Video URL: https://www.youtube.com/watch?v=V7AYmOBahsU
didn't you get an offer to sell the company for 400 million dollars yeah I did what it made you super rich why didn't you say yes you're very good at this Sophia also founder of Nasty Gal A best-selling author and a Powerhouse in the entrepreneurial world I was rebellious from a very early age I was a stripper I wasn't even 21 I used someone else's ID to work there built an online business the first thing I sold online was stolen get a whole shopping cart of stuff put them on Amazon for 10 cents less than the other resellers and then gotten arrested for shoplifting I'm a little dark I realized I could connect my creativity to something legitimate started Nasty Gal selling vintage namastico went from 150 000 a year to doing 150 000 over lunch I didn't realize the amount of responsibility I had being the poster child of Entrepreneurship then I was this girl boss but my naivete and lack of experience did send me to the grade nasty y'all fell apart after 10 years my husband of like a year left the headlines weren't nice 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 out of bed it's challenged my confidence and I'm still like I don't belong here but I don't belong here is also a really great motivator I don't belong here means I don't fit in but that's going to be a superpower I can do things differently what was the plan in life at that point gosh before this episode starts I have a small favor to ask from you two months ago 74 of people that watch this channel didn't subscribe we're now down to 69 my goal is 50 so if you've ever liked any 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 bigger the channel gets as you've seen the bigger the guests get thank you and enjoy this episode [Music] take me back to those suburbs in San Diego and give me your earliest context wow I was born in San Diego Sharp Memorial Hospital only child eternally and only child I think wound up having the personality
of a probably seven children and the challenge of maybe seven children for my parents um we moved a few times you know our house was like it was it was happy-ish when I was young I lived in San Diego till I was seven and it's a beautiful place and I so wish we would have stayed there but we moved to beautiful Sacramento California and that was really the Suburban experience where you know when you're a kid a little kid you don't know what a suburb is and chasing the ice cream man is great but once you get older living in the suburbs if you have any amount of curiosity about the world the homogeneous you know nature of living in the suburbs is something that totally crushed me I knew there was more out there and I didn't know what it was but I wanted I like wanted out from a very early age what what did you what did you want at a very early age when you say you wanted out oh yeah what did you want yeah I wanted out of my family home it wasn't happy my parents didn't get along I was playing referee you know really yeah what what age starting at like 10 or something I mean yeah it was just it wasn't a super happy place and they yeah they didn't get along they didn't always agree on how to raise me and I think when your parents you know everybody's relationship has issues and everybody's not everybody's but most people's parents you know sometimes don't get along when you have a sibling I think you can go be like um that's funny or they're whatever let's just go play with Legos or something like that or let's go ride bikes but I think being isolated in a house that wasn't super happy as an only child made it worse and I just remember so many drives silent car drives where I was in the back seat alone and I just remember like the silence and the the light of the street lights like washing over the car just in in Silence with my parents in the two front seat um yeah they're really like only affectionate after like an argument and even then it was like I don't know hand-holding or something they were very strict as well
I had to beg to go to a boy's birthday party in sixth grade we weren't super religious but my mom grew up in the 50s in a Greek Orthodox household um just not puritanical because that sounds less cultural than Greek Orthodoxy but uh strict you know what about money yeah arguments happened in my household when I was younger because of money yeah I mean my dad sold my dad did loans and my mom sold houses but track homes in the suburbs and they were both working with Builders and Banks and manufactured homes and so on the weekends by the time I was I don't know maybe 10 my mom was working in the model homes that are all kind of dressed up and you can tour them and pick your manufactured home and change a couple things and there's like a fake keyboard in there just all kinds of funny things to play with and then so I was with my dad on weekends and my and they both worked entirely commission so I've never seen either of my parents work for a salary and my mom's dad didn't work 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 family who wouldn't necessarily call themselves entrepreneurs but they're people who ate what they killed and that's what I witnessed money was good I think when I was like you know when we were in San Diego and I think it got tougher over time I remember very vividly being in a credit counselor's office I just can't believe they brought me but there was no I don't know where they would have put me watching them cut up their credit cards like cut their credit cards in half and put them in a clear jar with like other people's cut up credit cards and file for chapter 11. bankruptcy yep did you know what was going on no I still don't know what happened I don't know are you able to look back on that that first sort of chapter of your life and figure out how it had a lasting impact on various elements of who you are today I think it allowed me to even though it was so challenging younger in life to learn how to assimilate into different
environments um to I guess entertain myself independently to realize that Authority was like adults were not trained to be parents and weren't any further along with their maturity sometimes than I was at my age you know I looked at teachers and thought wow you know you have domain expertise you know some stuff but I can tell that like you're morally bankrupt and I don't trust you and why have I been put in your you know in your hands um I think the thing that had the biggest impact on me is how critical my dad was so he's half Italian and half Portuguese and his dad was a mean mean guy and my dad's very charismatic and I love him and he's super chill now but when I was young he had a lot of pressure on him and he didn't really have the best model of what a great parent looked like and I can't say he was a bad parent you know he did his best I know that both my parents did their best with the materials that they had the ingredients that they had to be parents but it instilled in me this unfortunate but also very fortunate always peeling back another layer of the onion examining myself but also real internalized drive to do better in a self-criticism that has worked very well for me that's been challenging it's challenged my confidence over time but it also has been a superpower to in some ways I don't know in some ways hold myself accountable because I'm always I almost want to say second guessing myself but also very um in a very I guess someone said Jesuit way at one point but a way where I can see both sides of everything you know challenging my doubts and my ego but the problem with that is sometimes it's hard to differentiate between the two what is you know fiction and what isn't and what of my self-critiques are accurate because I want to be and I think I am a pretty self-aware person and even with the things that I'm not great at I'm like super proud of that because I've got a ton of advantages and things that I'm
really great at but I think it was the criticism I experienced early on in life for so long that instilled that in me and I've learned how to turn it into something that's more balanced than what it was when I inherited it when you inherited it when it was handed to me the model I had the level of critique that I had that didn't have the Counterpoint that I'm able to provide for myself you're talking about your funnel there yeah he would critique you yes when you say critique do you mean oh that's that's naughty don't do that no no like that's not how you do something or why why'd you do it like that or can you not or you know I mean I love my dad and and he's you know as both of my parents have gotten older they split when I was 17 and I've just watched them both become such better people I remember congratulating them when they finally split up and was so glad at 17 years old and I was also like I'm out of here see ya you seem to become a bit of a rebel you know from from when you moved out of your parents house for the next couple of years the behavior looked really rebellious oh yeah no I mean I was rebellious from a very early age I remember in middle school a teacher I was eating an apple in class I was eating an apple it was healthy I was hungry I've got agency over my body I didn't know what that word meant I'm hungry I'm gonna eat food I'm human I'm hungry I'm gonna eat food in the middle of class but like who how could you tell someone not to eat when they're hungry it's like a simple bodily function and it keeps me healthy and it's gonna make me a better student and it's and I and the teacher told me to throw the Apple away and I just started the apple and of course I had the attention of the entire class and I got up and I sauntered over to the trash can super slowly and I just like ate the apple all the way to the core like super fast finished the apple and was like dink in the trash can um so I was like that if if someone said
