NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239
2484 segments
didn't you get an offer to sell the
company for 400 million dollars yeah I
did what it made you super rich why
didn't you say yes
you're very good at this Sophia also
founder of Nasty Gal A best-selling
author and a Powerhouse in the
entrepreneurial world I was rebellious
from a very early age I was a stripper I
wasn't even 21 I used someone else's ID
to work there built an online business
the first thing I sold online was stolen
get a whole shopping cart of stuff put
them on Amazon for 10 cents less than
the other resellers and then gotten
arrested for shoplifting
I'm a little dark I realized I could
connect my creativity to something
legitimate started Nasty Gal selling
vintage namastico went from 150 000 a
year to doing 150 000 over lunch I
didn't realize the amount of
responsibility I had being the poster
child of Entrepreneurship then I was
this girl boss but my naivete and lack
of experience did send me to the grade
nasty y'all fell apart after 10 years my
husband of like a year left the
headlines weren't nice
what is it like from a mental health
perspective it's hard to pull yourself
out of a hole when you don't want to get
out of bed it's challenged my confidence
and I'm still like I don't belong here
but I don't belong here is also a really
great motivator I don't belong here
means I don't fit in but that's going to
be a superpower I can do things
differently
what was the plan in life at that point
gosh
before this episode starts I have a
small favor to ask from you two months
ago 74 of people that watch this channel
didn't subscribe we're now down to 69 my
goal is 50 so if you've ever liked any
of the videos we've posted if you like
this channel can you do me a quick favor
and hit the Subscribe button it helps
this channel more than you know and the
bigger the channel gets as you've seen
the bigger the guests get thank you and
enjoy this episode
[Music]
take me back to those suburbs in San
Diego and give me your earliest context
wow I was born in San Diego Sharp
Memorial Hospital only child
eternally and only child
I think wound up having the personality
of a probably seven children and the
challenge of maybe seven children for my
parents
um
we moved a few times you know our house
was like it was it was happy-ish when I
was young I lived in San Diego till I
was seven and it's a beautiful place and
I so wish we would have stayed there but
we moved to beautiful
Sacramento California and that was
really the Suburban experience where you
know when you're a
kid a little kid you don't know what a
suburb is and chasing the ice cream man
is great but once you get older living
in the suburbs if you have any amount of
curiosity about the world the
homogeneous you know nature of living in
the suburbs is something that totally
crushed me I knew there was more out
there and I didn't know what it was but
I wanted I like wanted out from a very
early age
what what did you what did you want at a
very early age when you say you wanted
out oh yeah what did you want yeah I
wanted out of my family home it wasn't
happy my parents didn't get along I was
playing referee you know really yeah
what what age
starting at like 10 or something
I mean
yeah it was just it wasn't a super happy
place and they yeah they didn't get
along they didn't always agree on how to
raise me and I think when your parents
you know everybody's relationship has
issues and everybody's not everybody's
but most people's parents you know
sometimes don't get along when you have
a sibling I think you can go be like um
that's funny or they're whatever let's
just go play with Legos or something
like that or let's go ride bikes but I
think being isolated in a house that
wasn't super happy as an only child made
it worse and I just remember so many
drives silent car drives where I was in
the back seat alone
and I just remember like the silence and
the the light of the street lights
like washing over the car just in in
Silence with my parents in the two front
seat
um yeah they're really like only
affectionate
after like an argument and even then it
was like I don't know hand-holding or
something they were very strict as well
I had to beg to go to a boy's birthday
party in sixth grade
we weren't super religious but my mom
grew up in the 50s in a Greek Orthodox
household
um just
not puritanical because that sounds less
cultural than Greek Orthodoxy but uh
strict you know what about money
yeah arguments happened in my household
when I was younger because of money
yeah I mean my dad sold my dad did loans
and my mom sold houses but track homes
in the suburbs and they were both
working with Builders and Banks and
manufactured homes and so on the
weekends by the time I was I don't know
maybe 10 my mom was working in the model
homes
that are all kind of dressed up and you
can tour them and pick your manufactured
home and change a couple things and
there's like a fake keyboard in there
just all kinds of
funny things to play with and then so I
was with my dad on weekends and my and
they both worked entirely commission so
I've never seen either of my parents
work for a salary and my mom's dad
didn't work for salary and my dad's dad
owned a motel and they all grew up on a
motel so there's like generations of my
family who wouldn't necessarily call
themselves entrepreneurs but they're
people who ate what they killed and
that's what I witnessed
money was good I think when I was like
you know when we were in San Diego and I
think it got tougher over time I
remember very vividly
being in a credit counselor's office I
just can't believe they brought me but
there was no I don't know where they
would have put me watching them
cut up their credit cards like cut their
credit cards in half and put them in a
clear jar with like other people's cut
up credit cards and file for chapter 11.
bankruptcy yep did you know what was
going on no
I still don't know what happened I don't
know
are you able to look back on that
that first sort of chapter of your life
and figure out how it had a lasting
impact on various elements of who you
are today
I think it allowed me to even though it
was so challenging younger in life to
learn how to assimilate into different
environments
um to I guess entertain myself
independently to realize that Authority
was
like adults were not trained to be
parents and weren't any further along
with their maturity sometimes than I was
at my age you know I looked at teachers
and thought wow you know you have domain
expertise you know some stuff but I can
tell that like you're morally bankrupt
and I don't trust you and why have I
been put in your
you know in your hands
um
I think the thing that had the biggest
impact on me is how critical my dad was
so he's half Italian and half Portuguese
and his dad was a mean mean guy
and my dad's very charismatic and I love
him and he's super chill now but when I
was young he had a lot of pressure
on him and he didn't really have the
best model of what a great parent looked
like and I can't say he was a bad parent
you know he did his best I know that
both my parents did their best with the
materials that they had the ingredients
that they had to be parents
but it instilled in me this
unfortunate but also very fortunate
always peeling back another layer of the
onion examining myself but also real
internalized drive to do better in a
self-criticism that has worked very well
for me that's been challenging it's
challenged my confidence over time but
it also has been a superpower to in some
ways I don't know in some ways hold
myself accountable because I'm always I
almost want to say second guessing
myself
but also very
um
in a very I guess someone said Jesuit
way at one point but
a way where I can see both sides of
everything you know challenging my
doubts and my ego
but the problem with that is sometimes
it's hard to differentiate between the
two what is
you know fiction and what isn't and what
of my self-critiques are accurate
because I want to be and I think I am a
pretty self-aware person
and even with the things that I'm not
great at I'm like super proud of that
because I've got
a ton of advantages and things that I'm
really great at but I think it was the
criticism I experienced early on in life
for so long that instilled that in me
and I've learned how to turn it into
something that's more balanced than
what it was when I inherited it
when you inherited it
when it was handed to me the model I had
the level of critique that I had that
didn't have the Counterpoint that I'm
able to provide for myself you're
talking about your funnel there yeah he
would critique you yes
when you say critique do you mean
oh that's that's naughty don't do that
no
no like that's not how you do something
or why why'd you do it like that or can
you not or
you know I mean I love my dad and
and he's you know as both of my parents
have gotten older they split when I was
17 and I've just watched them
both become such better people
I remember congratulating them when they
finally split up and was so glad at 17
years old and I was also like I'm out of
here
see ya
you seem to become a bit of a rebel
you know from from when you moved out of
your parents house
for the next couple of years the
behavior looked really rebellious oh
yeah no I mean I was rebellious from a
very early age
I remember in middle school a teacher I
was eating an apple in class I was
eating an apple it was healthy I was
hungry I've got agency over my body I
didn't know what that word meant I'm
hungry I'm gonna eat food I'm human I'm
hungry I'm gonna eat food in the middle
of class
but like who how could you tell someone
not to eat when they're hungry it's like
a simple bodily function and it keeps me
healthy and it's gonna make me a better
student and it's
and I and the teacher told me to throw
the Apple away
and I just started the apple and of
course I had the attention of the entire
class
and I got up and I sauntered over to the
trash can super slowly and I just like
ate the apple all the way to the core
like super fast finished the apple and
was like dink in the trash can
um so I was like that if if someone said
not to do something I did the thing that
they didn't say I couldn't do that was
similar it was peripheral
and then by the time I got to high
school I was going to the anarchist book
fair in San Francisco I was sure
capitalism was you know the worst thing
ever
I was very angsty I thought that
adulthood it's funny there's a Netflix
series about my life and the first thing
that the character says is adulthood is
where dreams go to die and it's so weird
to reference your own Netflix series
like who does that but
that's how I that's how I felt I wasn't
trying to be a child but I also didn't
want to go work in an office I also
wasn't ambitious so somehow along the
way that lack of desire to live a
conventional life became something that
turned into ambition because I not even
ambition just curiosity something that I
was good at and you know eventually
built a business but um
I uh in high school in high school
I remember there being Bells like right
there's a bell that rings and you go
from from one room to another room all
day a bell rings you sit at a desk a
bell rings
and you stand up and you Shuffle over to
the other room
and then you sit down and you like
memorize some stuff
and then you like this is my youth I was
sure I was being trained for something
super mediocre not that I wanted
Excellence I just wanted out
why are you like that because you know
