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didn't you get an offer to sell the company for 400 million dollars yeah I did what it made you super rich why
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didn't you say yes you're very good at this Sophia also founder of Nasty Gal A best-selling
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author and a Powerhouse in the entrepreneurial world I was rebellious from a very early age I was a stripper I
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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
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get a whole shopping cart of stuff put them on Amazon for 10 cents less than the other resellers and then gotten
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arrested for shoplifting I'm a little dark I realized I could connect my creativity to something
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legitimate started Nasty Gal selling vintage namastico went from 150 000 a
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year to doing 150 000 over lunch I didn't realize the amount of responsibility I had being the poster
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child of Entrepreneurship then I was this girl boss but my naivete and lack of experience did send me to the grade
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nasty y'all fell apart after 10 years my husband of like a year left the headlines weren't nice
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what is it like from a mental health perspective it's hard to pull yourself out of a hole when you don't want to get
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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
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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
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differently what was the plan in life at that point gosh
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before this episode starts I have a small favor to ask from you two months ago 74 of people that watch this channel
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didn't subscribe we're now down to 69 my goal is 50 so if you've ever liked any
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of the videos we've posted if you like this channel can you do me a quick favor and hit the Subscribe button it helps this channel more than you know and the
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bigger the channel gets as you've seen the bigger the guests get thank you and enjoy this episode
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[Music]
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take me back to those suburbs in San Diego and give me your earliest context
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wow I was born in San Diego Sharp Memorial Hospital only child
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eternally and only child I think wound up having the personality of a probably seven children and the
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challenge of maybe seven children for my parents um
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we moved a few times you know our house was like it was it was happy-ish when I
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was young I lived in San Diego till I was seven and it's a beautiful place and
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I so wish we would have stayed there but we moved to beautiful Sacramento California and that was
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really the Suburban experience where you know when you're a kid a little kid you don't know what a
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suburb is and chasing the ice cream man is great but once you get older living
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in the suburbs if you have any amount of curiosity about the world the
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homogeneous you know nature of living in the suburbs is something that totally
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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
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early age what what did you what did you want at a very early age when you say you wanted
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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
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playing referee you know really yeah what what age
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starting at like 10 or something I mean yeah it was just it wasn't a super happy
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place and they yeah they didn't get along they didn't always agree on how to
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raise me and I think when your parents you know everybody's relationship has issues and everybody's not everybody's
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but most people's parents you know sometimes don't get along when you have a sibling I think you can go be like um
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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
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think being isolated in a house that wasn't super happy as an only child made
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it worse and I just remember so many drives silent car drives where I was in
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the back seat alone and I just remember like the silence and the the light of the street lights
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like washing over the car just in in Silence with my parents in the two front
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seat um yeah they're really like only affectionate after like an argument and even then it
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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
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party in sixth grade we weren't super religious but my mom
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grew up in the 50s in a Greek Orthodox household um just
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not puritanical because that sounds less cultural than Greek Orthodoxy but uh
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strict you know what about money yeah arguments happened in my household
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when I was younger because of money yeah I mean my dad sold my dad did loans
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and my mom sold houses but track homes in the suburbs and they were both working with Builders and Banks and
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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
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homes that are all kind of dressed up and you can tour them and pick your manufactured
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home and change a couple things and there's like a fake keyboard in there just all kinds of
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funny things to play with and then so I was with my dad on weekends and my and
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they both worked entirely commission so I've never seen either of my parents work for a salary and my mom's dad
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didn't work for salary and my dad's dad owned a motel and they all grew up on a motel so there's like generations of my
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family who wouldn't necessarily call themselves entrepreneurs but they're people who ate what they killed and
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that's what I witnessed money was good I think when I was like
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you know when we were in San Diego and I think it got tougher over time I
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remember very vividly being in a credit counselor's office I just can't believe they brought me but
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there was no I don't know where they would have put me watching them cut up their credit cards like cut their
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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.
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bankruptcy yep did you know what was going on no
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I still don't know what happened I don't know are you able to look back on that
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that first sort of chapter of your life and figure out how it had a lasting impact on various elements of who you
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are today I think it allowed me to even though it
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was so challenging younger in life to learn how to assimilate into different environments
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um to I guess entertain myself independently to realize that Authority
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was like adults were not trained to be parents and weren't any further along
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with their maturity sometimes than I was at my age you know I looked at teachers
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and thought wow you know you have domain expertise you know some stuff but I can
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tell that like you're morally bankrupt and I don't trust you and why have I
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been put in your you know in your hands
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um I think the thing that had the biggest impact on me is how critical my dad was
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so he's half Italian and half Portuguese and his dad was a mean mean guy
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and my dad's very charismatic and I love him and he's super chill now but when I
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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
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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
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materials that they had the ingredients that they had to be parents but it instilled in me this
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unfortunate but also very fortunate always peeling back another layer of the
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onion examining myself but also real internalized drive to do better in a
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self-criticism that has worked very well for me that's been challenging it's
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challenged my confidence over time but it also has been a superpower to in some
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ways I don't know in some ways hold myself accountable because I'm always I
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almost want to say second guessing myself but also very
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um in a very I guess someone said Jesuit way at one point but
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a way where I can see both sides of everything you know challenging my
