlett?

  Do you think anyone else questioned it?

• 40:37Speaker 01

  What?

• 40:38Steven Bartlett?

  Do you think anyone else questioned it?

• 40:39Speaker 01

  No. No.

• 40:43Speaker 01

  But if you really think about it, it's pretty wild, right?

• 40:47Steven Bartlett?

  That eBay store that you start in your free time when you're working that job that you took to fix the hair and

• 40:56Steven Bartlett?

  it was successful.

• 40:58Speaker 01

  Yeah.

• 40:58Steven Bartlett?

  And, you know, you kind of frame it as you saw maybe a price arbitrage or whatever, but it's more than that, right? It's more than that. To be successful at that time, I'm sure a lot of people saw that price arbitrage and they didn't build a nasty girl. So when you reflect on why and how you were particularly successful, how'd you diagnose that?

• 41:19Speaker 01

  I reverse engineered everything everyone else did and did a better job and did it with my signature on it.

• 41:26Steven Bartlett?

  Do you think, and I'm thinking now about that bell again in school, where you were like analyzing the bell when no one else was, do you think that kind of default to thinking in terms of first principles, like asking the question, why, why the fuck do we do it that way? Has been part of the reason why that eBay store was successful?

• 41:43Speaker 01

  I think so. I think most people that started an eBay store are copying what other people are doing. They might reverse engineer some things and see what their competitors are doing. And I did that. But I just did it 10 times better with a totally different spirit, with excellent copywriting, with great styling and great models and increasingly better photography. And I would, I was extremely resourceful. I would buy stuff on eBay and sell it for more than I paid for it. I was searching for Yves Saint Laurent, just misspelled, you know?

• 42:21Steven Bartlett?

  That's wrong. But even that's first principle thinking, that's like. You've got a convention on one end, which says just like, do what's being done. And then you've got these like first principle thinkers who kind of think first about what they know to be true. And they're really good at filtering out convention. They can kind of see through it at the truth. Whereas convention like is safety, it's comfort, it guarantees you a pre tried blueprint. So people follow that. But then these other little rebels, they have this almost inbuilt ability to just like fucking see through to that that that truth that nobody can see. And in that case, I mean, that's a great idea, but even caring more about the copy. And you having your own belief as to why the copy mattered or the photography, like why photography really, really mattered.

• 43:05Speaker 01

  On eBay.

• 43:06Steven Bartlett?

  Yeah, on eBay, which a lot of people wouldn't have had like that's.

• 43:09Speaker 01

  And it was called Nasty Gal. The spirit of it was really irreverent. At the time, the eBay sellers were selling like, you know, it was called Mama Stone Vintage was a really big one. And it was all very hippie dippy and vintagey. And mine was vintagey, but it was like very hard hitting, edgy. I named it after an album by a woman named Betty Davis, who had an album called Nasty Gal. She was so stylish in the seventies, put out some incredible records, was married to Miles Davis for a short period and was allegedly too wild for him.

• 43:47Speaker 01

  Her lyrics are just so, and I was stripping her music when I was like 20 and then I was like, cool, nasty gal. And it cut through the noise. And I think when you start a business and you don't need to survive, you might have more time to navel gaze. Or you might do things super conventionally. But when you need to survive, there are certain things that other people have done right, that you can see, you know, accelerate what it is that you may do on your own, but learn from them. And then also take and make your own way. I think had I tried to do things completely differently than everybody else, I wouldn't, I wouldn't have survived.

• 44:32Speaker 01

  I would have been dead in the water.

• 44:34Steven Bartlett?

  Speaking to something really interesting there, which is like this balancing act between naivety, which is great for innovation, and then convention, which is great for staying alive. I'm talking about like the nasty girl needing a CFO.

• 44:48Speaker 01

  Yeah.

• 44:49Steven Bartlett?

  You see what I mean? Or like, that's what how I feel when being a young founder, 21 years old, start this business, it grows incredibly quickly. Okay, the naivety made us interesting, but our naivety will also send us to the grave here if we're not.

• 45:00Speaker 01

  Yeah.

• 45:00Steven Bartlett?

  If we don't know what we don't know.

• 45:01Speaker 01

  I've been to hell. I've been, I died and now I'm in the afterlife. It did send me to the grave. My naivete and lack of experience did send me to the grave.

• 45:10Steven Bartlett?

  It happened so fast. That's a quote. It was shocking how fast it all happened. Nasty Girl went from doing $150,000 a year to doing $150,000 a day and then $150,000 over lunch.

• 45:25Speaker 01

  Mm hmm. Yeah, $150,000 over lunch. It was either a day or over lunch that we all worked out of this warehouse. It was a bunch of kids in the East Bay, in Emeryville. I had this 7,000 square foot warehouse, which I thought was the hugest thing. And I was like, when we hit $150,000 a day, God, was it a day? It must have been the holidays. I was like, I'm gonna get a bounce house. You know those things that people jump on, the inflatable things?

• 45:52Steven Bartlett?

  Oh, a bouncy castle.

• 45:53Speaker 01

  That children jump on. It was an upside down horse and its legs were in the air. When you jumped on it, the legs like.

• 45:59Steven Bartlett?

  That's what you wanted?

• 46:00Speaker 01

  And in between, you know, on our breaks, we got to jump in the bounce house. I was like 23, 24 years old. It did happen really quickly.

• 46:10Steven Bartlett?

  To be fair, now you say it. When we raised investment for the first time, the first thing I bought was a 13,000 pound slide. Big blue slide, which we had in our office. That was the first thing I bought before we got desks. So talking about naivete.

