NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239

Didn't you get an offer to sell the. company for $400 million? Yeah, I did. What would it have made you? Super [ __ ] rich. Why didn't you say yes? You're very good at this. Sophia. Amoruso. founder of Nasty Gal, a best-selling. author, and a powerhouse in the. entrepreneurial world. 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. Nasty Gal went from $150,000 a year to. doing $150,000 over lunch. 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. Headlines.

weren't nice. Then Netflix comes out. You just got played. What is it like for you from a mental. health perspective? It's hard to pull yourself out of a hole. when you don't want to get out of bed. It's 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. What was the plan in life at that point? Oh gosh.

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Sophia, take me back to those suburbs in San. Diego and give me your earliest. contacts. Well, 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. Um.

we moved a few times, you know, our. house was like it was 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. homogeneous, 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 was, but. I wanted I like wanted out from a very. early age. What what did you what did you want out. of a very early age? When you say you. wanted out? Oh, yeah. What did you want? Yeah, I wanted out of my family home. It. wasn't happy. My parents didn't get along. I was.

playing referee, you know. Really? Yeah. What What age? 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, "Mhm, 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, 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, hand-holding or. something. They were very strict, as. well. I had to beg to go to a. boy's birthday party in sixth grade.

We weren't super religious, but my mom. grew up in the '50s in a. Greek Orthodox household. Um. just. not puritanical, cuz that sounds less. cultural than Greek Orthodoxy, but uh. strict, you know. What about money? What about money? Yeah. of arguments happened in my household. when I was younger because of money. Yeah. I mean, my dad sold My dad did.

loans, and my mom sold houses, but tract 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 things. There's. 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. My. mom's dad didn't work 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'd. have 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. Bankruptcy. Yep. Did you know what was going on?

No. I still don't know what hap- I don't. know. 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? I think it allowed me to even though it. was so challenging younger in life. to learn how to assimilate into. different environments. Um 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?". Um.

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. um 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. um. 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 super proud of that cuz. 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.

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. When you inherited it? When it was handed to me. You know, it's. 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. You're talking about your father here? Yeah. He He would critique you? Yes. When you say critique, do do you mean.

Oh, that's that's naughty. Don't do. that. 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 I was so glad at 17.

years old and I was also like, I'm out. of here. See you. You seem to become a bit of a rebel. You know, from from when you moved out. of your parents' house. The next couple of years, I the behavior. looked really rebellious. 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 my I.

didn't know what that word meant. I'm. hungry. I'm going to eat food. I'm. human. I'm hungry. I'm going to eat food. in the middle of class. 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 going. to make me a better student and it's. and I and the teacher told me to throw. the apple away. 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. 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 I 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 because I. not 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 mediocre. Not that I. wanted excellence. I just wanted out. Why are you like that? Cuz you know the. all the other kids were cool. 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 actually hatched out of a disco. ball. But that's the way. That's how I came out. I I had um Gabor Maté here who's this. like. I think he's just interviewed Prince. Harry actually. Um in 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, the parents are arguing, we. actually interpret that as there being. something that to do with us. Mhm. 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. Mhm. Mhm. Yeah, I took Adderall this. morning. Well, they Well, yeah. Just to prepare for the podcast. Just. kidding. No, I have major ADD. ADD? 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. How did you realize it was a real thing. a couple of years ago? I I've been I mean, you know, I go to a. psychiatrist and I talk about what's.

going on with my brain and. um do what I can to help myself. um holistically, but also I know I'm. also predisposed to depression. I'm not. predisposed. I've suffered with. depression my whole life. Since when? 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. Um.

and that's not something, you know, it's. hard to pull yourself out of a hole when. you don't want to 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. 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. I think we're all struggling to be a. well-rounded person. I don't know. Some people seem to like. have these parents that teach them that.

and they come out and they're like. Yeah. you know, boop boop boop boop boop boop. and it's not. you know, that's almost diminishing to. be like la la la la. 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. Did you ever You said. a curious phrase now, which. made me um. ponder. You said, "I'm a little dark.". Uh-huh. What do you mean by I'm a little dark? Hm. Hm. Why you giggling? You're making me think. you are a little dark. I am. I'm not evil. God.