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doubts and my ego but the problem with that is sometimes
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it's hard to differentiate between the two what is you know fiction and what isn't and what
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of my self-critiques are accurate because I want to be and I think I am a pretty self-aware person
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and even with the things that I'm not great at I'm like super proud of that because I've got
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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
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for so long that instilled that in me and I've learned how to turn it into
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something that's more balanced than what it was when I inherited it
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when you inherited it when it was handed to me the model I had
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the level of critique that I had that didn't have the Counterpoint that I'm able to provide for myself you're
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talking about your funnel there yeah he would critique you yes when you say critique do you mean
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oh that's that's naughty don't do that no no like that's not how you do something
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or why why'd you do it like that or can you not or
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you know I mean I love my dad and and he's you know as both of my parents
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have gotten older they split when I was 17 and I've just watched them both become such better people
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I remember congratulating them when they finally split up and was so glad at 17
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years old and I was also like I'm out of here see ya you seem to become a bit of a rebel
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you know from from when you moved out of your parents house for the next couple of years the
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behavior looked really rebellious oh yeah no I mean I was rebellious from a very early age
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I remember in middle school a teacher I was eating an apple in class I was
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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
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hungry I'm gonna eat food I'm human I'm hungry I'm gonna eat food in the middle of class
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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
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healthy and it's gonna make me a better student and it's and I and the teacher told me to throw
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the Apple away and I just started the apple and of course I had the attention of the entire
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class and I got up and I sauntered over to the
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trash can super slowly and I just like ate the apple all the way to the core
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like super fast finished the apple and was like dink in the trash can
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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
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similar it was peripheral and then by the time I got to high
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school I was going to the anarchist book fair in San Francisco I was sure
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capitalism was you know the worst thing ever I was very angsty I thought that
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adulthood it's funny there's a Netflix series about my life and the first thing that the character says is adulthood is
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where dreams go to die and it's so weird to reference your own Netflix series like who does that but
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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
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wasn't ambitious so somehow along the way that lack of desire to live a
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conventional life became something that turned into ambition because I not even ambition just curiosity something that I
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was good at and you know eventually built a business but um I uh in high school in high school
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I remember there being Bells like right there's a bell that rings and you go
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from from one room to another room all day a bell rings you sit at a desk a
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bell rings and you stand up and you Shuffle over to the other room
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and then you sit down and you like memorize some stuff and then you like this is my youth I was
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sure I was being trained for something super mediocre not that I wanted Excellence I just wanted out
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why are you like that because you know all the other kids will come out like that I actually came out I came out like
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that yeah it is not I mean her I'm I might have some hereditary just kind of
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like Italian I'm not sure what or something it's not it wasn't a nurture
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thing that was a nature thing or I don't know I just like
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came out I actually hatched out of a disco ball but that's the way that's how I came out I had a gabo mate here who's
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this like I think he's just interviewed Prince Harry actually um in uh in a little like pay-per-view
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therapy session or whatever and Gabriel Mata said something to me that I've been pondering ever since he said that as children we're like narcissists and
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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 were arguing we
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actually interpret that as there being something that to do with us and that's the way we view the world as a survival
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mechanism and he says one of the things that happens when we're in a where you were a young child and we're in a house
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where there's lots of arguing and lots of drama and shouting is we learn to
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avert our attention as a way to help us deal with emotional distress and that develops into something they call ADD
00:15:07
and ADHD so I took Adderall this morning hmm hahaha
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well they will yeah just to prepare for the podcast just kidding now I've major
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add but they diagnosed me as a kid and I was
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like no this is mind control forget it I'm not focused because I thought it was situational I thought it
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was my environment and it maybe was partially because I wasn't interested in what was happening
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and distracted because I was curious about other things but also it's a real thing and it wasn't
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until a few years ago that I finally realized it was a thing and sought treatment and
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it's helped but it's helped like marginally it's not I had to realize it was a real thing a
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couple of years ago I've I've been I mean you know I go to a psychiatrist and I talk about what's
00:16:00
going on with my brain and um do what I can to help myself
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um holistically but also I know I'm also predisposed to depression not
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predisposed I've suffered with depression my whole life since when my whole life I don't I can't remember
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an age where I wasn't depressed I just
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I wasn't always miserable but I've I'm kind of a dark I'm a little dark
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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
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that's you know to have the willpower to just get over depression and put on a
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happy face and whatever people do get an ice bath and jump in the sauna and meditate and
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you know I am still struggling to be the well-rounded person but I'm functional I think we're all struggling to be a
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well-rounded person I don't know some people seem to like have these parents that teach them that and they come out
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and they're like yeah you know and it's not you know that's almost diminishing
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to be like but but I'm yeah there's people who just
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seem to you know and some people come out of the womb like that I know parents that are creative chaotic I know people
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who are well-rounded whose parents were addicted to drugs and somehow they just
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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
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said it curious phrase now which made me um Ponder you said I'm a little dark uh-huh
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what do you mean by I'm a little dark hmm
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why are you giggling you're making me think you are a little dog I am I'm not evil God uh I'm not a witch
00:18:03
I I guess I've just
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you know like I said I've struggled with depression I'm not a bubbly person I'm not someone
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you know as a child my mom has said you only laughed when something was really
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funny you know I think kids run around like laughing and smiling because they're like children or something but I
00:18:27
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
00:18:33
an adult it's become something that requires it's just being genuine and maybe I'm not I think maybe I'm not
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impressed maybe in general I'm just skeptical you went to see a psychiatrist when you were 16. oh I went to see a
