The Diary Of A CEO with Steven Bartlett: E239: NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso

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

Yeah, I did.

I would have made you super rich.

Why didn't you say yes?

You're very good at this.

Sophia!

And Aruso!

Founder of the Nasty Gallant, a best-selling author,

and a powerhouse in the entrepreneurial world.

I was rebellious from a very early age.

I was a stripper.

I wasn't even 21.

I used someone else's ID to work there.

Built an online business.

And the first thing I sold online was stolen.

Get a whole shopping cart of stuff.

Put them on Amazon for $0.10 less than the other resellers.

And then gotten arrested for shoplifting.

I'm a little dark.

I realized I could connect my creativity to something legitimate.

Started Nasty Gall, selling vintage.

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

I didn't realize the amount of responsibility I had

being the poster child of entrepreneurship.

Then I was this girl boss,

but my naivete and lack of experience did send me to the grave.

Nasty Gall fell apart after 10 years.

My husband of like a year left.

The headlines weren't nice.

Then Netflix comes out.

You just got played.

What is it like from a mental perspective?

It's hard to pull yourself out of a hole

when you don't want to get out of bed.

It's challenged my confidence.

And I'm still like, I don't belong here,

but I don't belong here is also a really great motivator.

I don't belong here means I don't fit in,

but that's going to be a super power.

I can do things differently.

What was the plan in life at that point?

Oh gosh.

Sophia, take me back to those suburbs in San Diego

and give me your earliest context.

Wow.

I was born in San Diego at Sharp Memorial Hospital.

Only child, eternally an only child.

I think wound up having the personality of a probably seven children

and the challenge of maybe seven children for my parents.

We moved a few times, you know, our house was like,

it was, it was happy ish when I was young.

I lived in San Diego till I was seven

and it's a beautiful place.

And I so wish we would have stayed there,

but we moved to beautiful Sacramento, California.

And that was really the suburban experience where,

you know, when you're a kid, a little kid,

you don't know what a suburb is

and chasing the ice cream man is great.

But once you get older, living in the suburbs,

if you have any amount of curiosity about the world,

the homogenous, you know, nature of living in the suburbs

is something that totally crushed me.

I knew there was more out there and I didn't know what it was,

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

What did you, what did you want at a very early age

when you say you wanted out?

Oh, yeah.

What did you want?

Yeah, I wanted out of my family home.

It wasn't happy.

My parents didn't get along.

I was playing referee, you know?

Really?

Yeah.

At what age?

Starting at like 10 or something.

I mean, yeah, it was just,

it wasn't a super happy place and they, yeah,

they didn't get along.

They didn't always agree on how to raise me.

And I think when your parents, you know,

everybody's relationship has issues and everybody's,

not everybody's, but most people's parents,

you know, sometimes don't get along.

When you have a sibling, I think you can go be like,

that's funny.

Or they're whatever, let's just go play with Legos

or something like that.

Or let's go ride bikes.

But I think being isolated in a house that wasn't super happy

as an only child made it worse.

And I just remember so many drives, silent car drives,

where I was in the backseat alone and I just remember

like the silence and the light of the street lights,

it's like washing over the car, just in silence with my parents

in the two front seats.

You know, they were really like only affectionate

after like an argument.

And even then it was like, I don't know,

hand holding or something.

They were very strict as well.

I had to beg to go to a boy's birthday party in sixth grade.

We weren't super religious, but my mom grew up in the 50s

in a Greek Orthodox household, just not puritanical

because that sounds less cultural than Greek Orthodoxy,

but strict, you know.

What about money?

A lot of them, a lot of arguments happened in my household

when I was younger because of money.

Yeah, I mean, my dad sold, my dad did loans

and my mom sold houses, but track homes in the suburbs

and they were both working with builders and banks

and manufactured homes.

And so on the weekends, by the time I was, I don't know,

maybe 10, my mom was working in the model homes

that are all kind of dressed up and you can tour them

and pick your manufactured home and change a couple things.

And there was like a fake keyboard in there

and just all kinds of funny things to play with.

And then so I was with my dad on weekends

and they both worked entirely commission.

So I've never seen either of my parents work for a salary

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

and my dad's dad owned a motel

and they all grew up on a motel.

So there's like generations of my family

who wouldn't necessarily call themselves entrepreneurs

but they're people who ate what they killed

and that's what I witnessed.

Money was good, I think when I was like,

you know, when we were in San Diego

and I think it got tougher over time.

I remember very vividly being in a credit counselor's office.

I just can't believe they brought me

but there was no, I don't know where they would have put me.

Watching them cut up their credit cards,

like cut their credit cards in half

and put them in a clear jar with like other people's,

cut up credit cards and file for chapter 11.

Bankruptcy.

Yep.

Did you know what was going on?

No.

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

As an adult, are you able to look back on that,

that first sort of chapter of your life

and figure out how it had a lasting impact

on various elements of who you are today?

I think it allowed me to,

even though it was so challenging younger in life,

to learn how to assimilate into different environments,

to, I guess, entertain myself independently,

to realize that authority was,

like adults were not trained to be parents

and weren't any further along with their maturity sometimes,

then I was at my age, I looked at teachers and thought,

wow, you have domain expertise, you know some stuff,

but I can tell that you're morally bankrupt

and I don't trust you

and why have I been put in your hands?

I think the thing that had the biggest impact on me

is how critical my dad was.

So he's half Italian and half Portuguese

and his dad was a mean, mean guy.

And my dad's very charismatic and I love him

and he's super chill now,

but when I was young he had a lot of pressure on him

and he didn't really have the best model

of what a great parent looked like

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

you know, he did his best.

I know that both of my parents did their best

with the materials that they had,

the ingredients that they had to be parents,

but it instilled in me this unfortunate

but also very fortunate

always peeling back another layer of the onion,

examining myself,

but also a real internalized drive

to do better and a self-criticism

that has worked very well for me.

That's been challenging.

It's challenged my confidence over time,

but it also has been a superpower to,

in some ways, I don't know,

in some ways hold myself accountable

because I'm always,

I almost want to say second guessing myself.

But also very,

in a very, I guess, someone said Jesuit way at one point,

but a way where I can see both sides of everything,

you know, challenging my doubts and my ego,

but the problem with that is sometimes

it's hard to differentiate between the two.

What is, you know, fiction and what isn't

and what of my self-critiques are accurate

because I want to be,

and I think I am a pretty self-aware person.

And even with the things that I'm not great at,

I'm super proud of that

because I've got a ton of advantages

and things that I'm really great at.

But I think it was the criticism I experienced

early on in life for so long

that instilled that in me,

and I've learned how to turn it into something

that's more balanced than what it was

when I inherited it.

When you inherited it?

When it was handed to me, you know,

the model I had,

the level of critique that I had

that didn't have the counterpoint

that I'm able to provide for myself.

You're talking about your father here?

Yeah.

He would critique you?

Yes.

When you say critique, do you mean...

Oh, that's naughty.

Don't do that.

No.

No, like, that's not how you do something.

Or why did you do it like that?

Or can you not?

Or, you know...

I mean, I love my dad,

and he's...

You know, as both of my parents have gotten older,

they split when I was 17,

and I've just watched them

both become such better people.

I remember congratulating them

when they finally split up

and was so glad

at 17 years old, and I was also like,

I'm out of here.

Yeah.

You seem to become a bit of a rebel,

you know, from when you moved out

of your parents' house

for the next couple of years.

The behavior looked really rebellious.

Oh, yeah. No. I mean, I was rebellious

from a very early age.

I remember

in middle school, a teacher,

I was eating an apple in class.

I was eating an apple. It was healthy.

I was hungry. I've got agency over my body.

I didn't know what that word meant.

I'm hungry. I'm going to eat food. I'm a human.

I'm hungry. I'm going to eat food

in the middle of class.

But, like, who...

How could you tell someone not to eat

when they're hungry? It's like a simple bodily function.

And it keeps me healthy

and it's going to make me a better student.