Uh I'm not a witch. I. I guess I have. 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 cuz they're like children or. something, but I had to have a reason. I'm not sure why, and it's still kind of.

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. Maybe in general, I'm. just skeptical. You went to see a psychiatrist when you. were 16? Oh, I went to see a psychiatrist when I. was like. 10. I mean, I was I was in therapy. when I was like 10, 11. With what symptoms? 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. It 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. It was. also just very.

a very willful. independent thinker who didn't fit into. a traditional educational environment. 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 Wellbutrin and I'm not going to. take It's like an antidepressant. I. didn't take it. I was like, no, I'm not. taking any of this. When did they when Wait, and like. That was by high school.

So, you were 16-ish around that time. when they. Yeah, 15, 16 and I was like, this is. it's I don't feel like myself. I feel wired and weird and. I got I. like I think I got Ritalin. Someone. tried to buy it off me in like high. school and I was like, what do you what? I don't even get it. I was like, I'm. just throwing this stuff in the trash. I. didn't. And then so you so you get. diagnosed and prescribed antidepressant. at 16-ish. Mhm. Your parents break up at 17-ish. You.

leave the. I move out. You move out. I move out at 17 before I graduate high. school. I was home-schooling, so I got. my diploma in the mail. I thought. 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. Uh. So, I moved into a closet. You moved into a closet? Under the stairs for $60 a month. With a sleeping bag. this? Uh these guys that were like in bands. and artists who I'd met going to shows. cuz I was really into music and went. downtown in Sacramento and saw music and.

What was the plan in life at that point? Was there a plan? You know, you're like. 17, 18. told me there was a plan. Mhm. I wanted to go to. I first wanted to go to Reed College, but that was expensive. But then I wanted to go to the Evergreen. College. So, by the time I was 18, 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 going to go to. college, I was going to 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 going to. do anything for me. You described this chapter of your life. as being very lost. 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 a you know, some Disney character that 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 17, 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. 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. That's an interesting turn of events.

Turn of events. Yeah. That was an interesting turn of. events. And. Now this 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. I was Yeah, I was looking for some place. to belong and I never found it and I. kind of love that. Cuz it's forced me to make my own and. forced me to stay creative thinker. And.

also, I don't know. I This isn't fair, but the. people in some of those communities like. peaked and never left. It's like, you. know, I listen 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. Like that sounds. that sounds. awful to me. So, I'm. I'm glad I didn't find a comfy place. And it's been uncomfortable since then. How long did you try the stripping. thing? I don't know. I mean, when you're in. your late teens, early 20s, 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. You know, they say. I read in your book where 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. Mhm. 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. that you learned from stripping that you. think is probably stayed with you.

today? 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.

18 who 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 I didn't sleep with anybody till I. was 19. So I just I was kind of late and. by 20 I was. stripping in Portland. That escalated quickly. 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. Uh. I like when I was on birth control, I. went off birth control for like 1 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. Yeah, I'm like, I don't know.

Who's watching? And uh and I wound up. I wound up pregnant. So, I'm like 20, maybe 19, and. I went to this sliding scale women's. clinic. and. but but it 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 they were just I kept following up. to be 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. going to 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 it to. 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. Um but at least it's like this, right? It's been like this.

You know, doesn't. This doesn't ever go that low. 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 [ __ ] with us. We're not the. teacher.". Yeah, it was like, "Okay, like maybe. just figure out how to go to get along, you know?". It wasn't like, "Wow, I'm going to go. have a career and do. everything I'm I'm going to 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. Shoplifting. Mhm. Why'd you make that sound? I don't know. It was fun. What was your favorite thing to steal? I don't endorse shoplifting. Neither do I. 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 uh. 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. I did it at grocery. stores. I I furnished apartments. I. walked out of places with like little. 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. And I was like, yes, this is this is. luxury. It's worth jail time. So that was, yeah. And. 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. and participating in. cart 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 an ex-. some kind of quasi political lazy excuse. for just not working hard. Anyway, I. learned from some of the best. Um I had. a friend who had written a book called. Evasion, literally.