not to do something I did the thing that they didn't say I couldn't do that was similar it was peripheral and then by the time I got to high school I was going to the anarchist book fair in San Francisco I was sure capitalism was you know the worst thing ever I was very angsty I thought that adulthood it's funny there's a Netflix series about my life and the first thing that the character says is adulthood is where dreams go to die and it's so weird to reference your own Netflix series like who does that but that's how I that's how I felt I wasn't trying to be a child but I also didn't want to go work in an office I also wasn't ambitious so somehow along the way that lack of desire to live a conventional life became something that turned into ambition because I not even ambition just curiosity something that I was good at and you know eventually built a business but um I uh in high school in high school I remember there being Bells like right there's a bell that rings and you go from from one room to another room all day a bell rings you sit at a desk a bell rings and you stand up and you Shuffle over to the other room and then you sit down and you like memorize some stuff and then you like this is my youth I was sure I was being trained for something super mediocre not that I wanted Excellence I just wanted out why are you like that because you know all the other kids will come out like that I actually came out I came out like that yeah it is not I mean her I'm I might have some hereditary just kind of like Italian I'm not sure what or something it's not it wasn't a nurture thing that was a nature thing or I don't know I just like came out I actually hatched out of a disco ball but that's the way that's how I came out I had a gabo mate here who's this like I think he's just interviewed Prince Harry actually um in uh in a little like pay-per-view 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 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 actually interpret that as there being something that to do with us and that's the way we view the world as a survival mechanism and he says one of the things that happens when we're in a where you were a young child and we're in a house where there's lots of arguing and lots of drama and shouting is we learn to avert our attention as a way to help us deal with emotional distress and that develops into something they call ADD and ADHD so I took Adderall this morning hmm hahaha well they will yeah just to prepare for the podcast just kidding now I've major add but they diagnosed me as a kid and I was like no this is mind control forget it I'm not focused because I thought it was situational I thought it was my environment and it maybe was partially because I wasn't interested in what was happening and distracted because I was curious about other things but also it's a real thing and it wasn't until a few years ago that I finally realized it was a thing and sought treatment and it's helped but it's helped like marginally it's not I had to realize it was a real thing a couple of years ago I've I've been I mean you know I go to a psychiatrist and I talk about what's going on with my brain and um do what I can to help myself um holistically but also I know I'm also predisposed to depression not predisposed I've suffered with depression my whole life since when my whole life I don't I can't remember an age where I wasn't depressed I just I wasn't always miserable but I've I'm kind of a dark I'm a little dark um and that's not something you know it's hard to pull yourself out of a hole when you don't want to get out of bed like that's you know to have the willpower to just get over depression and put on a happy face and whatever people do get an ice bath and jump in the sauna and meditate and you know I am still struggling to be the
well-rounded person but I'm functional I think we're all struggling to be a well-rounded person I don't know some people seem to like have these parents that teach them that and they come out and they're like yeah you know and it's not you know that's almost diminishing to be like but but I'm yeah there's people who just seem to you know and some people come out of the womb like that I know parents that are creative chaotic I know people who are well-rounded whose parents were addicted to drugs and somehow they just wound up like that and how to attribute that to your parents it's that's a hard correlation to make did you ever you said it curious phrase now which made me um Ponder you said I'm a little dark uh-huh what do you mean by I'm a little dark hmm 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 I I guess I've just you know like I said I've struggled with depression I'm not a bubbly person I'm not someone you know as a child my mom has said you only laughed when something was really funny you know I think kids run around like laughing and smiling because they're like children or something but I had to have a reason I'm not sure why and it's still kind of like that and maybe it's I don't know as an adult it's become something that requires it's just being genuine and maybe I'm not I think maybe I'm not impressed maybe in general I'm just skeptical you went to see a psychiatrist when you were 16. oh I went to see a psychiatrist when I was like 10. I mean I was in therapy when I was like 10 11. with what's trying to be diagnosed like what's wrong with her why can't she stay on task why is she so weird why doesn't she get along why is she distracted so I have report cards that say chooses to disturb others you know doesn't stay on task it's stuff like that it was like I was always like you know not paying attention curious about
something else engaged with something else it wasn't always to be rebellious sometimes it was very good-natured and I would get in trouble for things that I didn't think were bad or intend to be bad it was also just very a very willful independent thinker who didn't fit into a traditional educational environment and you know that's something for whatever reason seemed to be needed to be diagnosed but then I was like no no I'm not taking Wellbutrin and I'm not going to take it's like an antidepressant I didn't take it I was like no I'm not taking any of this when did they win right that was by high school so you were 16-ish around that time when they yeah 15 16 and I was like this is it's I don't feel like myself feel wired and weird and I got like I think I got Ritalin and someone tried to buy it off me in like high school and I was like what do you what I don't even get it I was like I'm just throwing this stuff in the trash I didn't and then so you so you get diagnosed and prescribed antidepressant at 16ish your 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 homeschooling so I got my diploma in the mail I thought the like most embarrassing thing would be would be to wear the cap and gown I was like what is that I don't understand what's the tassel why do you have to wear a robe what is this robe I I wouldn't have been proud standing in a group doing some group thing I'm not a group person even though I've built a lot of really powerful communities I'm not I don't assimilate well into groups and I think groups are responsible for the most heinous things in like human history so uh [Laughter] so I moved into a closet you moved into a closing under the stairs for sixty dollars a month uh these guys that were like in bands and artists who had met going to shows because I was really into music and went downtown in Sacramento and saw music and what was the plan in life at that point was there a plan you know you're like 17 years no you told me there was a plan I
wanted to go to first wanted to go to Reed College but that was expensive but then I wanted to go to the Evergreen College so by the time I was 18 I had moved to Olympia Washington to get residency to go to the state school called the Ever Supreme State College which is a super duper hippie state school that's interdisciplinary and there's no majors to the point of it not really being worth going but if I was gonna go to college I was going to go to a place like that but even state tuition was expensive so I lived in Washington state for a year to get state to get residency so I could go to that school and by the time I got residency I was like this school's not gonna do anything for me you described this chapter of your life as being very lost super lost super lost I was looking for my I kind of hate this word tribe I was looking for people like me I thought I would find people like me and then all would be well like uh you know some Disney character that you know ugly duckling or someone who loses you know they're lost from the wolf pack I don't know what these movies are and then they find their family and people understand them and so from the time I was 17 I moved from Downtown Sacramento to Olympia Washington lived in two places there Seattle lived in two places there San Francisco lived in one or two places there Oakland with my alcoholic fry cook boyfriend I had met in Olympia we couldn't get jobs and my parents were like yeah we can't help you with college stuff so then we moved to Portland I was a stripper I was lost I was lost that's an interesting time a ton of events yeah that was an interesting turn of events and that chapter of your life in some ways mirrors the transience of the start of your life you said you moved to like eight eight or ten different schools when you were young and then when you leave the nest you end up bouncing around as in your own words like looking for your family I was yeah I was looking for