• 46:25Speaker 01

  I bought, I paid off my mom's mortgage.

• 46:27Steven Bartlett?

  Oh, did you? I couldn't do that with invested capital, but.

• 46:32Speaker 01

  No, it wasn't with investor capital. No, it was the first time I made money.

• 46:36Steven Bartlett?

  Yeah, my slide was with investor.

• 46:38Speaker 01

  Okay, yeah, no, no.

• 46:39Steven Bartlett?

  They actually, those investors did really well. They got bought out within six months. So they got a big return.

• 46:43Speaker 01

  Good job.

• 46:44Steven Bartlett?

  Yeah.

• 46:44Speaker 01

  What do you attribute at such a young age? I'm just going to interview you for a second. Because you couldn't have had a ton of experience under leaders to give you a model of what leadership looked like. You were naive, you know, could you, I couldn't empathize with the people I was managing because I had never experienced leadership. And I just showed up and I did what I, what needed to happen and what I said I was going to do. I didn't understand that people needed to be held accountable because I held myself accountable, especially C-level executives and grownups whose careers were longer than I had been alive. Like, how did you do that at such a young age?

• 47:21Steven Bartlett?

  Well, I think I, I think I messed up. I think like for the first two years, I hired people that were very, very inexperienced. And I reflect and I go, I think I did that because I thought they were easier to manage. And I couldn't fathom the concept that I could hire someone who was two times my age and three times my experience. And A, they'd want to come here and B, with us, with our slide and dogs and tree and basketball court and ball pool. And they would like take us seriously, but also like be like, maybe there was an insecurity about how I'd manage them. And so what ends up happening is you hide lots of like young people. You know, I remember the BBC did an article saying, is this the youngest company in Britain? Because I think we were like somewhere, but our average age was maybe 20 or something. And we had like, we had like a hundred, almost a hundred people, you know, and you feel the strain of that.

• 48:04Steven Bartlett?

  You feel things breaking. This is where you go, convention is right about some things, processes, HR, finance. You feel things breaking at the seams a little bit because of the growth. And then at some point, an adult enters the room and you go, oh, I get, I get this. And so we hired some, some really, really great people. And the great thing is great people hire great people. So we went from being this kind of very lopsided inexperienced organization to being a balanced one. And I say balanced because it's my belief that to own the future, you have to understand the present, which is why you want to hire a 16-year-old that gets TikTok or whatever. And you also need to hire someone that's maybe much double their age, experienced in client services and understands the old rules of the game.

• 48:48Steven Bartlett?

  If you understand both games, you can understand the game of the future, I think. So made a lot of mistakes. And when I nearly went under several times and had to call people and beg for money in the lead up to payday, but. Somehow managed to survive, but going back to you now.

• 49:05Steven Bartlett?

  I feel like we missed a part because you know, you're at the you went from starting that store to bouncing around on that bouncy castle thing. We call it bouncy castle.

• 49:13Speaker 01

  Okay.

• 49:16Speaker 01

  Horse castle.

• 49:16Steven Bartlett?

  Between there, between that bouncing on that horse castle and the starting the store. What, what happened?

• 49:25Speaker 01

  So. First year, just on eBay, did seventy five thousand dollars in revenue. I was the only employee. It was just, you know, it was pure cash. All of the money just went back into the business. I didn't even know what expensive things I would have wanted. I didn't, I'd never eaten an oyster. You know, I was drinking like. Budweiser or an eat, eat, still like subsisting on Boston Market and like Starbucks. So I didn't spend any of that money. I thought building a business, and I think for the most part it is.

• 49:58Speaker 01

  Was selling things for more than you bought them for and not spending all the money. That's it. That's all. And so I bought things. I sold them for more than I paid for them and no one else would have given me money. Parents weren't going to give me money. I don't even think I had a credit card at that age. I didn't understand what venture capital was and I was living in the Bay Area. And had I not built the company to eventually, you know, twenty eight million dollar run rate, super profitably, I would never have known. And so, yeah, year two, left eBay about halfway through and launched my own website, nastygalvintage.com. And did two hundred and fifty thousand dollars in revenue.

• 50:42Speaker 01

  The next year did one point one million. The next year did six and a half. The next year did twelve and I was coming off a twelve million dollar a year. Revenue, owned a hundred percent of the company.

• 50:57Speaker 01

  Had a bunch of kids working for me. And that's when venture capitalists came in. And at that point, you know, we were selling non-vintage stuff. What really allowed the company to scale was going to trade shows and showrooms and curating from the market, based on what I had learned from my customer, having sold vintage to them. So I knew them very, very well. And that gave me the ability to then go by greater breadth and depth in things I knew they would love.

• 51:28Steven Bartlett?

  And that's what, 2011, 12? Venture capital comes in?

• 51:33Speaker 01

  2012 was when Index Ventures invested $60 million.

• 51:36Steven Bartlett?

  $60 million?

• 51:38Speaker 01

  On a $350 million valuation.

• 51:40Steven Bartlett?

  On a business with a $28 million run rate?

• 51:43Speaker 01

  Yeah.

• 51:43Steven Bartlett?

  You were profitable at that time?

• 51:44Speaker 01

  Mm-hmm.

• 51:46Steven Bartlett?

  Significantly?

• 51:47Speaker 01

  Pretty significantly. I have a-

• 51:49Steven Bartlett?

  10% or 20% of them?

• 51:51Speaker 01

  I don't know. I don't know. I didn't even look at that. I was, I never had to learn to read a P and L because my company was profitable and I just, you know, generally knew how much it cost to run. I didn't, and I, and I didn't, I didn't buy expensive office chairs.

