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

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

Transcript

2484 segments

0:00

didn't you get an offer to sell the

0:01

company for 400 million dollars yeah I

0:03

did what it made you super rich why

0:06

didn't you say yes

0:07

you're very good at this Sophia also

0:10

founder of Nasty Gal A best-selling

0:13

author and a Powerhouse in the

0:15

entrepreneurial world I was rebellious

0:17

from a very early age I was a stripper I

0:20

wasn't even 21 I used someone else's ID

0:21

to work there built an online business

0:23

the first thing I sold online was stolen

0:26

get a whole shopping cart of stuff put

0:28

them on Amazon for 10 cents less than

0:30

the other resellers and then gotten

0:32

arrested for shoplifting

0:34

I'm a little dark I realized I could

0:36

connect my creativity to something

0:38

legitimate started Nasty Gal selling

0:41

vintage namastico went from 150 000 a

0:44

year to doing 150 000 over lunch I

0:46

didn't realize the amount of

0:47

responsibility I had being the poster

0:49

child of Entrepreneurship then I was

0:51

this girl boss but my naivete and lack

0:54

of experience did send me to the grade

0:56

nasty y'all fell apart after 10 years my

0:58

husband of like a year left the

1:00

headlines weren't nice

1:05

what is it like from a mental health

1:07

perspective it's hard to pull yourself

1:08

out of a hole when you don't want to get

1:10

out of bed it's challenged my confidence

1:12

and I'm still like I don't belong here

1:13

but I don't belong here is also a really

1:16

great motivator I don't belong here

1:18

means I don't fit in but that's going to

1:20

be a superpower I can do things

1:22

differently

1:24

what was the plan in life at that point

1:27

gosh

1:32

before this episode starts I have a

1:33

small favor to ask from you two months

1:36

ago 74 of people that watch this channel

1:38

didn't subscribe we're now down to 69 my

1:42

goal is 50 so if you've ever liked any

1:45

of the videos we've posted if you like

1:46

this channel can you do me a quick favor

1:48

and hit the Subscribe button it helps

1:50

this channel more than you know and the

1:51

bigger the channel gets as you've seen

1:53

the bigger the guests get thank you and

1:55

enjoy this episode

1:57

[Music]

2:05

take me back to those suburbs in San

2:08

Diego and give me your earliest context

2:11

wow I was born in San Diego Sharp

2:15

Memorial Hospital only child

2:18

eternally and only child

2:20

I think wound up having the personality

2:22

of a probably seven children and the

2:25

challenge of maybe seven children for my

2:28

parents

2:29

um

2:30

we moved a few times you know our house

2:33

was like it was it was happy-ish when I

2:36

was young I lived in San Diego till I

2:38

was seven and it's a beautiful place and

2:41

I so wish we would have stayed there but

2:44

we moved to beautiful

2:46

Sacramento California and that was

2:49

really the Suburban experience where you

2:52

know when you're a

2:53

kid a little kid you don't know what a

2:55

suburb is and chasing the ice cream man

2:57

is great but once you get older living

3:00

in the suburbs if you have any amount of

3:03

curiosity about the world the

3:06

homogeneous you know nature of living in

3:09

the suburbs is something that totally

3:11

crushed me I knew there was more out

3:13

there and I didn't know what it was but

3:16

I wanted I like wanted out from a very

3:18

early age

3:19

what what did you what did you want at a

3:22

very early age when you say you wanted

3:23

out oh yeah what did you want yeah I

3:26

wanted out of my family home it wasn't

3:28

happy my parents didn't get along I was

3:32

playing referee you know really yeah

3:35

what what age

3:37

starting at like 10 or something

3:39

I mean

3:41

yeah it was just it wasn't a super happy

3:45

place and they yeah they didn't get

3:49

along they didn't always agree on how to

3:51

raise me and I think when your parents

3:53

you know everybody's relationship has

3:55

issues and everybody's not everybody's

3:57

but most people's parents you know

3:59

sometimes don't get along when you have

4:02

a sibling I think you can go be like um

4:05

that's funny or they're whatever let's

4:08

just go play with Legos or something

4:10

like that or let's go ride bikes but I

4:13

think being isolated in a house that

4:17

wasn't super happy as an only child made

4:22

it worse and I just remember so many

4:26

drives silent car drives where I was in

4:31

the back seat alone

4:33

and I just remember like the silence and

4:36

the the light of the street lights

4:40

like washing over the car just in in

4:44

Silence with my parents in the two front

4:46

seat

4:48

um yeah they're really like only

4:50

affectionate

4:51

after like an argument and even then it

4:53

was like I don't know hand-holding or

4:56

something they were very strict as well

4:58

I had to beg to go to a boy's birthday

5:00

party in sixth grade

5:03

we weren't super religious but my mom

5:06

grew up in the 50s in a Greek Orthodox

5:09

household

5:11

um just

5:12

not puritanical because that sounds less

5:15

cultural than Greek Orthodoxy but uh

5:19

strict you know what about money

5:22

yeah arguments happened in my household

5:25

when I was younger because of money

5:27

yeah I mean my dad sold my dad did loans

5:32

and my mom sold houses but track homes

5:36

in the suburbs and they were both

5:37

working with Builders and Banks and

5:40

manufactured homes and so on the

5:42

weekends by the time I was I don't know

5:45

maybe 10 my mom was working in the model

5:47

homes

5:48

that are all kind of dressed up and you

5:50

can tour them and pick your manufactured

5:53

home and change a couple things and

5:55

there's like a fake keyboard in there

5:57

just all kinds of

5:58

funny things to play with and then so I

6:01

was with my dad on weekends and my and

6:04

they both worked entirely commission so

6:06

I've never seen either of my parents

6:08

work for a salary and my mom's dad

6:11

didn't work for salary and my dad's dad

6:13

owned a motel and they all grew up on a

6:16

motel so there's like generations of my

6:18

family who wouldn't necessarily call

6:20

themselves entrepreneurs but they're

6:21

people who ate what they killed and

6:24

that's what I witnessed

6:26

money was good I think when I was like

6:29

you know when we were in San Diego and I

6:32

think it got tougher over time I

6:35

remember very vividly

6:37

being in a credit counselor's office I

6:39

just can't believe they brought me but

6:41

there was no I don't know where they

6:42

would have put me watching them

6:46

cut up their credit cards like cut their

6:49

credit cards in half and put them in a

6:50

clear jar with like other people's cut

6:53

up credit cards and file for chapter 11.