some place to belong and I never found it and I kind of love that because it's forced me to make my own and force me to stay creative thinker and also I don't know I this isn't fair but the people in some of those communities like peaked and never left it's like you know I listen to pop punk in high school can you imagine I'm sorry if anybody listening is like never graduated from listening to pop punk but if you don't graduate to metal or some other it's not even more sophisticated but like less juvenile varieties of rock it's the same as finding you know some comfortable Community when you're 20 and then never leaving like that sounds that sounds awful to me so I'm I'm glad I didn't find a comfy place and it's been uncomfortable since then how long did you try this stripping thing I don't know I mean when you're in your late teens early 20s time just feels like it felt like a decade that I was you know bouncing around to these places probably three or five months it was fun I loved it nobody pulled anything I never got messed with I drank my white Russians and ate the Subway sandwich from next door and played photo hunt and I wasn't even 21 I used someone else's ID to work there and I got to dance to music that I liked I made money I didn't really have to engage with anybody and I got really comfortable with my body in a way that I hadn't before and that was cool yeah they say I've read a new book where you said that you believe you hold the world record for having the most shitty jobs like back to back throughout that period of your life they say you know I've learned this from this podcast that every job teaches you something and that thing can be applied to business there's always a sort of a transferable skill or whatever learn what was the transferable skill but you learn from stripping that you think has probably stayed with you today I think that even though I wasn't didn't have the upper body strength to be the traditional one upside down swinging around what I could do I mean it was like
Shuffle around and whatever was enough and still charismatic enough and still great enough to entertain other people and then being comfortable with my body it's like exposure therapy you know I was the girl at 18 it would like make out with someone and then if I was like naked or something I'd like put on my clothes to go to the bathroom or something I was like not I didn't sleep with anybody until I was 19. so I was just I was kind of late by 20 I was tripping in Portland I'll tell you the crescendo of that experience so dating with dating Wade the alcoholic fry cook who was 10 years older than me uh I like I was on birth control I went off birth control for like one day and there was almost we were hardly even you know engaging in the way that someone might like get pregnant like so briefly like that day yeah I'm like I don't know who's watching and uh and I wound up I want it pregnant so I'm like 20. Maybe 19. and I went to the sliding scale Women's Clinic and but but it was the only day I could get in but it also happened to be the day of my court date because I had gotten arrested for shoplifting so I had to have the Women's Clinic write an excuse to the court telling them why this poor girl couldn't make it to her court date and the whole thing got they were just I kept following up to be like when is it rescheduled and I think they all just felt so bad for me it kind of vanished but that was that was like okay no more shortcuts it wasn't like I'm gonna go be a CEO but it also just taught me that breaking some rules puts you in other people's hands and I was you know being arrested I'm not as autonomous as I would have liked to have been and you know even with stripping to a certain extent it was a shortcut I was trying to evade like working hard but it was also
a lot of fun but that was really that was a low point it's had lots of low points um but at least it's like this right it's been like this you know doesn't it doesn't ever go that low there's clearly um a slight issue here with authority and it feels to me like the ultimate Authority which is the law eventually was like he can't [ __ ] with us we're not the teacher yeah it was like okay like maybe just figure out how to get along you know it wasn't like wow I'm gonna go have a career and do everything I'm I'm gonna just do everything differently but also I just didn't want to cut Corners I didn't want to end up not in control of my environment or stuck in jail or something stupid shoplifting mm-hmm why'd you make that sound I don't know it was fun what was your favorite thing to steal I don't endorse shoplifting neither do I my rationale for shoplifting was that there was so much excess in you know our culture that it would never make a dent to steal organic tampons from Fred Meyer which is like Target in Portland or whatever so I uh when I did get caught and this was my favorite thing was just walking out with stuff so I would get a whole shopping cart of stuff I had a little teeny tiny little razor thingy so I knew where the sensors were and I would cut them off they were there and pile a shopping cart high and just walk out with no bags or anything I did it at grocery stores I I furnished apartments I walked out of places with like literal rugs this High just walked out because nobody expects you to be that like obvious about it they're looking for somebody who's like putting stuff in their pockets and when I did get caught I had like a George Foreman grill I think a basketball organic tampons some food really nice shower curtain rings they were metal and
then they had like ceramic they were heavy and they had like a ceramic thing that said hot and then the other one said cold and I was like yes this is this is luxury It's Worth jail time so that was yeah and you know I built an online business and the first thing I sold online was stolen so another thing and I learned this from people who were professionally trying to like avoid getting jobs and participating in capitalistic culture which is a privilege it's lazy it's it was it was yeah I was really young and I just didn't want to work you know it was some kind of quasi-political lazy excuse for just not working hard anyway I learned from some of the best um I had a friend who had written a book called evasion literally and I would go into Barnes and Noble and they had a no chase policy like I knew what the policies were at these places because if their employees Chase someone shoplifting it's gonna cost them way much more if they get like knifed or something than it would for them to lose a few books and so I would go on Amazon and I would look at the best-selling books this is in 2002 2003 it's like and even look at the ratio of most expensive book to least pages so I could stack them as many of them as high as possible and I would just walk to the front like the front of the store would have all the best sellers and huge stacks and I would just like piled them hide I look like an employee like who's carrying a huge stack of books I was right in the front of the store and I just like walked my car and I'd put them on Amazon for 10 cents less than all the other resellers I'd sell them overnight I'd ship a Media Mail and I'd pay my 350 a month rent why weren't you scared I think I was but it's when you get scared that you get caught and it's when you hesitate you fail it's the same thing if you're snowboarding and you're like oh it's kind of icy let me look down you're just like catch an edge you're surfing and you look at the nose of the board right
so even that's what you're a life lesson I guess I guess we'll say I'm not proud of this I was really young and I was finding my way I never stole from individuals that was like not on thesis for me no I couldn't justify it I would never feel comfortable doing it um but big box retailers I was like over the last couple of how long maybe four months I've been changing my diet shall 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 things that's really come through for me which has caused a big change in my life is the need for us to have these superfoods these green Foods these vegetables and then a company I love so much and a company I'm an investor in and then a company that sponsors this podcast and I'm on the board of recently announced a new product which absolutely spoke to exactly where I was in my life and that is huel and they announced Daily Greens Daily Greens is a product that contains 91 superfoods nutrients and plant-based ingredients which helps me meet that dietary requirement with the convenience that hewell always offers unfortunately it's only currently available in the US but I hope I pray that it'll be with you guys in the UK too so if you're in the US check it out it's an incredible product I've been having it here in La for the last couple of weeks and it's a game changer ladies and gentlemen our newest brand partnership will come it's no surprise to regular listeners on this podcast the first episode of 2023 I was joined by the incredible Professor Tim Spector to hear more about his work at a company called Zoe using data to understand our bodies better so that we can live more fulfilled higher potential lives Zoe was born from the truth that our overall health is impacted by our gut health by helping you to understand how your body is working so it can help you to reduce your risk of long-term disease and increase your energy levels for me this is the future and that is why I became an investor in the company and that is why they are now a sponsor of this podcast you can read up about everything they're doing and you can pre-order your Zoe program at joinzoe.com and they've