And. I would go into Barnes & Noble. and they had a no chase policy. Like I. knew what the policies were at these. places. Because if their employees chase. 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. best selling books. This is in 2002, 2003. It's like.

and. even look at the ratio of. most expensive book to least 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 best sellers in huge stacks. and I would just like. pile them high to I look 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 walk 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 a media. mail and I'd pay my $350 a month rent. Why weren't you scared? 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. uh-oh it's kind of icy let me look down. you're just like. catch an edge. You're surfing and you. look at the nose of the board. right? So you think that's what you.

a life lesson? I guess I guess. 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. And you can justify. It's not No, I couldn't justify it. I. would never feel comfortable doing it. Um but big box retailers I was like hm. Over the last couple of how long maybe. four months I've been changing my diet. shall I say. Many of you who've really.

been paying attention this to this. podcast will know why. I've sat here. with some incredible health experts and. one of the things that's really come. through for me which has caused a big. change in my life is the need for us to. have these superfoods these green foods. these vegetables and then. a company I love so much and a company. I'm an investor in and then a company. that sponsors this podcast and that I'm. on the board of. recently announced a new product which. absolutely spoke to exactly where I was. in my life and that is Huel and they. announced daily greens. Daily greens is.

a product that contains 91 superfoods, nutrients, and plant-based ingredients, which helps me meet that dietary. requirement with the convenience that. Huel always offers. Unfortunately, it's only currently. available in the US, but I hope. I pray that it'll be with you guys in. the UK, too. So, if you're in the US, check it out. It's an incredible. product. I've been having it here in LA. for the last couple of weeks, and it's a. game-changer. Ladies and gentlemen, our. newest brand partnership will come as no. surprise to regular listeners on this. podcast. The first episode of 2023,

I was joined by the incredible Professor. Tim Spector to hear more about his work. at a company called Zoe, using data to. understand our bodies better so that we. can live more fulfilled, higher. potential lives. Zoe was born from the truth that our. overall health is impacted by our gut. health. By helping you to understand how. your body is working, Zoe can help you. to reduce your risk of long-term disease. and increase your energy levels. For me, this is the future, and that is why I. became an investor in the company, and. that is why they are now a sponsor of.

this podcast. You can read up about. everything they're doing, and you can. pre-order your Zoe program at. joinzoe.com. And they've been kind enough to offer an. exclusive 10% off code, CEO10. So, you. can put that code in at checkout, CEO10. Thank you so much. Let's get back to the. episode. So, by this time you're getting a little. bit acquainted with the internet and. selling things on the internet clearly. cuz you're selling stolen stuff. Uh yeah. Vintage. Mhm. Why Why vintage? Why did you start to.

sell vintage clothes? Yeah, so by 2006, 6, I had gotten some real jobs, you know, after after I'd worked in shoe. stores and record stores and photo labs. and. Subway again, I dry dry cleaners, I. How did you get on with those jobs? They didn't last very long. I like jobs. very appetizing though, so record.

stores, photo labs, book stores. I 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 79 New Montgomery Street Street. called the Academy of Art University. 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. Is this your hernia? Yeah. The hern. The hern? 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 um 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. 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. with group health insurance with a job. 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. Were you doing anything sort of criminal. at this point? job, no. So all of your money came from that job. and. Yeah. And so there there was a. three-month waiting period for health.

insurance. And while I was there, I had time to. I had some time downtime in this lobby. and there's a computer. And uh 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. 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.

$9.99 and these things were going for. like $200, $300. And they were just. making it look like something that. Sienna Miller or some boho at the time. it was like boho, Olsen twins, Sienna. Miller kind of vibes. And they would do. that, put the stuff online, and the. customer determined the price. And it was so much money. And so I. thought, okay. So, I waited my 3 months. for my health insurance cuz there was a. 3-month waiting period, got the hernia. fixed.