6:56

bankruptcy yep did you know what was

7:00

going on no

7:03

I still don't know what happened I don't

7:04

know

7:06

are you able to look back on that

7:09

that first sort of chapter of your life

7:11

and figure out how it had a lasting

7:13

impact on various elements of who you

7:15

are today

7:16

I think it allowed me to even though it

7:20

was so challenging younger in life to

7:22

learn how to assimilate into different

7:24

environments

7:26

um to I guess entertain myself

7:28

independently to realize that Authority

7:31

was

7:32

like adults were not trained to be

7:35

parents and weren't any further along

7:38

with their maturity sometimes than I was

7:41

at my age you know I looked at teachers

7:43

and thought wow you know you have domain

7:46

expertise you know some stuff but I can

7:48

tell that like you're morally bankrupt

7:51

and I don't trust you and why have I

7:53

been put in your

7:56

you know in your hands

7:59

um

8:00

I think the thing that had the biggest

8:02

impact on me is how critical my dad was

8:06

so he's half Italian and half Portuguese

8:10

and his dad was a mean mean guy

8:13

and my dad's very charismatic and I love

8:16

him and he's super chill now but when I

8:20

was young he had a lot of pressure

8:22

on him and he didn't really have the

8:25

best model of what a great parent looked

8:28

like and I can't say he was a bad parent

8:30

you know he did his best I know that

8:33

both my parents did their best with the

8:35

materials that they had the ingredients

8:37

that they had to be parents

8:39

but it instilled in me this

8:42

unfortunate but also very fortunate

8:45

always peeling back another layer of the

8:49

onion examining myself but also real

8:53

internalized drive to do better in a

8:56

self-criticism that has worked very well

8:58

for me that's been challenging it's

9:01

challenged my confidence over time but

9:04

it also has been a superpower to in some

9:07

ways I don't know in some ways hold

9:09

myself accountable because I'm always I

9:13

almost want to say second guessing

9:14

myself

9:15

but also very

9:19

um

9:20

in a very I guess someone said Jesuit

9:22

way at one point but

9:25

a way where I can see both sides of

9:28

everything you know challenging my

9:31

doubts and my ego

9:34

but the problem with that is sometimes

9:36

it's hard to differentiate between the

9:38

two what is

9:40

you know fiction and what isn't and what

9:42

of my self-critiques are accurate

9:45

because I want to be and I think I am a

9:47

pretty self-aware person

9:49

and even with the things that I'm not

9:51

great at I'm like super proud of that

9:53

because I've got

9:54

a ton of advantages and things that I'm

9:56

really great at but I think it was the

9:59

criticism I experienced early on in life

10:01

for so long that instilled that in me

10:04

and I've learned how to turn it into

10:06

something that's more balanced than

10:09

what it was when I inherited it

10:12

when you inherited it

10:14

when it was handed to me the model I had

10:18

the level of critique that I had that

10:20

didn't have the Counterpoint that I'm

10:22

able to provide for myself you're

10:24

talking about your funnel there yeah he

10:25

would critique you yes

10:27

when you say critique do you mean

10:31

oh that's that's naughty don't do that

10:33

no

10:34

no like that's not how you do something

10:36

or why why'd you do it like that or can

10:39

you not or

10:41

you know I mean I love my dad and

10:45

and he's you know as both of my parents

10:48

have gotten older they split when I was

10:50

17 and I've just watched them

10:52

both become such better people

10:55

I remember congratulating them when they

10:58

finally split up and was so glad at 17

11:01

years old and I was also like I'm out of

11:03

here

11:03

see ya

11:05

you seem to become a bit of a rebel

11:08

you know from from when you moved out of

11:10

your parents house

11:12

for the next couple of years the

11:14

behavior looked really rebellious oh

11:16

yeah no I mean I was rebellious from a

11:18

very early age

11:19

I remember in middle school a teacher I

11:24

was eating an apple in class I was

11:26

eating an apple it was healthy I was

11:28

hungry I've got agency over my body I

11:30

didn't know what that word meant I'm

11:32

hungry I'm gonna eat food I'm human I'm

11:33

hungry I'm gonna eat food in the middle

11:35

of class

11:37

but like who how could you tell someone

11:40

not to eat when they're hungry it's like

11:41

a simple bodily function and it keeps me

11:45

healthy and it's gonna make me a better

11:47

student and it's

11:49

and I and the teacher told me to throw

11:51

the Apple away

11:53

and I just started the apple and of

11:55

course I had the attention of the entire

11:57

class

11:58

and I got up and I sauntered over to the

12:03

trash can super slowly and I just like

12:07

ate the apple all the way to the core

12:09

like super fast finished the apple and

12:12

was like dink in the trash can

12:15

um so I was like that if if someone said

12:17

not to do something I did the thing that

12:20

they didn't say I couldn't do that was

12:22

similar it was peripheral

12:25

and then by the time I got to high

12:28

school I was going to the anarchist book

12:29

fair in San Francisco I was sure

12:33

capitalism was you know the worst thing

12:35

ever

12:36

I was very angsty I thought that

12:40

adulthood it's funny there's a Netflix

12:42

series about my life and the first thing

12:44

that the character says is adulthood is

12:46

where dreams go to die and it's so weird

12:48

to reference your own Netflix series

12:50

like who does that but

12:52

that's how I that's how I felt I wasn't

12:55

trying to be a child but I also didn't

12:57

want to go work in an office I also

12:59

wasn't ambitious so somehow along the

13:02

way that lack of desire to live a

13:05

conventional life became something that

13:07

turned into ambition because I not even

13:10

ambition just curiosity something that I

13:13

was good at and you know eventually

13:14

built a business but um

13:17

I uh in high school in high school

13:21

I remember there being Bells like right

13:25

there's a bell that rings and you go

13:26

from from one room to another room all

13:29

day a bell rings you sit at a desk a

13:33

bell rings

13:34

and you stand up and you Shuffle over to

13:37

the other room

13:39

and then you sit down and you like

13:40

memorize some stuff

13:42

and then you like this is my youth I was

13:45

sure I was being trained for something

13:46

super mediocre not that I wanted

13:48

Excellence I just wanted out

13:51

why are you like that because you know

13:53

all the other kids will come out like

13:55

that I actually came out I came out like

13:57

that yeah it is not I mean her I'm I

14:02

might have some hereditary just kind of

14:05

like Italian I'm not sure what or

14:09

something it's not it wasn't a nurture

14:11

thing that was

14:13

a nature thing or I don't know I just

14:16

like

14:17

came out I actually hatched out of a

14:19

disco ball but that's the way that's how

14:22

I came out I had a gabo mate here who's

14:25

this like I think he's just interviewed

14:27

Prince Harry actually

14:29

um in uh in a little like pay-per-view

14:32

therapy session or whatever and Gabriel

14:33

Mata said something to me that I've been

14:34

pondering ever since he said that

14:36

as children we're like narcissists and

14:38

we are that way because it helped us to

14:40

survive so we think that everything is

14:42

about us when we're like babies and

14:43

young so the parents were arguing we

14:45

actually interpret that as there being

14:47

something that to do with us and that's

14:49

the way we view the world as a survival

14:50

mechanism and he says one of the things

14:52

that happens when we're in a where you

14:54

were a young child and we're in a house

14:55

where there's lots of arguing and lots

14:57

of drama and shouting is we learn to

15:01

avert our attention as a way to help us

15:04

deal with emotional distress and that

15:06

develops into something they call ADD

15:07

and ADHD so I took Adderall this morning

15:10

hmm

15:12

hahaha

15:13

well they will yeah just to prepare for

15:15

the podcast just kidding now I've major

15:18

add

15:22

but they diagnosed me as a kid and I was

15:24

like no this is mind control

15:26

forget it I'm not focused because I

15:28

thought it was situational I thought it

15:30

was my environment and it maybe was

15:32

partially because I wasn't interested in

15:34

what was happening

15:36

and distracted because I was curious

15:38

about other things

15:39

but also it's a real thing and it wasn't

15:42

until

15:43

a few years ago that I finally realized

15:46

it was a thing and sought treatment and

15:49

it's helped but it's helped like

15:50

marginally it's not

15:52

I had to realize it was a real thing a

15:54

couple of years ago

15:56

I've I've been I mean you know I go to a

15:58

psychiatrist and I talk about what's

16:00

going on with my brain and

16:04

um do what I can to help myself

16:08

um holistically but also I know I'm also

16:12

predisposed to depression not

16:14

predisposed I've suffered with

16:16

depression my whole life since when

16:19

my whole life I don't I can't remember

16:21

an age where I wasn't

16:23

depressed I just

16:26

I wasn't always miserable but I've I'm

16:29

kind of a dark I'm a little dark

16:31

um

16:32

and that's not something you know it's

16:34

hard to pull yourself out of a hole when

16:36

you don't want to get out of bed like

16:39

that's you know to have the willpower to

16:42

just get over depression and put on a

16:45

happy face and whatever people do get an

16:47

ice bath and jump in the sauna and

16:49

meditate and

16:51

you know I am still struggling to be the

16:53

well-rounded person but I'm functional I

16:55

think we're all struggling to be a

16:57

well-rounded person I don't know some

16:58

people seem to like have these parents

17:00

that teach them that and they come out

17:02

and they're like yeah you know and it's

17:05

not you know that's almost diminishing

17:08

to be like

17:09

but

17:11

but I'm yeah there's people who just

17:14

seem to you know and some people come

17:16

out of the womb like that I know parents

17:18

that are creative chaotic I know people

17:21

who are well-rounded whose parents were

17:23

addicted to drugs and somehow they just

17:27

wound up like that and how to attribute

17:29

that to your parents it's that's a hard

17:31

correlation to make did you ever you

17:33

said it curious phrase now which

17:36

made me um

17:38

Ponder you said I'm a little dark uh-huh

17:43

what do you mean by I'm a little dark

17:46

hmm

17:55

why are you giggling you're making me

17:56

think you are a little dog I am I'm not

17:58

evil God uh I'm not a witch

18:03

I

18:06

I guess I've

18:07

just

18:09

you know like I said I've struggled with

18:11

depression

18:12

I'm not a bubbly person I'm not someone

18:16

you know as a child my mom has said you

18:20

only laughed when something was really

18:21

funny you know I think kids run around

18:23

like laughing and smiling because

18:25

they're like children or something but I

18:27

had to have a reason

18:29

I'm not sure why and it's still kind of

18:31

like that and maybe it's I don't know as

18:33

an adult it's become something that

18:35

requires it's just being genuine and

18:38

maybe I'm not I think maybe I'm not

18:41

impressed maybe in general I'm just

18:44

skeptical you went to see a psychiatrist

18:46

when you were 16. oh I went to see a

18:48

psychiatrist when I was like 10. I mean

18:51

I was in therapy

18:53

when I was like 10 11. with what's

18:56

trying to be diagnosed like what's wrong

18:58

with her why can't she stay on task why

19:00

is she so weird why doesn't she get

19:02

along

19:03

why is she distracted so I have report

19:05

cards

19:06

that say

19:08

chooses to disturb others you know

19:11

doesn't stay on task it's stuff like

19:14

that it was like I was always like you

19:16

know not paying attention curious about

19:18

something else engaged with something

19:19

else it wasn't always to be rebellious

19:22

sometimes it was very good-natured and I

19:25

would get in trouble for things that I

19:26

didn't think were bad or intend to be

19:28

bad it was also just very a very willful

19:33

independent thinker who didn't fit into

19:37

a traditional educational environment

19:39

and

19:41

you know that's something

19:43

for whatever reason seemed to be needed

19:46

to

19:47

be diagnosed

19:49

but then I was like no no I'm not taking

19:52

Wellbutrin and I'm not going to take

19:54

it's like an antidepressant I didn't

19:56

take it I was like no I'm not taking any

19:58

of this when did they win right that was

20:00

by high school so you were 16-ish around

20:02

that time when they yeah 15 16 and I was

20:04

like this is

20:07

it's I don't feel like myself feel wired

20:11

and weird and

20:12

I got like I think I got Ritalin and

20:14

someone tried to buy it off me in like

20:16

high school and I was like what do you

20:17

what I don't even get it I was like I'm

20:20

just throwing this stuff in the trash I

20:22

didn't

20:24

and then so you so you get diagnosed and

20:26

prescribed antidepressant at 16ish your

20:30

parents break up at 17ish you leave them

20:32

I move out you move out I move out at

20:34

17. before I graduate high school I was

20:37

homeschooling so I got my diploma in the

20:38

mail I thought the like most

20:41

embarrassing thing would be would be to

20:42

wear the cap and gown I was like what is

20:45

that I don't understand what's the

20:47

tassel why do you have to wear a robe

20:49

what is this robe

20:51

I I wouldn't have been proud standing in

20:53

a group doing some group thing I'm not a

20:55

group person even though I've built a

20:57

lot of really powerful communities I'm

21:00

not I don't assimilate well into groups

21:02

and I think groups are responsible for

21:03

the most heinous things in like human

21:05

history so uh

21:08

[Laughter]