And it's...

And the teacher told me to throw the apple away.

And I just started the apple.

And, of course, I had the attention

of the entire class.

And I got up

and I

sauntered over

to the trash can

super slowly.

And I just, like, ate the apple

all the way to the core, like, super fast.

Finished the apple and was, like, dink

in the trash can.

So I was like that.

If someone said not to do something,

I did the thing that they didn't say I couldn't do

that was similar.

It was peripheral.

And then by the time I got to high school,

I was going to the Anarchist Book Fair

in San Francisco.

I was sure capitalism

was, you know, the worst thing ever.

I was very angsty.

I thought that

adulthood, it's funny,

there's a Netflix series about my life

and the first thing that the character says

is adulthood is where dreams go to die.

And it's so weird to reference your own Netflix series.

Like, who does that?

But that's how I

felt. I wasn't trying to be a child,

but I also didn't want to go

work in an office. I also wasn't ambitious.

So somehow

along the way that

lack of desire to live a conventional

life became something that turned into ambition

because I

didn't even ambition just curiosity, something that

I was good at and, you know,

eventually built a business.

But I,

in high school,

in high school,

I remember

bells, like right, there's a bell that rings

and you go from one room to another room

all day.

A bell rings.

You sit at a desk, a bell rings

and you stand up

and you shuffle over to the other room

and then you sit down

and you like memorize some stuff

and then you like, this is my youth?

I was sure I was being trained for something

super mediocre, not that I wanted excellence,

I just wanted out.

Why are you like that?

Because, you know, all the other kids were cool.

I came out like that.

I actually came out, I came out like that.

Yeah, it is not,

I mean, I might have

some hereditary

just kind of like Italian,

I'm not sure what,

or something, it's not,

it wasn't a nurture thing, that was

a nature thing, or I don't know, I just

like came out,

I actually hatched out of a disco ball,

but that's the way

that's how I came out.

I had a Gabal Mate here

who's this like, I think he's just interviewed Prince Harry

actually,

in a little like, pay-per-view

therapy session or whatever, and Gabal Mate said something to me

that I've been pondering ever since, he said that

as children, we're like narcissists

and we are that way because it helped us

to survive, so we think that everything is about us

when we're like babies and young, so if the parents

were arguing, we actually interpret that

as there being something that to do with us

and that's the way we view the world as a survival mechanism,

he says one of the things that

happens when we're a young child

and we're in a house where there's lots of arguing

and lots of drama and shouting, is

we learn to

avert our attention

as a way to help us deal with the

emotional distress, and that develops into something

they call ADD and ADHD.

Yeah, I took Adderall this morning.

Well, yeah.

Just to prepare for the podcast, just kidding,

you know, I have major

ADD.

ADD.

But they diagnosed me as a kid and I was like,

no, this is mind control.

Forget it, I'm not focused because

I thought it was situational, I thought it was my environment

and it

maybe was partially because I wasn't interested

in what was happening

and distracted because I was curious

about other things, but also

it's a real thing and it wasn't until

a few years ago that I finally

realized it was a thing

and sought treatment

and it's helped, but it's helped marginally.

It's not

helped. How did you realize it was a real thing

a couple of years ago?

I mean, I go to

a psychiatrist and I talk about

what's going on with my brain

and

do what I can to

help myself

holistically,

but also I know

I'm also predisposed to depression.

I'm not predisposed. I've suffered

with depression my whole life.

Since when? My whole life.

I can't remember an age where

I wasn't

depressed.

I wasn't always miserable

but I'm kind of a dark.

I'm a little dark

and that's not something

it's hard to pull yourself out of a hole

when you don't want to get out of bed.

Like that's

I don't have the willpower

to just get over depression

and put on a happy face

and whatever people do get in an ice bath

and jump in the sauna and meditate

and

I'm still struggling to be the well-rounded person

but I'm functional.

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

I don't know. Some people seem to

have these parents that teach them that

and they come out and they're like

boop boop boop boop boop boop

and that's almost

punishing to be like

but

yeah, there's people

who just seem to you know

and some people come out of the womb like that.

I know parents that are creative,

chaotic, I know people

who are well-rounded, whose parents were

addicted to drugs and somehow

they just wound up like that

and how to attribute that to

your parents, that's a hard correlation

to make.

Did you ever, you said a curious phrase

made me

ponder, you said I'm a little dark.

Uh-huh.

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

Why are you giggling? You're making me think

you are a little dark. I am.

I'm not evil.

I'm not a witch.

I

am a

I guess I have

just

you know like I said I've struggled with depression

I'm not a bubbly person

I'm

not someone you know as a child my mom

has said

you only laughed when something was really funny

you know I think kids run around like laughing

and smiling because they're like children

or something but I had to have a reason

I'm not

sure why and it's still kind of like that

and maybe it's I don't know as an adult

it's become something that requires

it's just being genuine

and maybe I'm not

I think maybe I'm not impressed

maybe in general I'm just

skeptical. You went to see a psychiatrist

when you were 16. Oh I went to see

a psychiatrist when I was like

10. I mean I was

in therapy when I was like 10

11. With what symptoms?

Trying to be diagnosed like what's wrong with her

why can't she stay on task

why is she so weird why doesn't she get along

why is she distracted

so I have report cards

that say

chooses to disturb others

you know doesn't stay on

task it's stuff like that

it was like I was always like

you know not paying attention curious

about something else engaged with something else

it wasn't always to be rebellious

sometimes it was very good natured

and I would get in trouble for things that I

didn't think were bad or intend to be

bad it was also just very

a very willful

independent

thinker

who didn't fit into a traditional

educational environment

and you know

that's something

for whatever reason seem to be

needed to

be diagnosed

but then I was like no

I'm not taking well mutrin

and I'm not gonna take it's like an antidepressant

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

of this

that was by high school so you were 16

around that time when they yeah 15

16 and I was like this is

it's

I don't feel like myself

feel wired and weird and

I got out like I think

I got riddling and someone tried to buy it off me

and like high school and I was like what do you what

I don't even get it it's like

I'm just throwing this stuff in the trash

and

then so you get

diagnosed and prescribed antidepressant at

16 ish

your parents break up at 17 ish

I move out

I move out at 17 before I graduate

high school I was homeschooling so I got my

diploma in the mail I thought

like most embarrassing thing would be

would be to wear the cap and gown I was

like what is that I don't understand

what's the tassel

why do you have to wear a robe what is this robe

I wouldn't

proud standing in a group doing some

group thing I'm not a group person

even though I've built a lot of really

powerful communities

I'm not I don't assimilate well into groups and

I think groups are responsible for the most

painst things in like human history so

so I moved into a closet

you moved into a closet under the stairs

for $60 a month

with a sleeping bag

these guys that were like in bands

and artists

who had met going to shows

because I was really into music

and went downtown in Sacramento

and saw music and

what was the plan in life at that point

was there a plan you know you're like 17-18

no he told me there was a plan

I wanted to go to

first wanted to go to Reed College but that was

expensive

but then I wanted to go to the Evergreen College

so by the time I was 18

I had moved to Olympia Washington to get

residency to go to the state

school called the Evergreen State College

which is a

super duper hippie

state school that's interdisciplinary

and there's no majors

to the point of it not

really being worth

going but if I was gonna go

to college I was gonna go to a place like that

but even state tuition

was expensive so I lived in

Washington state for a year

to get state to get residency

so I could go to that school

and by the time I got residency

I was like this school's not gonna

do anything for me

You described this chapter of your life as being very lost

Super lost

super lost I was looking for my

I kind of hate this word

tribe

I was looking for people like me

I thought I would find people like me and then

all would be well like

you know some Disney character

that you know ugly duckling

or someone who

loses you know they're lost from the wolf

pack I don't know what these movies are

and then they find their family and

people understand them and so

from the time I was 17

I moved from

downtown Sacramento to Olympia

Washington lived in two places there

Seattle lived in two places there

San Francisco

lived in one or two places there

Oakland with my alcoholic

fry cook boyfriend

and I had met in Olympia

we couldn't get jobs and

my parents were like yeah

we can't help you with college stuff

so

then we moved to

Portland I was a stripper

I was lost I was lost

That's an interesting turn of events

Yeah

that was an interesting turn of events

and

That chapter of your life in some ways

mirrors the transience of the start of your life

you said you moved to like 8

or 10 different schools when you were young

and then when you leave the nest you end up bouncing around

as in your own words like

looking for your family

I was yeah I was looking for some place

to belong and I never found it and I kind of

love that

cause it's forced me to make

my own and forced me to stay a creative thinker

and also I don't know

this isn't fair but the people

in some of those communities

like peaked and never left it's like

you know I listen to pop punk in high school

can you imagine

I'm sorry if anybody listening is like

never graduated from listening to pop punk

but if you don't graduate

to metal or

some other

it's not even more sophisticated but

like less juvenile

varieties of rock

it's the same as finding

you know some

comfortable community when you're

20 and then never leaving

that sounds

awful to me so

I'm glad I didn't find

a comfy place

and it's been uncomfortable since then

How long did you try the stripping thing?