00:18:48
psychiatrist when I was like 10. I mean I was in therapy when I was like 10 11. with what's
00:18:56
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
00:19:02
along why is she distracted so I have report cards that say
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chooses to disturb others you know doesn't stay on task it's stuff like
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that it was like I was always like you know not paying attention curious about something else engaged with something
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else it wasn't always to be rebellious sometimes it was very good-natured and I
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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
00:19:33
independent thinker who didn't fit into a traditional educational environment
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and you know that's something for whatever reason seemed to be needed
00:19:46
to be diagnosed but then I was like no no I'm not taking
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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
00:19:58
of this when did they win right that was by high school so you were 16-ish around that time when they yeah 15 16 and I was
00:20:04
like this is it's I don't feel like myself feel wired
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and weird and I got like I think I got Ritalin and someone tried to buy it off me in like
00:20:16
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
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didn't and then so you so you get diagnosed and prescribed antidepressant at 16ish your
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parents break up at 17ish you leave them I move out you move out I move out at 17. before I graduate high school I was
00:20:37
homeschooling so I got my diploma in the mail I thought the like most embarrassing thing would be would be to
00:20:42
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
00:20:49
what is this robe I I wouldn't have been proud standing in a group doing some group thing I'm not a
00:20:55
group person even though I've built a lot of really powerful communities I'm not I don't assimilate well into groups
00:21:02
and I think groups are responsible for the most heinous things in like human history so uh
00:21:08
[Laughter] so I moved into a closet you moved into a closing under the
00:21:14
stairs for sixty dollars a month uh these guys that were like in bands
00:21:20
and artists who had met going to shows because I was really into music and went
00:21:27
downtown in Sacramento and saw music and what was the plan in life at that point
00:21:32
was there a plan you know you're like 17 years no you told me there was a plan I wanted to go to
00:21:37
first wanted to go to Reed College but that was expensive but then I wanted to go to the Evergreen
00:21:43
College so by the time I was 18 I had moved to Olympia Washington to get residency to go to the state school
00:21:50
called the Ever Supreme State College which is a super duper hippie state
00:21:56
school that's interdisciplinary and there's no majors to the point of it not really being
00:22:03
worth going but if I was gonna go to college I was going to go to a place like that but
00:22:09
even state tuition was expensive so I lived in Washington state for a year to
00:22:14
get state to get residency so I could go to that school and by the time
00:22:20
I got residency I was like this school's not gonna do anything for me you
00:22:25
described this chapter of your life as being very lost super lost super lost I was looking for
00:22:30
my I kind of hate this word tribe I was looking for people like me I
00:22:37
thought I would find people like me and then all would be well like uh you know some Disney character that you know ugly
00:22:44
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
00:22:50
find their family and people understand them and so from the time I was 17 I
00:22:56
moved from Downtown Sacramento to Olympia Washington lived in two places there
00:23:01
Seattle lived in two places there San Francisco lived in one or two places there
00:23:08
Oakland with my alcoholic fry cook boyfriend I had met in Olympia we
00:23:14
couldn't get jobs and my parents were like yeah we can't help you with college
00:23:20
stuff so then we moved to Portland I was a stripper I was lost I was lost
00:23:28
that's an interesting time a ton of events yeah that was an interesting turn of events
00:23:34
and that chapter of your life in some ways mirrors the transience of the start of your life you said you moved to like
00:23:41
eight eight or ten different schools when you were young and then when you leave the nest you end up bouncing around as in your own words
00:23:48
like looking for your family I was yeah I was looking for some place to belong and I never found
00:23:53
it and I kind of love that because it's forced me to make my own and force me to stay creative thinker
00:24:00
and also I don't know I this isn't fair but the people in some of those communities like
00:24:06
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
00:24:13
listening is like never graduated from listening to pop punk but if you don't graduate to metal or some other it's not
00:24:22
even more sophisticated but like less juvenile varieties of rock it's the same
00:24:28
as finding you know some comfortable Community when you're 20 and
00:24:35
then never leaving like that sounds that sounds awful to me so I'm I'm glad I
00:24:41
didn't find a comfy place and it's been uncomfortable since then
00:24:47
how long did you try this stripping thing I don't know I mean when you're in your late teens early 20s
00:24:54
time just feels like it felt like a decade that I was you know bouncing
00:24:59
around to these places probably three or five months it was fun I loved it nobody
00:25:05
pulled anything I never got messed with I drank my white Russians and ate the
00:25:11
Subway sandwich from next door and played photo hunt and I wasn't even 21 I
00:25:17
used someone else's ID to work there and I got to dance to music that I liked
00:25:23
I made money I didn't really have to engage with anybody and I got really comfortable with my
00:25:29
body in a way that I hadn't before and that was cool yeah they say
00:25:35
I've read a new book where you said that you believe you hold the world record for having the most shitty
00:25:42
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 and that
00:25:49
thing can be applied to business there's always a sort of a transferable skill or whatever learn what was the transferable
00:25:55
skill but you learn from stripping that you think has probably stayed with you
00:26:01
today I think that even though I wasn't didn't
00:26:06
have the upper body strength to be the traditional one upside down swinging around
00:26:12
what I could do I mean it was like Shuffle around and whatever was enough
00:26:18
and still charismatic enough and still great enough to entertain other people
00:26:25
and then being comfortable with my body it's like exposure therapy you know I was the girl at
00:26:32
18 it would like make out with someone and then if I was like naked or
00:26:37
something I'd like put on my clothes to go to the bathroom or something I was like
00:26:43
not I didn't sleep with anybody until I was 19. so I was just I was kind of late by 20 I was
00:26:50
tripping in Portland I'll tell you the crescendo of that experience so dating with dating Wade
00:26:58
the alcoholic fry cook who was 10 years older than me uh
00:27:04
I like I was on birth control I went off birth control for like one day and there
00:27:10
was almost we were hardly even you know engaging in the way that someone might
00:27:18
like get pregnant like so briefly like
00:27:23
that day yeah I'm like I don't know
00:27:30
who's watching and uh and I wound up I want it pregnant
00:27:36
so I'm like 20. Maybe 19. and
00:27:43
I went to the sliding scale Women's Clinic and but but it was the only day I could get
00:27:50
in but it also happened to be the day of my court date because I had
00:27:55
gotten arrested for shoplifting so I had to have the Women's Clinic
00:28:01
write an excuse to the court telling them why this poor girl couldn't make it
00:28:08
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
00:28:13
think they all just felt so bad for me it kind of vanished but that was that was like okay no more shortcuts it
00:28:20
wasn't like I'm gonna go be a CEO but it also just
00:28:26
taught me that breaking some rules puts you in other
00:28:33
people's hands and I was you know being arrested I'm not as autonomous as I
00:28:40
would have liked to have been and you know even with stripping to a certain extent it was a shortcut I was trying to
00:28:46
evade like working hard but it was also a lot of fun but that was really that
00:28:52
was a low point it's had lots of low points um but at least it's like this right
00:28:58
it's been like this you know doesn't
00:29:03
it doesn't ever go that low there's clearly um a slight issue here with authority and it feels to me like
00:29:10
the ultimate Authority which is the law eventually was like he can't [ __ ] with us we're not the teacher yeah it was
00:29:15
like okay like maybe just figure out how to get along you know it wasn't like wow I'm gonna go have a
00:29:22
career and do everything I'm I'm gonna just do everything differently but also
00:29:27
I just didn't want to cut Corners I didn't want to end up
00:29:33
not in control of my environment or stuck in jail or something stupid shoplifting
00:29:40
mm-hmm why'd you make that sound I don't know it was fun
00:29:46
what was your favorite thing to steal I don't endorse shoplifting neither do I
00:29:52
my rationale for shoplifting was that there was so much excess
00:29:58
in you know our culture that it would never make a dent to steal organic
00:30:04
tampons from Fred Meyer which is like Target in Portland or whatever
00:30:09
so I uh when I did get caught and this was my favorite thing was just walking out with
00:30:16
stuff so I would get a whole shopping cart of stuff I had a little teeny tiny little
00:30:21
razor thingy so I knew where the sensors were and I would cut them off they were
00:30:27
there and pile a shopping cart high and just
00:30:33
walk out with no bags or anything I did it at grocery stores I I furnished
00:30:38
apartments I walked out of places with like literal rugs this High just walked
00:30:44
out because nobody expects you to be that like obvious about it they're
00:30:50
looking for somebody who's like putting stuff in their pockets and when I did get caught
00:30:57
I had like a George Foreman grill I think a basketball organic tampons some food really nice
00:31:05
shower curtain rings they were metal and then they had like ceramic they were heavy and they had like a ceramic thing
00:31:11
that said hot and then the other one said cold and I was like yes this is this is luxury
00:31:17
It's Worth jail time so that was yeah and you know I built an online business and
00:31:24
the first thing I sold online was stolen so another thing and I learned this from
00:31:30
people who were professionally trying to like avoid getting jobs and participating in
00:31:37
capitalistic culture which is a privilege it's lazy it's it was it was yeah I was really
00:31:44
young and I just didn't want to work you know it was some kind of quasi-political
00:31:50
lazy excuse for just not working hard anyway I learned from some of the best