21:10

so I moved into a closet

21:12

you moved into a closing under the

21:14

stairs for sixty dollars a month

21:18

uh these guys that were like in bands

21:20

and artists who had met going to shows

21:24

because I was really into music and went

21:27

downtown in Sacramento and saw music and

21:30

what was the plan in life at that point

21:32

was there a plan you know you're like 17

21:33

years no you told me there was a plan I

21:36

wanted to go to

21:37

first wanted to go to Reed College but

21:40

that was expensive

21:42

but then I wanted to go to the Evergreen

21:43

College so by the time I was 18 I had

21:46

moved to Olympia Washington to get

21:48

residency to go to the state school

21:50

called the Ever Supreme State College

21:52

which is a super duper hippie state

21:56

school that's interdisciplinary and

21:58

there's no majors

22:00

to the point of it not really being

22:03

worth

22:04

going but if I was gonna go to college I

22:07

was going to go to a place like that but

22:09

even state tuition was expensive so I

22:12

lived in Washington state for a year to

22:14

get state to get residency

22:17

so I could go to that school and by the

22:19

time

22:20

I got residency I was like this school's

22:21

not gonna do anything for me you

22:25

described this chapter of your life as

22:26

being very lost

22:28

super lost super lost I was looking for

22:30

my I kind of hate this word

22:32

tribe

22:35

I was looking for people like me I

22:37

thought I would find people like me and

22:38

then all would be well like uh you know

22:41

some Disney character that you know ugly

22:44

duckling or someone who loses you know

22:47

they're lost from the wolf pack I don't

22:49

know what these movies are and then they

22:50

find their family and people understand

22:52

them and so from the time I was 17 I

22:56

moved from

22:58

Downtown Sacramento to Olympia

23:00

Washington lived in two places there

23:01

Seattle lived in two places there San

23:04

Francisco

23:05

lived in one or two places there

23:08

Oakland with my alcoholic fry cook

23:11

boyfriend I had met in Olympia we

23:14

couldn't get jobs and my parents were

23:17

like yeah we can't help you with college

23:20

stuff so then we moved to Portland

23:25

I was a stripper I was lost I was lost

23:28

that's an interesting time a ton of

23:30

events yeah that was an interesting turn

23:33

of events

23:34

and that chapter of your life in some

23:37

ways mirrors the transience of the start

23:39

of your life you said you moved to like

23:41

eight eight or ten different schools

23:43

when you were young

23:44

and then when you leave the nest you end

23:45

up bouncing around as in your own words

23:48

like looking for

23:49

your family I was yeah I was looking for

23:51

some place to belong and I never found

23:53

it and I kind of love that

23:55

because it's forced me to make my own

23:58

and force me to stay creative thinker

24:00

and also

24:01

I don't know I this isn't fair but the

24:03

people in some of those communities like

24:06

peaked and never left it's like you know

24:08

I listen to pop punk in high school can

24:11

you imagine I'm sorry if anybody

24:13

listening is like never graduated from

24:15

listening to pop punk but if you don't

24:17

graduate to metal or some other it's not

24:22

even more sophisticated but like less

24:24

juvenile varieties of rock it's the same

24:28

as finding you know some

24:31

comfortable Community when you're 20 and

24:35

then never leaving like that sounds that

24:37

sounds awful to me so I'm I'm glad I

24:41

didn't find a comfy place

24:44

and it's been uncomfortable since then

24:47

how long did you try this stripping

24:48

thing

24:49

I don't know I mean when you're in your

24:51

late teens early 20s

24:54

time just feels like it felt like a

24:57

decade that I was you know bouncing

24:59

around to these places probably three or

25:01

five months it was fun I loved it nobody

25:05

pulled anything I never got messed with

25:08

I drank my white Russians and ate the

25:11

Subway sandwich from next door and

25:14

played photo hunt and I wasn't even 21 I

25:17

used someone else's ID to work there

25:19

and I got to dance to music that I liked

25:23

I made money I didn't really have to

25:25

engage with anybody

25:27

and I got really comfortable with my

25:29

body in a way that I hadn't before and

25:32

that was cool

25:33

yeah they say

25:35

I've read a new book where you said that

25:37

you believe you hold the

25:40

world record for having the most shitty

25:42

jobs like back to back throughout that

25:43

period of your life they say you know

25:45

I've learned this from this podcast that

25:46

every job teaches you something and that

25:49

thing can be applied to business there's

25:50

always a sort of a transferable skill or

25:52

whatever learn what was the transferable

25:55

skill

25:56

but you learn from stripping that you

25:58

think has probably stayed with you

26:01

today

26:03

I think that even though I wasn't didn't

26:06

have the upper body strength to be the

26:08

traditional one upside down swinging

26:11

around

26:12

what I could do I mean it was like

26:14

Shuffle around and whatever was enough

26:18

and still charismatic enough and still

26:21

great enough to

26:23

entertain other people

26:25

and then being comfortable with my body

26:27

it's like exposure therapy you know I

26:30

was the girl at

26:32

18 it would like make out with someone

26:35

and then if I was like naked or

26:37

something I'd like

26:39

put on my clothes to go to the bathroom

26:41

or something I was like

26:43

not I didn't sleep with anybody until I

26:46

was 19. so I was just I was kind of late

26:48

by 20 I was

26:50

tripping in Portland

26:53

I'll tell you the crescendo of that

26:55

experience so dating with dating Wade

26:58

the

26:59

alcoholic fry cook who was 10 years

27:01

older than me

27:03

uh

27:04

I like I was on birth control I went off

27:07

birth control for like one day and there

27:10

was almost we were hardly even you know

27:15

engaging in the way that someone might

27:18

like get pregnant like so briefly like

27:23

that day

27:27

yeah I'm like I don't know

27:30

who's watching and uh and I wound up I

27:34

want it pregnant

27:36

so I'm like 20.