been kind enough to offer an exclusive 10 off code CEO 10. so you can put that code in at checkout CEO 10. thank you so much let's get back to the episode so by this time you're getting a little bit acquainted with the internet and selling things on the internet clearly because you're selling stolen stuff yeah yeah vintage mm-hmm why why vintage why did you start to sell vintage clothes yeah so by 2000 six I had gotten some real jobs now after after I'd worked in shoe stores and record stores and Photo Labs and Subway again I like dry cleaners I how did you get on with those jobs it didn't last very long I like job-free alphabetized things though so record stores Photo Labs bookstores like paper makes me feel important for some reason mailing things I don't know it worked out with my eBay store and the last job I had was in the lobby of an art school in San Francisco at 79 new Montgomery Street called The Academy of Art University it was a job I got because I needed to get health insurance and at the time you couldn't get health insurance with a pre-existing condition you is this your hernia yeah the Hearn the Hearn yeah so a hernia if you don't know what it is is a place it's a hole in your muscle wall that your guts poke out of and it makes a little bump and I had one kind of in my groin area I called an inguinal hernia and it didn't hurt but they're kind of dangerous because they can like if your muscle tense is up or something they can get strangulated and necrotic which is a disgusting word so I had to get it fixed but before I got it fixed it was kind of fun I shaved everything but the hernia my poor boyfriend my poor boyfriend and um yeah it was entertaining it was kind of funny to have like a small lump in my pants for a few weeks or something but at the time you could not get health insurance with a pre-existing condition even with depression if you had medical records that said you had depression and your insurance lapsed insurance companies would decline you now that's
not the case you can have a pre-existing condition apply for health insurance you'll be given health insurance you could only get health insurance with a pre-existing condition like a hernia with group health insurance with a job so I had to go find a job that had health insurance and I got this job in the lobby of the art school as a campus safety host which was a different way of saying you're cheaper than a unionized security guard and I wore a starchy white shirt it was like a men's clothing I had to wear this awful uniform with like a magnetic thing here that had my name and the school's logo on it and check students in and say hi you need to sign in can I see your ID that was were you doing anything sort of criminal at this point my job no so all of your money came from that job and yeah and so there was a three month waiting period for health insurance and while I was there I had time to I had some down time in this Lobby and there's a computer and uh there's no Facebook or Instagram at the time this is 2006. and I was starting to get friend requests from these eBay sellers on MySpace I wore only vintage I was like you know root and toot and Scootin to like oldies and rock and roll and dive bars and subsisting on burritos I loved vintage I wore vintage I wasn't necessarily into fashion and I didn't want to be in fashion but I loved style and I loved vintage and I loved thrifting and I saw what they were doing and their auction prices were crazy like I thought hate Street was expensive because I had shopped at thrift stores and found great stuff and saw what their auctions were going for and these were actual prices that the customer was determining they would start the auction price at 9.99 and these things were going for like 200 300 and they were just making it look like something that Sienna Miller some boho at the time it was like boho Olsen twins Sienna Miller kind of Vibes and they would do that put this stuff online and the customer determined the price and it was so much money and so I thought okay so I waited my three months for my health insurance because
there was a three-month waiting period it got the Hearn fixed and I started an eBay store and I wasn't trying to be an entrepreneur I was trying to legitimately not work for anybody and that's when I realized that I could connect my curiosity and Independence and creativity and resourcefulness to something legitimate that made money that I learned from every step I was taking and started nastygal selling vintage out of my boyfriend's apartment before that point would people have called you lazy or unmotivated I didn't know any people who would have said something like that because my friends were just like me so objectively then objectively I think just lost I think it would be a judgment to say I was lazy I can relate to so much of what you've said especially all the stuff about Authority like I just decided to stop going to school and I was polite about it but I I've always had a challenge with authority every job I had throughout through that period of my life lasted for three months I was just cool center hopping get to the bonus threshold quit gives me two months where 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 because I think people would have looked at me in school and stuff and said like written me off oh it's he's lazy well like my thesis is that everyone most people are lazy and you should be lazy for things that you absolutely hate 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 tried to write a second book and published two books after girl boss which was a thing I can't I cannot be assigned something I it either comes out or it's not there that's the do you think that's the the rebel in you that is but it's why everything I do is so inspired and honest and I don't want to be like I'm unique but because you never accepted or learned compliance it's an actual representation of who I am and what I think and how I feel and my perspective instead of a manufactured version because somebody
has given me an assignment like you didn't even want the bell in school to tell you what to do no the gift in a curse though right I mean it's pretty logical that you would question a bell ringing and someone moving from one room the same room to the next room every single day what do you think anyone else no no but if you really think about it it's pretty wild right that that eBay store that you start with in your free time when you're working that job you took to fix the Heron um it was successful yeah and you know you kind of frame it as you saw maybe a price Arbitrage or whatever but but it's more than that right it's more than that to be successful at that time I'm not sure a lot of people saw that price Arbitrage and they didn't build a nasty girl so when you reflect on why and how you were particularly successful how did you diagnose that I reverse engineered everything everyone else did and did a better job and did it with my signature on it do you think and I'm thinking now about that Bell again in school where you were like analyzing the Bell where no one else was do you think that kind of default to thinking in terms of first principles like asking the question why why the [ __ ] do we do it that way has been part of the reason why that eBay store was successful I think so I think most people that started an eBay store are copying what other people are doing they might reverse engineer some things and see what their competitors are doing and I did that but I just did it 10 times better with a totally different spirit with excellent copywriting with great styling great models and increasingly better photography and I would I was extremely resourceful I would buy stuff on eBay and sell it for more than I paid for it I was searching for Eve's son Laurent just misspelled you know the song but even that's the first principle thinking that's like
but you've got a convention on one end which says just like do what's being done and then you've got these like first principle thinkers who kind of think first about what they know to be true and they're really good at filtering out convention they can kind of see throughout the truth whereas convention like is safety it's Comfort it's it guarantees you a pre-tried blueprint so people follow that but then these other little Rebels they they have this almost inbuilt ability to just like [ __ ] see through to the that that truth that nobody can see and in that case I mean that's a great idea but even caring more about the copy and you having your own belief as to why the copy matted or the photography like why photography really really mattered on eBay yeah on eBay which a lot of people would have had like that's um and it was called Nasty Gal the spirit of it was really irreverent at the time the eBay sellers were selling like you know is called Mama Stone vintage was a really big one and it was all very hippy dippy and vintagey and mine was vintagey but it was like very hard-hitting edgy I named it after an album by a woman named Betty Davis who had an album called Nasty Gal she was so stylish uh in the 70s put out some incredible records was married to Miles Davis for a short period and was allegedly too wild for him her lyrics are just so and I was stripping her music when I was like 20 and then I was like cool nasty girl and it cut through the noise and I think when you start a business and you don't need to survive you might have more time to Naval gaze or you might do things super conventionally but when you need to survive there are certain things that other people have done right that you can see you know accelerate what it is that you may do on your own but learn from them and then also take and make your own way I think had I tried to do things completely differently than everybody else I wouldn't I wouldn't have survived I would have been dead in the water speaking to something really interesting there which is like this Balancing Act between naivety which is great for innovation and then convention which is