00:31:58
um I had a friend who had written a book called evasion literally and
00:32:03
I would go into Barnes and Noble and they had a no chase policy like I
00:32:09
knew what the policies were at these places because if their employees Chase someone shoplifting it's gonna cost them
00:32:15
way much more if they get like knifed or something than it would for them to lose a few books
00:32:21
and so I would go on Amazon and I would look at the
00:32:26
best-selling books this is in 2002 2003 it's like and
00:32:33
even look at the ratio of most expensive book to least pages so I could stack
00:32:39
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
00:32:45
the best sellers and huge stacks and I would just like piled them hide I look like an employee
00:32:51
like who's carrying a huge stack of books I was right in the front of the store and I just like walked my car and
00:32:57
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
00:33:04
I'd pay my 350 a month rent why weren't you scared
00:33:10
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
00:33:16
the same thing if you're snowboarding and you're like oh it's kind of icy let me look down
00:33:22
you're just like catch an edge you're surfing and you look at the nose of the board
00:33:28
right so even that's what you're a life lesson I guess I guess we'll say I'm not proud
00:33:34
of this I was really young and I was finding my way I never
00:33:39
stole from individuals that was like not on thesis for me
00:33:45
no I couldn't justify it I would never feel comfortable doing it um but big box retailers I was like over
00:33:54
the last couple of how long maybe four months I've been changing my diet shall
00:33:59
I say many of you have really been paying attention to this podcast will know why I've sat here with some incredible Health experts and one of the
00:34:06
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
00:34:11
superfoods these green Foods these vegetables and then a company I love so
00:34:16
much and a company I'm an investor in and then a company that sponsors this podcast and I'm on the board of recently
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announced a new product which absolutely spoke to exactly where I was in my life and that is huel and they announced
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00:34:35
and plant-based ingredients which helps me meet that dietary requirement with the convenience that hewell always
00:34:41
offers unfortunately it's only currently available in the US but I hope I pray that it'll be with you guys in
00:34:48
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
00:34:55
ladies and gentlemen our newest brand partnership will come it's no surprise to regular listeners on this podcast the
00:35:00
first episode of 2023 I was joined by the incredible Professor Tim Spector to
00:35:06
hear more about his work at a company called Zoe using data to understand our bodies better so that we can live more
00:35:12
fulfilled higher potential lives Zoe was born from the truth that our overall health is impacted by our gut health by
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00:35:48
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 because
00:35:53
you're selling stolen stuff yeah yeah vintage mm-hmm
00:35:59
why why vintage why did you start to sell vintage clothes yeah so by 2000
00:36:06
six I had gotten some real jobs now after
00:36:12
after I'd worked in shoe stores and record stores and Photo Labs and Subway again
00:36:18
I like dry cleaners I how did you get on with those jobs
00:36:26
it didn't last very long I like job-free alphabetized things though so record stores
00:36:32
Photo Labs bookstores like paper makes me feel important for some reason
00:36:37
mailing things I don't know it worked out with my eBay store
00:36:42
and the last job I had was in the lobby of an art school in San Francisco at 79
00:36:48
new Montgomery Street called The Academy of Art University it was a job I got because I needed to get health insurance
00:36:54
and at the time you couldn't get health insurance with a pre-existing condition you is this your hernia yeah the Hearn
00:37:04
the Hearn yeah so a hernia if you don't know what it is is a place it's a hole
00:37:10
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 I
00:37:17
called an inguinal hernia and it didn't hurt but they're kind of dangerous because they can like if your
00:37:24
muscle tense is up or something they can get strangulated and necrotic which is a disgusting word
00:37:30
so I had to get it fixed but before I got it fixed it was kind of fun I shaved everything but the hernia
00:37:37
my poor boyfriend my poor boyfriend and um yeah it was entertaining it was kind
00:37:43
of funny to have like a small lump in my pants for a few weeks or something
00:37:49
but at the time you could not get health insurance with a pre-existing condition even with depression if you had medical
00:37:55
records that said you had depression and your insurance lapsed insurance companies would decline you now that's
00:38:01
not the case you can have a pre-existing condition apply for health insurance you'll be given health insurance you
00:38:07
could only get health insurance with a pre-existing condition like a hernia
00:38:14
with group health insurance with a job so I had to go
00:38:20
find a job that had health insurance and I got this job in the lobby of the
00:38:25
art school as a campus safety host which was a different way of saying you're cheaper than a unionized security guard
00:38:32
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
00:38:40
here that had my name and the school's logo on it and check students in and say
00:38:47
hi you need to sign in can I see your ID that was were you doing anything sort of criminal at this point my job no so all
00:38:53
of your money came from that job and yeah and so there was a three month
00:38:59
waiting period for health insurance and while I was there I had time to
00:39:05
I had some down time in this Lobby and there's a computer and uh there's no Facebook or Instagram
00:39:10
at the time this is 2006. and I was starting to get friend
00:39:17
requests from these eBay sellers on MySpace I wore only vintage I was like you know
00:39:23
root and toot and Scootin to like oldies and rock and roll and dive bars and
00:39:28
subsisting on burritos I loved vintage I wore vintage I wasn't necessarily into fashion and I didn't want to be in
00:39:36
fashion but I loved style and I loved vintage and I loved thrifting
00:39:41
and I saw what they were doing and their auction prices were crazy like I thought hate Street was expensive
00:39:49
because I had shopped at thrift stores and found great stuff and saw what their auctions were going
00:39:55
for and these were actual prices that the customer was determining they would start the auction price at
00:40:00
9.99 and these things were going for like 200 300 and they were just making
00:40:05
it look like something that Sienna Miller some boho at the time it was like
00:40:10
boho Olsen twins Sienna Miller kind of Vibes and they would do that put this
00:40:18
stuff online and the customer determined the price and it was so much money and
00:40:24
so I thought okay so I waited my three months for my health insurance because there was a three-month waiting period it got the Hearn fixed and I started an
00:40:32
eBay store and I wasn't trying to be an entrepreneur I was trying to legitimately not work for anybody and
00:40:40
that's when I realized that I could connect my curiosity and Independence
00:40:45
and creativity and resourcefulness
00:40:50
to something legitimate that made money that I learned from every step I was taking and
00:40:59
started nastygal selling vintage out of my boyfriend's apartment before that
00:41:04
point would people have called you lazy or unmotivated
00:41:09
I didn't know any people who would have said something like that because my friends were just like me so objectively
00:41:17
then objectively I think just lost I think it would be a
00:41:22
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
00:41:28
going to school and I was polite about it but I I've always had a challenge with authority every job I had throughout through that period of my
00:41:34
life lasted for three months I was just cool center hopping get to the bonus threshold quit gives me two months where
00:41:40
I don't have to get a job call up another course employed those people yeah I'm one of them and it's funny
00:41:46
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
00:41:51
well like my thesis is that everyone most people are lazy and you should be lazy for things that you absolutely hate
00:41:57
doing okay you should be so yeah I'm only motivated by things I'm curious about if someone assigns me something like I've
00:42:03
tried to write a second book and published two books after girl boss which was a thing
00:42:10
I can't I cannot be assigned something I it either comes out or it's not there
00:42:18
that's the do you think that's the the rebel in you that is but it's why everything I do is so inspired and honest and
00:42:25
I don't want to be like I'm unique but because you never accepted or learned compliance it's an actual representation
00:42:31
of who I am and what I think and how I feel and my perspective instead of a
00:42:37
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
00:42:44
the gift in a curse though right I mean it's pretty logical that you would question
00:42:50
a bell ringing and someone moving from one room the same room to the next room
00:42:56
every single day what do you think anyone else no no
00:43:03
but if you really think about it it's pretty wild right that that eBay store that you start with
00:43:09
in your free time when you're working that job you took to fix the Heron
00:43:15
um it was successful yeah and you know you kind of frame it
00:43:21
as you saw maybe a price Arbitrage or whatever but but it's more than that right it's more than that to be
00:43:27
successful at that time I'm not sure a lot of people saw that price Arbitrage and they didn't build a nasty girl so
00:43:32
when you reflect on why and how you were particularly successful how did
00:43:37
you diagnose that I reverse engineered everything everyone else did and did a better job and did it
00:43:44
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
00:43:51
Bell where no one else was do you think that kind of default to thinking in terms of first principles like asking
00:43:56
the question why why the [ __ ] do we do it that way has been part of the reason why that eBay store was successful
00:44:03
I think so I think most people that started an eBay store
00:44:08
are copying what other people are doing they might reverse engineer some things
00:44:14
and see what their competitors are doing and I did that but I just did it 10 times better with a totally different
00:44:20
spirit with excellent copywriting with great styling great models and
00:44:26
increasingly better photography and I would I was extremely resourceful I
00:44:33
would buy stuff on eBay and sell it for more than I paid for it I was searching for Eve's son Laurent just misspelled
00:44:40
you know the song but even that's the first principle
00:44:45
thinking that's like but you've got a convention on one end which says just like do what's being
00:44:50
done and then you've got these like first principle thinkers who kind of think first about what they know to be
00:44:55
true and they're really good at filtering out convention they can kind of see throughout the truth whereas
00:45:01