all the other kids will come out like
that I actually came out I came out like
that yeah it is not I mean her I'm I
might have some hereditary just kind of
like Italian I'm not sure what or
something it's not it wasn't a nurture
thing that was
a nature thing or I don't know I just
like
came out I actually hatched out of a
disco ball but that's the way that's how
I came out I had a gabo mate here who's
this like I think he's just interviewed
Prince Harry actually
um in uh in a little like pay-per-view
therapy session or whatever and Gabriel
Mata said something to me that I've been
pondering ever since he said that
as children we're like narcissists and
we are that way because it helped us to
survive so we think that everything is
about us when we're like babies and
young so the parents were arguing we
actually interpret that as there being
something that to do with us and that's
the way we view the world as a survival
mechanism and he says one of the things
that happens when we're in a where you
were a young child and we're in a house
where there's lots of arguing and lots
of drama and shouting is we learn to
avert our attention as a way to help us
deal with emotional distress and that
develops into something they call ADD
and ADHD so I took Adderall this morning
hmm
hahaha
well they will yeah just to prepare for
the podcast just kidding now I've major
add
but they diagnosed me as a kid and I was
like no this is mind control
forget it I'm not focused because I
thought it was situational I thought it
was my environment and it maybe was
partially because I wasn't interested in
what was happening
and distracted because I was curious
about other things
but also it's a real thing and it wasn't
until
a few years ago that I finally realized
it was a thing and sought treatment and
it's helped but it's helped like
marginally it's not
I had to realize it was a real thing a
couple of years ago
I've I've been I mean you know I go to a
psychiatrist and I talk about what's
going on with my brain and
um do what I can to help myself
um holistically but also I know I'm also
predisposed to depression not
predisposed I've suffered with
depression my whole life since when
my whole life I don't I can't remember
an age where I wasn't
depressed I just
I wasn't always miserable but I've I'm
kind of a dark I'm a little dark
um
and that's not something you know it's
hard to pull yourself out of a hole when
you don't want to get out of bed like
that's you know to have the willpower to
just get over depression and put on a
happy face and whatever people do get an
ice bath and jump in the sauna and
meditate and
you know I am still struggling to be the
well-rounded person but I'm functional I
think we're all struggling to be a
well-rounded person I don't know some
people seem to like have these parents
that teach them that and they come out
and they're like yeah you know and it's
not you know that's almost diminishing
to be like
but
but I'm yeah there's people who just
seem to you know and some people come
out of the womb like that I know parents
that are creative chaotic I know people
who are well-rounded whose parents were
addicted to drugs and somehow they just
wound up like that and how to attribute
that to your parents it's that's a hard
correlation to make did you ever you
said it curious phrase now which
made me um
Ponder you said I'm a little dark uh-huh
what do you mean by I'm a little dark
hmm
why are you giggling you're making me
think you are a little dog I am I'm not
evil God uh I'm not a witch
I
I guess I've
just
you know like I said I've struggled with
depression
I'm not a bubbly person I'm not someone
you know as a child my mom has said you
only laughed when something was really
funny you know I think kids run around
like laughing and smiling because
they're like children or something but I
had to have a reason
I'm not sure why and it's still kind of
like that and maybe it's I don't know as
an adult it's become something that
requires it's just being genuine and
maybe I'm not I think maybe I'm not
impressed maybe in general I'm just
skeptical you went to see a psychiatrist
when you were 16. oh I went to see a
psychiatrist when I was like 10. I mean
I was in therapy
when I was like 10 11. with what's
trying to be diagnosed like what's wrong
with her why can't she stay on task why
is she so weird why doesn't she get
along
why is she distracted so I have report
cards
that say
chooses to disturb others you know
doesn't stay on task it's stuff like
that it was like I was always like you
know not paying attention curious about
something else engaged with something
else it wasn't always to be rebellious
sometimes it was very good-natured and I
would get in trouble for things that I
didn't think were bad or intend to be
bad it was also just very a very willful
independent thinker who didn't fit into
a traditional educational environment
and
you know that's something
for whatever reason seemed to be needed
to
be diagnosed
but then I was like no no I'm not taking
Wellbutrin and I'm not going to take
it's like an antidepressant I didn't
take it I was like no I'm not taking any
of this when did they win right that was
by high school so you were 16-ish around
that time when they yeah 15 16 and I was
like this is
it's I don't feel like myself feel wired
and weird and
I got like I think I got Ritalin and
someone tried to buy it off me in like
high school and I was like what do you
what I don't even get it I was like I'm
just throwing this stuff in the trash I
didn't
and then so you so you get diagnosed and
prescribed antidepressant at 16ish your
parents break up at 17ish you leave them
I move out you move out I move out at
17. before I graduate high school I was
homeschooling so I got my diploma in the
mail I thought the like most
embarrassing thing would be would be to
wear the cap and gown I was like what is
that I don't understand what's the
tassel why do you have to wear a robe
what is this robe
I I wouldn't have been proud standing in
a group doing some group thing I'm not a
group person even though I've built a
lot of really powerful communities I'm
not I don't assimilate well into groups
and I think groups are responsible for
the most heinous things in like human
history so uh
[Laughter]
so I moved into a closet
you moved into a closing under the
stairs for sixty dollars a month
uh these guys that were like in bands
and artists who had met going to shows
because I was really into music and went
downtown in Sacramento and saw music and
what was the plan in life at that point
was there a plan you know you're like 17
years no you told me there was a plan I
wanted to go to
first wanted to go to Reed College but
that was expensive
but then I wanted to go to the Evergreen
College so by the time I was 18 I had
moved to Olympia Washington to get
residency to go to the state school
called the Ever Supreme State College
which is a super duper hippie state
school that's interdisciplinary and
there's no majors
to the point of it not really being
worth
going but if I was gonna go to college I
was going to go to a place like that but
even state tuition was expensive so I
lived in Washington state for a year to
get state to get residency
so I could go to that school and by the
time
I got residency I was like this school's
not gonna do anything for me you
described this chapter of your life as
being very lost
super lost super lost I was looking for
my I kind of hate this word
tribe
I was looking for people like me I
thought I would find people like me and
then all would be well like uh you know
some Disney character that you know ugly
duckling or someone who loses you know
they're lost from the wolf pack I don't
know what these movies are and then they
find their family and people understand
them and so from the time I was 17 I
moved from
Downtown Sacramento to Olympia
Washington lived in two places there
Seattle lived in two places there San
Francisco
lived in one or two places there
Oakland with my alcoholic fry cook
boyfriend I had met in Olympia we
couldn't get jobs and my parents were
like yeah we can't help you with college
stuff so then we moved to Portland
I was a stripper I was lost I was lost
that's an interesting time a ton of
events yeah that was an interesting turn
of events
and that chapter of your life in some
ways mirrors the transience of the start
of your life you said you moved to like
eight eight or ten different schools
when you were young
and then when you leave the nest you end
up bouncing around as in your own words
like looking for
your family I was yeah I was looking for
some place to belong and I never found
it and I kind of love that
because it's forced me to make my own
and force me to stay creative thinker
and also
I don't know I this isn't fair but the
people in some of those communities like
peaked and never left it's like you know
I listen to pop punk in high school can
you imagine I'm sorry if anybody
listening is like never graduated from
listening to pop punk but if you don't
graduate to metal or some other it's not
even more sophisticated but like less
juvenile varieties of rock it's the same
as finding you know some
comfortable Community when you're 20 and
then never leaving like that sounds that
sounds awful to me so I'm I'm glad I
didn't find a comfy place
and it's been uncomfortable since then
how long did you try this stripping
thing
I don't know I mean when you're in your
late teens early 20s
time just feels like it felt like a
decade that I was you know bouncing
around to these places probably three or
five months it was fun I loved it nobody
pulled anything I never got messed with
I drank my white Russians and ate the
Subway sandwich from next door and
played photo hunt and I wasn't even 21 I
used someone else's ID to work there
and I got to dance to music that I liked
I made money I didn't really have to
engage with anybody
and I got really comfortable with my
body in a way that I hadn't before and
that was cool
yeah they say
I've read a new book where you said that
you believe you hold the
world record for having the most shitty
jobs like back to back throughout that
period of your life they say you know
I've learned this from this podcast that
every job teaches you something and that
thing can be applied to business there's
always a sort of a transferable skill or
whatever learn what was the transferable
skill
but you learn from stripping that you
think has probably stayed with you
today
I think that even though I wasn't didn't
have the upper body strength to be the
traditional one upside down swinging
around
what I could do I mean it was like
Shuffle around and whatever was enough
and still charismatic enough and still
great enough to
entertain other people
and then being comfortable with my body
it's like exposure therapy you know I
was the girl at
18 it would like make out with someone
and then if I was like naked or
something I'd like
put on my clothes to go to the bathroom
or something I was like
not I didn't sleep with anybody until I
was 19. so I was just I was kind of late
by 20 I was
tripping in Portland
I'll tell you the crescendo of that
experience so dating with dating Wade
the
alcoholic fry cook who was 10 years
older than me
uh
I like I was on birth control I went off
birth control for like one day and there
was almost we were hardly even you know
engaging in the way that someone might
like get pregnant like so briefly like
that day
yeah I'm like I don't know
who's watching and uh and I wound up I
want it pregnant
so I'm like 20.