• 52:06Steven Bartlett?

  Did you, did you know your, like, gross margins on your?

• 52:08Speaker 01

  On the products, yeah. On the operating margins, no. I don't, I don't think, I didn't understand what operating margin was.

• 52:16Steven Bartlett?

  It's pretty incredible that you can be running a business that's generating, that has a $28 million a year run rate and not know what operating margins you're dealing with or what your net profit is.

• 52:25Speaker 01

  It's a luxury, but it was also a disadvantage. Once we plowed $60 million into the business and things got a lot more complex and a lot less profitable.

• 52:36Steven Bartlett?

  You talk about the $60 million going into Nasty Gun in 2020, 2012. What did it break?

• 52:44Speaker 01

  Hmm. I mean, we no longer had to live within our means. That's what investor money does unless you maintain profitability and keep that money in the bank for, you know, another time or pocket all of it as a founder.

• 53:01Speaker 01

  We, you know, I had hired a COO at that time. I had a top tier investor on my board and very little like historicals, data, financials to base the future growth on. But it had been exploding, just continued to be exploding. And with that capital behind us, we could grow even faster. And the expectation was that the next year, we would grow from 28 million in revenue to 128 million dollars in revenue. We just rounded up by 100 million and then we hired into that and we bought into it.

• 53:44Steven Bartlett?

  Oh, you believed it and everyone.

• 53:46Speaker 01

  I had grownups forecasting this stuff with me. I relied on them. It's why I brought them in. You hired the right ones. Clearly I didn't pick the right ones or I'm not sure what happened, but I remember sitting in a room with them and us deciding, I didn't push for it. This wasn't, you know, we're gonna just grow by 100 million dollars this year. And someone put a plan together and this is, we hired 100 people. It was like the Tower of Babel. You know that story? You don't know? It's like a biblical story where people are building this tower or something, but they all speak different languages. And I could be completely wrong. I don't think I am.

• 54:29Speaker 01

  But none of them get along or understand one another. And it was, it was, it's just a mess trying to integrate 100 people into a company in a year, especially a company with no processes and no real intentional culture that had been established, no real intentional anything other than the brand, the spirit of the brand, what needed to be done. It was, it was like a family business that just got really big. It was, I was a kid.

• 55:02Steven Bartlett?

  How are you feeling in terms of, at this point, in terms of what's going on around you? Sixty million dollars has just come into the bank account. You're looking at it thinking, that's a big fucking number. You're, you know, because you have a valuation of three hundred and fifty?

• 55:17Speaker 01

  Yeah, I'm worth two hundred and eighty million dollars on paper at this point.

• 55:20Steven Bartlett?

  So that, and wherever you go, they'll lead with that and remind you of it. And you'll be treated as such, even though it's paper and it's not real, it's not the cash in your bank account. How, how does that make you feel when you, you know, then they put you on the front cover of Forbes?

• 55:33Speaker 01

  Yeah.

• 55:34Steven Bartlett?

  How does that make you feel?

• 55:37Speaker 01

  It was a blast. I didn't do any of it to have glory or go on a victory lap. And I wound up with it and I embraced it and I had a lot of fun. It distracted me. You know, the book in twenty fourteen turned into a phenomenon. You know, it was champagne clinks for some milestone with the company or new hire, promotion, any given time. I, people would come up to me and say, congratulations. And I had to ask which thing they were congratulating me for. It was, it was just like oysters for everybody. Finally, you know, I, I got better taste in wine. I got better taste, period. Thank God.

• 56:22Speaker 01

  But now I spend less money with a good taste that I had to spend a lot of money to acquire. A lot of my own.

• 56:31Steven Bartlett?

  But did, did you feel, did you feel like it made sense? Like the, the image that's been, that had been built of you at the time, that the world is now like, oh my God. Did, is that what was going on inside?

• 56:44Speaker 01

  I think it made sense. I think it was a freak show. I was a community college dropout who bootstrapped a business to twenty eight million dollars in revenue, super profitably. You know, investors came out of the woodwork, you know, and top tier ones anointed me as someone who could pull it off. And I didn't know what I was signing up for or what I was supposed to pull off, but.

• 57:09Speaker 01

  It was considered a rags to riches story and.

• 57:14Steven Bartlett?

  Imposter syndrome. Any of that?

• 57:17Speaker 01

  For sure. Yeah. I mean, I still walk in rooms and I'm here. I was talking to your team and I was like, oh, my gosh, you guys have really big people. I hope I can keep up. I say like a lot. I'm intimidated. I hope I can provide some value. What are the comments on YouTube going to say? Is this going to be a valuable conversation? I really hope people like it, you know? And she was like, what? You wouldn't be here if that wasn't the case. What? What are you talking about? You're great. But I get nervous, right?

• 57:51Speaker 01

  I get nervous on stages and I'm still like, you know, I don't, I don't belong here. But the I don't belong here is also a really great motivator. The I don't belong here is I snuck in the back door. I don't belong here means I can do things differently. I don't belong here means I don't fit in. But that's going to be a superpower. And I think it's okay to feel like an outsider or an impostor sometimes because you find yourself in places where

• 58:25Speaker 01

  you have an outside perspective and are able to learn things.

• 58:31Speaker 01

  Unlike the people who were invited to the table, who all showed up there with the same pedigree. And then you get to make

• 58:40Speaker 01

  oblique connections between who you are, where you came from, and then the door, the room that you just snuck into as an impostor. And that is radical.

• 58:52Steven Bartlett?

  Would you remove that self doubting voice if I put a button in front of you and said you press this, you'll never doubt yourself again?