27:38

Maybe 19. and

27:43

I went to the sliding scale Women's

27:44

Clinic

27:46

and

27:47

but but it was the only day I could get

27:50

in but it also happened to be

27:52

the day of my court date because I had

27:55

gotten arrested for shoplifting

27:59

so I had to have the Women's Clinic

28:01

write an excuse to the court telling

28:05

them why this poor girl couldn't make it

28:08

to her court date and the whole thing

28:09

got they were just I kept following up

28:11

to be like when is it rescheduled and I

28:13

think they all just felt so bad for me

28:14

it kind of vanished but that was that

28:18

was like okay no more shortcuts it

28:20

wasn't like I'm gonna go be a CEO but it

28:24

also

28:25

just

28:26

taught me that

28:29

breaking some rules puts you in other

28:33

people's hands and I was you know being

28:37

arrested I'm not as autonomous as I

28:40

would have liked to have been and you

28:43

know even with stripping to a certain

28:44

extent it was a shortcut I was trying to

28:46

evade like working hard but it was also

28:49

a lot of fun but that was really that

28:52

was a low point it's had lots of low

28:54

points

28:55

um but at least it's like this right

28:58

it's been like this

29:01

you know doesn't

29:03

it doesn't ever go that low

29:06

there's clearly um a slight issue here

29:08

with authority and it feels to me like

29:10

the ultimate Authority which is the law

29:12

eventually was like he can't [ __ ] with

29:14

us we're not the teacher yeah it was

29:15

like okay like maybe just figure out how

29:17

to get along you know

29:20

it wasn't like wow I'm gonna go have a

29:22

career and do

29:23

everything I'm I'm gonna just do

29:25

everything differently but also

29:27

I just didn't want to cut Corners I

29:30

didn't want to

29:32

end up

29:33

not in control of my environment or

29:36

stuck in jail or something stupid

29:38

shoplifting

29:40

mm-hmm

29:41

why'd you make that sound I don't know

29:43

it was fun

29:46

what was your favorite thing to steal

29:50

I don't endorse shoplifting neither do I

29:52

my rationale for shoplifting was that

29:56

there was so much excess

29:58

in you know our culture that it would

30:02

never make a dent to steal organic

30:04

tampons from Fred Meyer which is like

30:06

Target

30:07

in Portland or whatever

30:09

so

30:11

I uh

30:12

when I did get caught and this was my

30:14

favorite thing was just walking out with

30:16

stuff

30:17

so I would get a whole shopping cart of

30:19

stuff I had a little teeny tiny little

30:21

razor thingy so I knew where the sensors

30:25

were and I would cut them off they were

30:27

there

30:28

and pile a shopping cart high and just

30:33

walk out with no bags or anything I did

30:36

it at grocery stores I I furnished

30:38

apartments I walked out of places with

30:41

like literal rugs this High just walked

30:44

out because nobody expects you to be

30:46

that like obvious about it they're

30:50

looking for somebody who's like putting

30:51

stuff in their pockets

30:53

and when I did get caught

30:57

I had like a George Foreman grill

30:59

I think a basketball

31:01

organic tampons some food really nice

31:05

shower curtain rings they were metal and

31:07

then they had like ceramic they were

31:09

heavy and they had like a ceramic thing

31:11

that said hot and then the other one

31:12

said cold and I was like yes this is

31:15

this is luxury

31:17

It's Worth jail time so that was yeah

31:19

and

31:22

you know I built an online business and

31:24

the first thing I sold online was stolen

31:27

so another thing and I learned this from

31:30

people who were professionally trying to

31:32

like avoid getting jobs and

31:35

participating in

31:37

capitalistic culture which is a

31:39

privilege it's lazy

31:42

it's it was it was yeah I was really

31:44

young and I just didn't want to work you

31:48

know it was some kind of quasi-political

31:50

lazy excuse for just not working hard

31:53

anyway I learned from some of the best

31:58

um I had a friend who had written a book

31:59

called evasion literally and

32:03

I would go into Barnes and Noble

32:06

and they had a no chase policy like I

32:09

knew what the policies were at these

32:10

places because if their employees Chase

32:12

someone shoplifting it's gonna cost them

32:15

way much more if they get like knifed or

32:18

something than it would for them to lose

32:19

a few books

32:21

and so I would go on Amazon

32:24

and I would look at the

32:26

best-selling books this is in 2002 2003

32:30

it's like and

32:33

even look at the ratio of most expensive

32:37

book to least pages so I could stack

32:39

them as many of them as high as possible

32:42

and I would just walk to the front like

32:44

the front of the store would have all

32:45

the best sellers and huge stacks and I

32:48

would just like

32:50

piled them hide I look like an employee

32:51

like who's carrying a huge stack of

32:53

books I was right in the front of the

32:55

store and I just like walked my car and

32:57

I'd put them on Amazon for 10 cents less

33:00

than all the other resellers I'd sell

33:02

them overnight I'd ship a Media Mail and

33:04

I'd pay my 350 a month rent

33:07

why weren't you scared

33:10

I think I was but it's when you get

33:12

scared that you get caught

33:14

and it's when you hesitate you fail it's

33:16

the same thing

33:17

if you're snowboarding and you're like

33:19

oh it's kind of icy let me look down

33:22

you're just like catch an edge you're

33:24

surfing and you look at the nose of the

33:27

board

33:28

right

33:29

so even that's what you're a life lesson

33:31

I guess I guess we'll say I'm not proud

33:34

of this

33:35

I was really young and I was finding my

33:37

way I never

33:39

stole from individuals that was like not

33:42

on thesis for me

33:45

no I couldn't justify it I would never

33:48

feel comfortable doing it

33:50

um but big box retailers I was like over

33:54

the last couple of how long maybe four

33:56

months I've been changing my diet shall

33:59

I say many of you have really been

34:01

paying attention to this podcast will

34:02

know why I've sat here with some

34:04

incredible Health experts and one of the

34:06

things that's really come through for me

34:07

which has caused a big change in my life

34:08

is the need for us to have these

34:11

superfoods these green Foods these

34:13

vegetables and then a company I love so

34:16

much and a company I'm an investor in

34:18

and then a company that sponsors this

34:20

podcast and I'm on the board of recently

34:22

announced a new product which absolutely

34:25

spoke to exactly where I was in my life

34:27

and that is huel and they announced

34:29

Daily Greens Daily Greens is a product

34:31

that contains 91 superfoods nutrients

34:35

and plant-based ingredients which helps

34:37

me meet that dietary requirement with

34:39

the convenience that hewell always

34:41

offers unfortunately it's only currently

34:43

available in the US but I hope

34:46

I pray that it'll be with you guys in

34:48

the UK too so if you're in the US check

34:50

it out it's an incredible product I've

34:51

been having it here in La for the last

34:53

couple of weeks and it's a game changer

34:55

ladies and gentlemen our newest brand

34:57

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34:58

to regular listeners on this podcast the

35:00

first episode of 2023 I was joined by

35:03

the incredible Professor Tim Spector to

35:06

hear more about his work at a company

35:07

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35:10

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35:12

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35:15

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35:17

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35:18

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35:20

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35:22

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35:24

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35:28

an investor in the company and that is

35:30

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35:31

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35:33

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35:35

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35:38

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35:40

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35:48

much let's get back to the episode so by

35:50

this time you're getting a little bit

35:51

acquainted with the internet and selling

35:52

things on the internet clearly because

35:53

you're selling stolen stuff yeah yeah

35:56

vintage mm-hmm

35:59

why why vintage why did you start to

36:02

sell vintage clothes

36:04

yeah so by 2000

36:06

six

36:08

I had gotten some real jobs now after

36:12

after I'd worked in shoe stores and

36:14

record stores and Photo Labs and

36:16

Subway again

36:18

I like dry cleaners

36:21

I

36:23

how did you get on with those jobs

36:26

it didn't last very long I like job-free

36:29

alphabetized things though so record

36:30

stores

36:32

Photo Labs bookstores like paper makes

36:36

me feel important for some reason

36:37

mailing things I don't know it worked

36:40

out with my eBay store

36:42

and the last job I had was in the lobby

36:45

of an art school in San Francisco at 79

36:48

new Montgomery Street called The Academy

36:50

of Art University it was a job I got

36:53

because I needed to get health insurance

36:54

and at the time you couldn't get health

36:57

insurance with a pre-existing condition

36:59

you is this your hernia yeah the Hearn

37:04

the Hearn yeah so a hernia if you don't

37:07

know what it is is a place it's a hole

37:10

in your muscle wall that your guts poke

37:12

out of and it makes a little bump and I

37:15

had one kind of in my groin area I

37:17

called an inguinal hernia

37:19

and it didn't hurt but they're kind of

37:22

dangerous because they can like if your

37:24

muscle tense is up or something they can

37:26

get strangulated and necrotic which is a

37:29

disgusting word

37:30

so I had to get it fixed but before I

37:32

got it fixed it was kind of fun I shaved

37:34

everything but the hernia

37:37

my poor boyfriend my poor boyfriend and

37:41

um yeah it was entertaining it was kind

37:43

of funny to have like a small lump in my

37:45

pants for

37:46

a few weeks or something

37:49

but at the time you could not get health

37:51

insurance with a pre-existing condition

37:52

even with depression if you had medical

37:55

records that said you had depression and

37:56

your insurance lapsed insurance

37:58

companies would decline you now that's

38:01

not the case you can have a pre-existing

38:03

condition apply for health insurance

38:04

you'll be given health insurance you

38:07

could only get health insurance with a

38:10

pre-existing condition like a hernia

38:14

with group health insurance with a job

38:18

so I had to go

38:20

find a job that had health insurance

38:23

and I got this job in the lobby of the

38:25

art school as a campus safety host which

38:28

was a different way of saying you're

38:30

cheaper than a unionized security guard

38:32

and I wore a starchy white shirt it was

38:35

like a men's clothing I had to wear this

38:37

awful uniform with like a magnetic thing

38:40

here that had my name and the school's

38:42

logo on it and check students in and say

38:47

hi you need to sign in can I see your ID

38:49

that was were you doing anything sort of

38:51

criminal at this point my job no so all

38:53

of your money came from that job and

38:56

yeah and so there was a three month

38:59

waiting period for health insurance

39:02

and while I was there I had time to

39:05

I had some down time in this Lobby and

39:07

there's a computer

39:08

and uh there's no Facebook or Instagram

39:10

at the time this is

39:12

2006.