Maybe 19. and
I went to the sliding scale Women's
Clinic
and
but but it was the only day I could get
in but it also happened to be
the day of my court date because I had
gotten arrested for shoplifting
so I had to have the Women's Clinic
write an excuse to the court telling
them why this poor girl couldn't make it
to her court date and the whole thing
got they were just I kept following up
to be like when is it rescheduled and I
think they all just felt so bad for me
it kind of vanished but that was that
was like okay no more shortcuts it
wasn't like I'm gonna go be a CEO but it
also
just
taught me that
breaking some rules puts you in other
people's hands and I was you know being
arrested I'm not as autonomous as I
would have liked to have been and you
know even with stripping to a certain
extent it was a shortcut I was trying to
evade like working hard but it was also
a lot of fun but that was really that
was a low point it's had lots of low
points
um but at least it's like this right
it's been like this
you know doesn't
it doesn't ever go that low
there's clearly um a slight issue here
with authority and it feels to me like
the ultimate Authority which is the law
eventually was like he can't [ __ ] with
us we're not the teacher yeah it was
like okay like maybe just figure out how
to get along you know
it wasn't like wow I'm gonna go have a
career and do
everything I'm I'm gonna just do
everything differently but also
I just didn't want to cut Corners I
didn't want to
end up
not in control of my environment or
stuck in jail or something stupid
shoplifting
mm-hmm
why'd you make that sound I don't know
it was fun
what was your favorite thing to steal
I don't endorse shoplifting neither do I
my rationale for shoplifting was that
there was so much excess
in you know our culture that it would
never make a dent to steal organic
tampons from Fred Meyer which is like
Target
in Portland or whatever
so
I uh
when I did get caught and this was my
favorite thing was just walking out with
stuff
so I would get a whole shopping cart of
stuff I had a little teeny tiny little
razor thingy so I knew where the sensors
were and I would cut them off they were
there
and pile a shopping cart high and just
walk out with no bags or anything I did
it at grocery stores I I furnished
apartments I walked out of places with
like literal rugs this High just walked
out because nobody expects you to be
that like obvious about it they're
looking for somebody who's like putting
stuff in their pockets
and when I did get caught
I had like a George Foreman grill
I think a basketball
organic tampons some food really nice
shower curtain rings they were metal and
then they had like ceramic they were
heavy and they had like a ceramic thing
that said hot and then the other one
said cold and I was like yes this is
this is luxury
It's Worth jail time so that was yeah
and
you know I built an online business and
the first thing I sold online was stolen
so another thing and I learned this from
people who were professionally trying to
like avoid getting jobs and
participating in
capitalistic culture which is a
privilege it's lazy
it's it was it was yeah I was really
young and I just didn't want to work you
know it was some kind of quasi-political
lazy excuse for just not working hard
anyway I learned from some of the best
um I had a friend who had written a book
called evasion literally and
I would go into Barnes and Noble
and they had a no chase policy like I
knew what the policies were at these
places because if their employees Chase
someone shoplifting it's gonna cost them
way much more if they get like knifed or
something than it would for them to lose
a few books
and so I would go on Amazon
and I would look at the
best-selling books this is in 2002 2003
it's like and
even look at the ratio of most expensive
book to least pages so I could stack
them as many of them as high as possible
and I would just walk to the front like
the front of the store would have all
the best sellers and huge stacks and I
would just like
piled them hide I look like an employee
like who's carrying a huge stack of
books I was right in the front of the
store and I just like walked my car and
I'd put them on Amazon for 10 cents less
than all the other resellers I'd sell
them overnight I'd ship a Media Mail and
I'd pay my 350 a month rent
why weren't you scared
I think I was but it's when you get
scared that you get caught
and it's when you hesitate you fail it's
the same thing
if you're snowboarding and you're like
oh it's kind of icy let me look down
you're just like catch an edge you're
surfing and you look at the nose of the
board
right
so even that's what you're a life lesson
I guess I guess we'll say I'm not proud
of this
I was really young and I was finding my
way I never
stole from individuals that was like not
on thesis for me
no I couldn't justify it I would never
feel comfortable doing it
um but big box retailers I was like over
the last couple of how long maybe four
months I've been changing my diet shall
I say many of you have really been
paying attention to this podcast will
know why I've sat here with some
incredible Health experts and one of the
things that's really come through for me
which has caused a big change in my life
is the need for us to have these
superfoods these green Foods these
vegetables and then a company I love so
much and a company I'm an investor in
and then a company that sponsors this
podcast and I'm on the board of recently
announced a new product which absolutely
spoke to exactly where I was in my life
and that is huel and they announced
Daily Greens Daily Greens is a product
that contains 91 superfoods nutrients
and plant-based ingredients which helps
me meet that dietary requirement with
the convenience that hewell always
offers unfortunately it's only currently
available in the US but I hope
I pray that it'll be with you guys in
the UK too so if you're in the US check
it out it's an incredible product I've
been having it here in La for the last
couple of weeks and it's a game changer
ladies and gentlemen our newest brand
partnership will come it's no surprise
to regular listeners on this podcast the
first episode of 2023 I was joined by
the incredible Professor Tim Spector to
hear more about his work at a company
called Zoe using data to understand our
bodies better so that we can live more
fulfilled higher potential lives Zoe was
born from the truth that our overall
health is impacted by our gut health by
helping you to understand how your body
is working so it can help you to reduce
your risk of long-term disease and
increase your energy levels for me this
is the future and that is why I became
an investor in the company and that is
why they are now a sponsor of this
podcast you can read up about everything
they're doing and you can pre-order your
Zoe program at joinzoe.com and they've
been kind enough to offer an exclusive
10 off code CEO 10. so you can put that
code in at checkout CEO 10. thank you so
much let's get back to the episode so by
this time you're getting a little bit
acquainted with the internet and selling
things on the internet clearly because
you're selling stolen stuff yeah yeah
vintage mm-hmm
why why vintage why did you start to
sell vintage clothes
yeah so by 2000
six
I had gotten some real jobs now after
after I'd worked in shoe stores and
record stores and Photo Labs and
Subway again
I like dry cleaners
I
how did you get on with those jobs
it didn't last very long I like job-free
alphabetized things though so record
stores
Photo Labs bookstores like paper makes
me feel important for some reason
mailing things I don't know it worked
out with my eBay store
and the last job I had was in the lobby
of an art school in San Francisco at 79
new Montgomery Street called The Academy
of Art University it was a job I got
because I needed to get health insurance
and at the time you couldn't get health
insurance with a pre-existing condition
you is this your hernia yeah the Hearn
the Hearn yeah so a hernia if you don't
know what it is is a place it's a hole
in your muscle wall that your guts poke
out of and it makes a little bump and I
had one kind of in my groin area I
called an inguinal hernia
and it didn't hurt but they're kind of
dangerous because they can like if your
muscle tense is up or something they can
get strangulated and necrotic which is a
disgusting word
so I had to get it fixed but before I
got it fixed it was kind of fun I shaved
everything but the hernia
my poor boyfriend my poor boyfriend and
um yeah it was entertaining it was kind
of funny to have like a small lump in my
pants for
a few weeks or something
but at the time you could not get health
insurance with a pre-existing condition
even with depression if you had medical
records that said you had depression and
your insurance lapsed insurance
companies would decline you now that's
not the case you can have a pre-existing
condition apply for health insurance
you'll be given health insurance you
could only get health insurance with a
pre-existing condition like a hernia
with group health insurance with a job
so I had to go
find a job that had health insurance
and I got this job in the lobby of the
art school as a campus safety host which
was a different way of saying you're
cheaper than a unionized security guard
and I wore a starchy white shirt it was
like a men's clothing I had to wear this
awful uniform with like a magnetic thing
here that had my name and the school's
logo on it and check students in and say
hi you need to sign in can I see your ID
that was were you doing anything sort of
criminal at this point my job no so all
of your money came from that job and
yeah and so there was a three month
waiting period for health insurance
and while I was there I had time to
I had some down time in this Lobby and
there's a computer
and uh there's no Facebook or Instagram
at the time this is
2006.