• 58:58Speaker 01

  No, it's so boring. I had a coach recently and he was lovely. We did five sessions. He was like $5,000 a month and I was like, taxes. I'd buy something else to save on taxes and.

• 59:16Speaker 01

  He was like, can you imagine? He asked me that word or he asked me that question and I was like, but what would I struggle with? What, who would I be if I didn't have challenges? And I was happy all the time. It's like the scaffolding would fall apart or something.

• 59:35Speaker 01

  That's a story I tell myself.

• 59:39Speaker 01

  But it's fun to have a dark counterpoint, to hold yourself accountable and be like, maybe it is that or not that. And I think that counterpoint is an opportunity to gain self-awareness.

• 59:56Steven Bartlett?

  Do you think it's additive to your performance or reductive?

• 59:59Speaker 01

  I think it can slow me down and I can make really slow decisions because I doubt myself. But beyond that, I think I've found a way to harness it that really works for me.

• 1:00:16Steven Bartlett?

  Have you, have you developed like a decision-making framework to help you navigate the two voices in your head? It's funny because when you're describing your mother and your father, it felt like those were the two voices. Your mother would seem to be very supportive. Your dad somewhat critical at times or pessimistic. Have you found a way of being able to juggle those voices?

• 1:00:36Steven Bartlett?

  So that you can make decisions decisively and quickly?

• 1:00:40Speaker 01

  No.

• 1:00:41Steven Bartlett?

  No.

• 1:00:42Speaker 01

  No. So I can, I can have these conversations. And when I, you know, when I do make a decision, I've learned to be slower with making decisions because I either make them extremely quickly or slowly on accident. And so I want to be very deliberate in the decisions that I make now and think more critically rather than, you know, navel gaze or be reactive to something. I went to this retreat, even though it's not really a luxury experience, with 30 other people called the Hoffman Process. And it's seven days with no phone, no internet, no books, no music. You were 30 other people and you're going through this process

• 1:01:25Speaker 01

  of mapping your patterns from your childhood against your parents and how, how you inherited that. And it's all directly correlated and basically graduating from your, your emotional child into an emotional adult.

• 1:01:42Speaker 01

  Super embarrassing, weird process, like so dorky. And everybody came with something different to work on or what emerged for them. You know, I, I feel unloved. I feel unlovable. I don't feel unlovable. My thing, and it sounds really weak, was like, I don't trust myself. I don't think I'm deceiving myself, but I think I can rationalize a lot of things to the point where I'll tolerate them too long. Um, and that's gone for relationships that went for my most recent relationship. Um, and so that's a strange thing. I don't trust myself because I do have these

• 1:02:24Speaker 01

  voices, it sounds, I don't have voices in my head, but I can see things from any perspective and not be totally attached to either one, to the point of being slow and asking for too much advice.

• 1:02:43Steven Bartlett?

  In that retreat, did you, did you have to sort of like go upstream and figure out where that belief started? Is that the point of that retreat?

• 1:02:50Speaker 01

  Mm-hmm.

• 1:02:51Steven Bartlett?

  Did you figure it out? Did you go upstream?

• 1:02:52Speaker 01

  What a good question. You're very good at this.

• 1:02:55Steven Bartlett?

  Oh, thank you.

• 1:02:56Speaker 01

  Yeah, I think it was that my parents didn't agree on how to raise me, that I felt misunderstood, that my good intentions were sometimes construed as troublemaking, that the fact that I didn't fit into the environment I was raised in, I was, I was not accepted and I was some kind of weird deviant when I was just being myself and felt punished for being myself. And I think that gave me like a lack of confidence or something, and I don't identify with being an unconfident person. But when it comes to decision-making, when everyone around you is telling you something, a different story about yourself than you have,

• 1:03:40Speaker 01

  and doesn't understand why you operate the way you do, that is really with integrity and in line with who I was and what I needed to be successful as a child. If other people like live in a different world and don't understand that those are your needs, you just feel wildly alone and think, wow, I am a freak. And that Found its way into my career through the public too, which has been super fun being told I'm something that I'm mostly not.

• 1:04:18Steven Bartlett?

  What have you been told you are?

• 1:04:20Speaker 01

  Oh, gosh.

• 1:04:24Speaker 01

  So Nasty Gal fell apart after 10 years. It was a, it was a quick rise and it was, it was a, it was a, it was a slow rise. And it was a relatively quick fall, couple of years in the making. And when it did fall, the headlines were crazy because I'd had all this press from this book I published. And being the poster child of entrepreneurship, going on the victory lap. National Enquirer said, had a picture of me and it said rags to riches, like straight up tabloid, American dream stuff. Like a caricature. And I didn't realize the amount of responsibility I had to like other people as an example, like I kinda did.

• 1:05:08Speaker 01

  But as some symbol for entrepreneurship or my generation, you know, generation of the entrepreneurs coming up behind me. Or at least what the press thought I was responsible for.

• 1:05:21Speaker 01

  The, you know, there were headlines like, does the failure of Nasty Gal mean millennials aren't ready to lead? It's like, wait, how is one example representative of a generation?

• 1:05:36Speaker 01

  And I've also read headlines like when the Netflix series came out. The worst thing about Netflix's Girlboss is its source material.

• 1:05:47Speaker 01

  Not even the show, just me.

• 1:05:55Speaker 01

  But I'm not bad. I don't believe, I don't believe it.

• 1:06:00Steven Bartlett?

  How does that make you feel at the time, though?