convention like is safety it's Comfort it's it guarantees you a pre-tried
00:45:06
blueprint so people follow that but then these other little Rebels they they have this almost inbuilt
00:45:11
ability to just like [ __ ] see through to the that that truth that nobody can see and in that case I mean that's a
00:45:17
great idea but even caring more about the copy and you having your own belief as to why the copy matted or the photography like why photography really
00:45:24
really mattered on eBay yeah on eBay which a lot of people would have had like that's um and it was called Nasty
00:45:30
Gal the spirit of it was really irreverent at the time the eBay sellers
00:45:36
were selling like you know is called Mama Stone vintage was a really big one and it was all very hippy dippy and
00:45:42
vintagey and mine was vintagey but it was like very hard-hitting edgy
00:45:48
I named it after an album by a woman named Betty Davis who had an album
00:45:53
called Nasty Gal she was so stylish uh in the 70s put out some
00:46:00
incredible records was married to Miles Davis for a short period and was allegedly too wild for him
00:46:08
her lyrics are just so and I was stripping her music when I was like 20 and then I was like cool nasty girl and
00:46:16
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
00:46:22
to Naval gaze or you might do things super conventionally but when
00:46:29
you need to survive there are certain things that other people have done right that you can see you know accelerate
00:46:36
what it is that you may do on your own but learn from them and then also take
00:46:43
and make your own way I think had I tried to do things completely differently than everybody else
00:46:49
I wouldn't I wouldn't have survived I would have been dead in the water speaking to something really interesting
00:46:56
there which is like this Balancing Act between naivety which is great for innovation and then convention which is
00:47:02
great for staying alive I'm talking about like the the nasty girl needing a
00:47:07
CFO yeah you see what I mean or like that's what how I feel when being a young founder 21 years old start this business
00:47:13
it grows incredibly quickly okay the naivety made us interesting but our naivety will also send us to the Grave
00:47:19
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
00:47:25
afterlife I it did send me to the Grave my naivete and lack of experience did send me to the Grave it happened so fast
00:47:33
that's a quote um it was shocking how fast it all happened nasty girl went from doing 150
00:47:40
000 a year to doing 150 000 a day and then 150 000 over lunch
00:47:46
yeah 150 000 over lunch it was either a day or over lunch that
00:47:52
we all worked out of this Warehouse it was a bunch of kids in the East Bay in Emeryville I had the 7 000 square
00:47:58
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
00:48:05
have been the holidays I was like I'm gonna get a bounce house you know those things that people jump on the
00:48:11
inflatable things the children that children jump on it was an upside down horse and its legs were in the air when
00:48:18
he jumped on it the legs like that's what you wanted and in between you know on our breaks we
00:48:23
got to jump in the bounce house I was like 23 24 years old it did happen really
00:48:30
quickly to be fair now you say it when we raised investment for the first time the first thing I bought was a 13 000
00:48:37
pound slide big blue slide which we had in our office that was the first thing I bought
00:48:42
before we got desks so talking about neither today I bought I paid off my mom's mortgage oh did you okay I
00:48:50
couldn't do that with investor Capital no it wasn't with investor Capital no it was the first time I made money yeah my
00:48:57
slide was with investor one okay yeah no no they actually those investors did really well they got bought out within six months so they got a big return but
00:49:03
good job yeah what do you attribute at such a young age I'm just gonna interview you for a second because you
00:49:10
couldn't have had a ton of experience under leaders to give you a model of what leadership looked like you were
00:49:16
naive you know could you I couldn't empathize with the people I was managing because I
00:49:22
had never experienced leadership and I just showed up and I did what I I what needed to happen and what I said I was
00:49:28
going to do I didn't understand that people needed to be held accountable because I held myself accountable especially c-level Executives and
00:49:34
grown-ups whose careers were longer than I had been alive like how did you do
00:49:40
that at such a young age well I think I I think I messed up I think like for the first two years I hired people that were
00:49:45
very very inexperienced I reflect and I go I think I did that because I thought they were easier to manage and I
00:49:51
couldn't fathom the concept that I could hire someone who was two times my age
00:49:56
and three times my experience and Avid want to come here and be with us with that with our sliding dogs and tree and
00:50:01
basketball court and ball pool and they would like take us seriously but also like be like maybe there was an
00:50:07
insecurity about how I'd manage them and so what ends up happening is you I hired lots of like young people
00:50:12
you know a member of the BBC did an article saying is this the youngest company in Britain because I think we were like somewhere but our average age
00:50:18
was maybe 20 or something and we had like we had like 100 almost 100 people you know and you feel the strain of that
00:50:25
you feel things breaking this is where you go convention is right about some things
00:50:30
processes HR Finance you feel things breaking at the seams a little bit because of the growth um and then at
00:50:36
some point an adult enters the room and you go oh I get this and so we hired some some
00:50:44
really really great people and the great thing is great people hire great people so we went from being this kind of very
00:50:49
lopsided inexperienced organization to being a balanced one and I say balance because it's my belief that to own the
00:50:54
future you have to understand the present which is why you want to hire a 16 year old that gets Tick Tock or whatever and you also need to hire
00:51:01
someone that's maybe double their age experienced in client services and understands the old rules
00:51:08
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 when I
00:51:14
nearly went under several times and had to call people and beg for money um in the lead up to Payday but
00:51:20
somehow managed to survive but go back to you now um I feel that we missed a park because
00:51:27
you know you write the reception you went from starting that store to bouncing around on that bouncy castle
00:51:32
thing we call it bouncy castle okay horse Castle between that between that
00:51:39
bouncing on that horse castle and the starting the store what happened
00:51:45
so first year just on eBay did 75 000 in Revenue I was
00:51:52
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
00:51:58
expensive things I would have wanted I didn't I had never eaten an oyster you know I was drinking like
00:52:04
Budweiser or you could still like subsisting on Boston Market and like
00:52:09
Starbucks so I didn't spend any of that money I thought building a business and I think
00:52:15
for the most part it is uh was selling things for more than you bought
00:52:21
them for and not spending all the money that's it that's all and so I bought things I sold
00:52:28
them for more than I paid for them and no one else would have given me money parents weren't gonna give me money
00:52:33
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
00:52:41
and had I not built the company to eventually you know 28 million dollar run rate super profitably I would never
00:52:49
have known and so yeah year two left eBay about
00:52:54
halfway through and launched my own website nastygalvintage.com and did 250 000 in Revenue
00:53:02
the next year did 1.1 million the next year did six and a half
00:53:07
the next year did 12 and I was coming off a 12 million dollar a year uh
00:53:13
Revenue owned 100 of the company had a bunch of kids working for me
00:53:20
and that's when Venture capitalists came in and at that point you know
00:53:25
we were selling non-vintage stuff what really allowed the company to scale was going to trade shows and showrooms and
00:53:31
curating from the market based on what I had learned from my customer having sold vintage to them so I knew them very very
00:53:38
well and that gave me the ability to then go by greater breadth and depth in
00:53:45
things I knew they would love and that's what 2011-12
00:53:51
Venture Capital comes in 2012 was when index Ventures invested 60 million dollars 60 million dollars on a 350
00:53:59
million dollar valuation on a business with a 28 million run rate yeah you're profitable at that time
00:54:06
significantly pretty significantly I have a 10 or 20 nothing I don't know I don't know I
00:54:12
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
00:54:18
you know generally knew how much it cost to run I didn't it and I and I didn't I
00:54:24
didn't buy expensive office chairs did you did you know you like gross margins on on your on the product yeah on the
00:54:30
operating margins no I don't I don't think I didn't understand what operating margin was
00:54:36
um pretty incredible that you can be running a business that's generating has a 28 million dollar a year run rate and not know what operating margins you're
00:54:43
dealing with or what your net profit is it's a luxury but it was also a disadvantage once we plowed 60 million
00:54:50
dollars into the business and things got a lot more complex and a lot less profitable
00:54:56
you talk about the 60 million going into nastygon in 2020 to 2012.
00:55:02
what did it break hmm I mean we no longer had to live within our means
00:55:10
that's what investor money does unless you maintain profitability and keep that money in the bank for you know another
00:55:17
time or pocket all of it as a founder we you know I had hired a COO at that
00:55:25
time I had a top tier investor on my board
00:55:30
and very little like historicals data
00:55:36
financials to base the future growth on but it had
00:55:42
been exploding just continue to be exploding and with that Capital behind us we could grow even faster
00:55:48
and the expectation was that the next year we would grow from 28 million in
00:55:55
Revenue to 128 million dollars in Revenue we just rounded up by 100 million and then we hired into that and
00:56:03
we bought into it oh you believed it and everyone I had grown-ups forecasting this stuff with me
00:56:09
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
00:56:16
sure what happened but I remember sitting in a room with them and
00:56:21
us deciding I didn't push for it this wasn't you know we're gonna just grow by 100 million
00:56:28
dollars this year and someone put a plan together and this is we hired 100 people it was like the
00:56:33
Tower of Babel you know that story you don't know it's like a biblical story where
00:56:39
uh people are building this Tower or something but they all speak different languages and I I could be completely
00:56:47
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
00:56:54
a mess trying to integrate 100 people into a company in a year especially a company with no processes
00:57:01
and no real intentional culture that had been established
00:57:06
no real intentional anything other than the brand
00:57:12