and I was starting to get friend
requests from these eBay sellers on
MySpace
I wore only vintage I was like you know
root and toot and Scootin to like oldies
and rock and roll and dive bars and
subsisting on burritos I loved vintage I
wore vintage I wasn't necessarily into
fashion and I didn't want to be in
fashion but I loved style and I loved
vintage
and I loved thrifting
and I saw what they were doing
and their auction prices were crazy like
I thought hate Street was expensive
because I had shopped at thrift stores
and found great stuff
and saw what their auctions were going
for and these were actual prices that
the customer was determining
they would start the auction price at
9.99 and these things were going for
like 200 300 and they were just making
it look like something that Sienna
Miller some boho at the time it was like
boho Olsen twins Sienna Miller kind of
Vibes and they would do that put this
stuff online and the customer determined
the price and it was so much money and
so I thought okay so I waited my three
months for my health insurance because
there was a three-month waiting period
it got the Hearn fixed and I started an
eBay store and I wasn't trying to be an
entrepreneur I was trying to
legitimately not work for anybody and
that's when I realized that I could
connect my curiosity and Independence
and creativity and resourcefulness
to something
legitimate that made money that I
learned from every step I was taking and
started nastygal selling vintage out of
my boyfriend's apartment before that
point
would people have called you lazy
or unmotivated
I didn't know any people who would have
said something like that because my
friends were just like me so objectively
then objectively
I think just lost I think it would be a
judgment to say I was lazy
I can relate to so much of what you've
said especially all the stuff about
Authority like I just decided to stop
going to school and I was polite about
it but I I've always had a challenge
with authority every job I had
throughout through that period of my
life lasted for three months I was just
cool center hopping get to the bonus
threshold quit gives me two months where
I don't have to get a job call up
another course employed those people
yeah I'm one of them and it's funny
because I think people would have looked
at me in school and stuff and said
like written me off oh it's he's lazy
well like my thesis is that everyone
most people are lazy and you should be
lazy for things that you absolutely hate
doing
okay you should be so yeah I'm only
motivated by things I'm curious about if
someone assigns me something like I've
tried to write a second book and
published two books after girl boss
which was a thing
I can't I cannot be assigned something I
it either comes out or it's not there
that's the do you think that's the the
rebel in you
that is but it's why everything I do is
so inspired and honest and
I don't want to be like I'm unique but
because you never accepted or learned
compliance it's an actual representation
of who I am and what I think and how I
feel and my perspective instead of a
manufactured version because somebody
has given me an assignment like you
didn't even want the bell in school to
tell you what to do no
the gift in a curse though right
I mean it's pretty logical that you
would question
a bell ringing and someone moving from
one room the same room to the next room
every single day what do you think
anyone else no
no
but if you really think about it it's
pretty wild right
that that eBay store that you start with
in your free time when you're working
that job
you took to fix the Heron
um
it was successful
yeah and you know you kind of frame it
as you saw maybe a price Arbitrage or
whatever but but it's more than that
right it's more than that to be
successful at that time I'm not sure a
lot of people saw that price Arbitrage
and they didn't build a nasty girl so
when you reflect on why and how
you were particularly successful how did
you diagnose that
I reverse engineered everything everyone
else did and did a better job and did it
with my
signature on it do you think and I'm
thinking now about that Bell again in
school where you were like analyzing the
Bell where no one else was do you think
that kind of default to thinking in
terms of first principles like asking
the question why why the [ __ ] do we do
it that way has been part of the reason
why that eBay store was successful
I think so
I think
most people that started an eBay store
are copying what other people are doing
they might reverse engineer some things
and see what their competitors are doing
and I did that but I just did it 10
times better with a totally different
spirit with excellent copywriting with
great styling great models and
increasingly better photography and I
would I was extremely resourceful I
would buy stuff on eBay and sell it for
more than I paid for it I was searching
for Eve's son Laurent just misspelled
you know
the song
but even that's the first principle
thinking that's like
but you've got a convention on one end
which says just like do what's being
done and then you've got these like
first principle thinkers who kind of
think first about what they know to be
true and they're really good at
filtering out convention they can kind
of see throughout the truth whereas
convention like is safety it's Comfort
it's it guarantees you a pre-tried
blueprint so people follow that but then
these other little Rebels
they they have this almost inbuilt
ability to just like [ __ ] see through
to the that that truth that nobody can
see and in that case I mean that's a
great idea but even caring more about
the copy and you having your own belief
as to why the copy matted or the
photography like why photography really
really mattered on eBay yeah on eBay
which a lot of people would have had
like that's um and it was called Nasty
Gal the spirit of it was really
irreverent at the time the eBay sellers
were selling like you know is called
Mama Stone vintage was a really big one
and it was all very hippy dippy and
vintagey and mine was vintagey but it
was like very hard-hitting edgy
I named it after an album by a woman
named Betty Davis who had an album
called Nasty Gal she was
so stylish uh in the 70s put out some
incredible records was married to Miles
Davis for a short period
and was allegedly too wild for him
her lyrics are just so and I was
stripping her music when I was like 20
and then I was like cool nasty girl and
it cut through the noise and I think
when you start a business and you don't
need to survive you might have more time
to Naval gaze or you might do things
super conventionally
but when
you need to survive there are certain
things that other people have done right
that you can see you know accelerate
what it is that you may do on your own
but learn from them and then also take
and make your own way I think had I
tried to do things completely
differently than everybody else
I wouldn't I wouldn't have survived I
would have been dead in the water
speaking to something really interesting
there which is like this Balancing Act
between naivety which is great for
innovation and then convention which is
great for staying alive I'm talking
about like the the nasty girl needing a
CFO
yeah you see what I mean or like that's
what how I feel when being a young
founder 21 years old start this business
it grows incredibly quickly okay the
naivety made us interesting but our
naivety will also send us to the Grave
here if we're not yeah if we don't know
what we don't know I've been to Hell
I've been I died and now I'm in the
afterlife I it did send me to the Grave
my naivete and lack of experience did
send me to the Grave it happened so fast
that's a quote
um it was shocking how fast it all
happened nasty girl went from doing 150
000 a year to doing 150 000 a day and
then 150 000 over lunch
yeah 150 000 over lunch
it was either a day or over lunch that
we all worked out of this Warehouse it
was a bunch of kids in the East Bay
in Emeryville I had the 7 000 square
foot Warehouse which I thought was the
hugest thing and I was like when we hit
150 000 a day God was it a day it must
have been the holidays I was like I'm
gonna get a bounce house you know those
things that people jump on the
inflatable things the children that
children jump on it was an upside down
horse and its legs were in the air when
he jumped on it the legs like that's
what you wanted
and in between you know on our breaks we
got to jump in the bounce house I was
like
23 24 years old it did happen really
quickly to be fair now you say it when
we raised investment for the first time
the first thing I bought was a 13 000
pound slide
big blue slide which we had in our
office that was the first thing I bought
before we got desks so talking about
neither today I bought I paid off my
mom's mortgage oh did you okay I
couldn't do that with investor Capital
no it wasn't with investor Capital no it
was the first time I made money yeah my
slide was with investor one okay yeah no
no they actually those investors did
really well they got bought out within
six months so they got a big return but
good job yeah what do you attribute at
such a young age I'm just gonna
interview you for a second because you
couldn't have had a ton of experience
under leaders to give you a model of
what leadership looked like you were
naive
you know could you I couldn't empathize
with the people I was managing because I
had never experienced leadership and I
just showed up and I did what I I what
needed to happen and what I said I was
going to do I didn't understand that
people needed to be held accountable
because I held myself accountable
especially c-level Executives and
grown-ups whose careers were longer than
I had been alive like how did you do