• 1:06:04Speaker 01

  By the time that Netflix series came out, I had been this hero as an entrepreneur. Then I was this girl boss because I wrote a book called Girl Boss and it was pink. And I was like this and I looked like I knew what was up, but I was like 27. And then there was the me whose company fell apart, the CEO. There was the girl boss who had built a toxic culture or just no intentional culture at all that like warped into something that wasn't perfect, but wasn't, I still don't think it was the worst. And now this person, this conflation of all of those things with this girl on the scripted comedy,

• 1:06:48Speaker 01

  which came out four months after I left Nasty Gal. So the biggest kind of personality or whatever, identity crisis was, you know, I'm on the cover of Forbes in June, I think of 2016, July of 2016. My husband of like a year's like, may I change my mind? And I'm like, oh my God, that wedding was so expensive. It was devastating, but I'm just like, God, that wedding was so expensive. It was a great party.

• 1:07:13Steven Bartlett?

  So in that space of like 12 months, you're on Forbes, husband leaves, Netflix comes out, Nasty Gal goes under.

• 1:07:20Speaker 01

  Nasty Gal goes under, then Netflix comes out. So the show had been shot when things are all like up and to the right. And, you know, we were working through challenges. There had been some layoffs, but the company was still, you know, a hundred million dollars a year. You know, not profitable anymore, but a great brand and something that was valuable. And eventually, um, yeah, like fell apart. And that the, there was really a conflation of the hero, the failure. And now this girl, four months later. Who's a caricature of a person I was when I was 22 in a scripted comedy,

• 1:08:05Speaker 01

  playing someone named Sophia, starring in eBay store called Nasty Gal. When for the first time in 10 years in my adult life, since I was 22 years old, I'm no longer associated with the thing that I had built. And now there are 130 million homes in 195 countries, watching a story of someone that I was no longer and no longer had trying to move on and to move on when there's a full PR campaign about who you used to be.

• 1:08:41Steven Bartlett?

  You're someone who's, as you said, you've had a long history with mental health challenges.

• 1:08:47Steven Bartlett?

  What is it like in that 12 month period? What's going on from a mental health perspective?

• 1:08:52Speaker 01

  Hmm, I had fallen in love again. I think I was still like traveling. I started another company. I maintain my mental health partially because I keep going. You know, I don't stop and like lick my wounds. I think I was also, I was also on antidepressants. I wasn't jumping for joy, but I also knew that there was a huge community that still supported me, who had read my book, 500,000 women who bought it. And I went on to start a company called Girlboss, right as the Netflix series was hitting, put on our first conference. And I had my podcast and I moved on quickly.

• 1:09:37Speaker 01

  And even though the headlines weren't nice,

• 1:09:43Speaker 01

  the people who followed me, my friends, my relationships, everybody in my network, nobody bailed. Like the girls who were inspired by Girlboss were refreshed that I had face planted publicly because everyone else is face planting in private. And in the same way that watching some random community college dropout from Sacramento, start a business with an internet connection and a computer, gave them license to, you know, yes, they were inspired, but also embrace their own failures because the hero face planted publicly.

• 1:10:28Speaker 01

  And that can also inspire people.

• 1:10:34Steven Bartlett?

  This is hopefully the most cliche question I ask, but I wanna, I wanna know because you have a, from your, from that experience, you have amazing feedback. You have amazing insight, invaluable insight, I would say, because when I think about the things, obviously, that have taught me the most, it's not, it's not when things go right. That's a validation of your hypothesis. It's when things go tragically wrong and you go, oh, okay, fuck. You have all of this new information about, which has corrected your hypothesis. So when you, if we go back and think about that fundraiser, for example, a lot of people will hear that you raised a company, raised investment at 350 million and think, amazing, that's when people clap, right? They, they get the champagne out of their oysters.

• 1:11:15Steven Bartlett?

  For people listening that aren't in business, they might not understand how that can also be a key reason why the company ultimately went under. The 350 million, why, why did our big valuation hurt you?

• 1:11:26Speaker 01

  Yeah, I think the 350 million dollar valuation, as celebrated as it was and how wealthy I was on paper, was the, was the nail in the coffin. I think it was, it was then in 2012 where we were overvalued and the expectations that was, was that the next round of fundraising that we do is at a, over a billion dollar valuation? And so the company's doing, you know, on an upswing to 28 million dollars in revenue. That's like over 10 times revenue and it's a fashion business. This isn't a technology business. This isn't Uber. This isn't an infinitely scalable marketplace. It's e-commerce.

• 1:12:10Speaker 01

  It was a different era of e-commerce. It was pretty early. It was the era of fab.com, which like imploded and One Kings Lang and Beechman and Shoe Dazzle. There was no playbook. There were no e-comm veterans or, you know, performance marketing people who had been in those jobs for even very long. I was hiring executives who'd worked at like Macy's, right? Nobody had like e-comm, it wasn't called direct to consumer at the time. It was very, very different. There was no Shopify and.

• 1:12:43Speaker 01

  We were overvalued and I didn't know that. I didn't even negotiate, you know, hardly negotiate. I didn't shop a term sheet around and say, I'm gonna pick the highest price from different investors. I only had one term sheet and I was like, great, I like you.

• 1:12:57Steven Bartlett?

  Index fund shares, which are a phenomenal.