39:14

and I was starting to get friend

39:17

requests from these eBay sellers on

39:19

MySpace

39:20

I wore only vintage I was like you know

39:23

root and toot and Scootin to like oldies

39:27

and rock and roll and dive bars and

39:28

subsisting on burritos I loved vintage I

39:31

wore vintage I wasn't necessarily into

39:33

fashion and I didn't want to be in

39:36

fashion but I loved style and I loved

39:39

vintage

39:40

and I loved thrifting

39:41

and I saw what they were doing

39:43

and their auction prices were crazy like

39:46

I thought hate Street was expensive

39:49

because I had shopped at thrift stores

39:51

and found great stuff

39:53

and saw what their auctions were going

39:55

for and these were actual prices that

39:56

the customer was determining

39:58

they would start the auction price at

40:00

9.99 and these things were going for

40:02

like 200 300 and they were just making

40:05

it look like something that Sienna

40:08

Miller some boho at the time it was like

40:10

boho Olsen twins Sienna Miller kind of

40:13

Vibes and they would do that put this

40:18

stuff online and the customer determined

40:20

the price and it was so much money and

40:24

so I thought okay so I waited my three

40:26

months for my health insurance because

40:27

there was a three-month waiting period

40:28

it got the Hearn fixed and I started an

40:32

eBay store and I wasn't trying to be an

40:34

entrepreneur I was trying to

40:37

legitimately not work for anybody and

40:40

that's when I realized that I could

40:42

connect my curiosity and Independence

40:45

and creativity and resourcefulness

40:50

to something

40:52

legitimate that made money that I

40:54

learned from every step I was taking and

40:59

started nastygal selling vintage out of

41:02

my boyfriend's apartment before that

41:04

point

41:05

would people have called you lazy

41:07

or unmotivated

41:09

I didn't know any people who would have

41:11

said something like that because my

41:13

friends were just like me so objectively

41:17

then objectively

41:19

I think just lost I think it would be a

41:22

judgment to say I was lazy

41:25

I can relate to so much of what you've

41:26

said especially all the stuff about

41:27

Authority like I just decided to stop

41:28

going to school and I was polite about

41:30

it but I I've always had a challenge

41:32

with authority every job I had

41:33

throughout through that period of my

41:34

life lasted for three months I was just

41:36

cool center hopping get to the bonus

41:38

threshold quit gives me two months where

41:40

I don't have to get a job call up

41:42

another course employed those people

41:44

yeah I'm one of them and it's funny

41:46

because I think people would have looked

41:47

at me in school and stuff and said

41:49

like written me off oh it's he's lazy

41:51

well like my thesis is that everyone

41:54

most people are lazy and you should be

41:56

lazy for things that you absolutely hate

41:57

doing

41:58

okay you should be so yeah I'm only

42:00

motivated by things I'm curious about if

42:02

someone assigns me something like I've

42:03

tried to write a second book and

42:06

published two books after girl boss

42:08

which was a thing

42:10

I can't I cannot be assigned something I

42:14

it either comes out or it's not there

42:18

that's the do you think that's the the

42:19

rebel in you

42:21

that is but it's why everything I do is

42:23

so inspired and honest and

42:25

I don't want to be like I'm unique but

42:27

because you never accepted or learned

42:29

compliance it's an actual representation

42:31

of who I am and what I think and how I

42:34

feel and my perspective instead of a

42:37

manufactured version because somebody

42:38

has given me an assignment like you

42:40

didn't even want the bell in school to

42:41

tell you what to do no

42:44

the gift in a curse though right

42:46

I mean it's pretty logical that you

42:48

would question

42:50

a bell ringing and someone moving from

42:54

one room the same room to the next room

42:56

every single day what do you think

42:58

anyone else no

43:01

no

43:03

but if you really think about it it's

43:04

pretty wild right

43:07

that that eBay store that you start with

43:09

in your free time when you're working

43:10

that job

43:11

you took to fix the Heron

43:15

um

43:16

it was successful

43:18

yeah and you know you kind of frame it

43:21

as you saw maybe a price Arbitrage or

43:23

whatever but but it's more than that

43:25

right it's more than that to be

43:27

successful at that time I'm not sure a

43:28

lot of people saw that price Arbitrage

43:29

and they didn't build a nasty girl so

43:32

when you reflect on why and how

43:34

you were particularly successful how did

43:37

you diagnose that

43:39

I reverse engineered everything everyone

43:41

else did and did a better job and did it

43:44

with my

43:45

signature on it do you think and I'm

43:48

thinking now about that Bell again in

43:49

school where you were like analyzing the

43:51

Bell where no one else was do you think

43:52

that kind of default to thinking in

43:54

terms of first principles like asking

43:56

the question why why the [ __ ] do we do

43:58

it that way has been part of the reason

44:00

why that eBay store was successful

44:03

I think so

44:04

I think

44:06

most people that started an eBay store

44:08

are copying what other people are doing

44:11

they might reverse engineer some things

44:14

and see what their competitors are doing

44:16

and I did that but I just did it 10

44:18

times better with a totally different

44:20

spirit with excellent copywriting with

44:23

great styling great models and

44:26

increasingly better photography and I

44:29

would I was extremely resourceful I

44:33

would buy stuff on eBay and sell it for

44:34

more than I paid for it I was searching

44:37

for Eve's son Laurent just misspelled

44:40

you know

44:41

the song

44:43

but even that's the first principle

44:45

thinking that's like

44:47

but you've got a convention on one end

44:48

which says just like do what's being

44:50

done and then you've got these like

44:52

first principle thinkers who kind of

44:53

think first about what they know to be

44:55

true and they're really good at

44:56

filtering out convention they can kind

44:58

of see throughout the truth whereas

45:01

convention like is safety it's Comfort

45:02

it's it guarantees you a pre-tried

45:06

blueprint so people follow that but then

45:08

these other little Rebels

45:09

they they have this almost inbuilt

45:11

ability to just like [ __ ] see through

45:13

to the that that truth that nobody can

45:16

see and in that case I mean that's a

45:17

great idea but even caring more about

45:19

the copy and you having your own belief

45:21

as to why the copy matted or the

45:22

photography like why photography really

45:24

really mattered on eBay yeah on eBay

45:27

which a lot of people would have had

45:28

like that's um and it was called Nasty

45:30

Gal the spirit of it was really

45:32

irreverent at the time the eBay sellers

45:36

were selling like you know is called

45:38

Mama Stone vintage was a really big one

45:40

and it was all very hippy dippy and

45:42

vintagey and mine was vintagey but it

45:44

was like very hard-hitting edgy

45:48

I named it after an album by a woman

45:50

named Betty Davis who had an album

45:53

called Nasty Gal she was

45:56

so stylish uh in the 70s put out some

46:00

incredible records was married to Miles

46:02

Davis for a short period

46:04

and was allegedly too wild for him

46:08

her lyrics are just so and I was

46:10

stripping her music when I was like 20

46:12

and then I was like cool nasty girl and

46:16

it cut through the noise and I think

46:17

when you start a business and you don't

46:19

need to survive you might have more time

46:22

to Naval gaze or you might do things

46:24

super conventionally

46:26

but when

46:29

you need to survive there are certain

46:31

things that other people have done right

46:34

that you can see you know accelerate

46:36

what it is that you may do on your own

46:40

but learn from them and then also take

46:43

and make your own way I think had I

46:46

tried to do things completely

46:47

differently than everybody else

46:49

I wouldn't I wouldn't have survived I

46:53

would have been dead in the water

46:54

speaking to something really interesting

46:56

there which is like this Balancing Act

46:57

between naivety which is great for

47:00

innovation and then convention which is

47:02

great for staying alive I'm talking

47:04

about like the the nasty girl needing a

47:07

CFO

47:08

yeah you see what I mean or like that's

47:10

what how I feel when being a young

47:12

founder 21 years old start this business

47:13

it grows incredibly quickly okay the

47:15

naivety made us interesting but our

47:17

naivety will also send us to the Grave

47:19

here if we're not yeah if we don't know

47:21

what we don't know I've been to Hell

47:23

I've been I died and now I'm in the

47:25

afterlife I it did send me to the Grave

47:27

my naivete and lack of experience did

47:29

send me to the Grave it happened so fast

47:33

that's a quote

47:35

um it was shocking how fast it all

47:37

happened nasty girl went from doing 150

47:40

000 a year to doing 150 000 a day and

47:43

then 150 000 over lunch

47:46

yeah 150 000 over lunch

47:49

it was either a day or over lunch that

47:52

we all worked out of this Warehouse it

47:53

was a bunch of kids in the East Bay

47:56

in Emeryville I had the 7 000 square

47:58

foot Warehouse which I thought was the

48:00

hugest thing and I was like when we hit

48:02

150 000 a day God was it a day it must

48:05

have been the holidays I was like I'm

48:06

gonna get a bounce house you know those

48:09

things that people jump on the

48:11

inflatable things the children that

48:14

children jump on it was an upside down

48:15

horse and its legs were in the air when

48:18

he jumped on it the legs like that's

48:19

what you wanted

48:21

and in between you know on our breaks we

48:23

got to jump in the bounce house I was

48:25

like

48:26

23 24 years old it did happen really

48:30

quickly to be fair now you say it when

48:33

we raised investment for the first time

48:34

the first thing I bought was a 13 000

48:37

pound slide

48:39

big blue slide which we had in our

48:41

office that was the first thing I bought

48:42

before we got desks so talking about

48:45

neither today I bought I paid off my

48:47

mom's mortgage oh did you okay I

48:50

couldn't do that with investor Capital

48:52

no it wasn't with investor Capital no it

48:54

was the first time I made money yeah my

48:57

slide was with investor one okay yeah no

48:59

no they actually those investors did

49:00

really well they got bought out within

49:02

six months so they got a big return but

49:03

good job yeah what do you attribute at

49:06

such a young age I'm just gonna

49:07

interview you for a second because you

49:10

couldn't have had a ton of experience

49:12

under leaders to give you a model of

49:14

what leadership looked like you were

49:16

naive

49:17

you know could you I couldn't empathize

49:20

with the people I was managing because I

49:22

had never experienced leadership and I

49:24

just showed up and I did what I I what

49:26

needed to happen and what I said I was

49:28

going to do I didn't understand that

49:29

people needed to be held accountable

49:31

because I held myself accountable

49:32

especially c-level Executives and

49:34

grown-ups whose careers were longer than

49:37

I had been alive like how did you do

49:40

that at such a young age well I think I

49:42

I think I messed up I think like for the

49:43

first two years I hired people that were

49:45

very very inexperienced I reflect and I

49:47

go I think I did that because I thought

49:49

they were easier to manage and I

49:51

couldn't fathom the concept that I could

49:53

hire someone who was two times my age

49:56

and three times my experience and Avid

49:58

want to come here and be with us with

49:59

that with our sliding dogs and tree and

50:01

basketball court and ball pool and they

50:04

would like take us seriously but also

50:05

like be like maybe there was an

50:07

insecurity about how I'd manage them and

50:09

so what ends up happening is you I hired

50:11

lots of like young people

50:12

you know a member of the BBC did an

50:14

article saying is this the youngest

50:15

company in Britain because I think we

50:17

were like somewhere but our average age

50:18

was maybe 20 or something and we had

50:20

like we had like 100 almost 100 people

50:22

you know and you feel the strain of that

50:25

you feel things breaking this is where

50:27

you go

50:28

convention is right about some things

50:30

processes HR Finance you feel things

50:33

breaking at the seams a little bit

50:34

because of the growth um and then at

50:36

some point an adult enters the room

50:39

and you go oh

50:41

I get this and so we hired some some

50:44

really really great people and the great

50:45

thing is great people hire great people

50:47

so we went from being this kind of very

50:49

lopsided inexperienced organization to

50:51

being a balanced one and I say balance

50:52

because it's my belief that to own the

50:54

future you have to understand the

50:55

present which is why you want to hire a

50:57

16 year old that gets Tick Tock or

50:59

whatever and you also need to hire

51:01

someone that's maybe

51:02

double their age experienced in client

51:05

services and understands the old rules

51:08

of the game if you understand both games

51:10

you can understand the game of the

51:11

future I think so

51:12

um made a lot of mistakes and when I

51:14

nearly went under several times and had

51:16

to call people and beg for money

51:18

um in the lead up to Payday but

51:20

somehow managed to survive but go back

51:23

to you now

51:25

um I feel that we missed a park because

51:27

you know you write the reception you

51:29

went from starting that store to

51:30

bouncing around on that bouncy castle

51:32

thing we call it bouncy castle okay

51:36

horse Castle between that between that

51:39

bouncing on that horse castle and the

51:41

starting the store

51:43

what happened

51:45

so

51:47

first year

51:49

just on eBay did 75 000 in Revenue I was

51:52

the only employee it was just you know

51:53

it was pure cash

51:55

all of the money just went back into the

51:57

business I didn't even know what

51:58

expensive things I would have wanted I

52:00

didn't I had never eaten an oyster you

52:02

know I was drinking like

52:04

Budweiser or you could still like

52:07

subsisting on Boston Market and like

52:09

Starbucks

52:11

so I didn't spend any of that money I

52:13

thought building a business and I think

52:15

for the most part it is

52:17

uh was

52:19

selling things for more than you bought

52:21

them for and not spending all the money

52:24

that's it

52:25

that's all and so I bought things I sold

52:28

them for more than I paid for them and

52:30

no one else would have given me money

52:31

parents weren't gonna give me money

52:33

I don't even think I had a credit card

52:35

at that age

52:36

I didn't understand what Venture Capital

52:38

was and I was living in the Bay Area

52:41

and had I not built the company to

52:43

eventually you know 28 million dollar

52:45

run rate super profitably I would never

52:49

have known

52:50

and so yeah year two left eBay about

52:54

halfway through and launched my own

52:55

website nastygalvintage.com

52:58

and did 250 000 in Revenue

53:02

the next year did 1.1 million the next

53:05

year did six and a half

53:07

the next year did 12 and I was coming

53:10

off a 12 million dollar a year uh

53:13

Revenue

53:14

owned 100 of the company

53:17

had a bunch of kids working for me

53:20

and that's when Venture capitalists came

53:22

in and at that point you know

53:25

we were selling non-vintage stuff what

53:28

really allowed the company to scale was

53:30

going to trade shows and showrooms and

53:31

curating from the market based on what I

53:34

had learned from my customer having sold

53:36

vintage to them so I knew them very very

53:38

well and that gave me the ability to

53:40

then go by greater breadth and depth in

53:45

things I knew they would love

53:48

and that's what 2011-12

53:51

Venture Capital comes in 2012 was when

53:54

index Ventures invested 60 million

53:56

dollars 60 million dollars on a 350

53:59

million dollar valuation on a business

54:01

with a 28 million run rate yeah you're

54:04

profitable at that time

54:06

significantly

54:07

pretty significantly I have a 10 or 20

54:10

nothing I don't know I don't know I

54:12

didn't even look at that I was I I never

54:14

had to learn to read a p l because my

54:16

company was profitable and I just

54:18

you know generally knew how much it cost

54:20

to run I didn't it and I and I didn't I

54:24

didn't buy expensive office chairs did

54:26

you did you know you like gross margins

54:28

on on your on the product yeah on the

54:30

operating margins no I don't I don't

54:32

think I didn't understand what operating

54:34

margin was

54:36

um pretty incredible that you can be

54:37

running a business that's generating has

54:39

a 28 million dollar a year run rate and

54:41

not know what operating margins you're

54:43

dealing with or what your net profit is

54:45

it's a luxury but it was also a

54:48

disadvantage once we plowed 60 million

54:50

dollars into the business and things got

54:52

a lot more complex and a lot less

54:54

profitable

54:56

you talk about the 60 million going into

54:58

nastygon in 2020 to 2012.