that at such a young age well I think I
I think I messed up I think like for the
first two years I hired people that were
very very inexperienced I reflect and I
go I think I did that because I thought
they were easier to manage and I
couldn't fathom the concept that I could
hire someone who was two times my age
and three times my experience and Avid
want to come here and be with us with
that with our sliding dogs and tree and
basketball court and ball pool and they
would like take us seriously but also
like be like maybe there was an
insecurity about how I'd manage them and
so what ends up happening is you I hired
lots of like young people
you know a member of the BBC did an
article saying is this the youngest
company in Britain because I think we
were like somewhere but our average age
was maybe 20 or something and we had
like we had like 100 almost 100 people
you know and you feel the strain of that
you feel things breaking this is where
you go
convention is right about some things
processes HR Finance you feel things
breaking at the seams a little bit
because of the growth um and then at
some point an adult enters the room
and you go oh
I get this and so we hired some some
really really great people and the great
thing is great people hire great people
so we went from being this kind of very
lopsided inexperienced organization to
being a balanced one and I say balance
because it's my belief that to own the
future you have to understand the
present which is why you want to hire a
16 year old that gets Tick Tock or
whatever and you also need to hire
someone that's maybe
double their age experienced in client
services and understands the old rules
of the game if you understand both games
you can understand the game of the
future I think so
um made a lot of mistakes and when I
nearly went under several times and had
to call people and beg for money
um in the lead up to Payday but
somehow managed to survive but go back
to you now
um I feel that we missed a park because
you know you write the reception you
went from starting that store to
bouncing around on that bouncy castle
thing we call it bouncy castle okay
horse Castle between that between that
bouncing on that horse castle and the
starting the store
what happened
so
first year
just on eBay did 75 000 in Revenue I was
the only employee it was just you know
it was pure cash
all of the money just went back into the
business I didn't even know what
expensive things I would have wanted I
didn't I had never eaten an oyster you
know I was drinking like
Budweiser or you could still like
subsisting on Boston Market and like
Starbucks
so I didn't spend any of that money I
thought building a business and I think
for the most part it is
uh was
selling things for more than you bought
them for and not spending all the money
that's it
that's all and so I bought things I sold
them for more than I paid for them and
no one else would have given me money
parents weren't gonna give me money
I don't even think I had a credit card
at that age
I didn't understand what Venture Capital
was and I was living in the Bay Area
and had I not built the company to
eventually you know 28 million dollar
run rate super profitably I would never
have known
and so yeah year two left eBay about
halfway through and launched my own
website nastygalvintage.com
and did 250 000 in Revenue
the next year did 1.1 million the next
year did six and a half
the next year did 12 and I was coming
off a 12 million dollar a year uh
Revenue
owned 100 of the company
had a bunch of kids working for me
and that's when Venture capitalists came
in and at that point you know
we were selling non-vintage stuff what
really allowed the company to scale was
going to trade shows and showrooms and
curating from the market based on what I
had learned from my customer having sold
vintage to them so I knew them very very
well and that gave me the ability to
then go by greater breadth and depth in
things I knew they would love
and that's what 2011-12
Venture Capital comes in 2012 was when
index Ventures invested 60 million
dollars 60 million dollars on a 350
million dollar valuation on a business
with a 28 million run rate yeah you're
profitable at that time
significantly
pretty significantly I have a 10 or 20
nothing I don't know I don't know I
didn't even look at that I was I I never
had to learn to read a p l because my
company was profitable and I just
you know generally knew how much it cost
to run I didn't it and I and I didn't I
didn't buy expensive office chairs did
you did you know you like gross margins
on on your on the product yeah on the
operating margins no I don't I don't
think I didn't understand what operating
margin was
um pretty incredible that you can be
running a business that's generating has
a 28 million dollar a year run rate and
not know what operating margins you're
dealing with or what your net profit is
it's a luxury but it was also a
disadvantage once we plowed 60 million
dollars into the business and things got
a lot more complex and a lot less
profitable
you talk about the 60 million going into
nastygon in 2020 to 2012.
what did it break hmm
I mean we
no longer had to live within our means
that's what investor money does unless
you maintain profitability and keep that
money in the bank for you know another
time or pocket all of it as a founder
we you know I had hired a COO at that
time I had a top tier investor on my
board
and
very little like historicals data
financials
to base the future growth on but it had
been exploding just continue to be
exploding and with that Capital behind
us we could grow even faster
and the expectation was that the next
year we would grow from 28 million in
Revenue to 128 million dollars in
Revenue we just rounded up by 100
million and then we hired into that and
we bought into it
oh you believed it and everyone I had
grown-ups forecasting this stuff with me
I relied on them it's why I brought them
in you hired the right ones clearly I
didn't pick the right ones or I'm not
sure what happened but I remember
sitting in a room with them
and
us deciding I didn't push for it this
wasn't you know
we're gonna just grow by 100 million
dollars this year and
someone put a plan together and this is
we hired 100 people it was like the
Tower of Babel you know that story
you don't know it's like a biblical
story where
uh people are building this Tower or
something but they all speak different
languages and I I could be completely
wrong I don't think I am
but none of them get along or understand
one another and it was it was it's just
a mess trying to integrate 100 people
into a company in a year
especially a company with no processes
and no real intentional culture
that had been established
no real intentional anything other than
the brand
the spirit of the brand
what needed to be done it was it was
like a family business that just got
really big it was
I was a kid
how are you feeling in terms of at this
point in terms of what's going on around
you 60 million dollars has just come
into the bank account you're looking at
me thinking that's a big [ __ ] number
you're you know because you have a
valuation of 350
yeah I'm worth 280 million dollars on
paper at this point so that and wherever
you go they'll lead with that and remind
you of it and you'll be treated as such
even though it's paper and it's not
realism yeah it's in your bank account
how does that make you feel when you you
know then they put you in the front
cover of Forbes yeah how does that make
you feel
it was a blast
um I didn't do any of it to have Glory
or go on a Victory lap and I wound up
with it and I embraced it and I had a
lot of fun it distracted me
you know the book in 2014 turned into a
phenomenon
you know it was champagne clinks for
some Milestone with a company or new
hire
promotion any given time
I people would come up to me and say
congratulations and I had to ask which
thing they were congratulating me for
it was
it was just like oysters for everybody
finally you know I I got better taste in
wine I got better taste period thank God
but now I spend less money with a good
taste that I had to spend a lot of money
to acquire
a lot of my own
but did you feel
did you feel like it made sense
like the the image that's been that had
been built of you at the time that the
world is now like oh my god did it is
that what was going on inside I think it
made sense I think it was a freak Show I
was a Community College Dropout who
bootstrapped a business to 28 million
dollars in Revenue super profitably
you know investors came out of the
woodwork you know top tier ones anointed
me as
someone who could pull it off and I
didn't know what I was signing up for or
what I was supposed to pull off but
it it was considered a rags to riches
story and imposter syndrome
any of that for sure yeah I mean I still
walk in rooms and I'm here I was
talking to your team and I was like oh
my gosh you guys have really big people
I hope I can keep up I say like a lot
I'm intimidated I hope I can provide
some value what are the comments on
YouTube gonna say is this going to be a
valuable conversation I really hope
people like it
you know and she was like what you
wouldn't be here if that wasn't the case
what what are you talking about you're
great
but I get nervous right
um I get nervous on stages
and I'm still like you know I don't I
don't belong here but I don't belong
here is also a really great motivator
the I don't belong here is I snuck in
the back door
I don't belong here means
I can do things differently I don't
belong here means I don't fit in
but that's going to be a superpower and
I think it's okay to feel like an
outsider
or an imposter sometimes because you
find yourself in places where
you learn you have an outside