great for staying alive I'm talking about like the the nasty girl needing a 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 it grows incredibly quickly okay the naivety made us interesting but our naivety will also send us to the Grave here if we're not yeah if we don't know what we don't know I've been to Hell I've been I died and now I'm in the afterlife I it did send me to the Grave my naivete and lack of experience did send me to the Grave it happened so fast that's a quote um it was shocking how fast it all happened nasty girl went from doing 150 000 a year to doing 150 000 a day and then 150 000 over lunch yeah 150 000 over lunch it was either a day or over lunch that we all worked out of this Warehouse it was a bunch of kids in the East Bay in Emeryville I had the 7 000 square foot Warehouse which I thought was the hugest thing and I was like when we hit 150 000 a day God was it a day it must have been the holidays I was like I'm gonna get a bounce house you know those things that people jump on the inflatable things the children that children jump on it was an upside down horse and its legs were in the air when he jumped on it the legs like that's what you wanted and in between you know on our breaks we got to jump in the bounce house I was like 23 24 years old it did happen really quickly to be fair now you say it when we raised investment for the first time the first thing I bought was a 13 000 pound slide big blue slide which we had in our office that was the first thing I bought before we got desks so talking about neither today I bought I paid off my mom's mortgage oh did you okay I 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 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 good job yeah what do you attribute at such a young age I'm just gonna interview you for a second because you couldn't have had a ton of experience
under leaders to give you a model of what leadership looked like you were naive you know could you I couldn't empathize with the people I was managing because I had never experienced leadership and I just showed up and I did what I I what needed to happen and what I said I was going to do I didn't understand that people needed to be held accountable because I held myself accountable especially c-level Executives and grown-ups whose careers were longer than I had been alive like how did you do that at such a young age well I think I I think I messed up I think like for the first two years I hired people that were very very inexperienced I reflect and I go I think I did that because I thought they were easier to manage and I couldn't fathom the concept that I could hire someone who was two times my age and three times my experience and Avid want to come here and be with us with that with our sliding dogs and tree and basketball court and ball pool and they would like take us seriously but also like be like maybe there was an insecurity about how I'd manage them and so what ends up happening is you I hired lots of like young people 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 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 you feel things breaking this is where you go convention is right about some things processes HR Finance you feel things breaking at the seams a little bit because of the growth um and then at some point an adult enters the room and you go oh I get this and so we hired some some really really great people and the great thing is great people hire great people so we went from being this kind of very lopsided inexperienced organization to being a balanced one and I say balance because it's my belief that to own the future you have to understand the present which is why you want to hire a 16 year old that gets Tick Tock or whatever and you also need to hire someone that's maybe double their age experienced in client services and understands the old rules
of the game if you understand both games you can understand the game of the future I think so um made a lot of mistakes and when I nearly went under several times and had to call people and beg for money um in the lead up to Payday but somehow managed to survive but go back to you now um I feel that we missed a park because you know you write the reception you went from starting that store to bouncing around on that bouncy castle thing we call it bouncy castle okay horse Castle between that between that bouncing on that horse castle and the starting the store what happened so first year just on eBay did 75 000 in Revenue I was the only employee it was just you know it was pure cash all of the money just went back into the business I didn't even know what expensive things I would have wanted I didn't I had never eaten an oyster you know I was drinking like Budweiser or you could still like subsisting on Boston Market and like Starbucks so I didn't spend any of that money I thought building a business and I think for the most part it is uh was selling things for more than you bought them for and not spending all the money that's it that's all and so I bought things I sold them for more than I paid for them and no one else would have given me money parents weren't gonna give me money I don't even think I had a credit card at that age I didn't understand what Venture Capital was and I was living in the Bay Area and had I not built the company to eventually you know 28 million dollar run rate super profitably I would never have known and so yeah year two left eBay about halfway through and launched my own website nastygalvintage.com and did 250 000 in Revenue the next year did 1.1 million the next year did six and a half the next year did 12 and I was coming off a 12 million dollar a year uh Revenue owned 100 of the company
had a bunch of kids working for me and that's when Venture capitalists came in and at that point you know we were selling non-vintage stuff what really allowed the company to scale was going to trade shows and showrooms and curating from the market based on what I had learned from my customer having sold vintage to them so I knew them very very well and that gave me the ability to then go by greater breadth and depth in things I knew they would love and that's what 2011-12 Venture Capital comes in 2012 was when index Ventures invested 60 million dollars 60 million dollars on a 350 million dollar valuation on a business with a 28 million run rate yeah you're profitable at that time significantly pretty significantly I have a 10 or 20 nothing I don't know I don't know I didn't even look at that I was I I never had to learn to read a p l because my company was profitable and I just you know generally knew how much it cost to run I didn't it and I and I didn't I didn't buy expensive office chairs did you did you know you like gross margins on on your on the product yeah on the operating margins no I don't I don't think I didn't understand what operating margin was 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 dealing with or what your net profit is it's a luxury but it was also a disadvantage once we plowed 60 million dollars into the business and things got a lot more complex and a lot less profitable you talk about the 60 million going into nastygon in 2020 to 2012. what did it break hmm I mean we no longer had to live within our means that's what investor money does unless you maintain profitability and keep that money in the bank for you know another time or pocket all of it as a founder we you know I had hired a COO at that time I had a top tier investor on my board and very little like historicals data financials to base the future growth on but it had been exploding just continue to be
exploding and with that Capital behind us we could grow even faster and the expectation was that the next year we would grow from 28 million in Revenue to 128 million dollars in Revenue we just rounded up by 100 million and then we hired into that and we bought into it oh you believed it and everyone I had grown-ups forecasting this stuff with me I relied on them it's why I brought them in you hired the right ones clearly I didn't pick the right ones or I'm not sure what happened but I remember sitting in a room with them and us deciding I didn't push for it this wasn't you know we're gonna just grow by 100 million dollars this year and someone put a plan together and this is we hired 100 people it was like the Tower of Babel you know that story you don't know it's like a biblical story where uh people are building this Tower or something but they all speak different languages and I I could be completely wrong I don't think I am but none of them get along or understand one another and it was it was it's just a mess trying to integrate 100 people into a company in a year especially a company with no processes and no real intentional culture that had been established no real intentional anything other than the brand the spirit of the brand what needed to be done it was it was like a family business that just got really big it was I was a kid 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 into the bank account you're looking at me thinking that's a big [ __ ] number you're you know because you have a valuation of 350 yeah I'm worth 280 million dollars on paper at this point so that and wherever you go they'll lead with that and remind you of it and you'll be treated as such even though it's paper and it's not 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 cover of Forbes yeah how does that make you feel
it was a blast um I didn't do any of it to have Glory or go on a Victory lap and I wound up with it and I embraced it and I had a lot of fun it distracted me you know the book in 2014 turned into a phenomenon you know it was champagne clinks for some Milestone with a company or new hire promotion any given time I people would come up to me and say congratulations and I had to ask which thing they were congratulating me for it was it was just like oysters for everybody finally you know I I got better taste in wine I got better taste period thank God but now I spend less money with a good taste that I had to spend a lot of money to acquire a lot of my own but did you feel did you feel like it made sense like the the image that's been that had been built of you at the time that the world is now like oh my god did it is that what was going on inside I think it made sense I think it was a freak Show I was a Community College Dropout who bootstrapped a business to 28 million dollars in Revenue super profitably you know investors came out of the woodwork you know top tier ones anointed me as someone who could pull it off and I didn't know what I was signing up for or what I was supposed to pull off but it it was considered a rags to riches story and imposter syndrome any of that for sure yeah I mean I still walk in rooms and I'm here I was talking to your team and I was like oh my gosh you guys have really big people I hope I can keep up I say like a lot I'm intimidated I hope I can provide some value what are the comments on YouTube gonna say is this going to be a valuable conversation I really hope people like it you know and she was like what you wouldn't be here if that wasn't the case what what are you talking about you're great but I get nervous right um I get nervous on stages and I'm still like you know I don't I don't belong here but I don't belong here is also a really great motivator the I don't belong here is I snuck in