55:02

what did it break hmm

55:05

I mean we

55:07

no longer had to live within our means

55:10

that's what investor money does unless

55:12

you maintain profitability and keep that

55:14

money in the bank for you know another

55:17

time or pocket all of it as a founder

55:21

we you know I had hired a COO at that

55:25

time I had a top tier investor on my

55:29

board

55:30

and

55:32

very little like historicals data

55:36

financials

55:38

to base the future growth on but it had

55:42

been exploding just continue to be

55:44

exploding and with that Capital behind

55:46

us we could grow even faster

55:48

and the expectation was that the next

55:52

year we would grow from 28 million in

55:55

Revenue to 128 million dollars in

55:58

Revenue we just rounded up by 100

56:00

million and then we hired into that and

56:03

we bought into it

56:04

oh you believed it and everyone I had

56:07

grown-ups forecasting this stuff with me

56:09

I relied on them it's why I brought them

56:11

in you hired the right ones clearly I

56:14

didn't pick the right ones or I'm not

56:16

sure what happened but I remember

56:17

sitting in a room with them

56:19

and

56:21

us deciding I didn't push for it this

56:23

wasn't you know

56:25

we're gonna just grow by 100 million

56:28

dollars this year and

56:30

someone put a plan together and this is

56:32

we hired 100 people it was like the

56:33

Tower of Babel you know that story

56:36

you don't know it's like a biblical

56:37

story where

56:39

uh people are building this Tower or

56:42

something but they all speak different

56:44

languages and I I could be completely

56:47

wrong I don't think I am

56:49

but none of them get along or understand

56:52

one another and it was it was it's just

56:54

a mess trying to integrate 100 people

56:55

into a company in a year

56:57

especially a company with no processes

57:01

and no real intentional culture

57:04

that had been established

57:06

no real intentional anything other than

57:10

the brand

57:12

the spirit of the brand

57:14

what needed to be done it was it was

57:16

like a family business that just got

57:18

really big it was

57:19

I was a kid

57:23

how are you feeling in terms of at this

57:25

point in terms of what's going on around

57:27

you 60 million dollars has just come

57:30

into the bank account you're looking at

57:31

me thinking that's a big [ __ ] number

57:32

you're you know because you have a

57:35

valuation of 350

57:37

yeah I'm worth 280 million dollars on

57:40

paper at this point so that and wherever

57:42

you go they'll lead with that and remind

57:44

you of it and you'll be treated as such

57:45

even though it's paper and it's not

57:47

realism yeah it's in your bank account

57:49

how does that make you feel when you you

57:52

know then they put you in the front

57:53

cover of Forbes yeah how does that make

57:55

you feel

57:57

it was a blast

58:00

um I didn't do any of it to have Glory

58:02

or go on a Victory lap and I wound up

58:04

with it and I embraced it and I had a

58:05

lot of fun it distracted me

58:08

you know the book in 2014 turned into a

58:11

phenomenon

58:13

you know it was champagne clinks for

58:16

some Milestone with a company or new

58:18

hire

58:20

promotion any given time

58:23

I people would come up to me and say

58:26

congratulations and I had to ask which

58:29

thing they were congratulating me for

58:32

it was

58:34

it was just like oysters for everybody

58:36

finally you know I I got better taste in

58:40

wine I got better taste period thank God

58:43

but now I spend less money with a good

58:46

taste that I had to spend a lot of money

58:47

to acquire

58:49

a lot of my own

58:51

but did you feel

58:53

did you feel like it made sense

58:56

like the the image that's been that had

58:58

been built of you at the time that the

59:00

world is now like oh my god did it is

59:02

that what was going on inside I think it

59:05

made sense I think it was a freak Show I

59:07

was a Community College Dropout who

59:09

bootstrapped a business to 28 million

59:11

dollars in Revenue super profitably

59:14

you know investors came out of the

59:16

woodwork you know top tier ones anointed

59:19

me as

59:21

someone who could pull it off and I

59:23

didn't know what I was signing up for or

59:25

what I was supposed to pull off but

59:29

it it was considered a rags to riches

59:32

story and imposter syndrome

59:36

any of that for sure yeah I mean I still

59:39

walk in rooms and I'm here I was

59:43

talking to your team and I was like oh

59:45

my gosh you guys have really big people

59:47

I hope I can keep up I say like a lot

59:50

I'm intimidated I hope I can provide

59:54

some value what are the comments on

59:55

YouTube gonna say is this going to be a

59:57

valuable conversation I really hope

59:59

people like it

60:00

you know and she was like what you

60:02

wouldn't be here if that wasn't the case

60:04

what what are you talking about you're

60:06

great

60:07

but I get nervous right

60:10

um I get nervous on stages

60:13

and I'm still like you know I don't I

60:16

don't belong here but I don't belong

60:18

here is also a really great motivator

60:20

the I don't belong here is I snuck in

60:23

the back door

60:24

I don't belong here means

60:27

I can do things differently I don't

60:29

belong here means I don't fit in

60:31

but that's going to be a superpower and

60:34

I think it's okay to feel like an

60:37

outsider

60:38

or an imposter sometimes because you

60:42

find yourself in places where

60:45

you learn you have an outside

60:46

perspective and are able to learn things

60:51

unlike the people who are invited to the

60:53

table who all showed up there with the

60:55

same pedigree

60:56

and then you get to make

61:00

oblique connections

61:03

between who you are where you came from

61:05

and then the door the room that you just

61:07

snuck into as an imposter and that is

61:11

radical

61:13

would you remove that self-doubting

61:15

voice if I put a button in front of you

61:17

and said you press this you'll never

61:18

doubt yourself again no

61:20

that's so boring I had a coach recently

61:23

and he was lovely

61:25

waited five sessions it was like five

61:27

thousand dollars a month and I was like

61:29

taxes

61:31

I'll buy something else to save on taxes

61:34

and

61:36

he was like can you imagine he asked me

61:38

that word or he asked me that question

61:40

and I was like

61:41

but

61:43

what would I struggle with what who

61:46

would I be if I didn't have challenges

61:49

and I was happy all the time it's like

61:52

the scaffolding would fall apart or

61:53

something

61:55

that's a story I tell myself

62:00

but it's fun to have a

62:03

dark Counterpoint

62:05

to hold yourself accountable and be like

62:08

maybe it is that or not that

62:10

and I think that Counterpoint is an

62:12

opportunity to gain self-awareness

62:16

do you think it's additive to your

62:17

performance or reductive

62:20

I think it can slow me down and I can

62:21

make really

62:23

slow

62:24

decisions because I doubt myself

62:27

but

62:29

beyond that

62:30

I think I've found a way to harness it

62:33

that really works for me

62:36

have you developed like a decision

62:38

making framework to help you navigate

62:40

the two voices in your head it's funny

62:42

because when you're describing your

62:43

mother and your father it felt like

62:44

those were the two voices your mother

62:45

would seem to be very supportive your

62:47

dad somewhat critical at times or

62:49

pessimistic

62:51

um have you found a way of being able to

62:53

juggle those voices

62:56

um

62:56

so that you can make decisions

62:58

decisively and quickly

63:00

no no no

63:03

so I can I can have these conversations

63:06

and when I you know when I do make a

63:08

decision I've learned to be slower with

63:11

making decisions because I either make

63:12

them extremely quickly or

63:15

slowly on accident and so I want to be

63:18

very deliberate in the decisions that I

63:20

make now and think more critically

63:22

rather than you know Naval gaze or

63:25

be reactive to something I went to this

63:30

uh Retreat even though it's not really a

63:32

luxury experience with 30 other people

63:34

called the Hoffman process

63:36

and it's seven days with no phone no

63:40

Internet no books no music you're with

63:42

30 other people and you're going through

63:44

this process of mapping your patterns

63:46

from your childhood against your parents

63:49

and how how you inherited that and it's

63:52

all directly correlated and basically

63:55

graduating from your your

63:58

emotional child into an emotional adult

64:03

super embarrassing weird process like so

64:06

dorky and everybody came with something

64:08

different to work on or what emerged for

64:10

them you know I I feel unloved I feel

64:13

unlovable

64:15

I don't feel unlovable

64:16

my thing and it sounds really weak was

64:19

like I don't trust myself

64:21

I don't think I'm deceiving myself but I

64:24

think I can rationalize a lot of things

64:26

to the point where I'll tolerate them

64:29

too long

64:32

um and that's gone for relationships

64:33

that went from my most recent

64:35

relationship

64:37

um and so that's a strange thing I don't

64:40

trust myself because I do have these

64:44

voices it sounds I don't have voices in

64:47

my head

64:48

but I can see things from any

64:51

perspective and not be totally attached

64:55

to either one to the point of

64:58

being slow and asking for too much

65:01

advice

65:03

in that Retreat did you did you have to

65:05

sort of like go upstream and figure out

65:07

where that belief started is that the

65:10

point of that Retreat did you figure it

65:12

out did you go Upstream what a good

65:13

question

65:14

you're very good at this oh thank you

65:16

yeah I think it was that my parents

65:18

didn't agree

65:20

on how to raise me that I felt

65:22

misunderstood that my good intentions

65:25

were sometimes construed as

65:27

troublemaking that the fact that I

65:30

didn't fit into the environment I was

65:33

raised in

65:34

I was I was not accepted and I was some

65:38

kind of weird deviant when I was just

65:40

being myself and felt punished for being

65:42

myself and I think that

65:45

gave me like a lack of confidence or

65:47

something and I don't identify with

65:49

being an unconfident person but when it

65:51

comes to decision making when everyone

65:53

around you is telling you something a

65:55

different story about yourself than you

65:59

have

66:00

and doesn't understand why you operate

66:02

the way you do that is really with

66:06

integrity and in line with who I was and

66:09

what I needed to be successful as a

66:10

child if other people like live in a

66:13

different world and don't understand

66:15

that those are your needs you just feel

66:19

wildly alone and think wow I am a freak

66:23

and that

66:25

found its way into my career through the

66:28

public too which has been super fun

66:30

being told I'm something

66:33

that I'm

66:35

mostly not

66:38

what have you been told you are oh gosh

66:43

um

66:44

so nasty y'all fell apart after 10 years

66:46

it was it was a quick rise and it was it

66:50

was it was a it was a slow rise and it

66:52

was a relatively quick fall couple of

66:56

years in the making

66:58

and when it did fall the headlines were

67:02

crazy because I had all this press from

67:05

this book I published and being the

67:07

poster child of Entrepreneurship going

67:09

on the victory lab National Enquirer

67:11

said had you know picture of me and it

67:14

said Rags to Riches like straight up

67:16

tabloid American Dream stuff like a

67:19

caricature

67:21

and I didn't realize the amount of

67:22

responsibility I had to like other

67:25

people as an example like I kind of did

67:27

but as some symbol for entrepreneurship

67:30

for my generation you know generation of

67:33

the entrepreneurs coming up behind me or

67:36

at least

67:36

what the Press thought I was responsible

67:39

for

67:41

the you know there were headlines like

67:43

does the failure of nasty yell mean

67:46

Millennials aren't ready to lead

67:48

it's like wait how is one example

67:51

representative of a generation

67:56

and I've also read headlines like when

67:59

the Netflix series came out

68:01

the worst thing about Netflix's girl

68:03

boss is its source material

68:07

not even the show just me

68:15

but I'm not bad I don't believe I don't

68:17

believe it

68:20

how does that make you feel at the time

68:21

though

68:24

by the time that Netflix series came out

68:27

I had been this hero as an entrepreneur

68:30

then I was this girl boss because I

68:32

wrote a

68:33

book called girl boss and it was pink

68:35

and I was like this and I looked like I

68:38

knew it was up but it was like 27 and

68:40

then there was the me whose company fell

68:43

apart the CEO there was the girl boss

68:46

who had built a

68:47

toxic culture

68:49

or just no intentional culture at our

68:52

all that like warped into something that

68:54

wasn't perfect but wasn't I still don't

68:56

think it was the worst

68:58

and

68:59

now this person this conflation of all

69:02

of those things

69:04

with this girl on the scripted comedy

69:07

which came out four months after I left

69:10

Nasty Gal so the biggest kind of

69:12

personality or whatever identity crisis

69:15

was

69:17

you know I'm on the cover of Forbes in

69:20

June I think of 2016 July of 2016 my

69:23

husband of like a Year's like man I

69:26

changed my mind and I'm like oh my God

69:27

that wedding was so expensive it was

69:29

devastating but I'm just like God that

69:31

wedding was so expensive it was a great

69:32

party

69:33

so in that space of like 12 months

69:36

you're on Forbes husband leaves Netflix

69:38

comes out nasty girl goes under nasty

69:41

girl goes under then Netflix comes out

69:44

so the show had been shot when things

69:46

are all like up and to the right and you

69:49

know we were working through challenges

69:51

there had been some layoffs but the

69:52

company was still you know 100 million

69:54

dollars a year

69:55

you know not profitable anymore but a

69:59

great brand and something that was

70:00

valuable and

70:04

eventually

70:06

um yeah like fell apart and that the con

70:11

there was really a conflation of the the

70:13

hero the failure and now this girl four

70:17