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. Before that point, would people have called you lazy? Or unmotivated? I didn't know any people who would have. said something like that because. my friends were. just like me. So, people. Objectively then, if. Objectively. I think just lost. Lost. I I think it would be a judgment to say. I was lazy. 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 I've always had a challenge. with authority. Every job I had through. up through that period of my life lasted. for 3 months. I was I was just call. center hopping. Get to the bonus. threshold, quit, gives me 2 months where. I don't have to get a job, call up. another call center. those people. Yeah, I'm one of them. And and it's funny because I think. people would have looked at me in school. and stuff and said. like written me off, oh, it's he's lazy. Well, I like I 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, 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. That's the Do you think that's the the. rebel in you? It is. but it's why everything I do is so. inspired and honest and. I don't want to be like I'm unique, but. Cuz you never accepted or learned. compliance.

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. Like you didn't even want the bell in. school to tell you what to do. No. The gift and a curse though, right? I mean, it's pretty logical that you. would question. That's not. a bell ringing and someone moving from. one room the same room to the next room. every single day. questioned it? For what? Do you think anyone else questioned it? No.

No. But if you really think about it, it's. pretty wild, right? That that eBay store that you start with. in your free time when you working that. job. you took to fix the hair and. Mhm. Um. it was successful. Yeah. And you know. you kind of frame it as you saw maybe a. price arbitrage or whatever, but it but. it's more than that, right? It's more. than that. To be successful at that time. I'm not sure a lot of people saw that. price arbitrage and they didn't build a.

Nasty Gal. So, when you reflect on why. and how. you were particularly successful. how do you diagnose that? I reverse engineered everything everyone. else did and did a better job and did it. with my. signature on it. 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. [ __ ] do we do it that way has been part.

of the reason why that eBay store was. successful? 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. Misspelled. But even that's first principle. thinking. That's like. you've got a conventional 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's it. guarantees you a pre-tried blueprint. So. people follow that, but then these other. little rebels, they they have this almost inbuilt. ability to just like [ __ ] see through. to the 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. On eBay. Yeah, on eBay. Which a lot of people. wouldn't have had. Like that's a. And it was called Nasty Gal. The spirit.

of it was really. irreverent. Mhm. 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 70s, put out some incredible.

records, was married to Miles Davis for. a short period, and was allegedly too wild for him. Her lyrics are just so when I was. stripping her music when I was like 20. and then I 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's certain.

things that other people have done right. that you can see, you know, accelerate what it is that you. 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 it I wouldn't have survived. I would have been dead in the water. You're 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. Like I'm talking about. like the the the Nasty Gal. needing a CFO. Yeah. See what I mean? Or like that's 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. Yeah. if we don't know what we don't know. I've been to hell I've been I died and. now I'm in the afterlife. I did it did. send me to the grave. My naivety and. lack of experience did send me to the. grave.

It happened so fast. That's a quote. Um It was shocking how. fast it all happened. Nasty Gal went from doing $150,000 a. year to doing $150,000 a day, and then. $150,000 over lunch. Mhm. 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 going to get a bounce house.". You know those things. that people jump on, the inflatable. things that children. 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. That's what you wanted? 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. To be fair, now you say it. when we raised investment 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 naivety. I bought I paid off my mom's mortgage. Oh, did you? Okay. I couldn't do that with investor. capital, but. No, it wasn't with investor capital. No, it was the first time I made money. Yeah, my slide was with investor money. Okay, yeah, no. No. They actually those investors did really.

well. They they got bought out within 6. months, so they got a big return, but. Good job. Yeah. 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. had just showed up and I did what I 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 cuz I held myself. accountable, especially C-level. executives and grown-ups. whose longer than I had been alive. Like, how did you do that at such a. young age? Well, I think I I think I messed up. I. think like for the first 2 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 be with us with that 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 hired lots of like. young people. You know, I I remember the BBC did an. article saying is this the youngest. company in Britain cuz I think we were. like somewhere our average age was maybe. 20 or something. And we had like a we. had like a hundred almost a hundred. people. You know, and you feel the. strain of that. You feel things. breaking. You're And 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. Um. 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 organization experience. 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. a little much double their age, experienced in client services, and understands the old rules of the. game. If you understand both games, you. can understand the game of the future, I. think. So um made a lot of mistakes and. we nearly went under several times and. had to call people and beg for money um. in the lead-up to payday, but. somehow managed to. survive. But going back to you now, um I feel like we missed a part cuz you. know, you're at the recep you're. you went from starting that store to.

bouncing around on that bouncy castle. thing. We call it bouncy castle. Okay. Horse castle. Between that between that bouncing on. that horse castle. and the starting the store, what what happened? So. first year, just on eBay, did $75,000 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 had never eaten an oyster. You. know, I was drinking like. Budweiser and e- it's still like e-. 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, uh 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, $28 million 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 $250,000 in revenue.