I don't know

I mean when you're in your late teens

early 20s

time just feels

like it felt like a decade

that I was bouncing around to these places

probably 3 or 5 months

it was fun

I loved it nobody pulled anything

I never got

messed with I drank my white

russians and ate the subway sandwich

from next door

and played photo hunt

and I wasn't even 21 I used

someone else's ID to work there

and I got to dance to music

that I liked

I made money I didn't really have to engage

with anybody

and I got really comfortable with my body

in a way that I hadn't before

it was cool

You know they say

I read in your book

where you said that you

believe you hold the world record

for having the most shitty jobs

like back to back throughout that period of your life

they say you know I've learnt this from this podcast

that every job teaches you something

and that thing can be applied to business

there's always a sort of a transferable skill

or whatever learn

what was the transferable skill

that you learnt from stripping

today

I think that

even though I wasn't

didn't have the upper body strength to be

the traditional one upside

down swinging around

what I could do

I mean it was like shuffle around

and whatever

was enough and still

charismatic enough and still

great enough to entertain

other people

and then being comfortable with my body

like exposure therapy

you know I was the girl at

18

I would like make out with someone

and then if I was like naked or something

I'd like

put on my clothes to go to the bathroom

or something I was like

not

I didn't sleep with anybody until I was 19

so I was kind of late by 20

I was

stripping in Portland

I'll tell you the crescendo of that experience

so dating with

the alcoholic

fry cook who was 10 years older than me

I was on birth control

I went off birth control

for like one day

and there was almost

we were hardly even

you know engaging

in the way that someone might

like get pregnant

like so

briefly like that day

and then

no other day

yeah I'm like I don't know

who's watching

and I wound up

I wound up pregnant

so I'm like 20

maybe 19

and

I went to the sliding

scale women's clinic

and

but it was the only day I could get in

but it also happened to be

the day of my court date

because I had

gotten arrested for shoplifting

so I had to have the women's clinic

write an excuse

to the court

telling them why this poor girl

couldn't make it

to her court date and the whole thing got there

just I kept following up to be like when is it rescheduled

and I think they all just felt so bad

for me it kind of vanished

but that was that was like

okay no more shortcuts

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

but it also

just

taught me that

breaking

some rules puts you in

other people's hands

and I was

you know being arrested I'm not

as autonomous as I

would have liked to have been and

you know even with stripping to a certain extent

it was a shortcut I was trying to evade

like working hard but it was also

a lot of fun

but that was really

that was a low point

it had lots of low points

but at least it's like this right

it's been like this

you know

doesn't

this doesn't ever go that low

there's clearly a slight issue here with

authority and it feels to me like

the ultimate authority which is the law

eventually was like you can't fuck with us

we're not the teacher

I like maybe just figure out how to

get along

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

and do everything

I'm gonna just do everything differently

but also

I just didn't want to cut corners

I didn't want to

end up

not in control of my environment

or stuck in jail or something stupid

shoplifting

mm-hmm

where'd you make that sound

it was fun

what was your favorite thing to steal

I don't endorse shoplifting

neither do I

my rationale for shoplifting was

that there was so much excess

in

our culture

that it would never make a dent to steal

organic tampons from Fred Meyer

which is like Target

in Portland or whatever

so

when I did get caught

and this was my favorite thing was just walking out

with stuff

so I would get a whole shopping cart of stuff

I had a little teeny tiny little

razor thingy

so I knew where the sensors were

and I would cut them off they were there

and

pile a shopping cart

high and just walk out

with no bags or anything

I did it at grocery stores

I furnished apartments

places with literal rugs

this high

just walked out because nobody expects you to be

that

obvious about it

they're looking for somebody who's putting stuff

in their pockets

and when I did get caught

I had a George Foreman grill

I think a basketball

organic tampons

some food

really nice shower curtain rings

they were metal and then they had

ceramic they were heavy

and they had a ceramic thing that said hot

and then the other one said cold

and I was like yes this is

this is luxury

worth jail time

and

I built an online business

and the first thing

I sold online was stolen

so another thing

and I learned this from people who were professionally

trying to avoid

getting jobs and

participating in

capitalistic culture which is a privilege

it's lazy

it was

I was really young

and I just didn't want to work

you know it was some kind of quasi

political lazy excuse for

just not working hard

anyway I learned from

some of the best

I had a friend who had written a book called Evasion

literally

and

I went to Barnes & Noble

and they had a no chase policy

like I knew what the policies were at these places

because if their employees

chase someone shoplifting

it's gonna cost them way much more

if they get like a knife or something

than it would for them to lose a few books

and so I would

go on Amazon

and I would look at the

best selling books

this is in 2002

2003 it's like

and

even look at the ratio of

most expensive book to lease pages

so I could stack them

as many of them as high as possible

and I would just walk to the front

like the front of the store would have all the best

sellers and huge stacks

and I would just like

pile them high I look like an employee

like who's carrying a huge stack of books

I was right in the front of the store and I just like

walked my car and I

put them on Amazon for 10 cents less

than all the other resellers

I'd sell them overnight

I'd ship a media mail and I'd pay my

$350 a month rent

Why weren't you scared?

I think I was

but it's when you get scared that you get caught

and it's when you hesitate you fail

it's the same thing

if you're snowboarding and you're like

uh oh it's kind of icy

let me look down

you're just like pfft catch an edge

you're surfing and you look at the nose of the board

right

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

I guess I guess

I'm not proud of this

I was really young and I was finding my way

I never

stole from individuals

that was like not on thesis for me

who can justify it

no I couldn't justify it I would never

feel comfortable doing it

but big box retailers

I was like

over the last couple of how long

for months I've been

changing my diet shall I say

many of you who have really been paying attention

to this podcast will know why

I've sat here with some incredible health experts

and one of the things that's really come through for me

which has caused a big change in my life

is the need for us to have these super foods

these green foods, these vegetables

and then

a company I love so much

and a company I'm an investor in

and a company that's sponsored this podcast

and that I'm on the board of

absolutely spoke to exactly

where I was in my life and that is Huell

and they announced Daily Greens

Daily Greens is a product that contains

91 super foods

nutrients and plant based

ingredients which helps me meet that dietary

requirement with the convenience

that Huell always offers

unfortunately it's only currently available

in the US but I hope

I pray that it'll be with you guys

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

it's an incredible product I've been having it here

in LA for the last couple of weeks

and it's a game changer. Ladies and gentlemen

our newest brand partnership will come

it's no surprise to regular listeners on this podcast

the first episode of 2023

I was joined by the incredible

Professor Tim Spector to hear more

about his work at a company called Zoe

using data to understand

our bodies better so that we can live more

fulfilled higher potential lives

Zoe was born from the truth

that our overall health is impacted by our gut health

by helping you to understand

how your body is working

Zoe can help you to reduce your risk of long-term disease

and increase your energy levels

for me this is the future

and that is why I became an investor in the company

and that is why they are now a sponsor of this podcast

you can read up about everything they're doing

and you can pre-order your Zoe program

at joinzoe.com

and they've been kind enough to offer

an exclusive 10% off code

CEO10

so you can put that code in and check out

CEO10

thank you very much let's get back to the episode

so by this time you're getting a little bit acquainted with the internet

and selling things on the internet clearly

because you're selling stolen stuff

vintage

mm-hmm

why vintage, why did you start

to sell vintage clothes

yeah so by 2006

I had gotten some real jobs

after I had worked in shoe stores

and record stores and photo labs

subway

again

dry cleaners

I...