• 1:12:58Speaker 01

  I was like, you're awesome. You can, you get it. You know, what Danny said when he invested was something none of the other potential investors said. And that was, you have a community. And I was like, yeah, we do have a community. But when you have that much money,

• 1:13:17Speaker 01

  you don't know there's been a nail in the coffin or that there's a coffin and that like you might be on your way into it or maybe already laying in it, but just several years in the future. And

• 1:13:34Speaker 01

  when things are up and to the right, you don't see what's lurking kind of below the surface. So when the tide lowers, right, you see the mud, you see weird crab shells. Sometimes, hopefully not, you see trash. And it's only when things recede that you see the mud that's underneath. And when you're on a victory lap and you're hitting milestones, everything's great and everybody loves their jobs and you're a hero. And as soon as things

• 1:14:05Speaker 01

  go a different way, as soon as there's layoffs, yeah, there are things, kind of, there are things, there are things lurking below the surface that were dynamics that were already happening that because everything was going so well, you know, were harder to notice. And, you know, it's hard to be a CEO. It's hard to be a founder. I think something a lot of people don't realize is that you only know 10% of what's happening in your organization. I had hundreds of employees. And ultimately, everything was my responsibility. But I am held accountable for 100% of what's happening.

• 1:14:46Speaker 01

  And when something goes wrong or something's mismanaged or someone has a bad experience in the company, the assumption is that I have signed off on it. That that is how I want things to be. And these things are happening, you know, cattiness and. You know, fiefdoms and silos and duplications of effort and all the, you know, the entire spectrum of things that are no fun at a fast growing company. I didn't know were happening until we laid people off and then they were like, hey, we didn't like it there. I'm like, okay. And some of that was totally overblown.

• 1:15:27Speaker 01

  But also, anything that any employees ever said about me or I've read, even though I don't agree with all of it, has been an opportunity for me to learn and take from that how I could be better because there's truth to almost everything.

• 1:15:43Steven Bartlett?

  Didn't you get an offer to sell the company completely for $400 million?

• 1:15:46Speaker 01

  Yeah, I did. I owned 80% of it.

• 1:15:49Steven Bartlett?

  So that would have made you, you know, quick maths, I don't know, very fucking rich?

• 1:15:53Speaker 01

  Mm hmm. Super fucking rich.

• 1:15:56Steven Bartlett?

  And why, why didn't you say yes?

• 1:16:00Speaker 01

  I went to my investor and I said, what do you think about this? And he said, you need to ask for more. I controlled the board. I owned, you know, I owned the majority of the company, but I also took advice from people who I thought knew more from me. But I didn't know that my interests weren't necessarily aligned with the interests of my investor, whose interest is to, whether I'm worth it or not, have a piece of paper to show his investors that says I'm worth, instead of 350, look, they're now worth a billion. And they just make up these numbers and then they can show their people that your company is worth more. And that was his, that was in his best

• 1:16:42Speaker 01

  interest. And that's what he was giving me advice based on.

• 1:16:46Steven Bartlett?

  Are you mad that he said that?

• 1:16:48Speaker 01

  I'm not mad.

• 1:16:49Steven Bartlett?

  Do you wish you'd made a different decision? Is that a regret?

• 1:16:56Speaker 01

  It's a, it's a partial regret, but I also know that no deal actually happens. They're not a, a real acquisitive company. They could have tried to acquire the company. I don't even know if they've acquired anything, integrating it into their company. If I had an earn out based on them, you know, controlling it and me trying to hit performance benchmarks, even if I had sold the company to them, who knows how it would have played out, I would have made a bunch of money. My life could have been miserable, but 99% of the time deals fall through.

• 1:17:26Steven Bartlett?

  There's also in those situations, a lot of people trying to get into the data room. So they make an offer so they can see your numbers and what you're doing and how your business is working out. And then they pull the offer later, once they've had a look into the data room and due diligence.

• 1:17:38Speaker 01

  Yeah, and then copy.

• 1:17:39Steven Bartlett?

  Yeah, exactly.

• 1:17:40Speaker 01

  Yeah, so we didn't get that far. I don't regret it.

• 1:17:45Speaker 01

  But yeah, that was a big thing, you know? For me, that would have been a lot of money. For him, it was just a teeny tiny bit more than what he had paid for it. So that's not a lot of, it's not much of a markup for him.

• 1:17:59Steven Bartlett?

  What is the advice you're giving now to, to women that are, and men, that are looking to start companies that are within your community, the communities you're building, within your portfolio companies now that you're an investor?

• 1:18:12Steven Bartlett?

  You know, like I think, I can think of the first piece of advice that I give young founders when they come to me. I'm wondering what your like first piece of advice is?

• 1:18:21Speaker 01

  I think for bootstrap founders, the advice would be different. For founders in my portfolio companies who are raising venture capital, my advice would be get as far as you can before raising a single dollar. Validate your idea as soon as you can with the ugliest, like most basic, quickest thing. Your first product should be super ugly. Get it in front of people and get some idea of whether it's valuable or not before you go raise money, before you even try to market it. Talk to every customer, every potential customer and bootstrap it as long as you can, if you can, because when investors do come in, your company's going to be worth more than if

• 1:19:02Speaker 01

  you had raised money when you just had an idea and were asking for a check. When you do raise money.

• 1:19:11Speaker 01

  Having a reasonable valuation is important and a lot of founders optimize for price because bigger price an investor pays, the more ownership the founder has.

• 1:19:23Steven Bartlett?

  The more they're worth, right?

• 1:19:24Speaker 01

  The more they're worth and the more eventually they could make if they sell the company. But when you have a valuation that's in line with market, that makes you an attractive acquisition, something someone might pay a multiple for, that 10%, say you're diluted down to 10 or 20%, you sell your company for $500 million, you're in much better shape than raising 350 and owning 80% of it and going to zero or whatever. So, and I think where things are right now with venture is a place that is, is close to that. And founders aren't greedy, founders who are raising money in this market know it's really, really hard.