The next year did 1.1 million. The next year did six and a half. The next year did 12, and I was coming. off. a $12 million year uh revenue, owned 100% of the company, 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. b- go by greater breadth and depth in. things I knew they would love. And that's what 2011, 12. venture capital comes in? 2012 was when Index Ventures invested. $60 million. $60 million? On a $350 million valuation.

On a business with a $28 million run run. rate. Yeah. You're you're profitable at that time. Mhm. Significantly? Pretty significantly. I have a. 10% or 20% or something? I don't know. I don't know. I didn't. even look at that. I was I I never had. to learn to read a P&L because my. company was profitable and I just. you know, generally knew how much it. cost to run. I didn't it it and I and I didn't I. didn't buy expensive office chairs. Did you did you know your like gross. margins on your on your. On the products, yeah. On the operating.

margins, no. I don't I don't think I I. didn't understand what operating margin. was. Um. It's pretty incredible that you could be. running a business that's generating has. a $28 million a year run rate and not. know what operating margins you're. dealing with or what your net profit is. 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. You talk about the $60 million going. into Nasty Gal in 2020.

2012. What did it break? Mhm. 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. 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 a hundred million.

and then we hired into that and we. bought into it. Oh, you believed it and everyone but uh. I had grown-ups 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 going to just grow by a hundred. million dollars this year and.

someone put a plan together and this is. we hired a hundred people. It was like. the Tower of Babel. You know that story? You don't know? It's like a biblical. story where. uh people are building this tower or. something, but they all speak different. languages and I I could be completely. wrong. I don't think I am. But none of them get along or understand. one another and it was it was it's just. a mess trying to integrate a hundred. 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 a it was. like a family business that just got. really big. It was. I was a kid. 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. [ __ ] number. You're you're you know, because you have. a valuation of 350. Yeah. I'm worth $280 million on paper at. this point. 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. Yeah. How does that make you feel? It was a blast. Um 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 2014 turned into a. phenomenon. You know, it was champagne clinks for. some milestone with the company it 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. 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. But did did you feel. did you feel like it made sense? Like the the image that's been that that. had been built of you at the time that. the world is now like, "Oh my god, I.

have heard of her." Did is that what was. going on inside? I think it made sense. I think it was a. freak show. I was a community college. dropout who bootstrapped a business to. $28 million in revenue, super. profitably. You know, investors came out of the. woodwork, you know, 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. it it was considered a rags-to-riches.

story, and. Imposter syndrome? Any of that? 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? Um. 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. you learn you have an outside. perspective and are able to learn things. unlike the people who are invited to the. table, who all showed up there with the. same pedigree. And then you get to make.

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. Would you remove that self-doubting. voice if if I put a button in front of. you and said, "You press this, you'll. never doubt yourself again.". 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 I'll buy something else to save on. taxes.". And. 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.". That's a story I tell myself.

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. Do you think it's additive to your. performance or reductive? I think it can slow me down and I can. make really. slow. decisions. cuz I doubt myself. But. beyond that.

I think I've found a way to harness it. that really works for me. Have you Have you developed like a. decision-making framework to help you. navigate the two voices in your head? It's funny cuz 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. Um have you found a way of being able to. juggle those voices. um. so that you can make decisions. decisively and quickly?

No. No? Mhm. No. Still. 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 cuz 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.

uh retreat, even though it's not really. a luxury experience, with 30 other. people called the Hoffman process, and it's 7 days with no phone, no. internet, no books, no music. You're. with 30 other people, and you're going. through this process 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.