how did you get on with those jobs?

it didn't last very long

I like jobs very alphabetizing though

so record stores

photo labs

bookstores

like paper makes me feel important for some reason

mailing things I don't know

worked out with my eBay store

and the last job I had

was in the lobby of an art school

in San Francisco

at 79 New Montgomery Street

called the Academy of Art University

it was a job I got because I needed

to get health insurance and at the time

you couldn't get health insurance

with the pre-existing condition

you...

is this your hernia?

yeah the hern

yeah so a hernia if you don't know what it is

is a place

it's a hole in your muscle wall

where your butts poke out of and it makes a little

bump and I had one

kind of in my groin area

called an inguinal hernia

and it didn't hurt

but they're kind of dangerous because they can

like if your muscle tense is up or something

they can get strangulated and necrotic

which is a disgusting word

so I had to get it fixed

but before I got it fixed it was kind of fun

I shaved everything but the hernia

my poor boyfriend

my poor boyfriend

and

it was entertaining it was kind of funny to have

a small lump in my pants for

a few weeks or something

but at the time

you could not get health insurance with

pre-existing condition even with depression

if you had medical records that said you had

depression and your insurance lapsed

insurance companies would decline you now

that's not the case

you can have a pre-existing condition apply for

health insurance you'll be given health insurance

you could only

get health insurance

with a pre-existing condition

like a hernia

with group health insurance

with a job

so I had to go

find a job that had health insurance

and I got this job

in the lobby of the art school as a campus

safety host

which was a different way of saying

you're cheaper than a unionized security guard

and I wore a starchy white shirt

it was like a men's clothing

I had to wear this awful uniform

with like a magnetic

thing here that had my name

and the school's logo on it

and check students in

and say hi you need to sign in

can I see your ID that was

were you doing anything sort of criminal at this point?

my job no

so all of your money came from that

job and

and so there was a three month waiting period

for health insurance

and while I was there

I had to

I had some downtime in this lobby

and there was a computer

and there was no Facebook or Instagram at the time

this is

2006

and I

was starting to get friend requests from these ebay sellers

on my space

I wore only vintage

I was like you know

rootin tootin scootin to like oldies

and rock n roll and dive bars

and subsisting on burritos

I wasn't necessarily into fashion

and I didn't want to be in

fashion but I loved style

and I loved vintage

and I loved thrifting

and I saw what they were doing

and their auction prices were

crazy like I thought heat street was expensive

because I had

shopped at thrift stores and found great stuff

and saw what their

auctions were going for and these were actual prices

that the customer was determining

they would start the auction price at

$999 and these things were going

for like $200-$300

and they were just making it look like

something that

Sienna Miller or some boho at the time

it was like boho, Olsen twins

Sienna Miller kind of vibes

and

they would do that

put this stuff online and the customer

determined the price

and it was so much money

and so I thought okay so I waited

my three months for my health insurance

waiting period, got the hern fixed

and

I started an eBay store and I wasn't

trying to be an entrepreneur

I was trying to legitimately

not work for anybody

and that's when I realized

that I could connect my curiosity

and independence

and creativity

and resourcefulness

to

something legitimate

that made money that I learned from every step

that I was taking

and

started nasty gal

selling vintage out of my boyfriend's apartment

Before that point

would people have called you lazy

or unmotivated?

I didn't know any people who would have said something

like that because

my friends were just like me

so people

objectively

I think just lost

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

I can relate to so much of what you said

especially all the stuff about authority

I just decided to stop going to school

and I was polite about it but I've always had a

challenge with authority, every job I had

through that period of my life lasted for three months

I was just call centre whole thing

get to the bonus, threshold, quit

because it'd be two months where I don't have to get a job

call up another call centre

I'm one of them

and it's funny because I think people would have looked at me

in school and stuff and said

like written me off, oh he's lazy

my thesis is that

most people are lazy and you should be lazy

for things that you absolutely hate doing

because you should be

I'm only motivated by things I'm curious about

if someone assigns me something

I've tried to write a second book

I published two books after Girl Boss

which was a thing

I can't

I cannot be assigned something

it either comes out or it's not there

Do you think that's the rebel in you?

It is

but it's why everything I do is so inspired

and honest and

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

Because you never accepted or learnt compliance

It's an actual representation

of who I am and what I think

and how I feel in my perspective

instead of a manufactured version

because somebody has given me an assignment

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

No

It's a gift and a curse though right?

I mean it's pretty logical that you

would question

what a bell ringing

and someone moving from

one room, the same room to the next room

every single day

Do you think anyone else questioned it?

No

But if you really think about it

it's pretty wild right?

That e-base

store that you start in your free time

when you're working that job

you took to fix the heron

and

it was successful

and

you kind of frame it as you saw

maybe a price arbitrage or whatever

but it's more than that

to be successful at that time

I'm sure a lot of people saw that price arbitrage

and they didn't build a nasty girl

so when you reflect on why and how

you were particularly successful

how did you diagnose that?

I reverse engineered everything

everyone else did

and did a better job

and did it with my signature on it

Do you think

and I'm thinking now about that bell again in school

where you were like analyzing the bell when no one else was

do you think that kind of default

to thinking in terms of first principles

like asking the question why

why the fuck do we do it that way

has been part of the reason why that e-base store

was successful?