the back door I don't belong here means I can do things differently I don't belong here means I don't fit in but that's going to be a superpower and I think it's okay to feel like an outsider or an imposter sometimes because you find yourself in places where you learn you have an outside perspective and are able to learn things unlike the people who are invited to the table who all showed up there with the same pedigree and then you get to make oblique connections between who you are where you came from and then the door the room that you just snuck into as an imposter and that is radical would you remove that self-doubting voice if I put a button in front of you and said you press this you'll never doubt yourself again no that's so boring I had a coach recently and he was lovely waited five sessions it was like five thousand dollars a month and I was like taxes I'll buy something else to save on taxes and he was like can you imagine he asked me that word or he asked me that question and I was like but what would I struggle with what who would I be if I didn't have challenges and I was happy all the time it's like the scaffolding would fall apart or something that's a story I tell myself but it's fun to have a dark Counterpoint to hold yourself accountable and be like maybe it is that or not that and I think that Counterpoint is an opportunity to gain self-awareness do you think it's additive to your performance or reductive I think it can slow me down and I can make really slow decisions because I doubt myself but beyond that I think I've found a way to harness it that really works for me have you developed like a decision making framework to help you navigate the two voices in your head it's funny
because when you're describing your mother and your father it felt like those were the two voices your mother would seem to be very supportive your dad somewhat critical at times or pessimistic um have you found a way of being able to juggle those voices um so that you can make decisions decisively and quickly no no no so I can I can have these conversations and when I you know when I do make a decision I've learned to be slower with making decisions because I either make them extremely quickly or slowly on accident and so I want to be very deliberate in the decisions that I make now and think more critically rather than you know Naval gaze or be reactive to something I went to this uh Retreat even though it's not really a luxury experience with 30 other people called the Hoffman process and it's seven days with no phone no Internet no books no music you're with 30 other people and you're going through this process of mapping your patterns from your childhood against your parents and how how you inherited that and it's all directly correlated and basically graduating from your your emotional child into an emotional adult super embarrassing weird process like so dorky and everybody came with something different to work on or what emerged for them you know I I feel unloved I feel unlovable I don't feel unlovable my thing and it sounds really weak was like I don't trust myself I don't think I'm deceiving myself but I think I can rationalize a lot of things to the point where I'll tolerate them too long um and that's gone for relationships that went from my most recent relationship um and so that's a strange thing I don't trust myself because I do have these voices it sounds I don't have voices in my head but I can see things from any perspective and not be totally attached to either one to the point of being slow and asking for too much advice in that Retreat did you did you have to sort of like go upstream and figure out
where that belief started is that the 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 yeah I think it was that my parents didn't agree on how to raise me that I felt misunderstood that my good intentions were sometimes construed as troublemaking that the fact that I didn't fit into the environment I was raised in I was I was not accepted and I was some kind of weird deviant when I was just being myself and felt punished for being myself and I think that gave me like a lack of confidence or something and I don't identify with being an unconfident person but when it comes to decision making when everyone around you is telling you something a different story about yourself than you have and doesn't understand why you operate the way you do that is really with integrity and in line with who I was and what I needed to be successful as a child if other people like live in a different world and don't understand that those are your needs you just feel wildly alone and think wow I am a freak and that found its way into my career through the public too which has been super fun being told I'm something that I'm mostly not what have you been told you are oh gosh um so nasty y'all fell apart after 10 years it was it was a quick rise and it was it was it was a it was a slow rise and it was a relatively quick fall couple of years in the making and when it did fall the headlines were crazy because I had all this press from this book I published and being the poster child of Entrepreneurship going on the victory lab National Enquirer said had you know picture of me and it said Rags to Riches like straight up tabloid American Dream stuff like a caricature and I didn't realize the amount of responsibility I had to like other people as an example like I kind of did but as some symbol for entrepreneurship for my generation you know generation of the entrepreneurs coming up behind me or
at least what the Press thought I was responsible for the you know there were headlines like does the failure of nasty yell mean Millennials aren't ready to lead it's like wait how is one example representative of a generation and I've also read headlines like when the Netflix series came out the worst thing about Netflix's girl boss is its source material not even the show just me but I'm not bad I don't believe I don't believe it how does that make you feel at the time though by the time that Netflix series came out I had been this hero as an entrepreneur then I was this girl boss because I wrote a book called girl boss and it was pink and I was like this and I looked like I knew it was up but it was like 27 and then there was the me whose company fell apart the CEO there was the girl boss who had built a toxic culture or just no intentional culture at our all that like warped into something that wasn't perfect but wasn't I still don't think it was the worst and now this person this conflation of all of those things with this girl on the scripted comedy which came out four months after I left Nasty Gal so the biggest kind of personality or whatever identity crisis was you know I'm on the cover of Forbes in June I think of 2016 July of 2016 my husband of like a Year's like man I changed my mind and I'm like oh my God that wedding was so expensive it was devastating but I'm just like God that wedding was so expensive it was a great party so in that space of like 12 months you're on Forbes husband leaves Netflix comes out nasty girl goes under nasty girl goes under then Netflix comes out so the show had been shot when things are all like up and to the right and you know we were working through challenges there had been some layoffs but the company was still you know 100 million dollars a year you know not profitable anymore but a great brand and something that was
valuable and eventually um yeah like fell apart and that the con there was really a conflation of the the hero the failure and now this girl four months later who's a a caricature of a person I was when I was 22 in a scripted comedy playing someone named Sophia starting an eBay store called Nasty Gal when for the first time in 10 years in my adult life since I was 22 years old I am no longer associated with the thing that I had built and now there are 130 million homes in 195 countries watching a story of someone that I was no longer and no longer had trying to move on and to move on when there's a full PR campaign about who you used to be you're someone who's as you said you've had a long history with mental health challenges what is it like in like in that 12-month period what's going on from a mental health perspective I had fallen in love again I think it was still like traveling I started another company I maintain my mental health partially because I keep going you know I don't stop and like lick my wounds I think I was also I was also on antidepressants I wasn't jumping for joy but I also knew that there was a huge community that still supported me who had read my book 500 000 women who bought it and I went on to start a company called girl boss right as the Netflix series was hitting put on our first conference and I had my podcast and I moved on quickly and even though the headlines weren't nice the people who followed me my friends my relationships everybody in my network nobody bailed like the girls who were inspired by girl boss were refreshed that I had face planted publicly because everyone else is face planting in private and in the same way that watching some random Community College Dropout from Sacramento start a business with an internet connection and a computer gave them license to you know yes they were inspired but also