months later

70:18

who's a a caricature of a person I was

70:21

when I was 22 in a scripted comedy

70:25

playing someone named Sophia starting an

70:27

eBay store called Nasty Gal

70:29

when for the first time

70:31

in 10 years in my adult life since I was

70:34

22 years old I am no longer associated

70:37

with the thing that I had built and now

70:40

there are 130 million homes in 195

70:44

countries watching a story of someone

70:47

that I

70:49

was no longer and no longer had trying

70:54

to move on and to move on when there's a

70:57

full PR campaign about who you used to

70:59

be

71:02

you're someone who's as you said you've

71:03

had a long history with mental health

71:05

challenges

71:07

what is it like in like in that 12-month

71:09

period what's going on from a mental

71:12

health perspective

71:13

I had fallen in love again

71:15

I think it was still like traveling I

71:17

started another company

71:19

I maintain my mental health partially

71:22

because I keep going

71:24

you know I don't stop and like lick my

71:28

wounds I think I was also I was also on

71:31

antidepressants I wasn't

71:33

jumping for joy but I also knew that

71:38

there was a huge community that still

71:40

supported me who had read my book 500

71:43

000 women who bought it

71:45

and I went on to start a company called

71:48

girl boss

71:49

right as the Netflix series was hitting

71:52

put on our first conference

71:54

and I had my podcast and I moved on

71:56

quickly and even though the headlines

72:00

weren't nice

72:03

the people who followed me my friends my

72:06

relationships everybody in my network

72:07

nobody bailed

72:10

like the girls who were inspired by girl

72:12

boss were refreshed that I had face

72:15

planted publicly because everyone else

72:18

is face planting in private

72:21

and in the same way that watching some

72:24

random Community College Dropout from

72:26

Sacramento start a business with an

72:29

internet connection

72:30

and a computer gave them license

72:33

to you know yes they were inspired but

72:36

also

72:39

Embrace their own failures because the

72:40

hero

72:42

face planted

72:44

publicly

72:49

and that can also inspire people

72:54

this is hopefully the most cliche

72:56

question I ask but

72:57

um I wanna I wanna know because you have

73:00

a from your from that experience you

73:02

have amazing feedback you have amazing

73:05

Insight invaluable Insight I would say

73:07

because when I think about the things

73:08

obviously they've taught me the most

73:09

it's not it's not when things go right

73:11

that's a validation of your hypothesis

73:13

it's when things go tragically wrong and

73:15

you go oh okay [ __ ] you have all of this

73:17

new information about which is corrected

73:19

your hypothesis so when you if we go

73:21

back and think about that fundraise for

73:23

example

73:24

um a lot of people will hear that you

73:26

raise the company raise investment at

73:28

350 million and think

73:30

amazing that's when people clap right

73:32

they get the champagne out oysters

73:35

for people listening that aren't in

73:36

business they might not understand how

73:38

that can also be a key reason why the

73:40

company ultimately went under

73:42

the 350 million why why did our big

73:45

valuation hurt yeah

73:47

yeah I think the 350 million dollar

73:49

evaluation is celebrated as it was and

73:52

how wealthy I was on paper

73:54

um was the was the nail in the coffin I

73:57

think it was it was then in 2012 where

74:00

we were overvalued and the expectations

74:03

that was was that the next round of

74:06

fundraising that we do is at a over a

74:11

billion dollar valuation and so the

74:13

company's doing

74:14

you know on an upswing 228 million

74:17

dollars in Revenue that's like over 10

74:20

times revenue and it's a fashion

74:22

business this isn't a technology

74:23

business this isn't Uber this isn't an

74:27

infinitely scalable Marketplace it's

74:29

e-commerce it was a different era of

74:31

e-commerce it was pretty early it was

74:33

the era of fab.com which like imploded

74:36

and won King's Lane in beechment in

74:39

ShoeDazzle there was no Playbook there

74:41

were no Ecom veterans or

74:45

you know Performance Marketing people

74:47

who had been in those jobs for even very

74:49

long I was hiring Executives who had

74:52

worked at like Macy's right

74:54

um nobody had like econ it wasn't called

74:57

direct to Consumer at the time it was

74:59

very very different there's no Shopify

75:01

and

75:03

we were overvalued and I didn't know

75:05

that I didn't even negotiate you know

75:07

hardly negotiate I didn't shop a term

75:09

sheet around and say I'm gonna pick the

75:11

highest price from different investors I

75:14

only had one term sheet and I was like

75:16

great I like you index finishes I was

75:19

like you're awesome you can I you get it

75:22

you know what Danny said when he

75:24

invested

75:25

uh was something none of the other

75:27

potential investors said and that was

75:29

you have a community and I was like yeah

75:32

we do have a community

75:33

but when you have that much money

75:37

you don't know there's been a nail in

75:40

the coffin or that there's a coffin and

75:42

that like you might be on your way into

75:45

it or maybe already laying in it but

75:48

just several years in the future

75:51

and

75:54

when things are up and to the right

75:57

you don't see what's lurking kind of

76:00

below the surface so when the tide

76:02

lowers

76:03

right you see the mud you see weird crab

76:06

shells sometimes hopefully not you see

76:09

trash

76:10

and it's only when things recede that

76:14

you see the mud that's underneath and

76:15

when you're on a Victory lap and you're

76:17

hitting milestones

76:19

everything's great and everybody loves

76:20

their jobs and you're a hero and as soon

76:23

as things

76:25

Go a different way as soon as there's

76:27

layoffs yeah there are things kind of

76:30

there are things there are things

76:32

lurking below the surface that were

76:34

dynamics that were already happening

76:38

that

76:39

because everything was going so well

76:42

you know we're harder to notice and

76:46

you know it's hard to be a CEO

76:48

it's hard to be a founder

76:50

I think something a lot of people don't

76:53

realize is that you only know 10 of

76:56

what's happening in your organization

76:57

right hundreds of employees and

77:00

ultimately everything was my

77:01

responsibility

77:03

but I am held accountable for 100 of

77:05

what's Happening

77:06

and when something goes wrong or

77:08

something's mismanaged or someone has a

77:10

bad experience in the company the

77:12

assumption is that I have signed off on

77:15

it that that is how I want things to be

77:18

and these things are happening you know

77:21

cattiness and

77:23

you know fiefdoms and silos and

77:26

duplications of effort and all the you

77:29

know the entire

77:30

spectrum of things that are no fun at a

77:34

fast-growing company

77:36

I didn't know were happening until we

77:38

laid people off and then they were like

77:40

hey

77:41

we didn't like it there I'm like okay

77:43

and some of that was totally overblown

77:48

but also anything that any employees

77:51

ever said about me or I've read

77:54

even though I don't agree with all of it

77:56

has been an opportunity for me to learn

77:58

and take from that how I could be better

78:00

because there's truth to almost

78:02

everything didn't you get an offer to

78:04

sell the company completely for 400

78:06

million dollars yeah I did

78:07

I owned 80 of it so that would have made

78:11

you you know quick maths I don't know

78:13

very [ __ ] Rich super [ __ ] rich

78:16

and why why didn't you say yes

78:20

I went to my investor

78:22

and I said what do you think about this

78:26

and he said

78:28

you need to ask for more I controlled

78:30

the board I owned you know I own the

78:33

majority of the company but I also took

78:35

advice from people who I thought knew

78:37

more from me but I didn't know that my

78:40

interests weren't necessarily aligned

78:42

with the interests of my investor whose

78:44

interest is to

78:46

whether I'm worth it or not

78:48

have a piece of paper to show his

78:50

investors that says I'm worth instead of

78:52

350 look they're now worth a billion and

78:55

they just make up these numbers and then

78:57

they can show their people that your

78:59

company's worth more and that was his

79:01

that was in his best interest and that's

79:04

what he was giving me advice based on

79:06

are you mad that he said that

79:08

I'm not mad do you wish you made a

79:11

different decision

79:13

is that a regret

79:16

it's a it's a partial regret but I also

79:18

know that no deal actually happens

79:20

they're not a

79:22

a real acquisitive company they could

79:24

have tried to acquire the company I

79:26

don't even know if they've acquired

79:27

anything integrating it into their

79:29

company if I had an earn out based on

79:31

them you know controlling it and me

79:34

trying to hit performance benchmarks

79:37

even if I had sold the company to them

79:39

who knows how it would have played out I

79:40

would have made a bunch of money my life

79:42

could have been miserable but 99 of the

79:44

time deals fall through there's also in

79:47

those situations a lot of people trying

79:50

to get into the data room so they make

79:51

an offer so they can see your numbers

79:53

and what you're doing and how your

79:54

business is working out and then they

79:55

pull the offer later once they've had a

79:56

look into the data room and due

79:58

diligence yeah and then copy yeah

79:59

exactly yeah so we didn't get that far I

80:03

don't regret it

80:05

um

80:05

but yeah that was a big thing you know

80:09

for me that would have been a lot of

80:10

money for him it was just a teeny tiny

80:12

bit more than what he had paid for it so

80:14

that's not a lot of them it's not much

80:17

of a markup for him

80:19

what is the advice you're giving now to

80:22

to women that are and men that are

80:24

looking to start companies that are

80:25

within your community the communities

80:27

You're Building within your portfolio

80:29

companies now that you're an investor

80:31

um

80:32

you know like I think I can think of the

80:34

first piece of advice that I give young

80:36

Founders when they come to me I'm

80:37

wondering what your like first piece of

80:39

advice is

80:41

I think for bootstrap Founders the

80:42

advice would be different for Founders

80:44

in my portfolio companies who are

80:45

raising Venture Capital my advice would

80:47

be

80:49

get as far as you can before raising a

80:51

single dollar

80:52

validate your idea as soon as you can

80:54

with the ugliest

80:56

like most basic quickest thing or first

80:59

product should be super ugly get it in

81:01

front of people and get some idea of

81:04

whether it's valuable or not before you

81:06

go raise money before you even try to

81:08

Market it talk to you

81:11

every customer every potential customer

81:14

and bootstrap it as long as you can if

81:17

you can because when investors do come

81:20

in your company is going to be worth

81:21

more than if you would raise money when

81:24

you just had an idea and were asking for

81:27

a check

81:28

when you do raise money

81:31

having a reasonable valuation is

81:34

important and a lot of Founders optimize

81:35

for price because

81:38

bigger price an investor pays the more

81:41

ownership the founder has the more

81:44

they're worth right the more they're

81:45

worth and the more eventually they could

81:47

make if they sell the company

81:49

but when you have a valuation that's in

81:53

line with Market that makes you an

81:55

attractive acquisition something someone

81:58

might pay a multiple for that 10 percent

82:01

say you're diluted down to 10 or 20

82:03

percent but you sell your company for

82:06

500 million dollars you're in much

82:09

better shape than raising 350 and owning

82:12

80 percent of it and going to zero or

82:14

whatever so and I think where things are

82:17

right now with Venture is

82:20

a place that is is close to that and

82:23

Founders aren't greedy Founders who are

82:26

raising money in this market no it's

82:27

really really hard they don't want to be

82:30

overpriced because the people who raise

82:32

money over the last few years raised at

82:35

such a high valuation these founders

82:38

nobody's going to reinvest in them

82:39

they've blown through their money they

82:40

thought they were you know they're on an

82:42

upswing their company might be doing 2

82:44

million in Revenue but they're someone

82:46

told them they were worth 80 million

82:48

dollars and now nobody's going to give

82:50

the money I've as an angel investor I

82:52

have

82:54

three of these right now and it's like

82:57

Hail Mary's two of them have figured out

82:58

how to survive ones like we have another

83:00

term sheet I mean I've been there

83:04

what about the psychological advice

83:05

you'd give to her

83:08

um

83:09

I would say to listen to your gut

83:12

you know there's going to be a lot of

83:13

voices around you and there are people

83:15

who know more than you

83:17

and have experience and you should

83:20

listen to them but you should also

83:24

always maintain and continue to

83:27

cultivate a voice that

83:30

when you know it should is able to

83:34

supersede any advice that anybody gives

83:36

you

83:38

um I think it's easy to take all the

83:40

advice because you're an inexperienced

83:42

founder

83:43

and um

83:46

and into lose touch with your intuition

83:50

and it's probably what got you to where

83:52

you are as a Founder without the money

83:54

and without the experts

83:57

and if you just rely on the money and

83:59

the experts you're losing the thing that

84:01

made what you're doing Special in the

84:03

first place

84:05

which day was your hardest day over the

84:07

last

84:10

since you were since you first started

84:12

that store on eBay is there a day you

84:14

look back and go do you know what that

84:15

period or that day was just

84:18

the worst the hardest the darkest

84:24

see and it's weird the hardest day was

84:25

when my husband laughed

84:27

and I don't miss him and I don't wish we

84:29

were still together

84:31

I don't really think about him I mean

84:34

that was in 2016.