I think so

I think

most people that start an e-base store

are not being what other people are doing

they might reverse engineer some things

and see what their competitors are doing

and I did that

but I just did it ten times better

with a totally different spirit

with excellent copywriting

with great styling

great models and increasingly better photography

and

I was

extremely resourceful

I would buy stuff on ebay and sell it for more than I paid for it

I was searching for

just misspelled

you know

misspelled

even that's first principle thinking

you've got a convention

on one end which says do what's being done

and then you've got these first principle

thinkers who kind of think first about

what they know to be true

and they're really good at filtering out convention

they can kind of see through it at the truth

whereas convention is safety

it's comfort, it guarantees you

a pre-tried blueprint

so people follow that

but then these other little rebels

they have this almost inbuilt ability

to just like fucking see through

to that truth that nobody can see

and in that case I mean that's a great idea

but even caring more about the copy

and you having your own belief as to why the copy mattered

or the photography

like why photography really really mattered

on ebay

which a lot of people wouldn't have had

and it was called nasty gal

the spirit of it was really irreverent

at the time the ebay sellers were selling

like you know

it was called momma stone vintage

was a really big one and it was all very hippie-dippy

and vintagey and mine was vintagey

but it was like very

hard-hitting edgy

I named it after an album

by a woman named Betty Davis

who had an album

called nasty gal

she was so stylish

in the 70s

put out some incredible records

I married to Miles Davis for a short period

and was allegedly too

wild for him

her lyrics are just so

and I was stripping her music when I was like 20

and then I was like

cool nasty gal

and it cut through the noise and I think

when you start a business and you don't need to survive

you might have more time

to navel gaze

or you might do things super conventionally

but

when

you survive there are certain things

that other people have done right

that you can see

accelerate what it is that

you may do on your own

but learn from them

and then also take

and make your own way

I think had I tried to do things completely differently

than everybody else

I wouldn't have

survived I would have been dead in the water

Speaking to something really interesting there

which is like this balancing act between

naivety which is great for

innovation and then convention

which is great for staying alive

I'm talking about the nasty girl

needing a CFO

you see what I mean

that's how I feel being a young founder

21 years old start this business

it grows incredibly quickly

the naivety made us interesting

but our naivety will also send us to the grave here

if we don't know what we don't know

I've been

I died and now I'm in the afterlife

and it did send me to the grave

my naivety and lack of experience

did send me to the grave

It happened so fast

that's a quote

it was shocking how fast it all happened

nasty girl went from doing

$150,000 a year

to doing $150,000 a day

and then $150,000 over lunch

yeah $150,000 over lunch

it was either

a day or over lunch

we all worked out of this warehouse

with kids in the east bay

in Emeryville

I had this 7,000 square foot warehouse

which I thought was the hugest thing

and I was like when we hit $150,000 a day

God was it a day

it must have been the holidays

I was like I'm gonna get a bounce house

you know those things

that people jump on the inflatable things

that children jump on

it was an upside down horse

and its legs were in the air

when you jumped on it the legs

on our breaks we got to jump

in the bounce house

I was like 23

24 years old

it did happen really quickly

to be fair, now you say it

when we raised investment for the first time

the first thing I bought was a 13,000 pound

slide

big blue slide which we had in our office

that was the first thing I bought before we got desks

talking about naivete

I paid off my mom's mortgage

oh did you

spend that with investor capital

no it wasn't with investor capital

no it was the first time I

made money

okay yeah no

they actually those investors did really well

they got bought out within six months

good job

what do you attribute at such a young age

I'm just gonna interview you for a second

because you couldn't have had a ton of

experience under leaders

to give you a model of what leadership looked like

you were naive

I couldn't empathize

with the people I was managing because I had never

experienced leadership and I just

showed up and I did what

needed to happen and what I said I was gonna do

I didn't understand that people needed to be held accountable

because I held myself accountable

especially C level executives

and grownups whose careers

were longer than I had been

alive like how did you do that at such a young age

well I think I

messed up I think like for the first two years

I hired people that were very very inexperienced

and I reflect and I go I think I did that

because I thought they were easier to manage

and I couldn't fathom

the concept that I could hire someone

who was two times my age

and three times my experience and A they'd want

to come here and B with us with with our slide

and dogs and tree and basketball court

and ball pool

and they would like take us seriously but also like B

like maybe there was an insecurity about how I'd manage

them and so what ends up happening

is you hide lots of like young people

you know I remember the BBC did an article

saying is this the youngest company in Britain

because I think we were like somewhere but our average age

was maybe 20 or something

and we had like we had like a hundred

almost a hundred people you know and you feel

the strain of that you feel things breaking

you know this is where you go

convention is right about some things

processes HR finance

you feel things breaking at the seams a little bit

because of the growth and then

at some point an adult enters

the room and you go oh

I get I get this

and so we hired some some really

really great people and the great thing is great

people hire great people so we went from being

this kind of very lopsided and experienced

organization to being a balanced one and I say

balanced because it's my belief that to own the

future you have to understand the present

which is why you want to hire a 16 year old that gets

tick tock or whatever and you also

need to hire someone that's maybe

much double their age

experienced in client services

and understand the old rules of the game

if you understand both games you can

understand the game of the future I think so

made a lot of mistakes and

when I nearly went under several times and had to

call people and beg for money

in the lead up to payday but

somehow managed to

survive but going back to you now

I feel

that we missed a part because you know you're at the

you went from starting that store

to bouncing around on that bouncy castle thing

we call it bouncy castle

horse castle between there

between that bouncing on that horse castle

and the starting the store

what what happened

so

first year

just on eBay did $75,000 in revenue

I was the only employee it was just

pure cash all of the money

just went back into the business I didn't even know

what expensive things I would have wanted

I had never eaten an oyster

you know I was drinking like

Budweiser

still like eat subsisting on Boston

market and like Starbucks

so I didn't spend any of that money

I thought building a

business and I think for the most

part it is

was

selling things for more than you bought them for

and not spending all the money

that's it

that's all and so I bought things

I sold them for more than I paid for them

and no one else would have given me money

parents were gonna give me money

I think I had a credit card at that age

I didn't understand what

venture capital was and I was living in the Bay Area

and

had I not bought the company to eventually

you know $28 million run rate

super profitably

I would never have known

and so

yeah year two

left eBay about halfway through and launched my own website

nastygalvintage.com

and did

$250,000 in revenue

the next year did 1.1 million

the next year did

six and a half

the next year did 12 and I was coming off

a $12 million a year

revenue

owned 100% of the company

I had a bunch of kids

working for me

and that's when venture capitalists came in

and at that point

you know

we were selling non-vintage stuff

what really allowed the company to scale was going

to trade shows and showrooms and curating

from the market based on what I had learned

from my customer having sold

vintage to them so I knew

them very very well and that gave me the ability

to then go by

greater breadth and depth

in

things I knew they would love

and that's what

2011-12

venture capital comes in

2012 was when index ventures invested

$60 million

on a $350 million valuation

on a business with a $28 million

run rate

you were profitable at that time

significantly

pretty significantly

I don't know

I didn't even look at that

I never had to learn to read a P&L

because my company was profitable

and I just generally knew

how much it cost to run

and I didn't buy

expensive office chairs

did you know your gross margins

on the products?

on the operating margins?

I didn't understand what an operating margin was

pretty incredible that you can be running a business

that has a $28 million

a year run rate and not know

what operating margins you're dealing with

or what your net profit is

it's a luxury but it was also a disadvantage

once we plowed

$60 million into the business and things got

a lot more complex

and less profitable

You talk about that $60 million

going into NASDAQ in 2020

2012

what did it break?