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. 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. In that retreat, did you did you have to. sort of like go upstream and figure out. where that belief started? Is that the. the of that retreat? Mhm. Did you figure it out? Did you go. upstream? Mhm, what a good question. You're very good at this. Oh, thank you. 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 trouble. making, 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.

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. What have you been told you are? Oh, gosh. Um. 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 years in. the making. And when it did fall, the headlines were.

crazy cuz 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 you know, 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 kind. of did, but as some symbol for.

entrepreneurship or my generation, you. know, the generation of the. entrepreneurs coming up behind me or at. least. what the press thought I was responsible. for. 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? And I've also read headlines like. when the Netflix series came out,

the worst thing about Netflix is. Girlboss is its source material. Not even the show, just me. But I'm not bad. I don't believe I don't. believe it. How does that make you feel at the time. though? By the time that Netflix series came. out, I had been this hero as an entrepreneur,

then I was this Girlboss cuz I wrote a. book called Girlboss 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. Girlboss who had built a. toxic culture. or just no intentional culture at all. all that like warped into something that. wasn't perfect, but wasn't 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. 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 is like. "Nah, I changed 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. So in that space of like 12 months. you're on Forbes, husband leaves, Netflix comes out, Nasty Gal goes under. Nasty Gal goes under, then Netflix comes. out. Ah. Ooh. So the show had been shot when things. were all like up into the right. And you know, we were working through. challenges. There'd been some layoffs, but the company was still, you know, $100 million 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 the hero, the failure, and now. this. girl four months later. who's a a caricature of a person I was. when I was 22 in a scripted comedy. playing someone named Sophia starting an. 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.

You're someone who's, as you said, you've had a long history with mental. health challenges. What is it like in that in that 12-month. period? What's going on from a mental. health perspective? Mhm. I'd 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. And. even though the headlines weren't nice,

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. And that can also inspire people. This is hopefully the most cliche. question I ask, but. I want to I want to 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.". Mhm. You have all of this new information. about which has corrected your. hypothesis. So, when you if we go back. and think about that fundraise for. example, um. 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 and they. toast to this. 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 a big. valuation hurt you? Yeah. Yeah, I think the 350 million-dollar. valuation is celebrated as it was and. how wealthy I was on paper, um 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 228 million. dollars. in revenue. That's like over 10 times. revenue. And it's a fashion. This isn't. a technology business. This isn't Uber. This isn't an infinitely scalable. marketplace. It's e-commerce. 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 Lane. and and Beachmint and ShoeDazzle. There. was no playbook. There were no e-com. veterans. or. you know, performance marketing people. who had been in those jobs for even very. long. I was hiring executives who had. worked at like Macy's, right? Um nobody. had like e-com it wasn't called direct. to consumer at the time. It was very. very different. There was no Shopify.

And. 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 going to pick. the highest price from different. investors. I only had one term sheet and. I was like, great. I like you. Index Ventures which are in. like, you're awesome. You can I you get. it. You know, what Danny said when he. invested. uh 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. 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. when things are up into 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. 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'm held accountable for 100% of. what's happening. 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, 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. Didn't you get an offer to sell the. company completely for $400 million? Yeah. Yeah, I did. I owned 80% of it. So, that would have made you, you know, quick maths, I don't know, very [ __ ]. rich. Mhm. Mhm. Super [ __ ] rich. And why why didn't you say yes? 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's worth more,

and that was his That was in his best. interest, and that's what he was giving. me advice based on. Are you mad that he said that? I'm not mad. Do you wish you made a different. decision? Is that a regret? 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 earnout 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 get been miserable, but. 99% of the time deals fall through. Then you 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 in the to the data. room and due diligence. Yeah, and then copy it. lot. Yeah, exactly.

Yeah. So, we didn't get that far. I. don't regret it. Um. 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. 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?