• 1:20:09Speaker 01

  They don't want to be overpriced because the people who raised money over the last few years, raised at such a high valuation, these founders, nobody's going to reinvest in them. They've blown through their money. They thought they were, you know, they're on an upswing. Their company might be doing 2 million in revenue, but they're, someone told them they were worth $80 million? And now nobody's going to give them money. I've, as an angel investor, I have three of these right now. And it's like Hail Marys. Two of them have figured out how to survive. One's like, we have another term sheet. I mean, I've been there.

• 1:20:44Steven Bartlett?

  What about the psychological advice you'd give to a founder?

• 1:20:49Speaker 01

  I would say to listen to your gut. You know, there's going to be a lot of voices around you and there are people who know more than you and have experience and you should listen to them. But you should also always maintain and continue to cultivate a voice that, when you know it should, is able to supersede any advice that anybody gives you.

• 1:21:18Speaker 01

  I think it's easy to take all the advice because you're an inexperienced founder. And, um, and, and to lose touch with your intuition. And it's probably what got you to where you are as a founder, without the money and without the experts.

• 1:21:37Speaker 01

  And if you just rely on the money and the experts, you're losing the thing that made what you're doing special in the first place.

• 1:21:45Steven Bartlett?

  Which day was your hardest day over the last?

• 1:21:49Steven Bartlett?

  Since you first started that store on eBay? Is there a day you look back and go, do you know what? That period or that day was just the worst, the hardest, the darkest?

• 1:22:03Speaker 01

  Honestly, and it's weird, the hardest day was when my husband left. And I don't miss him and I don't wish we were still together. I don't really think about him. I mean, that was in twenty sixteen. But I had agreed to take a big swing in my personal life and make a huge commitment. And I thought that bumps in the road were like to be celebrated. I thought it was like, wow, okay, you're not feeling great about things. We're going to work through this and we're going to be so much better as a result of it. Because I see commitments as things that go up and down. And if you're in a commitment together, you're committed to working through those things. And it all comes out in the wash because you have that level of commitment to the other person.

• 1:22:49Speaker 01

  And that wasn't the case for him. And so I, I felt like I was like hallucinating. You know, I like went to a hotel for a week. I couldn't be in the house. It felt like a crime scene with his stuff around. And yeah, three, a whole, a whole week at the Beverly Hills Hotel with three poodles is quite the scene with, um, yeah, chain smoking in the courtyard in a bathrobe.

• 1:23:16Steven Bartlett?

  Has that experience put you off being a CEO of a big company?

• 1:23:20Speaker 01

  I mean, yeah, everything I've experienced has put me off from being the CEO of a big company. I'll never do it again.

• 1:23:24Steven Bartlett?

  Why?

• 1:23:25Speaker 01

  I don't, I just, I don't want to. That's not the job I want. I'm an early stage founder. I'm a master at creating brands that cut through the noise.

• 1:23:35Steven Bartlett?

  What happens though, if you're running a number of businesses now?

• 1:23:40Steven Bartlett?

  You've got your funds.

• 1:23:45Speaker 01

  Yep, business class.

• 1:23:46Steven Bartlett?

  Business class, but what happens say business class, what happens if it becomes globally, you know, globally successful, then you're back to being a big CEO again, though? Or you step out of the way?

• 1:23:58Speaker 01

  I would have to work really hard to make it that and I would have to invest in that and hire into it. That wouldn't happen by mistake. I have one employee on business class. Business class is super profitable. I launch it twice a year. It's pre-recorded. So business class is my entrepreneurship program, but I have two cohorts a year. April, I'm launching it and I launch in the fall. And it's an incredible product, but it's also something that is relatively self-led for the students. It's eight hours of video and 300 pages of worksheets and over 60 hours of interviews with me like this with entrepreneurs. And,

• 1:24:40Speaker 01

  you know, students get lifetime access. So, you know, they can take it over the first seven weeks. They can take it over the course of a year or the next few years. But it's not something that requires a ton of my time outside promoting it twice a year. And I built it for that. I built it for that. I'm using Kajabi and Drip for email and, you know, whatever Zapier and a variety of tools that allow it to be relatively low lift, light on human capital, still a lot of effort to promote. And something I do engage with throughout the year and two weekly calls with students and post in the lounge, which is our

• 1:25:21Steven Bartlett?

  But you're intentionally keeping it.

• 1:25:23Speaker 01

  That's it. No, yeah, I'm playing, I'm, I'm, I'm not playing small with business class. I'm playing to my strengths. That's big. And with trust fund, it's venture fund that I'm raising right now. It's a $10 million fund. What I get to do is not run a big company and keep trying to apply this stuff that I've learned over, you know, Over time, I get to go from zero to one over and over and over again with early-stage companies. And out of fund, I get to be in the weeds. If I hired a bunch of people, they don't want me to be in the weeds. Executives don't want you to micromanage, but I get to look at all the decks and I get to text the founders and say, here's what I think you should do. I can be helpful.

• 1:26:08Speaker 01

  And it's so rewarding to harvest all of my hardship on behalf of a new generation of founders and help them see around the corners that I wish someone had shown me around. And I get to keep my firm small. Even if I have a $50 million fund, I can do that with a few people. And I'm using the assets that I have. I'm the product. My relationships and my network and my access to deal flow is my product. My expertise and ability to help founders is my product. Million social followers and being able to amplify them is my product. The engaged community I have who's interested in the kinds of things I'm investing in will actually use them is my product.

• 1:26:52Speaker 01

  And I don't, I'm just, it's right here and it's an air table.

• 1:26:58Steven Bartlett?