hmm

I mean we

no longer had to live within our

means that's what investor money does

unless you maintain profitability

and keep that money in the bank for

another time

or pocket all of it as a founder

we

you know I had hired a COO

at that time

I had a top tier

investor on my board

and

very little like

historicals

data financials

to base

the future growth on

but it had been exploding

just continue to be exploding and with that capital behind us

we could grow even faster

and

the expectation was that

the next year we would grow from

$28 million in revenue

to $128 million

in revenue we just rounded up by

$100 million and then we hired

into that and we bought into it

oh you believed it and everyone

I had grown ups

forecasting this stuff with me I relied

on them it's why I brought them in you hired

the right ones

clearly I didn't pick the right ones or

not sure what happened but I remember sitting

in a room with them

and

us deciding I didn't push for it this

wasn't you know

we're going to just grow by $100 million

this year and

someone put a plan together and

this is we hired 100 people it was like the

Tower of Babel you know that story

you don't know it's like a biblical

story where

people are building this

tower or something but they all speak

languages and

I could be completely wrong

I don't think I am

but none of them get along or understand

one another and it was

it's just a mess trying to integrate 100 people

into a company in a year

especially a company with no processes

and

no real intentional culture

that had been established

no real intentional

anything other than

the brand

the spirit of the brand

what needed to be done

it was like a family business that just got

really big it was

I was a kid

how are you feeling in terms of

at this point in terms of what's going

on around you

$60 million has just come into the

bank account you're looking at it thinking that's a big

fucking number

because you have a valuation of $350

yeah

I'm worth $280 million on paper at this

point

and wherever you go they'll lead with that

and remind you of it and you'll be treated as such

even though it's paper and it's not real

it's not your bank account

how does that make you feel

then they put you on the front cover of Forbes

how does that make you feel

it was a blast

I didn't do

any of it to have glory

or go on a victory lap and I wound up

with it and I embraced it and I had a lot of fun

it distracted me

you know the book in 2014

turned into a phenomenon

you know

it was champagne clinks

for some milestone with the company

or new hire

promotion

at any given time

people would come up to me and say

congratulations

and I had to ask which thing

they were congratulating me for

it was

it was just like oysters for everybody

finally

you know I got better taste

in wine I got better taste period thank god

but now I spend less

money with a good taste

that I had to spend a lot of money to acquire

a lot of my own

but did you feel

did you feel like it made

sense

like the image that

had been built of you at the time that the world

is now like oh my god

is that what was going on inside

I think it made sense

I think it was a freak show

I was a community college dropout

who bootstrapped a business to 28 million dollars

in revenue

super profitably

investors came out of the woodwork

top tier ones anointed me

as

someone who could pull it off

and I didn't know what I was signing up for

or what I was supposed to pull off

but

it was

the richest story

imposter syndrome

any of that

for sure yeah

I mean I still walk in rooms

and I'm here I was

talking to your team and I was like oh my gosh

you guys have really big people

I hope I can keep up I say like a lot

I'm

intimidated I hope I can provide some

value what are the comments on youtube gonna say

is this gonna be a valuable

conversation I really hope people like it

you know and she was like

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

what are you talking about

you're great

but I get nervous

I get nervous on stages

and I'm still like

I don't belong here

but the I don't belong here

is also a really great motivator

the I don't belong here is

I snuck in the back door

I don't belong here means

I can do things differently

and a belong here means

I don't fit in

but that's gonna be a superpower

and I think

it's okay to feel like an outsider

or an imposter

sometimes because

you find yourself in places where

you have

an outside perspective and are able to learn

things

unlike the people

who are invited to the table who all showed up

there with the same pedigree

and then you get to make

oblique connections

between

who you are, where you came from and then the door

the room that you just snuck into

as an imposter

that is radical

would you remove that

self-doubting voice if I put a button

in front of you and said you press this you'll never die yourself again

no

it's so boring

I had a coach recently

and he was lovely

we did five sessions he was like $5,000 a month

and I was like

taxes

I'd buy something else to save on taxes

and

he was like can you imagine

he asked me that word

he asked me that question and I was like

but

what would I struggle with

who would I be if I

didn't have challenges

and I was happy all the time

the scaffolding would fall apart or something

that's a story

I tell myself

but it's fun to have

a dark counterpoint

to hold yourself accountable

maybe it is that or not that

and I think that counterpoint

is an opportunity to

gain self-awareness

do you think it's additive to your performance

or reductive

I think it can slow me down

and I can make really

slow decisions

because I doubt myself

but

beyond that

I think I've found a way to harness it

that really works for me

have you developed

a decision-making framework to help you navigate

the two voices in your head

it's funny because when you're describing your mother and your father

it felt like those were the two voices

your mother would seem to be very supportive

in what's critical at times

or pessimistic

have you found a way of being able to

juggle those voices

so that you can make decisions

decisively and quickly

no

no

so I can have these conversations

and when I do

make a decision

I've learned to be slower with making decisions

because I either make them extremely quickly

or

in an accident

so I want to be very deliberate

in the decisions that I make now

and think more critically

rather than navel gaze

or be reactive to something

I went to this

retreat

even though it's not really a luxury experience

with 30 other people called the Hoffman process

and it's seven days

with no phone

no internet, no books, no music

you're with 30 other people

through this process

of mapping your patterns from your childhood

against your parents

and how you inherited that

and it's all directly correlated

and basically

graduating from your

emotional child

into an emotional adult

super embarrassing

weird process

so dorky

and everybody came with something different to work on

or what emerged for them

I feel unloved

I don't feel unlovable

my thing

it sounds really weak

I don't trust myself

I don't think I'm deceiving myself

but I think I can rationalize a lot of things

to the point where

I'll tolerate them

too long

and that's gone for relationships

that went for my most recent relationship

and so that's a strange thing

I don't trust myself

because I do have these

voices

I don't have voices in my head

but

I can see things from any perspective

and not be

totally attached to either one

to the point of

being slow

and asking for too much advice

In that retreat

did you have to sort of

go upstream and figure out where that belief

started

is that the point of that retreat?

Did you figure it out? Did you go upstream?

What a good question

You're very good at this

I think it was that my parents didn't agree

on how to raise me

that I felt misunderstood

that my good intentions were sometimes

construed as

troublemaking

that the fact that I didn't fit into the environment

I was raised in

I was

not accepted and I was some kind of

weird deviant

when I was just being myself

and felt punished for being myself

and I think that

gave me like a lack of confidence or something

and I don't identify with being an

unconfident person

but when it comes to decision making

when everyone around you is telling you

a different story about yourself

than you have

and doesn't understand

why you operate the way you do

that is really

with integrity and in line with

who I was and what I needed to be successful

as a child

if other people like live in a different world

and don't understand

that those are your needs

you just feel wildly alone

and think wow I

am a freak

and that

found its way into my career

through the public too

which has been super fun being told I'm

something

that I'm

mostly not

what have you been told you are

oh gosh

um

so nasty y'all fell apart after 10 years

it was a quick rise

and it was

it was a slow rise

and it was a

relatively quick fall

couple years in the making

and when it did fall

the headlines were

crazy because I had had all this

press from this book I published

and being the poster child of entrepreneurship

going on the victory lap

national inquires had

had a picture of me and it said

rags to riches like straight up tabloid

American dream

stuff like a caricature

and I didn't realize

the amount of responsibility I had to like

other people as an example

like I kind of did

but as some symbol for entrepreneurship

or my generation

you know the generation of the

entrepreneurs coming up behind me or at least

what the press thought I was

responsible for

the

you know there were headlines like

does the failure of nasty y'all mean

millennials aren't ready to lead

it's like wait how is one example

representative

of a generation

and I've also read

headlines like

when the netflix series came out

the worst thing

about netflix's girl boss is its source

material

not even the show

just me

but I'm not bad

I don't believe it

how does that make you feel at the time though

by the time that netflix series came out

I had been this hero

as an entrepreneur

then I was this girl boss

because I wrote a

book called girl boss and it was pink and I

was like this and I looked like I knew it was up

but it was like 27

and then there was the me

whose company fell apart

the CEO there was the girl boss

who had built a

toxic culture

or just no intentional culture at all

that like warped into something that

wasn't perfect but wasn't

I still don't think it was the worst

and

now this person this conflation

of all of those things

with this girl on

the scripted comedy

which came out four months after I left

nasty y'all so the biggest

kind of personality or whatever

the humanity crisis

was

you know I'm on the cover of Forbes in

June I think of

2016 July of 2016

my husband of like a year's like

may I change my mind and I'm like oh my god

that wedding was so expensive it was devastating

but I'm just like god that wedding was so expensive

it was a great party

so in that space of like 12 months

you're on Forbes, husband leaves

netflix comes out, nasty girl

goes under

then netflix comes out

so the show had been shot when things

are all like up into the right

and you know we were working

through challenges there had been some layoffs

but the company was still you know

100 million dollars a year

you know not profitable anymore

but a great brand

and something that was valuable

and

eventually

yeah like

fell apart and

there was really a conflation

of the hero

the failure and now this

girl four months later

who's a caricature

of a person I was when I was

22 in a scripted

comedy playing someone named

Sophia starting an eBay store called

nasty gal when for the first

time in 10 years

in my adult life

since I was 22 years old

I'm no longer associated with

the thing that I had built

and now there are

130 million homes in

195 countries

watching a story of someone that I

was

no longer

and no longer

trying to move on to move on when

there's a full PR campaign

about who used to be

you're someone who's as you said you've had a long

history with mental health challenges

but

what is it like in that 12 month

period what's going on

from a mental perspective

I had fallen in love again

I think I was still like travelling

I started another company

I maintained my mental health

partially because I keep going

you know I don't stop

and like lick my wounds

I think I was also

I was also on anti-depressants

I wasn't

jumping for joy

but I also

knew that there was a huge

community that still supported me

who had read my book

500,000 women who bought it

and I went on to start

a company called Girl Boss

right as the Netflix series

was hitting put on our first conference

and I had my podcast

and I moved on quickly

and even though

the headlines weren't nice

the people who followed me

my friends, my relationships

everybody in my network

nobody bailed

like the girls who were inspired

by Girl Boss were refreshed

that I had face planted

publicly because everyone else

is face planting in private

and in the same way

that watching some

random community college dropout

from Sacramento start a business

with an internet connection

and a computer gave them license

to

yes they were inspired

but also

embrace their own failures

because the hero

face planted

publicly

and that can also

inspire people

This is hopefully the most cliche question

I ask but

I want to know

because you have

from that experience you have amazing feedback

you have amazing insight

invaluable insight I would say

because when I think about the things that have taught me the most

it's not when things go right

that's a validation of your hypothesis

it's when things go tragically wrong and you go oh okay fuck

you have all of this new information

about which is correct to your hypothesis

so if we go back

and think about that fundraise for example

a lot of people will hear

raise investment

at $350 million and think

amazing that's when people clap

they get the champagne out of their oysters

for people listening that aren't in business

they might not understand

how that can also be a key reason

why the company ultimately went under

the $350 million

why did a big valuation hurt you?