perspective and are able to learn things
unlike the people who are invited to the
table who all showed up there with the
same pedigree
and then you get to make
oblique connections
between who you are where you came from
and then the door the room that you just
snuck into as an imposter and that is
radical
would you remove that self-doubting
voice if I put a button in front of you
and said you press this you'll never
doubt yourself again no
that's so boring I had a coach recently
and he was lovely
waited five sessions it was like five
thousand dollars a month and I was like
taxes
I'll buy something else to save on taxes
and
he was like can you imagine he asked me
that word or he asked me that question
and I was like
but
what would I struggle with what who
would I be if I didn't have challenges
and I was happy all the time it's like
the scaffolding would fall apart or
something
that's a story I tell myself
but it's fun to have a
dark Counterpoint
to hold yourself accountable and be like
maybe it is that or not that
and I think that Counterpoint is an
opportunity to gain self-awareness
do you think it's additive to your
performance or reductive
I think it can slow me down and I can
make really
slow
decisions because I doubt myself
but
beyond that
I think I've found a way to harness it
that really works for me
have you developed like a decision
making framework to help you navigate
the two voices in your head it's funny
because when you're describing your
mother and your father it felt like
those were the two voices your mother
would seem to be very supportive your
dad somewhat critical at times or
pessimistic
um have you found a way of being able to
juggle those voices
um
so that you can make decisions
decisively and quickly
no no no
so I can I can have these conversations
and when I you know when I do make a
decision I've learned to be slower with
making decisions because I either make
them extremely quickly or
slowly on accident and so I want to be
very deliberate in the decisions that I
make now and think more critically
rather than you know Naval gaze or
be reactive to something I went to this
uh Retreat even though it's not really a
luxury experience with 30 other people
called the Hoffman process
and it's seven days with no phone no
Internet no books no music you're with
30 other people and you're going through
this process of mapping your patterns
from your childhood against your parents
and how how you inherited that and it's
all directly correlated and basically
graduating from your your
emotional child into an emotional adult
super embarrassing weird process like so
dorky and everybody came with something
different to work on or what emerged for
them you know I I feel unloved I feel
unlovable
I don't feel unlovable
my thing and it sounds really weak was
like I don't trust myself
I don't think I'm deceiving myself but I
think I can rationalize a lot of things
to the point where I'll tolerate them
too long
um and that's gone for relationships
that went from my most recent
relationship
um and so that's a strange thing I don't
trust myself because I do have these
voices it sounds I don't have voices in
my head
but I can see things from any
perspective and not be totally attached
to either one to the point of
being slow and asking for too much
advice
in that Retreat did you did you have to
sort of like go upstream and figure out
where that belief started is that the
point of that Retreat did you figure it
out did you go Upstream what a good
question
you're very good at this oh thank you
yeah I think it was that my parents
didn't agree
on how to raise me that I felt
misunderstood that my good intentions
were sometimes construed as
troublemaking that the fact that I
didn't fit into the environment I was
raised in
I was I was not accepted and I was some
kind of weird deviant when I was just
being myself and felt punished for being
myself and I think that
gave me like a lack of confidence or
something and I don't identify with
being an unconfident person but when it
comes to decision making when everyone
around you is telling you something a
different story about yourself than you
have
and doesn't understand why you operate
the way you do that is really with
integrity and in line with who I was and
what I needed to be successful as a
child if other people like live in a
different world and don't understand
that those are your needs you just feel
wildly alone and think wow I am a freak
and that
found its way into my career through the
public too which has been super fun
being told I'm something
that I'm
mostly not
what have you been told you are oh gosh
um
so nasty y'all fell apart after 10 years
it was it was a quick rise and it was it
was it was a it was a slow rise and it
was a relatively quick fall couple of
years in the making
and when it did fall the headlines were
crazy because I had all this press from
this book I published and being the
poster child of Entrepreneurship going
on the victory lab National Enquirer
said had you know picture of me and it
said Rags to Riches like straight up
tabloid American Dream stuff like a
caricature
and I didn't realize the amount of
responsibility I had to like other
people as an example like I kind of did
but as some symbol for entrepreneurship
for my generation you know generation of
the entrepreneurs coming up behind me or
at least
what the Press thought I was responsible
for
the you know there were headlines like
does the failure of nasty yell mean
Millennials aren't ready to lead
it's like wait how is one example
representative of a generation
and I've also read headlines like when
the Netflix series came out
the worst thing about Netflix's girl
boss is its source material
not even the show just me
but I'm not bad I don't believe I don't
believe it
how does that make you feel at the time
though
by the time that Netflix series came out
I had been this hero as an entrepreneur
then I was this girl boss because I
wrote a
book called girl boss and it was pink
and I was like this and I looked like I
knew it was up but it was like 27 and
then there was the me whose company fell
apart the CEO there was the girl boss
who had built a
toxic culture
or just no intentional culture at our
all that like warped into something that
wasn't perfect but wasn't I still don't
think it was the worst
and
now this person this conflation of all
of those things
with this girl on the scripted comedy
which came out four months after I left
Nasty Gal so the biggest kind of
personality or whatever identity crisis
was
you know I'm on the cover of Forbes in
June I think of 2016 July of 2016 my
husband of like a Year's like man I
changed my mind and I'm like oh my God
that wedding was so expensive it was
devastating but I'm just like God that
wedding was so expensive it was a great
party
so in that space of like 12 months
you're on Forbes husband leaves Netflix
comes out nasty girl goes under nasty
girl goes under then Netflix comes out
so the show had been shot when things
are all like up and to the right and you
know we were working through challenges
there had been some layoffs but the
company was still you know 100 million
dollars a year
you know not profitable anymore but a
great brand and something that was
valuable and
eventually
um yeah like fell apart and that the con
there was really a conflation of the the
hero the failure and now this girl four
months later
who's a a caricature of a person I was
when I was 22 in a scripted comedy
playing someone named Sophia starting an
eBay store called Nasty Gal
when for the first time
in 10 years in my adult life since I was
22 years old I am no longer associated
with the thing that I had built and now
there are 130 million homes in 195
countries watching a story of someone
that I
was no longer and no longer had trying
to move on and to move on when there's a
full PR campaign about who you used to
be
you're someone who's as you said you've
had a long history with mental health
challenges
what is it like in like in that 12-month
period what's going on from a mental
health perspective
I had fallen in love again
I think it was still like traveling I
started another company
I maintain my mental health partially
because I keep going
you know I don't stop and like lick my
wounds I think I was also I was also on
antidepressants I wasn't
jumping for joy but I also knew that
there was a huge community that still
supported me who had read my book 500
000 women who bought it
and I went on to start a company called
girl boss
right as the Netflix series was hitting
put on our first conference
and I had my podcast and I moved on
quickly and even though the headlines
weren't nice
the people who followed me my friends my
relationships everybody in my network
nobody bailed
like the girls who were inspired by girl
boss were refreshed that I had face
planted publicly because everyone else
is face planting in private
and in the same way that watching some
random Community College Dropout from
Sacramento start a business with an
internet connection
and a computer gave them license
to you know yes they were inspired but
also
Embrace their own failures because the
hero
face planted
publicly
and that can also inspire people
this is hopefully the most cliche
question I ask but
um I wanna I wanna know because you have
a from your from that experience you
have amazing feedback you have amazing
Insight invaluable Insight I would say
because when I think about the things
obviously they've taught me the most
it's not it's not when things go right
that's a validation of your hypothesis
it's when things go tragically wrong and
you go oh okay [ __ ] you have all of this
new information about which is corrected
your hypothesis so when you if we go
back and think about that fundraise for