84:37

but I had agreed to take a big swing in

84:42

my personal life and make a huge

84:44

commitment and I thought that bumps in

84:46

the road were like to be celebrated I

84:49

thought it was like wow okay you're not

84:51

feeling great about things we're gonna

84:53

work through this and we're going to be

84:54

so much better as a result of it because

84:56

I see

84:58

commitments as things that go up and

84:59

down and if you're in a commitment

85:01

together you're committed to working

85:04

through those things and it all comes

85:05

out in the wash because you have that

85:07

level of commitment to the other person

85:09

and that wasn't the case for him and so

85:12

I I felt like I was like hallucinating

85:15

you know I like went to a hotel for a

85:18

week I couldn't be in the house it felt

85:20

like a crime scene with his stuff around

85:23

and um yeah three a whole whole week at

85:27

the Beverly Hills Hotel with three

85:28

poodles

85:30

is quite the scene with them yeah chain

85:32

smoking in the courtyard and a bathrobe

85:36

has that experience put you off being a

85:38

CEO of a big company I mean ever yeah

85:41

everything I've experienced has put me

85:42

up from being a CEO of a big company

85:43

I'll never do it again

85:45

why I don't I just I don't want to

85:47

that's not the job I want I'm an early

85:49

stage founder I'm a master at creating

85:53

brands that cut through the noise what

85:56

happens though if one you know you're

85:57

running a number of businesses now

86:00

um you've got your fund

86:05

yep business class business class but

86:07

what what happens say business class

86:09

what happens if it becomes

86:11

globally

86:13

you know globally successful then

86:16

you're back to being a big CEO again

86:18

though are you step out I would have to

86:20

work really hard to make it that and I

86:21

would have to invest in that and hire

86:23

into it that wouldn't happen by mistake

86:27

I have one employee on business class

86:29

business class is super profitable I

86:32

launch it twice a year it's pre-recorded

86:34

so business class is my entrepreneurship

86:36

program but I have two courts a year I'm

86:39

uh April I'm launching it and I launch

86:42

in the fall and it's an incredible

86:46

product but it's also something that is

86:49

relatively self-led for the students

86:51

it's eight hours of video and 300 pages

86:53

of worksheets and over 60 hours of

86:55

interviews with me like this with

86:58

entrepreneurs

86:59

and you know students get lifetime

87:01

access so you know they can take it over

87:04

the first seven weeks they can take it

87:05

over the course of a year or the next

87:07

few years

87:08

but it's not something that requires a

87:11

ton of my time outside promoting it

87:12

twice a year and I built it for that I

87:15

built it for that I'm using kajabi and

87:19

drip for email and you know whatever

87:22

zapier and a variety of tools that allow

87:27

it to be relatively low lift light on

87:31

human capital still a lot of effort to

87:33

promote and something I do engage with

87:36

throughout the year and two weekly calls

87:39

with students and post in the lounge

87:40

which is our community keeping it that's

87:43

it no yeah I'm playing I'm I'm

87:46

I'm not playing small with business

87:49

class I'm playing to my strengths that's

87:52

big

87:53

and with trust fund it's Venture fun

87:55

that I'm raising right now it's a 10

87:57

million dollar fund what I get to do is

88:00

not run a big company and you can keep

88:01

trying to apply this stuff that I've

88:04

learned over you know

88:06

over time I get to go from zero to one

88:10

over and over and over again with early

88:12

stage companies and out of fun I get to

88:15

be in the weeds if I hired a bunch of

88:16

people I they don't want me to be in the

88:18

weeds Executives don't want you to

88:20

micromanage but I get to look at all the

88:22

decks and I get to text the founders and

88:25

say here's what I think you should do I

88:27

can be helpful and it's so rewarding to

88:30

harvest all of my hardship on behalf of

88:33

a new generation of Founders and help

88:36

them see around the corners that I wish

88:38

someone had shown me around

88:41

and I get to keep my firms small even if

88:45

I have a 50 million dollar fund I can do

88:47

that with a few people

88:49

um and I'm using the assets that I have

88:52

I'm the product my relationships and my

88:54

network and my access to dealflow is my

88:58

product my expertise and ability to help

89:00

Founders is my product million social

89:03

followers and being able to amplify them

89:05

is my product the engaged Community I

89:08

have who's interested in the kinds of

89:10

things I'm investing in will actually

89:11

use them is my product and I don't

89:15

I'm just it's right here and it's an air

89:17

table the intentionality is what I find

89:20

most surprising um inspiring because so

89:23

many people get dragged by the

89:24

Temptation of like external expectation

89:26

if it's great business class is great

89:28

but all accounts have been on the

89:29

website went on to so I saw that the

89:32

waiting list is open for 2023 it said

89:34

like join the waiting list for 2023 yeah

89:36

so it's launching in April okay the the

89:40

spring cohort launches in April so you

89:42

can enroll for like a 10-day period at

89:43

the at the end of April when things are

89:45

great we get dragged by our own success

89:49

what you're saying is you're going to be

89:51

intentional and you've designed it so

89:52

that that's impossible

89:54

so that you can't get Drax because

89:55

someone's going to come along and say we

89:57

love this we're going to give you a

89:58

check we love this we'll turn it into

89:59

some boxer shorts with some teddy bears

90:01

yeah no

90:03

no I I

90:06

have had the Pearl Village of knowing

90:08

what's on the other side of success and

90:10

that a lot of it is not what you sign up

90:12

for

90:13

and that when you are successful you're

90:15

stuck in it so I spend a lot of time

90:17

thinking about what success looks like

90:19

for me and what I want my life to look

90:21

like and how many people I want to have

90:22

around me and the kind of stakeholders I

90:24

want to have

90:25

so that I'm set up for Success when

90:27

trust fund is super successful which I

90:30

can stay Nimble with and with business

90:33

class I've engineered that Revenue was

90:35

down last year to the year prior

90:37

and that's so that's okay it's still

90:40

profitable I'm not gonna hire a bunch of

90:43

people or CEO or plow a ton of money

90:45

into it trying to solve problems and

90:47

pivot things so if I come along I say

90:49

I'm going to invest 10 millions of here

90:51

we're going to hire a CEO okay but you

90:54

take the money

90:55

yeah take the money just for the record

90:58

guys

90:59

when it's there

91:01

take Real Money Take Take the Money

91:06

magical thinking what is that yeah I

91:09

mean you can call it magical thinking

91:13

you can call it magical thinking you can

91:15

call it manifestation you can call it

91:17

prayer you can call it whatever you want

91:19

I think it's

91:21

you know casting the line out not

91:25

knowing what you're going to catch

91:27

trusting you're going to catch it and

91:28

we'll pull it back magical thinking is

91:30

like Indiana Jones where there's the

91:34

vast where's this there's the vast Chasm

91:37

between whatever and the Holy Grail and

91:40

he has to trust that there is a an

91:43

invisible bridge and he grabbed some

91:45

gravel and he throws it out across this

91:47

literal kind of Canyon and

91:52

the gravel just falls on a clear bridge

91:56

and he had to like trust that when he

92:00

walked across that he wouldn't fall and

92:02

so I see magical thinking as you know

92:06

Thinking Beyond what might be obvious

92:10

thinking you're capable of doing things

92:12

that you shouldn't be thinking you can

92:15

belong in places that you never thought

92:18

you could

92:19

thinking you can accomplish things that

92:22

you're completely unqualified to because

92:24

nobody's qualified to

92:25

being able to see yourself in a life

92:28

in a world that's beyond your wildest

92:31

imagination

92:32

and just staying there

92:37

we have a closing tradition on this

92:39

podcast where the last guest leaves a

92:40

question for the next guest your

92:41

question is unfortunately not the

92:43

hardest question in the world I really

92:44

wish you'd been given a real stitch up

92:45

one

92:46

um but yours is yours is fairly

92:48

straightforward question which is what

92:49

is your proudest moment

92:51

hmm

92:54

my proudest moment is

92:56

paying off my mom's mom's marriage I

92:59

mean that I can do that

93:00

that was crazy that was the first thing

93:02

I did

93:03

what about this then what's going to be

93:05

your proudest moment

93:09

hmm

93:11

it requires a little bit of magical

93:12

thinking

93:14

understanding what

93:17

is Meaningful in my life and actually

93:19

spending time on it you haven't figured

93:20

that out no there are meaningful things

93:22

but what is the people have kids and

93:25

that's like

93:26

obvious and I don't know if I'm gonna do

93:28

that

93:29

I am super agnostic about it it's really

93:31

strange

93:32

I'll be 39 in a month

93:35

um

93:36

but I think like finding that and

93:37

hanging on to it what is that what is is

93:41

there some big meaningful thing that I'm

93:43

gonna find and cling to till I die you

93:46

know and it's easy when it's family or

93:48

easy when it's a kid

93:49

and you can create these meaningful

93:51

things in your life

93:53

but what that what is that going to be

93:54

for me when I'm dying what is it what

93:58

will it all add up to I don't know

94:01

Sophia thank you so much for your time

94:02

and thank you for the inspiration you've

94:03

been an inspiration for me for many many

94:05

years and that's why I reached out to

94:06

you to sit here with you and you are

94:08

absolutely a superstar in many many

94:09

respects but um yeah you're built for

94:11

podcasting but also because of your um

94:13

inclination to be on open and honest and

94:15

vulnerable

94:17

um you're incredibly inspiring in the

94:18

stories you tell in the way that you

94:19

tell them so thank you so much it's a

94:21

real honor to meet you and I'm I'm

94:22

equally privileged that you said yes to

94:24

come and do this because oh my gosh and

94:25

I mean that I'm not I'm not just like

94:27

gassing you up or anything I mean no no

94:28

thank you you're super happy I can't

94:30

wait to see what you do with both trust

94:33

fund and business class because

94:35

um they look like exceptional projects

94:37

I've looked into the reviews of business

94:39

class and with your fund with the amount

94:41

of information you've learned from your

94:42

twisting turning professional career you

94:45

clearly have a huge um amount of

94:47

intellectual leverage and Firepower that

94:51

makes for a great

94:52

fund um founder so I look forward to

94:55

seeing what you do that thank you thanks

94:59

as you might know if the show's now

95:01

sponsored by Airbnb absolutely love

95:02

Airbnb always have always been a you

95:04

know saved my life on so many occasions

95:06

and my team when we first got in touch

95:07

with Airbnb were talking about how most

95:09

people don't realize that their place

95:11

where they currently live could become

95:13

an Airbnb and I guess the second

95:15

question there is how much could your

95:17

place be worth and it turns out you

95:19

could be sitting on an Airbnb gold mine

95:21

without even knowing it some people

95:23

Airbnb their entire homes when they're

95:25

away that's what I did in New York

95:26

whenever I left New York my place was on

95:28

Airbnb and people rented it out

95:29

sometimes for a day sometimes for two

95:31

days sometimes for a week and it's a

95:33

great way to cover some of the bills

95:34

while you're away so whether you're

95:35

looking to go on holiday or you just

95:37

want some extra cash for bills or you

95:39

want to buy something nice for a

95:40

valentine that you love whatever it

95:42

might be head over to airbnb.com UK host

95:45

and you can find out how much your

95:48

current property where you live can earn

95:50

while you're not there I suspect it

95:52

might blow your mind because it

95:53

certainly blew mine

95:54

[Music]

95:58

oh

96:00

[Music]

96:17

foreign

Interactive Summary

The video features an interview with Sophia Amoruso, the founder of Nasty Gal, author, and entrepreneur. Sophia shares her rebellious youth, her experiences as a stripper and shoplifter, and how she channeled her creativity and independence into building Nasty Gal. She discusses the rapid rise and subsequent fall of her company, emphasizing the challenges of fast growth, lack of experience, and the impact of venture capital. Sophia also touches on her mental health journey, her struggles with being misunderstood by authority figures, and her current endeavors as an investor and creator of Business Class.

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