Yeah I think

the $350 million valuation

is celebrated as it was

and how wealthy I was on paper

was the nail

in the coffin

it was then in 2012

where we were overvalued

and the expectations

that was

the next round of fundraising

that we do

is at over a billion dollar

valuation and so the company is doing

on an upswing

$228 million

in revenue

that's over 10 times revenue

in the fashion business

this isn't a technology business

this isn't Uber

this isn't an infinitely scalable marketplace

it's e-commerce

it was a different era of e-commerce

it was pretty early

it was the era of fab.com

which like imploded

and won Kingslang and Beechman

and ShoeDazzle

there was no playbook

there were no e-com veterans

or

I was hiring executives

who had worked at Macy's

nobody had

it wasn't called direct to consumer

at the time it was very very different

there was no Shopify

and

we were overvalued and I didn't know that

I didn't even hardly negotiate

I didn't shop a term sheet around

and say I'm going to pick the highest

price from different investors

I only had one term sheet and I was like

great I like you

yeah I was like you're awesome

you get it

you know what Danny said

when he invested

with something none of the other potential investors said

and that was you have a community

and I was like yeah

we do have a community

but when you have that much money

you don't know

there's been a nail in the coffin

or that there's a coffin

and that like you might be

on your way into it

or maybe already laying in it

but just several years

in the future

and

when things are up

into the right

you don't see what's lurking

kind of below the surface

so when the tide lowers

you see the mud

you see weird crab shells

sometimes hopefully not you see trash

and it's only when things

recede

you see the mud that's underneath

and when you're on a victory lap

and you're hitting milestones

everything's great and everybody loves their jobs

and you're a hero

and as soon as things

go a different way

as soon as there's layoffs

yeah there are things

there are things lurking below the surface

that were dynamics

that were already

happening that

because everything was going so well

you know we're harder to

notice and

you know it's hard to be a CEO

it's hard to be a founder

I think something

a lot of people don't realize is that

you only know 10%

of what's happening in your organization

I had hundreds of employees

and ultimately everything was my responsibility

but I'm held accountable

for 100% of what's happening

and when something goes wrong

or something's mismanaged

or someone has a bad experience in the company

the assumption is that

I have signed off on it

that that is how I want things

to be and these things are happening

you know cattiness

and you know

fiefdoms and silos

and duplications of effort

and all the you know the entire

spectrum of

things that are no fun

at a fast growing company

I didn't know were happening until

we laid people off

and then they were like hey

we didn't like it there

and some of that was

totally overblown

but also anything that any

employees ever said about me

or I've read

even though I don't agree with all of it

has been an opportunity for me to learn

and take from that how I could be better

because there's truth to

almost everything

Didn't you get an offer to sell the company

in dollars? Yeah I did

I owned 80% of it

So that would have made you

quick maths I don't know very fucking rich

Super fucking rich

And why

didn't you say yes?

I went to my investor

and I said

what do you think about this

and he said

you need to ask for more

I controlled the board

I owned the majority of the company

but I also took advice from people

who I thought knew more from me

but I didn't know that my

interests weren't necessarily aligned

with the interests of my investor

whose interest is to

whether I'm worth it or not

have a piece of paper to show his investors

that says I'm worth

instead of 350 look

they're now worth a billion and they just make

up these numbers and then they can show

their people that your company is worth

more and that was

in his best interest and that's what

he was giving me advice based on

Are you mad that he said that?

I'm not mad

Do you wish you made a different decision?

Is that a regret?

It's a partial regret

but I also know that no deal actually happens

they're not

a real acquisitive company

they could have tried to acquire the company

I don't even know if they've acquired anything

integrating it into their company if I had an earn out

based on

them controlling it

and me trying to hit performance

benchmarks even if I had

sold the company to them who knows how it would have

played out I would have made a bunch of money

my life could have been miserable but 99%

of the time deals fall through

There's also in those situations

a lot of people trying to

get into the data room so they make an offer

so they can see your numbers and what you're doing and how your business is working out

and then they pull the offer later

once they've had a look into the data room and due diligence

yeah and then copy it

yeah exactly

so we didn't get that far

I don't regret it

but

yeah that was a big thing

for me that would have been a lot of money for him

it was just a teeny tiny bit more than

what he had paid for it so that's not

a lot of them

it's not much of a markup for him

What is the advice you're giving now

to women that are

and men that are looking to start companies

in your community, the communities you're building

within your portfolio companies now that you're an investor

I can think of the

first piece of advice that I give

young founders when they come to me

I'm wondering what your first piece of advice is

I think for Bootstrap founders

the advice would be different

for founders in my portfolio companies

who are raising venture capital

my advice would be

get as far as you can before raising a single dollar

validate your idea

as soon as you can with the ugliest

like most basic

quickest thing your first product

should be super ugly get it in front of people

and get some idea

of whether it's valuable or not

before you go raise money

before you even try to market it

talk to every customer

every potential customer

and Bootstrap it

as long as you can if you can

because when investors do come in

your company is going to be worth more

than if you would raise money

when you just had an idea

and were asking for a check

when you do raise money

having a reasonable valuation

is important

and a lot of founders optimize for price

because

bigger price an investor pays

the more ownership

the founder has

the more they're worth right

the more they're worth and the more eventually

they could make if they sell the company

but when you have a valuation

that's in line with

market that makes you an attractive

acquisition

something someone might pay a multiple for

that 10%

say you're diluted down to 10 or 20%

if you sell your company

for 500 million dollars

you're in much better shape than

raising 350 and owning

80% of it and going to zero

or whatever

and I think where things are right now

where is

a place that is

close to that

and founders aren't greedy

founders who are raising money in this market

no it's really really hard

they don't want to be overpriced

because the people who raised money over the last few years

raised it such a high valuation

these founders

nobody's going to reinvest in them

they've blown through their money

they're on an upswing

their company might be doing 2 million in revenue

someone told them they were worth 80 million dollars

and now nobody's going to give them money

I've as an angel investor

I have

three of these right now

and it's like Hail Marys

two of them have figured out how to survive ones like

we have another term sheet

I mean I've been there

What about the psychological advice

you'd give to a client?

I would say to listen to your gut

you know there's going to be a lot of voices around you

and there are people who know more than you

and have

experience

and you should listen to them

but you should also

always maintain

and continue to cultivate

a voice that

when you know it

should is able to

supersede any advice that anybody

gives you

I think it's easy to

take all the advice because you're an

experienced founder

and

and to

lose touch with your intuition

and it's probably

what got you to where you are as a founder

without the money and without the experts

and if you

just rely on the money and the experts

you're losing the thing that

made what you're doing special in the first place

Which day was your hardest day over the last

year?