example
um a lot of people will hear that you
raise the company raise investment at
350 million and think
amazing that's when people clap right
they get the champagne out oysters
for people listening that aren't in
business they might not understand how
that can also be a key reason why the
company ultimately went under
the 350 million why why did our big
valuation hurt yeah
yeah I think the 350 million dollar
evaluation is celebrated as it was and
how wealthy I was on paper
um was the was the nail in the coffin I
think it was it was then in 2012 where
we were overvalued and the expectations
that was was that the next round of
fundraising that we do is at a over a
billion dollar valuation and so the
company's doing
you know on an upswing 228 million
dollars in Revenue that's like over 10
times revenue and it's a fashion
business this isn't a technology
business this isn't Uber this isn't an
infinitely scalable Marketplace it's
e-commerce it was a different era of
e-commerce it was pretty early it was
the era of fab.com which like imploded
and won King's Lane in beechment in
ShoeDazzle there was no Playbook there
were no Ecom veterans or
you know Performance Marketing people
who had been in those jobs for even very
long I was hiring Executives who had
worked at like Macy's right
um nobody had like econ it wasn't called
direct to Consumer at the time it was
very very different there's no Shopify
and
we were overvalued and I didn't know
that I didn't even negotiate you know
hardly negotiate I didn't shop a term
sheet around and say I'm gonna pick the
highest price from different investors I
only had one term sheet and I was like
great I like you index finishes I was
like you're awesome you can I you get it
you know what Danny said when he
invested
uh was something none of the other
potential investors said and that was
you have a community and I was like yeah
we do have a community
but when you have that much money
you don't know there's been a nail in
the coffin or that there's a coffin and
that like you might be on your way into
it or maybe already laying in it but
just several years in the future
and
when things are up and to the right
you don't see what's lurking kind of
below the surface so when the tide
lowers
right you see the mud you see weird crab
shells sometimes hopefully not you see
trash
and it's only when things recede that
you see the mud that's underneath and
when you're on a Victory lap and you're
hitting milestones
everything's great and everybody loves
their jobs and you're a hero and as soon
as things
Go a different way as soon as there's
layoffs yeah there are things kind of
there are things there are things
lurking below the surface that were
dynamics that were already happening
that
because everything was going so well
you know we're harder to notice and
you know it's hard to be a CEO
it's hard to be a founder
I think something a lot of people don't
realize is that you only know 10 of
what's happening in your organization
right hundreds of employees and
ultimately everything was my
responsibility
but I am held accountable for 100 of
what's Happening
and when something goes wrong or
something's mismanaged or someone has a
bad experience in the company the
assumption is that I have signed off on
it that that is how I want things to be
and these things are happening you know
cattiness and
you know fiefdoms and silos and
duplications of effort and all the you
know the entire
spectrum of things that are no fun at a
fast-growing company
I didn't know were happening until we
laid people off and then they were like
hey
we didn't like it there I'm like okay
and some of that was totally overblown
but also anything that any employees
ever said about me or I've read
even though I don't agree with all of it
has been an opportunity for me to learn
and take from that how I could be better
because there's truth to almost
everything didn't you get an offer to
sell the company completely for 400
million dollars yeah I did
I owned 80 of it so that would have made
you you know quick maths I don't know
very [ __ ] Rich super [ __ ] rich
and why why didn't you say yes
I went to my investor
and I said what do you think about this
and he said
you need to ask for more I controlled
the board I owned you know I own the
majority of the company but I also took
advice from people who I thought knew
more from me but I didn't know that my
interests weren't necessarily aligned
with the interests of my investor whose
interest is to
whether I'm worth it or not
have a piece of paper to show his
investors that says I'm worth instead of
350 look they're now worth a billion and
they just make up these numbers and then
they can show their people that your
company's worth more and that was his
that was in his best interest and that's
what he was giving me advice based on
are you mad that he said that
I'm not mad do you wish you made a
different decision
is that a regret
it's a it's a partial regret but I also
know that no deal actually happens
they're not a
a real acquisitive company they could
have tried to acquire the company I
don't even know if they've acquired
anything integrating it into their
company if I had an earn out based on
them you know controlling it and me
trying to hit performance benchmarks
even if I had sold the company to them
who knows how it would have played out I
would have made a bunch of money my life
could have been miserable but 99 of the
time deals fall through there's also in
those situations a lot of people trying
to get into the data room so they make
an offer so they can see your numbers
and what you're doing and how your
business is working out and then they
pull the offer later once they've had a
look into the data room and due
diligence yeah and then copy yeah
exactly yeah so we didn't get that far I
don't regret it
um
but yeah that was a big thing you know
for me that would have been a lot of
money for him it was just a teeny tiny
bit more than what he had paid for it so
that's not a lot of them it's not much
of a markup for him
what is the advice you're giving now to
to women that are and men that are
looking to start companies that are
within your community the communities
You're Building within your portfolio
companies now that you're an investor
um
you know like I think I can think of the
first piece of advice that I give young
Founders when they come to me I'm
wondering what your like first piece of
advice is
I think for bootstrap Founders the
advice would be different for Founders
in my portfolio companies who are
raising Venture Capital my advice would
be
get as far as you can before raising a
single dollar
validate your idea as soon as you can
with the ugliest
like most basic quickest thing or first
product should be super ugly get it in
front of people and get some idea of
whether it's valuable or not before you
go raise money before you even try to
Market it talk to you
every customer every potential customer
and bootstrap it as long as you can if
you can because when investors do come
in your company is going to be worth
more than if you would raise money when
you just had an idea and were asking for
a check
when you do raise money
having a reasonable valuation is
important and a lot of Founders optimize
for price because
bigger price an investor pays the more
ownership the founder has the more
they're worth right the more they're
worth and the more eventually they could
make if they sell the company
but when you have a valuation that's in
line with Market that makes you an
attractive acquisition something someone
might pay a multiple for that 10 percent
say you're diluted down to 10 or 20
percent but you sell your company for
500 million dollars you're in much
better shape than raising 350 and owning
80 percent of it and going to zero or
whatever so and I think where things are
right now with Venture is
a place that is is close to that and
Founders aren't greedy Founders who are
raising money in this market no it's
really really hard they don't want to be
overpriced because the people who raise
money over the last few years raised at
such a high valuation these founders
nobody's going to reinvest in them
they've blown through their money they
thought they were you know they're on an
upswing their company might be doing 2
million in Revenue but they're someone
told them they were worth 80 million
dollars and now nobody's going to give
the money I've as an angel investor I
have
three of these right now and it's like
Hail Mary's two of them have figured out
how to survive ones like we have another
term sheet I mean I've been there
what about the psychological advice
you'd give to her
um
I would say to listen to your gut
you know there's going to be a lot of
voices around you and there are people
who know more than you
and have experience and you should
listen to them but you should also
always maintain and continue to
cultivate a voice that
when you know it should is able to
supersede any advice that anybody gives
you
um I think it's easy to take all the
advice because you're an inexperienced
founder
and um
and into lose touch with your intuition
and it's probably what got you to where
you are as a Founder without the money
and without the experts
and if you just rely on the money and
the experts you're losing the thing that
made what you're doing Special in the
first place
which day was your hardest day over the
last
since you were since you first started
that store on eBay is there a day you
look back and go do you know what that
period or that day was just
the worst the hardest the darkest
see and it's weird the hardest day was
when my husband laughed
and I don't miss him and I don't wish we
were still together
I don't really think about him I mean
that was in 2016.