the spirit of the brand what needed to be done it was it was like a family business that just got
00:57:18
really big it was I was a kid
00:57:23
how are you feeling in terms of at this point in terms of what's going on around you 60 million dollars has just come
00:57:30
into the bank account you're looking at me thinking that's a big [ __ ] number you're you know because you have a
00:57:35
valuation of 350 yeah I'm worth 280 million dollars on paper at this point so that and wherever
00:57:42
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
00:57:47
realism yeah it's in your bank account how does that make you feel when you you know then they put you in the front
00:57:53
cover of Forbes yeah how does that make you feel it was a blast
00:58:00
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
00:58:05
lot of fun it distracted me you know the book in 2014 turned into a
00:58:11
phenomenon you know it was champagne clinks for some Milestone with a company or new
00:58:18
hire promotion any given time I people would come up to me and say
00:58:26
congratulations and I had to ask which thing they were congratulating me for
00:58:32
it was it was just like oysters for everybody finally you know I I got better taste in
00:58:40
wine I got better taste period thank God but now I spend less money with a good
00:58:46
taste that I had to spend a lot of money to acquire a lot of my own
00:58:51
but did you feel did you feel like it made sense
00:58:56
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 it is
00:59:02
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
00:59:09
bootstrapped a business to 28 million dollars in Revenue super profitably
00:59:14
you know investors came out of the woodwork you know top tier ones anointed me as
00:59:21
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
00:59:29
it it was considered a rags to riches story and imposter syndrome
00:59:36
any of that for sure yeah I mean I still walk in rooms and I'm here I was
00:59:43
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
00:59:50
I'm intimidated I hope I can provide some value what are the comments on YouTube gonna say is this going to be a
00:59:57
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
01:00:04
what what are you talking about you're great but I get nervous right
01:00:10
um I get nervous on stages and I'm still like you know I don't I
01:00:16
don't belong here but I don't belong here is also a really great motivator the I don't belong here is I snuck in
01:00:23
the back door I don't belong here means I can do things differently I don't
01:00:29
belong here means I don't fit in but that's going to be a superpower and
01:00:34
I think it's okay to feel like an outsider or an imposter sometimes because you
01:00:42
find yourself in places where you learn you have an outside perspective and are able to learn things
01:00:51
unlike the people who are invited to the table who all showed up there with the same pedigree
01:00:56
and then you get to make oblique connections
01:01:03
between who you are where you came from and then the door the room that you just snuck into as an imposter and that is
01:01:11
radical would you remove that self-doubting voice if I put a button in front of you
01:01:17
and said you press this you'll never doubt yourself again no that's so boring I had a coach recently
01:01:23
and he was lovely waited five sessions it was like five thousand dollars a month and I was like
01:01:29
taxes I'll buy something else to save on taxes and
01:01:36
he was like can you imagine he asked me that word or he asked me that question and I was like
01:01:41
but what would I struggle with what who would I be if I didn't have challenges
01:01:49
and I was happy all the time it's like the scaffolding would fall apart or something
01:01:55
that's a story I tell myself but it's fun to have a
01:02:03
dark Counterpoint to hold yourself accountable and be like maybe it is that or not that
01:02:10
and I think that Counterpoint is an opportunity to gain self-awareness
01:02:16
do you think it's additive to your performance or reductive I think it can slow me down and I can
01:02:21
make really slow decisions because I doubt myself
01:02:27
but beyond that I think I've found a way to harness it
01:02:33
that really works for me have you developed like a decision making framework to help you navigate
01:02:40
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
01:02:45
would seem to be very supportive your dad somewhat critical at times or pessimistic
01:02:51
um have you found a way of being able to juggle those voices um
01:02:56
so that you can make decisions decisively and quickly no no no
01:03:03
so I can I can have these conversations and when I you know when I do make a
01:03:08
decision I've learned to be slower with making decisions because I either make them extremely quickly or
01:03:15
slowly on accident and so I want to be very deliberate in the decisions that I make now and think more critically
01:03:22
rather than you know Naval gaze or be reactive to something I went to this
01:03:30
uh Retreat even though it's not really a luxury experience with 30 other people called the Hoffman process
01:03:36
and it's seven days with no phone no Internet no books no music you're with
01:03:42
30 other people and you're going through this process of mapping your patterns from your childhood against your parents
01:03:49
and how how you inherited that and it's all directly correlated and basically
01:03:55
graduating from your your emotional child into an emotional adult
01:04:03
super embarrassing weird process like so dorky and everybody came with something
01:04:08
different to work on or what emerged for them you know I I feel unloved I feel
01:04:13
unlovable I don't feel unlovable my thing and it sounds really weak was
01:04:19
like I don't trust myself I don't think I'm deceiving myself but I
01:04:24
think I can rationalize a lot of things to the point where I'll tolerate them too long
01:04:32
um and that's gone for relationships that went from my most recent relationship
01:04:37
um and so that's a strange thing I don't trust myself because I do have these
01:04:44
voices it sounds I don't have voices in my head but I can see things from any
01:04:51
perspective and not be totally attached to either one to the point of
01:04:58
being slow and asking for too much advice
01:05:03
in that Retreat did you did you have to sort of like go upstream and figure out where that belief started is that the
01:05:10
point of that Retreat did you figure it out did you go Upstream what a good question you're very good at this oh thank you
01:05:16
yeah I think it was that my parents didn't agree on how to raise me that I felt
01:05:22
misunderstood that my good intentions were sometimes construed as troublemaking that the fact that I
01:05:30
didn't fit into the environment I was raised in I was I was not accepted and I was some
01:05:38
kind of weird deviant when I was just being myself and felt punished for being myself and I think that
01:05:45
gave me like a lack of confidence or something and I don't identify with being an unconfident person but when it
01:05:51
comes to decision making when everyone around you is telling you something a different story about yourself than you
01:05:59
have and doesn't understand why you operate the way you do that is really with
01:06:06
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
01:06:13
different world and don't understand that those are your needs you just feel
01:06:19
wildly alone and think wow I am a freak and that
01:06:25
found its way into my career through the public too which has been super fun
01:06:30
being told I'm something that I'm mostly not
01:06:38
what have you been told you are oh gosh um
01:06:44
so nasty y'all fell apart after 10 years it was it was a quick rise and it was it
01:06:50
was it was a it was a slow rise and it was a relatively quick fall couple of
01:06:56
years in the making and when it did fall the headlines were
01:07:02
crazy because I had all this press from this book I published and being the poster child of Entrepreneurship going
01:07:09
on the victory lab National Enquirer said had you know picture of me and it said Rags to Riches like straight up
01:07:16
tabloid American Dream stuff like a caricature
01:07:21
and I didn't realize the amount of responsibility I had to like other people as an example like I kind of did
01:07:27
but as some symbol for entrepreneurship for my generation you know generation of
01:07:33
the entrepreneurs coming up behind me or at least what the Press thought I was responsible
01:07:39
for the you know there were headlines like does the failure of nasty yell mean
01:07:46
Millennials aren't ready to lead it's like wait how is one example
01:07:51
representative of a generation
01:07:56
and I've also read headlines like when the Netflix series came out
01:08:01
the worst thing about Netflix's girl boss is its source material
01:08:07
not even the show just me
01:08:15
but I'm not bad I don't believe I don't believe it
01:08:20
how does that make you feel at the time though by the time that Netflix series came out
01:08:27
I had been this hero as an entrepreneur then I was this girl boss because I
01:08:32
wrote a book called girl boss and it was pink and I was like this and I looked like I
01:08:38
knew it was up but it was like 27 and then there was the me whose company fell
01:08:43
apart the CEO there was the girl boss who had built a toxic culture
01:08:49
or just no intentional culture at our all that like warped into something that wasn't perfect but wasn't I still don't
01:08:56
think it was the worst and now this person this conflation of all
01:09:02
of those things with this girl on the scripted comedy
01:09:07
which came out four months after I left Nasty Gal so the biggest kind of
01:09:12
personality or whatever identity crisis was you know I'm on the cover of Forbes in
01:09:20
June I think of 2016 July of 2016 my husband of like a Year's like man I
01:09:26
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
01:09:32
party so in that space of like 12 months you're on Forbes husband leaves Netflix
01:09:38
comes out nasty girl goes under nasty girl goes under then Netflix comes out
01:09:44
so the show had been shot when things are all like up and to the right and you
01:09:49
know we were working through challenges there had been some layoffs but the company was still you know 100 million dollars a year
01:09:55
you know not profitable anymore but a great brand and something that was valuable and
01:10:04
eventually um yeah like fell apart and that the con
01:10:11
there was really a conflation of the the hero the failure and now this girl four
01:10:17
months later who's a a caricature of a person I was when I was 22 in a scripted comedy
01:10:25
playing someone named Sophia starting an eBay store called Nasty Gal when for the first time
01:10:31
in 10 years in my adult life since I was 22 years old I am no longer associated
01:10:37
with the thing that I had built and now there are 130 million homes in 195
01:10:44
countries watching a story of someone that I was no longer and no longer had trying
01:10:54
to move on and to move on when there's a full PR campaign about who you used to be
01:11:02
you're someone who's as you said you've had a long history with mental health challenges
01:11:07
what is it like in like in that 12-month period what's going on from a mental health perspective
01:11:13
I had fallen in love again I think it was still like traveling I started another company
01:11:19
I maintain my mental health partially because I keep going you know I don't stop and like lick my