Since you first started

that store on eBay

is there a day you look back and go do you know

that period or that day was just

the worst

the hardest the darkest

Honestly

and it's weird the hardest day was when my husband

left

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

still together

I don't really think about him

I mean that was in 2016

but

I

had agreed to take a big

swing in my personal life

and make a huge commitment

and I thought that bumps in the road were like

to be celebrated I thought it was like wow

okay you're not feeling great about things

we're gonna work through this and we're gonna be

so much better as a result of it because

I see

commitments as things that go up and down

and if you're in a commitment together

you're committed to working

through those things and it all comes out in the

wash because you have that level of

commitment to the other person and that wasn't

the case for him and so

I felt like I was like

hallucinating

you know I like went to a hotel

for a week I couldn't be in the house

it felt like a crime scene with his

stuff around

and yeah

a whole week at the Beverly Hills Hotel

with three poodles

is quite the scene with

chain smoking in the courtyard

in a bathrobe

has that experience put you off

being a CEO of a big company

I mean yeah everything I've experienced

has put me up for being a CEO of a big company

I'll never do it again

I don't want to that's not the job I want

I'm an early stage

founder I'm a master

at creating brands

that cut through the noise

what happens though if you're running

a number of businesses now

you've got your fund

business class

what happens if it becomes

globally

you know

globally successful then

you're back to being a big CEO again though

I would have to work really hard

to make it that and I would have to

invest in that and hire into it

that wouldn't happen

by mistake I have one employee

on business class

business class is super profitable

I launch it twice a year

it's pre-recorded so business class

is my entrepreneurship program

I have two accords a year

April I'm launching it

and I launch in the fall

and

it's an incredible product but it's also something

that is relatively

self-led for the students it's 8 hours

of video and 300 pages of worksheets

and over 60 hours of

interviews with me like this with

entrepreneurs

and you know students get lifetime

access so you know they can take it

over the first 7 weeks they can take it

over the course of a year or the next few years

but it's not

something that requires a ton of my time

outside promoting it twice a year

and I built it for that

I built it for that I'm using

Kajabi and drip

for email and

you know whatever Zappier

a variety of tools

that allow it to be

relatively low lift

light on human capital

still a lot of effort to promote

and something I do

engage with throughout the year

and to weekly calls of students

and post in the lounge which is our

community that's it no

I'm playing

I'm not playing small

with business class I'm playing

to my strengths that's big

and with trust fund

it's venture fund that I'm raising right now

it's a 10 million dollar fund

what I get to do is not run

a big company and keep trying

to apply this stuff that I've learned

over you know

over time

I get to go from 0 to 1

over and over and over again with early

stage companies and out of fund

I get to be in the weeds if I hired

a bunch of people I they don't want me to be in

the weeds executives don't want you to

micromanage but I get to look at all the

decks and I get to text the founders

and say here's what I think you should

do I can be helpful

and it's so rewarding to

harvest all of my hardship

on behalf of a new generation

of founders and help them

see around the corners that I wish

someone had shown me

around and

I get to keep my firm small

even if I have a 50 million dollar fund

I can do that with a few people

and

I'm using the assets that I have

I'm the product my relationships

and my network and my access to deal flow

is my product

my expertise and ability

to help founders is my product

million social followers

and being able to amplify them is my product

the engaged

community I have who's interested in the kinds of

things I'm investing in will actually use them

is my product and I don't

I'm just

it's right here and it's an air table

the intentionality is what I

find most surprising

because so many people get dragged

by the temptation of external expectation

if it's great business class is great

but all accounts have been on the website

went on to I saw that the

waiting list is open for 2023

it said like join the waiting list for 2023

yeah so it's launching in April

okay the spring cohort

launches in April so you can enroll

for like a 10 day period at the

end of April when things are great

we get dragged by our own success

mm-hmm what you're saying is

you're going to be intentional and you've designed

it so that that's impossible

so that you can't get dragged because someone's going to come

along and say we love this we're going to give you a check

we love this we'll turn it into some boxer shorts

or some teddy bears

yeah no no I

I

have had the privilege of knowing

what's on the other side of success

and that a lot of it is not what you sign up

for and that when you are

successful you're stuck in it

so I spent a lot of time thinking about what

success looks like for me and what I want

my life to look like and how many people I want to have

around me and the kind of stakeholders I want to

have so that I'm set up for success

when trust fund is super

successful which I can

stay nimble with

and with business class I've engineered

that revenue was down last year to the

year prior and that's so

that's okay it's still profitable

I'm not going to

hire a bunch of people or a CEO

or plow a ton of money into it

trying to solve problems and pivot things

so if I come along and say I'm going to invest 10 millions of

you we're going to hire a CEO

okay but you take the money

yeah

take the money just for the record

guys when it's

there take real

money take take the money

magical thinking

what is that

yeah I mean you can call it magical thinking

you can call it magical thinking

you can call it manifestation

you can call it prayer you can call it whatever you want

I think it's

you know casting

the line out

not knowing what you're going to catch trusting

you're going to catch it and we'll pull it back

magical thinking is like Indiana Jones

where

there's the vast

chasm between whatever

in the holy grail

and he has to trust that there is

an invisible bridge

and he grabs some gravel and he

throws it out across this

literal kind of canyon

and

the gravel

just falls on a clear bridge

and he had to

like trust that when he walked

across that he wouldn't fall

and so I see magical thinking

as you know

thinking

beyond what might be obvious

thinking you're capable of doing things

that you shouldn't be

thinking you can

belong in places that you never thought you could

thinking

you can accomplish things that you're completely

unqualified to because nobody's

qualified to

being able to see yourself in a life

in a world

that's beyond your wildest imagination

and just staying there

we have a closing tradition on this podcast

where the last guest leaves a question for the next guest

your question is unfortunately not the hardest question in the world

I really wish you'd been given a real stitch up one

but yours is

fairly straightforward question which is

what is your proudest moment?

my proudest moment is

paying off my mom's mortgage

I mean that I can do that

that was crazy

that was the first thing I did

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

this requires a little bit of magical thinking

understanding what

is meaningful in my life

and actually spending time on it

you haven't figured that out

there are meaningful things but what is the

people have kids and that's like

obvious and I don't know if I'm going to do that

I am super

agnostic about it, it's really strange

I'll be 39

in a month

but I think finding that and hanging on to it

what is

there some big meaningful thing

that I'm going to

find and cling to till I die

and it's easy when it's family

or easy when it's a kid

and you can create these meaningful things

in your life

but what is that going to be for me

when I'm dying, what is it

what will it all add up to

Sophia, thank you so much for your time

thank you for the inspiration

you've been an inspiration for me for many many many years

and that's why I reached out to you to sit here with you

and you are absolutely a superstar

in many many respects

but also because of your

inclination to be open and honest and vulnerable

you're incredibly inspiring

and the stories you tell in the way that you tell them

so thank you so much, it's a real honour to meet you

I'm equally privileged that you said yes to come

and do this

and I mean that, I'm not just like gassing you up or anything

I mean that, thank you

you're superb and I can't wait to see what you do

with both trust fund and business class

because they look like exceptional projects

I've looked into the reviews of business class

and with your fund

with the amount of information you've learnt

from your twisting turning professional career

you clearly have a huge amount of

intellectual leverage

and fire power

that makes for a great

fund founder

so I look forward to seeing what you do then

Thank you

As you might know

the shows now sponsored by Airbnb

absolutely love Airbnb, always have always been a

you know, saved my life on so many occasions

and my team when we first got in touch with Airbnb

were talking about how most people

don't realise that their place where they currently live

could become an Airbnb

and I guess the second question there

is how much could your place be worth

and it turns out you could be sitting on

an Airbnb gold mine without even knowing it

some people Airbnb their entire

homes when they're away, that's what I did in New York

when I left New York

my place was on Airbnb and people rented it out

sometimes for a day, sometimes for two days, sometimes for a week

and it's a great way to cover some of the bills

while you're away, so whether you're looking to go on holiday

or you just want some extra cash for bills

or you want to buy something nice for a Valentine

that you love, whatever it might be

head over to

Airbnb.co.uk

and you can find out how much your current property

where you live can earn while you're not there

I suspect

it might blow your mind because it's certainly blue mine.

Machine-generated transcript that may contain inaccuracies.