  The intentionality is what I find most inspiring because so many people get dragged by the temptation of like external expectation. If it's great, business class is great, but all accounts have been on the website. Went on to, I saw that the waiting list is open for 2023. It said like, join the waiting list for 2023.

• 1:27:16Speaker 01

  Yeah, so it's launching in April.

• 1:27:18Steven Bartlett?

  Okay.

• 1:27:19Speaker 01

  The spring cohort launches in April, so you can enroll for like a 10-day period at the end of April.

• 1:27:24Steven Bartlett?

  When things are great, we get dragged by our own success.

• 1:27:28Speaker 01

  Mm-hmm.

• 1:27:29Steven Bartlett?

  What you're saying is you're going to be intentional and you've designed it so that that's impossible, so that you can't get dragged. Because someone's going to come along and say, we love this, we're going to give you a check. We love this, we'll turn it into some boxer shorts or some teddy bears.

• 1:27:41Speaker 01

  Mm-mm. Yeah, no, no, I, I.

• 1:27:46Speaker 01

  I've had the privilege of knowing what's on the other side of success and that a lot of it is not what you sign up for. And that when you are successful, you're stuck in it. So I spent a lot of time thinking about what success looks like for me and what I want my life to look like and how many people I want to have around me and the kind of stakeholders I want to have. So that I'm set up for success when trust fund is super successful, which I can stay nimble with. And with business class I've engineered that revenue was down last year to the year prior. And that's, that's okay. It's still profitable. I'm not gonna hire a bunch of people or a CEO or plow a ton of money into it trying to solve problems and pivot things.

• 1:28:27Steven Bartlett?

  So if I come along and I say I'm gonna invest 10 million to you?

• 1:28:30Speaker 01

  We're gonna hire a CEO.

• 1:28:32Steven Bartlett?

  Okay, but you take the money.

• 1:28:35Speaker 01

  Yeah. Take the money, just for the record, guys. When it's there, take real money. Take, take the money.

• 1:28:45Steven Bartlett?

  Magical thinking.

• 1:28:47Speaker 01

  Mm hmm.

• 1:28:48Steven Bartlett?

  What is that?

• 1:28:49Speaker 01

  Yeah, I mean, you can call it magical thinking.

• 1:28:53Speaker 01

  You can call it magical thinking. You can call it manifestation. You can call it prayer. You can call it whatever you want. I think it's, you know, casting the line out, not knowing what you're gonna catch, trusting you're gonna catch it and will pull it back. Magical thinking is like Indiana Jones, where there's the vast, where's the, there's the vast chasm between whatever and the Holy Grail. And he has to trust that there is a, an invisible bridge. And he grabs some gravel and he throws it out across this literal kind of canyon. And the gravel just falls on a clear bridge.

• 1:29:36Speaker 01

  And he had to like trust that when he walked across that, he wouldn't fall. And so I see magical thinking as, you know. Thinking beyond what might be obvious, thinking you're capable of doing things that you shouldn't be, thinking you can belong in places that you never thought you could, thinking you can accomplish things that you're completely unqualified to because nobody's qualified to, being able to see yourself in a life, in a world that's beyond your wildest imagination and just staying there.

• 1:30:17Steven Bartlett?

  We have a closing tradition on this podcast where the last guest leaves a question for the next guest. Your question is unfortunately not the hardest question in the world. I really wish you'd been given a real stitch up one, but yours is fairly straightforward question, which is what is your proudest moment?

• 1:30:34Speaker 01

  My proudest moment is paying off my mom's mortgage. I mean, that I can do that? That was crazy. That was the first thing I did.

• 1:30:43Steven Bartlett?

  What about this then? What's going to be your proudest moment?

• 1:30:50Steven Bartlett?

  This requires a little bit of magical thinking.

• 1:30:54Speaker 01

  Understanding what is meaningful in my life and actually spending time on it.

• 1:31:00Steven Bartlett?

  You haven't figured that out?

• 1:31:01Speaker 01

  No, there are meaningful things, but what is the, people have kids and that's like obvious and I don't know if I'm going to do that. I am super agnostic about it. It's really strange. I'll be thirty nine in a month. But I think like finding that and hanging on to it, like what is the, what is, is there some big meaningful thing that I'm going to find and cling to till I die? You know, and it's easy when it's family or easy when it's a kid and you can create these meaningful things in your life, but what that, what is that going to be for me when I'm dying? What is it? What will it all add up to? I don't know.

• 1:31:40Steven Bartlett?

  Sophia, thank you so much for your time. Thank you for the inspiration. You've been an inspiration for me for many, many, many years. And that's why I reached out to you to sit here with you. And you are absolutely a superstar in many, many respects.

• 1:31:50Speaker 01

  Thank you.

• 1:31:50Steven Bartlett?

  You're built for podcasting, but also because of your inclination to be open and honest and vulnerable. You're incredibly inspiring in the stories you tell and the way that you tell them. So thank you so much. It's a real honor to meet you. And I'm equally privileged that you said yes to come and do this.

• 1:32:04Speaker 01

  Oh, my gosh.

• 1:32:05Steven Bartlett?

  And I mean that. I'm not gassing you up or anything. I mean that.

• 1:32:07Speaker 01

  No, no. Thank you.

• 1:32:09Steven Bartlett?

  You're superb. And I can't wait to see what you do with both trust fund and business class because they look like exceptional projects. I've looked into the reviews of business class and with your fund, with the amount of information you've learned from your twisting, turning professional career, you clearly have a huge amount of intellectual leverage and firepower that makes for a great fund founder. So I look forward to seeing what you do there.

• 1:32:35Speaker 01

  Thank you. Thanks.