01:11:28
wounds I think I was also I was also on antidepressants I wasn't
01:11:33
jumping for joy but I also knew that there was a huge community that still
01:11:40
supported me who had read my book 500 000 women who bought it and I went on to start a company called
01:11:48
girl boss right as the Netflix series was hitting put on our first conference
01:11:54
and I had my podcast and I moved on quickly and even though the headlines
01:12:00
weren't nice the people who followed me my friends my
01:12:06
relationships everybody in my network nobody bailed like the girls who were inspired by girl
01:12:12
boss were refreshed that I had face planted publicly because everyone else
01:12:18
is face planting in private and in the same way that watching some
01:12:24
random Community College Dropout from Sacramento start a business with an internet connection
01:12:30
and a computer gave them license to you know yes they were inspired but
01:12:36
also Embrace their own failures because the hero
01:12:42
face planted publicly
01:12:49
and that can also inspire people
01:12:54
this is hopefully the most cliche question I ask but um I wanna I wanna know because you have
01:13:00
a from your from that experience you have amazing feedback you have amazing Insight invaluable Insight I would say
01:13:07
because when I think about the things obviously they've taught me the most it's not it's not when things go right that's a validation of your hypothesis
01:13:13
it's when things go tragically wrong and you go oh okay [ __ ] you have all of this new information about which is corrected
01:13:19
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
01:13:26
raise the company raise investment at 350 million and think amazing that's when people clap right
01:13:32
they get the champagne out oysters for people listening that aren't in business they might not understand how
01:13:38
that can also be a key reason why the company ultimately went under the 350 million why why did our big
01:13:45
valuation hurt yeah yeah I think the 350 million dollar evaluation is celebrated as it was and
01:13:52
how wealthy I was on paper um was the was the nail in the coffin I
01:13:57
think it was it was then in 2012 where we were overvalued and the expectations
01:14:03
that was was that the next round of fundraising that we do is at a over a
01:14:11
billion dollar valuation and so the company's doing you know on an upswing 228 million
01:14:17
dollars in Revenue that's like over 10 times revenue and it's a fashion
01:14:22
business this isn't a technology business this isn't Uber this isn't an infinitely scalable Marketplace it's
01:14:29
e-commerce it was a different era of e-commerce it was pretty early it was the era of fab.com which like imploded
01:14:36
and won King's Lane in beechment in ShoeDazzle there was no Playbook there
01:14:41
were no Ecom veterans or you know Performance Marketing people
01:14:47
who had been in those jobs for even very long I was hiring Executives who had worked at like Macy's right
01:14:54
um nobody had like econ it wasn't called direct to Consumer at the time it was very very different there's no Shopify
01:15:01
and we were overvalued and I didn't know that I didn't even negotiate you know
01:15:07
hardly negotiate I didn't shop a term sheet around and say I'm gonna pick the highest price from different investors I
01:15:14
only had one term sheet and I was like great I like you index finishes I was like you're awesome you can I you get it
01:15:22
you know what Danny said when he invested uh was something none of the other potential investors said and that was
01:15:29
you have a community and I was like yeah we do have a community but when you have that much money
01:15:37
you don't know there's been a nail in the coffin or that there's a coffin and
01:15:42
that like you might be on your way into it or maybe already laying in it but
01:15:48
just several years in the future and
01:15:54
when things are up and to the right you don't see what's lurking kind of
01:16:00
below the surface so when the tide lowers right you see the mud you see weird crab
01:16:06
shells sometimes hopefully not you see trash and it's only when things recede that
01:16:14
you see the mud that's underneath and when you're on a Victory lap and you're hitting milestones
01:16:19
everything's great and everybody loves their jobs and you're a hero and as soon as things
01:16:25
Go a different way as soon as there's layoffs yeah there are things kind of
01:16:30
there are things there are things lurking below the surface that were dynamics that were already happening
01:16:38
that because everything was going so well you know we're harder to notice and
01:16:46
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
01:16:53
realize is that you only know 10 of what's happening in your organization right hundreds of employees and
01:17:00
ultimately everything was my responsibility but I am held accountable for 100 of
01:17:05
what's Happening and when something goes wrong or something's mismanaged or someone has a bad experience in the company the
01:17:12
assumption is that I have signed off on it that that is how I want things to be
01:17:18
and these things are happening you know cattiness and you know fiefdoms and silos and
01:17:26
duplications of effort and all the you know the entire spectrum of things that are no fun at a
01:17:34
fast-growing company I didn't know were happening until we laid people off and then they were like
01:17:40
hey we didn't like it there I'm like okay and some of that was totally overblown
01:17:48
but also anything that any employees ever said about me or I've read
01:17:54
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
01:18:00
because there's truth to almost everything didn't you get an offer to sell the company completely for 400
01:18:06
million dollars yeah I did I owned 80 of it so that would have made you you know quick maths I don't know
01:18:13
very [ __ ] Rich super [ __ ] rich and why why didn't you say yes
01:18:20
I went to my investor and I said what do you think about this
01:18:26
and he said you need to ask for more I controlled the board I owned you know I own the
01:18:33
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
01:18:40
interests weren't necessarily aligned with the interests of my investor whose interest is to
01:18:46
whether I'm worth it or not have a piece of paper to show his investors that says I'm worth instead of
01:18:52
350 look they're now worth a billion and they just make up these numbers and then
01:18:57
they can show their people that your company's worth more and that was his that was in his best interest and that's
01:19:04
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
01:19:11
different decision is that a regret
01:19:16
it's a it's a partial regret but I also know that no deal actually happens they're not a
01:19:22
a real acquisitive company they could have tried to acquire the company I don't even know if they've acquired
01:19:27
anything integrating it into their company if I had an earn out based on them you know controlling it and me
01:19:34
trying to hit performance benchmarks even if I had sold the company to them who knows how it would have played out I
01:19:40
would have made a bunch of money my life could have been miserable but 99 of the time deals fall through there's also in
01:19:47
those situations a lot of people trying to get into the data room so they make an offer so they can see your numbers
01:19:53
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 yeah and then copy yeah
01:19:59
exactly yeah so we didn't get that far I don't regret it
01:20:05
um but yeah that was a big thing you know for me that would have been a lot of
01:20:10
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 them it's not much
01:20:17
of a markup for him what is the advice you're giving now to to women that are and men that are
01:20:24
looking to start companies that are within your community the communities You're Building within your portfolio companies now that you're an investor
01:20:31
um 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
01:20:37
wondering what your like first piece of advice is I think for bootstrap Founders the advice would be different for Founders
01:20:44
in my portfolio companies who are raising Venture Capital my advice would be get as far as you can before raising a
01:20:51
single dollar validate your idea as soon as you can with the ugliest
01:20:56
like most basic quickest thing or first product should be super ugly get it in
01:21:01
front of people and get some idea of whether it's valuable or not before you go raise money before you even try to
01:21:08
Market it talk to you every customer every potential customer
01:21:14
and bootstrap it as long as you can if you can because when investors do come
01:21:20
in your company is going to be worth more than if you would raise money when you just had an idea and were asking for
01:21:27
a check when you do raise money having a reasonable valuation is
01:21:34
important and a lot of Founders optimize for price because bigger price an investor pays the more
01:21:41
ownership the founder has the more they're worth right the more they're worth and the more eventually they could
01:21:47
make if they sell the company but when you have a valuation that's in
01:21:53
line with Market that makes you an attractive acquisition something someone
01:21:58
might pay a multiple for that 10 percent say you're diluted down to 10 or 20
01:22:03
percent but you sell your company for 500 million dollars you're in much
01:22:09
better shape than raising 350 and owning 80 percent of it and going to zero or
01:22:14
whatever so and I think where things are right now with Venture is
01:22:20
a place that is is close to that and Founders aren't greedy Founders who are
01:22:26
raising money in this market no it's really really hard they don't want to be overpriced because the people who raise
01:22:32
money over the last few years raised at such a high valuation these founders
01:22:38
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
01:22:44
million in Revenue but they're someone told them they were worth 80 million dollars and now nobody's going to give
01:22:50
the money I've as an angel investor I have three of these right now and it's like
01:22:57
Hail Mary's two of them have figured out how to survive ones like we have another term sheet I mean I've been there
01:23:04
what about the psychological advice you'd give to her um
01:23:09
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
01:23:15
who know more than you and have experience and you should listen to them but you should also
01:23:24
always maintain and continue to cultivate a voice that
01:23:30
when you know it should is able to supersede any advice that anybody gives
01:23:36
you um I think it's easy to take all the advice because you're an inexperienced
01:23:42
founder and um and into lose touch with your intuition
01:23:50
and it's probably what got you to where you are as a Founder without the money and without the experts
01:23:57
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
01:24:03
first place which day was your hardest day over the last
01:24:10
since you were since you first started that store on eBay is there a day you look back and go do you know what that
01:24:15
period or that day was just the worst the hardest the darkest
01:24:24
see and it's weird the hardest day was when my husband laughed and I don't miss him and I don't wish we
01:24:29
were still together I don't really think about him I mean that was in 2016.