Embrace their own failures because the hero face planted publicly and that can also inspire people this is hopefully the most cliche question I ask but um I wanna I wanna know because you have a from your from that experience you have amazing feedback you have amazing Insight invaluable Insight I would say because when I think about the things obviously they've taught me the most it's not it's not when things go right that's a validation of your hypothesis it's when things go tragically wrong and you go oh okay [ __ ] you have all of this new information about which is corrected your hypothesis so when you if we go back and think about that fundraise for example um a lot of people will hear that you raise the company raise investment at 350 million and think amazing that's when people clap right they get the champagne out oysters for people listening that aren't in business they might not understand how that can also be a key reason why the company ultimately went under the 350 million why why did our big valuation hurt yeah yeah I think the 350 million dollar evaluation is celebrated as it was and how wealthy I was on paper um was the was the nail in the coffin I think it was it was then in 2012 where we were overvalued and the expectations that was was that the next round of fundraising that we do is at a over a billion dollar valuation and so the company's doing you know on an upswing 228 million dollars in Revenue that's like over 10 times revenue and it's a fashion business this isn't a technology business this isn't Uber this isn't an infinitely scalable Marketplace it's e-commerce it was a different era of e-commerce it was pretty early it was the era of fab.com which like imploded and won King's Lane in beechment in ShoeDazzle there was no Playbook there were no Ecom veterans or you know Performance Marketing people who had been in those jobs for even very long I was hiring Executives who had worked at like Macy's right um nobody had like econ it wasn't called direct to Consumer at the time it was
very very different there's no Shopify and we were overvalued and I didn't know that I didn't even negotiate you know hardly negotiate I didn't shop a term sheet around and say I'm gonna pick the highest price from different investors I 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 you know what Danny said when he invested uh was something none of the other potential investors said and that was you have a community and I was like yeah we do have a community but when you have that much money you don't know there's been a nail in the coffin or that there's a coffin and that like you might be on your way into it or maybe already laying in it but just several years in the future and when things are up and to the right you don't see what's lurking kind of below the surface so when the tide lowers right you see the mud you see weird crab shells sometimes hopefully not you see trash and it's only when things recede that you see the mud that's underneath and when you're on a Victory lap and you're hitting milestones everything's great and everybody loves their jobs and you're a hero and as soon as things Go a different way as soon as there's layoffs yeah there are things kind of there are things there are things lurking below the surface that were dynamics that were already happening that because everything was going so well you know we're harder to notice and you know it's hard to be a CEO it's hard to be a founder I think something a lot of people don't realize is that you only know 10 of what's happening in your organization right hundreds of employees and ultimately everything was my responsibility but I am held accountable for 100 of what's Happening and when something goes wrong or something's mismanaged or someone has a bad experience in the company the assumption is that I have signed off on it that that is how I want things to be
and these things are happening you know cattiness and you know fiefdoms and silos and duplications of effort and all the you know the entire spectrum of things that are no fun at a fast-growing company I didn't know were happening until we laid people off and then they were like hey we didn't like it there I'm like okay and some of that was totally overblown but also anything that any employees ever said about me or I've read even though I don't agree with all of it has been an opportunity for me to learn and take from that how I could be better because there's truth to almost everything didn't you get an offer to sell the company completely for 400 million dollars yeah I did I owned 80 of it so that would have made you you know quick maths I don't know very [ __ ] Rich super [ __ ] rich and why why didn't you say yes I went to my investor and I said what do you think about this and he said you need to ask for more I controlled the board I owned you know I own the majority of the company but I also took advice from people who I thought knew more from me but I didn't know that my interests weren't necessarily aligned with the interests of my investor whose interest is to whether I'm worth it or not have a piece of paper to show his investors that says I'm worth instead of 350 look they're now worth a billion and they just make up these numbers and then they can show their people that your company's worth more and that was his that was in his best interest and that's what he was giving me advice based on are you mad that he said that I'm not mad do you wish you made a different decision is that a regret it's a it's a partial regret but I also know that no deal actually happens they're not a a real acquisitive company they could have tried to acquire the company I don't even know if they've acquired anything integrating it into their company if I had an earn out based on them you know controlling it and me trying to hit performance benchmarks even if I had sold the company to them
who knows how it would have played out I would have made a bunch of money my life could have been miserable but 99 of the time deals fall through there's also in those situations a lot of people trying to get into the data room so they make an offer so they can see your numbers and what you're doing and how your business is working out and then they pull the offer later once they've had a look into the data room and due diligence yeah and then copy yeah exactly yeah so we didn't get that far I don't regret it um but yeah that was a big thing you know for me that would have been a lot of money for him it was just a teeny tiny bit more than what he had paid for it so that's not a lot of them it's not much of a markup for him what is the advice you're giving now to to women that are and men that are looking to start companies that are within your community the communities You're Building within your portfolio companies now that you're an investor um you know like I think I can think of the first piece of advice that I give young Founders when they come to me I'm wondering what your like first piece of advice is I think for bootstrap Founders the advice would be different for Founders in my portfolio companies who are raising Venture Capital my advice would be get as far as you can before raising a single dollar validate your idea as soon as you can with the ugliest like most basic quickest thing or first product should be super ugly get it in front of people and get some idea of whether it's valuable or not before you go raise money before you even try to Market it talk to you every customer every potential customer and bootstrap it as long as you can if you can because when investors do come in your company is going to be worth more than if you would raise money when you just had an idea and were asking for a check when you do raise money having a reasonable valuation is important and a lot of Founders optimize for price because bigger price an investor pays the more
ownership the founder has the more they're worth right the more they're worth and the more eventually they could make if they sell the company but when you have a valuation that's in line with Market that makes you an attractive acquisition something someone might pay a multiple for that 10 percent say you're diluted down to 10 or 20 percent but you sell your company for 500 million dollars you're in much better shape than raising 350 and owning 80 percent of it and going to zero or whatever so and I think where things are right now with Venture is a place that is is close to that and Founders aren't greedy Founders who are raising money in this market no it's really really hard they don't want to be overpriced because the people who raise money over the last few years raised at such a high valuation these founders nobody's going to reinvest in them they've blown through their money they thought they were you know they're on an upswing their company might be doing 2 million in Revenue but they're someone told them they were worth 80 million dollars and now nobody's going to give the money I've as an angel investor I have three of these right now and it's like Hail Mary's two of them have figured out how to survive ones like we have another term sheet I mean I've been there what about the psychological advice you'd give to her um I would say to listen to your gut you know there's going to be a lot of voices around you and there are people who know more than you and have experience and you should listen to them but you should also always maintain and continue to cultivate a voice that when you know it should is able to supersede any advice that anybody gives you um I think it's easy to take all the advice because you're an inexperienced founder and um and into lose touch with your intuition and it's probably what got you to where you are as a Founder without the money and without the experts and if you just rely on the money and the experts you're losing the thing that made what you're doing Special in the