but I had agreed to take a big swing in
my personal life and make a huge
commitment and I thought that bumps in
the road were like to be celebrated I
thought it was like wow okay you're not
feeling great about things we're gonna
work through this and we're going to be
so much better as a result of it because
I see
commitments as things that go up and
down and if you're in a commitment
together you're committed to working
through those things and it all comes
out in the wash because you have that
level of commitment to the other person
and that wasn't the case for him and so
I I felt like I was like hallucinating
you know I like went to a hotel for a
week I couldn't be in the house it felt
like a crime scene with his stuff around
and um yeah three a whole whole week at
the Beverly Hills Hotel with three
poodles
is quite the scene with them yeah chain
smoking in the courtyard and a bathrobe
has that experience put you off being a
CEO of a big company I mean ever yeah
everything I've experienced has put me
up from being a CEO of a big company
I'll never do it again
why I don't I just I don't want to
that's not the job I want I'm an early
stage founder I'm a master at creating
brands that cut through the noise what
happens though if one you know you're
running a number of businesses now
um you've got your fund
yep business class business class but
what what happens say business class
what happens if it becomes
globally
you know globally successful then
you're back to being a big CEO again
though are you step out I would have to
work really hard to make it that and I
would have to invest in that and hire
into it that wouldn't happen by mistake
I have one employee on business class
business class is super profitable I
launch it twice a year it's pre-recorded
so business class is my entrepreneurship
program but I have two courts a year I'm
uh April I'm launching it and I launch
in the fall and it's an incredible
product but it's also something that is
relatively self-led for the students
it's eight hours of video and 300 pages
of worksheets and over 60 hours of
interviews with me like this with
entrepreneurs
and you know students get lifetime
access so you know they can take it over
the first seven weeks they can take it
over the course of a year or the next
few years
but it's not something that requires a
ton of my time outside promoting it
twice a year and I built it for that I
built it for that I'm using kajabi and
drip for email and you know whatever
zapier and a variety of tools that allow
it to be relatively low lift light on
human capital still a lot of effort to
promote and something I do engage with
throughout the year and two weekly calls
with students and post in the lounge
which is our community keeping it that's
it no yeah I'm playing I'm I'm
I'm not playing small with business
class I'm playing to my strengths that's
big
and with trust fund it's Venture fun
that I'm raising right now it's a 10
million dollar fund what I get to do is
not run a big company and you can keep
trying to apply this stuff that I've
learned over you know
over time I get to go from zero to one
over and over and over again with early
stage companies and out of fun I get to
be in the weeds if I hired a bunch of
people I they don't want me to be in the
weeds Executives don't want you to
micromanage but I get to look at all the
decks and I get to text the founders and
say here's what I think you should do I
can be helpful and it's so rewarding to
harvest all of my hardship on behalf of
a new generation of Founders and help
them see around the corners that I wish
someone had shown me around
and I get to keep my firms small even if
I have a 50 million dollar fund I can do
that with a few people
um and I'm using the assets that I have
I'm the product my relationships and my
network and my access to dealflow is my
product my expertise and ability to help
Founders is my product million social
followers and being able to amplify them
is my product the engaged Community I
have who's interested in the kinds of
things I'm investing in will actually
use them is my product and I don't
I'm just it's right here and it's an air
table the intentionality is what I find
most surprising um inspiring because so
many people get dragged by the
Temptation of like external expectation
if it's great business class is great
but all accounts have been on the
website went on to so I saw that the
waiting list is open for 2023 it said
like join the waiting list for 2023 yeah
so it's launching in April okay the the
spring cohort launches in April so you
can enroll for like a 10-day period at
the at the end of April when things are
great we get dragged by our own success
what you're saying is you're going to be
intentional and you've designed it so
that that's impossible
so that you can't get Drax because
someone's going to come along and say we
love this we're going to give you a
check we love this we'll turn it into
some boxer shorts with some teddy bears
yeah no
no I I
have had the Pearl Village of knowing
what's on the other side of success and
that a lot of it is not what you sign up
for
and that when you are successful you're
stuck in it so I spend a lot of time
thinking about what success looks like
for me and what I want my life to look
like and how many people I want to have
around me and the kind of stakeholders I
want to have
so that I'm set up for Success when
trust fund is super successful which I
can stay Nimble with and with business
class I've engineered that Revenue was
down last year to the year prior
and that's so that's okay it's still
profitable I'm not gonna hire a bunch of
people or CEO or plow a ton of money
into it trying to solve problems and
pivot things so if I come along I say
I'm going to invest 10 millions of here
we're going to hire a CEO okay but you
take the money
yeah take the money just for the record
guys
when it's there
take Real Money Take Take the Money
magical thinking what is that yeah I
mean you can call it magical thinking
you can call it magical thinking you can
call it manifestation you can call it
prayer you can call it whatever you want
I think it's
you know casting the line out not
knowing what you're going to catch
trusting you're going to catch it and
we'll pull it back magical thinking is
like Indiana Jones where there's the
vast where's this there's the vast Chasm
between whatever and the Holy Grail and
he has to trust that there is a an
invisible bridge and he grabbed some
gravel and he throws it out across this
literal kind of Canyon and
the gravel just falls on a clear bridge
and he had to like trust that when he
walked across that he wouldn't fall and
so I see magical thinking as you know
Thinking Beyond what might be obvious
thinking you're capable of doing things
that you shouldn't be thinking you can
belong in places that you never thought
you could
thinking you can accomplish things that
you're completely unqualified to because
nobody's qualified to
being able to see yourself in a life
in a world that's beyond your wildest
imagination
and just staying there
we have a closing tradition on this
podcast where the last guest leaves a
question for the next guest your
question is unfortunately not the
hardest question in the world I really
wish you'd been given a real stitch up
one
um but yours is yours is fairly
straightforward question which is what
is your proudest moment
hmm
my proudest moment is
paying off my mom's mom's marriage I
mean that I can do that
that was crazy that was the first thing
I did
what about this then what's going to be
your proudest moment
hmm
it requires a little bit of magical
thinking
understanding what
is Meaningful in my life and actually
spending time on it you haven't figured
that out no there are meaningful things
but what is the people have kids and
that's like
obvious and I don't know if I'm gonna do
that
I am super agnostic about it it's really
strange
I'll be 39 in a month
um
but I think like finding that and
hanging on to it what is that what is is
there some big meaningful thing that I'm
gonna find and cling to till I die you
know and it's easy when it's family or
easy when it's a kid
and you can create these meaningful
things in your life
but what that what is that going to be
for me when I'm dying what is it what
will it all add up to I don't know
Sophia thank you so much for your time
and thank you for the inspiration you've
been an inspiration for me for many many
years and that's why I reached out to
you to sit here with you and you are
absolutely a superstar in many many
respects but um yeah you're built for
podcasting but also because of your um
inclination to be on open and honest and
vulnerable
um you're incredibly inspiring in the
stories you tell in the way that you
tell them so thank you so much it's a
real honor to meet you and I'm I'm
equally privileged that you said yes to
come and do this because oh my gosh and
I mean that I'm not I'm not just like
gassing you up or anything I mean no no
thank you you're super happy I can't
wait to see what you do with both trust
fund and business class because
um they look like exceptional projects
I've looked into the reviews of business
class and with your fund with the amount
of information you've learned from your
twisting turning professional career you
clearly have a huge um amount of
intellectual leverage and Firepower that
makes for a great
fund um founder so I look forward to
seeing what you do that thank you thanks
as you might know if the show's now
sponsored by Airbnb absolutely love
Airbnb always have always been a you
know saved my life on so many occasions
and my team when we first got in touch
with Airbnb were talking about how most
people don't realize that their place
where they currently live could become
an Airbnb and I guess the second
question there is how much could your
place be worth and it turns out you
could be sitting on an Airbnb gold mine
without even knowing it some people
Airbnb their entire homes when they're
away that's what I did in New York
whenever I left New York my place was on
Airbnb and people rented it out
sometimes for a day sometimes for two
days sometimes for a week and it's a
great way to cover some of the bills
while you're away so whether you're
looking to go on holiday or you just
want some extra cash for bills or you
want to buy something nice for a
valentine that you love whatever it
might be head over to airbnb.com UK host
and you can find out how much your
current property where you live can earn
while you're not there I suspect it
might blow your mind because it
certainly blew mine
[Music]
oh
[Music]
foreign
Ask follow-up questions or revisit key timestamps.
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.
Videos recently processed by our community