01:24:37
but I had agreed to take a big swing in
01:24:42
my personal life and make a huge commitment and I thought that bumps in the road were like to be celebrated I
01:24:49
thought it was like wow okay you're not feeling great about things we're gonna work through this and we're going to be
01:24:54
so much better as a result of it because I see commitments as things that go up and
01:24:59
down and if you're in a commitment together you're committed to working through those things and it all comes
01:25:05
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
01:25:12
I I felt like I was like hallucinating you know I like went to a hotel for a
01:25:18
week I couldn't be in the house it felt like a crime scene with his stuff around
01:25:23
and um yeah three a whole whole week at the Beverly Hills Hotel with three
01:25:28
poodles is quite the scene with them yeah chain smoking in the courtyard and a bathrobe
01:25:36
has that experience put you off being a CEO of a big company I mean ever yeah everything I've experienced has put me
01:25:42
up from 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
01:25:49
stage founder I'm a master at creating brands that cut through the noise what
01:25:56
happens though if one you know you're running a number of businesses now um you've got your fund
01:26:05
yep business class business class but what what happens say business class what happens if it becomes
01:26:11
globally you know globally successful then you're back to being a big CEO again
01:26:18
though are you step out I would have to work really hard to make it that and I would have to invest in that and hire
01:26:23
into it that wouldn't happen by mistake I have one employee on business class
01:26:29
business class is super profitable I launch it twice a year it's pre-recorded
01:26:34
so business class is my entrepreneurship program but I have two courts a year I'm uh April I'm launching it and I launch
01:26:42
in the fall and it's an incredible product but it's also something that is
01:26:49
relatively self-led for the students it's eight hours of video and 300 pages of worksheets and over 60 hours of
01:26:55
interviews with me like this with entrepreneurs and you know students get lifetime
01:27:01
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
01:27:07
few years but it's not something that requires a ton of my time outside promoting it
01:27:12
twice a year and I built it for that I built it for that I'm using kajabi and
01:27:19
drip for email and you know whatever zapier and a variety of tools that allow
01:27:27
it to be relatively low lift light on human capital still a lot of effort to
01:27:33
promote and something I do engage with throughout the year and two weekly calls
01:27:39
with students and post in the lounge which is our community keeping it that's it no yeah I'm playing I'm I'm
01:27:46
I'm not playing small with business class I'm playing to my strengths that's
01:27:52
big and with trust fund it's Venture fun that I'm raising right now it's a 10 million dollar fund what I get to do is
01:28:00
not run a big company and you can keep trying to apply this stuff that I've learned over you know
01:28:06
over time I get to go from zero to one over and over and over again with early
01:28:12
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
01:28:18
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
01:28:25
say here's what I think you should do I can be helpful and it's so rewarding to
01:28:30
harvest all of my hardship on behalf of a new generation of Founders and help
01:28:36
them see around the corners that I wish someone had shown me around
01:28:41
and I get to keep my firms small even if I have a 50 million dollar fund I can do
01:28:47
that with a few people um and I'm using the assets that I have I'm the product my relationships and my
01:28:54
network and my access to dealflow is my product my expertise and ability to help
01:29:00
Founders is my product million social followers and being able to amplify them is my product the engaged Community I
01:29:08
have who's interested in the kinds of things I'm investing in will actually use them is my product and I don't
01:29:15
I'm just it's right here and it's an air table the intentionality is what I find
01:29:20
most surprising um inspiring because so many people get dragged by the Temptation of like external expectation
01:29:26
if it's great business class is great but all accounts have been on the website went on to so I saw that the
01:29:32
waiting list is open for 2023 it said like join the waiting list for 2023 yeah so it's launching in April okay the the
01:29:40
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
01:29:45
great we get dragged by our own success what you're saying is you're going to be
01:29:51
intentional and you've designed it so that that's impossible so that you can't get Drax because someone's going to come along and say we
01:29:57
love this we're going to give you a check we love this we'll turn it into some boxer shorts with some teddy bears yeah no
01:30:03
no I I have had the Pearl Village of knowing
01:30:08
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
01:30:15
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
01:30:21
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
01:30:27
trust fund is super successful which I can stay Nimble with and with business
01:30:33
class I've engineered that Revenue was down last year to the year prior and that's so that's okay it's still
01:30:40
profitable I'm not gonna hire a bunch of people or CEO or plow a ton of money into it trying to solve problems and
01:30:47
pivot things so if I come along I say I'm going to invest 10 millions of here we're going to hire a CEO okay but you
01:30:54
take the money yeah take the money just for the record guys
01:30:59
when it's there take Real Money Take Take the Money
01:31:06
magical thinking what is that yeah I mean you can call it magical thinking
01:31:13
you can call it magical thinking you can call it manifestation you can call it prayer you can call it whatever you want
01:31:19
I think it's you know casting the line out not
01:31:25
knowing what you're going to catch trusting you're going to catch it and we'll pull it back magical thinking is like Indiana Jones where there's the
01:31:34
vast where's this there's the vast Chasm between whatever and the Holy Grail and
01:31:40
he has to trust that there is a an invisible bridge and he grabbed some gravel and he throws it out across this
01:31:47
literal kind of Canyon and the gravel just falls on a clear bridge
01:31:56
and he had to like trust that when he walked across that he wouldn't fall and
01:32:02
so I see magical thinking as you know Thinking Beyond what might be obvious
01:32:10
thinking you're capable of doing things that you shouldn't be thinking you can
01:32:15
belong in places that you never thought you could thinking you can accomplish things that
01:32:22
you're completely unqualified to because nobody's qualified to being able to see yourself in a life
01:32:28
in a world that's beyond your wildest imagination and just staying there
01:32:37
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
01:32:43
hardest question in the world I really wish you'd been given a real stitch up one um but yours is yours is fairly
01:32:48
straightforward question which is what is your proudest moment hmm
01:32:54
my proudest moment is paying off my mom's mom's marriage I mean that I can do that
01:33:00
that was crazy that was the first thing I did what about this then what's going to be your proudest moment
01:33:09
hmm it requires a little bit of magical thinking
01:33:14
understanding what is Meaningful in my life and actually spending time on it you haven't figured
01:33:20
that out no there are meaningful things but what is the people have kids and that's like
01:33:26
obvious and I don't know if I'm gonna do that I am super agnostic about it it's really
01:33:31
strange I'll be 39 in a month um but I think like finding that and
01:33:37
hanging on to it what is that what is is there some big meaningful thing that I'm
01:33:43
gonna find and cling to till I die you know and it's easy when it's family or easy when it's a kid
01:33:49
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
01:33:58
will it all add up to I don't know Sophia thank you so much for your time and thank you for the inspiration you've
01:34:03
been an inspiration for me for 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
01:34:09
respects but um yeah you're built for podcasting but also because of your um inclination to be on open and honest and
01:34:15
vulnerable um you're incredibly inspiring in the stories you tell in the way that you tell them so thank you so much it's a
01:34:21
real honor to meet you and I'm I'm equally privileged that you said yes to come and do this because oh my gosh and I mean that I'm not I'm not just like
01:34:27
gassing you up or anything I mean no no thank you you're super happy I can't wait to see what you do with both trust
01:34:33
fund and business class because um they look like exceptional projects I've looked into the reviews of business
01:34:39
class and with your fund with the amount of information you've learned from your twisting turning professional career you
01:34:45
clearly have a huge um amount of intellectual leverage and Firepower that
01:34:51
makes for a great fund um founder so I look forward to seeing what you do that thank you thanks
01:34:59
as you might know if the show's now sponsored by Airbnb absolutely love Airbnb always have always been a you
01:35:04
know saved my life on so many occasions and my team when we first got in touch with Airbnb were talking about how most people don't realize that their place
01:35:11
where they currently live could become an Airbnb and I guess the second question there is how much could your
01:35:17
place be worth and it turns out you could be sitting on an Airbnb gold mine without even knowing it some people
01:35:23
Airbnb their entire homes when they're away that's what I did in New York whenever I left New York my place was on
01:35:28
Airbnb and people rented it out sometimes for a day sometimes for two days sometimes for a week and it's a great way to cover some of the bills
01:35:34
while you're away so whether you're looking to go on holiday or you just want some extra cash for bills or you want to buy something nice for a
01:35:40
valentine that you love whatever it might be head over to airbnb.com UK host
01:35:45
and you can find out how much your current property where you live can earn while you're not there I suspect it
01:35:52
might blow your mind because it certainly blew mine [Music]
01:35:58
oh [Music]
01:36:17
foreign