first place which day was your hardest day over the last 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 period or that day was just the worst the hardest the darkest 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 were still together I don't really think about him I mean that was in 2016. but I had agreed to take a big swing in my personal life and make a huge commitment and I thought that bumps in the road were like to be celebrated I thought it was like wow okay you're not feeling great about things we're gonna work through this and we're going to be so much better as a result of it because I see commitments as things that go up and down and if you're in a commitment together you're committed to working through those things and it all comes out in the wash because you have that level of commitment to the other person and that wasn't the case for him and so I I felt like I was like hallucinating you know I like went to a hotel for a week I couldn't be in the house it felt like a crime scene with his stuff around and um yeah three a whole whole week at the Beverly Hills Hotel with three poodles is quite the scene with them yeah chain smoking in the courtyard and a bathrobe has that experience put you off being a CEO of a big company I mean ever yeah everything I've experienced has put me 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 stage founder I'm a master at creating brands that cut through the noise what happens though if one you know you're running a number of businesses now um you've got your fund yep business class business class but what what happens say business class what happens if it becomes globally you know globally successful then you're back to being a big CEO again though 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
into it that wouldn't happen by mistake I have one employee on business class business class is super profitable I launch it twice a year it's pre-recorded so business class is my entrepreneurship program but I have two courts a year I'm uh April I'm launching it and I launch in the fall and it's an incredible product but it's also something that is relatively self-led for the students it's eight hours of video and 300 pages of worksheets and over 60 hours of interviews with me like this with entrepreneurs and you know students get lifetime access so you know they can take it over the first seven weeks they can take it over the course of a year or the next few years but it's not something that requires a ton of my time outside promoting it twice a year and I built it for that I built it for that I'm using kajabi and drip for email and you know whatever zapier and a variety of tools that allow it to be relatively low lift light on human capital still a lot of effort to promote and something I do engage with throughout the year and two weekly calls with students and post in the lounge which is our community keeping it that's it no yeah I'm playing I'm I'm I'm not playing small with business class I'm playing to my strengths that's big and with trust fund it's Venture fun that I'm raising right now it's a 10 million dollar fund what I get to do is not run a big company and you can keep trying to apply this stuff that I've learned over you know over time I get to go from zero to one over and over and over again with early stage companies and out of fun I get to be in the weeds if I hired a bunch of people I they don't want me to be in the weeds Executives don't want you to micromanage but I get to look at all the decks and I get to text the founders and say here's what I think you should do I can be helpful and it's so rewarding to harvest all of my hardship on behalf of a new generation of Founders and help them see around the corners that I wish someone had shown me around and I get to keep my firms small even if I have a 50 million dollar fund I can do that with a few people um and I'm using the assets that I have I'm the product my relationships and my
network and my access to dealflow is my product my expertise and ability to help Founders is my product million social followers and being able to amplify them is my product the engaged Community I have who's interested in the kinds of things I'm investing in will actually use them is my product and I don't I'm just it's right here and it's an air table the intentionality is what I find most surprising um inspiring because so many people get dragged by the Temptation of like external expectation if it's great business class is great but all accounts have been on the website went on to so I saw that the 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 spring cohort launches in April so you can enroll for like a 10-day period at the at the end of April when things are great we get dragged by our own success what you're saying is you're going to be intentional and you've designed it so that that's impossible so that you can't get Drax because someone's going to come along and say we love this we're going to give you a check we love this we'll turn it into some boxer shorts with some teddy bears yeah no no I I have had the Pearl Village of knowing what's on the other side of success and that a lot of it is not what you sign up for and that when you are successful you're stuck in it so I spend a lot of time thinking about what success looks like for me and what I want my life to look like and how many people I want to have around me and the kind of stakeholders I want to have so that I'm set up for Success when trust fund is super successful which I can stay Nimble with and with business class I've engineered that Revenue was down last year to the year prior and that's so that's okay it's still 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 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 take the money yeah take the money just for the record guys when it's there
take Real Money Take Take the Money magical thinking what is that yeah I mean you can call it magical thinking you can call it magical thinking you can call it manifestation you can call it prayer you can call it whatever you want I think it's you know casting the line out not knowing what you're going to catch trusting you're going to catch it and we'll pull it back magical thinking is like Indiana Jones where there's the vast where's this there's the vast Chasm between whatever and the Holy Grail and he has to trust that there is a an invisible bridge and he grabbed some gravel and he throws it out across this literal kind of Canyon and the gravel just falls on a clear bridge and he had to like trust that when he walked across that he wouldn't fall and so I see magical thinking as you know Thinking Beyond what might be obvious thinking you're capable of doing things that you shouldn't be thinking you can belong in places that you never thought you could thinking you can accomplish things that you're completely unqualified to because nobody's qualified to being able to see yourself in a life in a world that's beyond your wildest imagination and just staying there we have a closing tradition on this podcast where the last guest leaves a question for the next guest your question is unfortunately not the hardest question in the world I really wish you'd been given a real stitch up one um but yours is yours is fairly straightforward question which is what is your proudest moment hmm my proudest moment is paying off my mom's mom's marriage I mean that I can do that that was crazy that was the first thing I did what about this then what's going to be your proudest moment hmm it requires a little bit of magical thinking understanding what is Meaningful in my life and actually spending time on it you haven't figured that out no there are meaningful things but what is the people have kids and
that's like obvious and I don't know if I'm gonna do that I am super agnostic about it it's really strange I'll be 39 in a month um but I think like finding that and hanging on to it what is that what is is there some big meaningful thing that I'm 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 and you can create these meaningful things in your life but what that what is that going to be for me when I'm dying what is it what will it all add up to I don't know Sophia thank you so much for your time and thank you for the inspiration you've 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 respects but um yeah you're built for podcasting but also because of your um inclination to be on open and honest and vulnerable um you're incredibly inspiring in the stories you tell in the way that you tell them so thank you so much it's a 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 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 fund and business class because um they look like exceptional projects I've looked into the reviews of business class and with your fund with the amount of information you've learned from your twisting turning professional career you clearly have a huge um amount of intellectual leverage and Firepower that makes for a great fund um founder so I look forward to seeing what you do that thank you thanks as you might know if the show's now sponsored by Airbnb absolutely love Airbnb always have always been a you 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 where they currently live could become an Airbnb and I guess the second question there is how much could your place be worth and it turns out you
could be sitting on an Airbnb gold mine without even knowing it some people 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 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 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 valentine that you love whatever it might be head over to airbnb.com UK host and you can find out how much your current property where you live can earn while you're not there I suspect it might blow your mind because it certainly blew mine [Music] oh [Music] foreign