Um. you know, like I think I 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. 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 you. 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 you had raised money when. you just had an idea and were asking for. a check. When you do raise money,

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. The more they're worth, right? 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. 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 Mary's. Two of them. have figured out how to survive. One's. like, "We have another term sheet." I.

mean, I've been there. What about the psychological advice. you'd give to a founder? Um. 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.

you when you know it should is able to. supersede any advice that anybody gives. you. Um I think it's easy to take all the. advice because you're an inexperienced. founder. And um. and into 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. 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. Which day was your hardest day of the. last. since you had 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. 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 20 16. 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. 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 um yeah, three a whole whole week at. the Beverly Hills Hotel with three. poodles.

is quite the scene with them. Yeah, chain-smoking in the courtyard in a. bathrobe. Has that experience put you off being a. CEO of a big company? I mean, I have Yeah, everything I've. experienced has put me off of being a. CEO of a big company. I'll never do it. again. Why? 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. What happens though if one of, you know, you're running a number of businesses. now? Um.

you've got your fund. Yeah, Business Class. Business Class. But what But what. happens to Business Class? What happens. if it becomes. globally, you know, globally successful? Then. you're back to being a big CEO again, no? Or you step out the way? 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. that I have two cohorts a year. I'm uh. 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 8 hours. of video and 300 pages of worksheets and. over 60 hours of. interviews with me like this with. entrepreneurs. And, you know, students get lifetime.

access. So, you know, they can take it. over the first 7 weeks, they can take it. over the course of a year or the next. few years. Um 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. Um and something I do engage. with throughout the year and do weekly. calls with students and post in the. lounge, which is our. But you're intentional in keeping it. That's it. No, yeah, I'm play 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, this 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 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 fun, I get. to be in the weeds. If I hired a bunch. of people, I 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." 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. Um 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 as. my product and I don't. I'm just it's right here and it's an. airtable. The intentionality is what's I find most. in surprising inspiring because so many. people get dragged by the temptation of. like external expectation. If it's. great, business class is great by all. accounts. I've been on the website.

Went on to I saw that the waiting list. is open for 2023. It said like join the. wait waiting list for 2023. When I go. Yeah, so it's launching in April. Okay. The the spring cohort launches in April. So, you can enroll for like a 10-day. period at the at the end of April. When things are great, we get dragged by. our own success. Mhm. 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 tie it into. some boxer shorts or some teddy bears.".

Mhm. Yeah. No. No, I I. have 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 spend 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 okay. It's still profitable. I'm not going to hire a bunch of people. or CEO or plow a ton of money into it. trying to solve problems and pivot. things. So, if I come along and I say I'm going. to invest 10 million, Safiya. We're going to hire a CEO. Okay, but you'd take the money. Yeah. Take the money. Just for the record, guys. When it's there.

take real money. Take take the money. Magical thinking. Mhm. What is that? Yeah, I mean you can call it magical. thinking. You can call it magical thinking. You. can call it manifestation. You can call. it prayer. You can call it whatever you. want. Think it's. you know, casting the line out not. knowing what you're going to catch. trusting you're going to catch it and. will pull it back. Magical thinking is.

like Indiana Jones where there's the. vast where there's 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. little kind of canyon. and. the gravel. just falls on a clear bridge and he had. to like trust that when he walked across.

that he wouldn't fall. And so, I see. magical thinking as, you 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. 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. Um but yours is. yours is fairly straightforward. question, which is what is your proudest. moment? Mhm. 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. What about this then? What's going to be. your proudest moment? Mhm. This requires a little bit of magical. thinking. Understanding what. is meaningful in my life and actually. spending time on it. Haven't figured that out? 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 39 in like a month. Um. 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. Sophia, thank you so much for your time. Um, 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. But, you're built for podcasting, but also. because of your, um, inclination to be. on open and honest and vulnerable. Um, 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 I'm I'm. equally privileged that you said yes to. come and do this cuz. Oh my god. And I mean that. I'm not gassing I'm not. just like gassing you up or anything. I. mean that. Thank you. You're super fab. And I can't wait to.

see what you do with both Trust Fund and. Business Class cuz um, they look like. exceptional projects. I 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, um, amount of. intellectual leverage and. firepower that makes for a great. fund, um, founder. So, I look forward to. seeing what you do there. Thank you. Thanks. As you might know, this show's now.

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