March 14, 2025 • 25 mins
Amy Nelson isn’t just an attorney and founder of The Riveter—she’s a force of nature. For years, she’s been in the ring with Amazon and the DOJ—and she’s winning. Oh, and did we mention she’s doing all this while raising four young daughters? Now, she’s bringing that same fire to our new monthly call-in show, Ask Amy. She’ll be answering your biggest, boldest questions about pivoting in business—no fluff, no BS, just straight talk for women ready to shake things up. DM the show with your questions and get ready. This is one you can’t afford to miss.
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Episode Transcript
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Speaker 1 (00:03):
Hey there you beautiful badass.
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You're welcome.
You're really good at theseanswers.
No wonder we're doing Ask Amy.
My God, I'm like can I get mynotebook out?
Well, amy Nelson, we just Imean, we had to just draw you
right back in.
Here I am, how are you?
I'm good.
(01:32):
How are you?
I would say welcome to the KeriCroft Show, but this is Ask Amy
.
This is Amy Nelson's show.
It's the Keri Cro up, what youwere putting down, and so what
we're going to do now, we'regoing to do a spot every month,
30 minutes or less.
People can call in, they can DM, they can write us and this is
(01:55):
a very highly concentrated,dialed in show about women
pivoting in business Men you'rewelcome.
You're welcome to come.
Speaker 2 (02:01):
Anyone's welcome.
Men can be here, it's fine, butthis is just.
Speaker 1 (02:03):
You know the riveter has been.
That's what it is right Womenpivoting in business.
So I'm telling you, when youhave her here in the hot seat,
you better be ringing in thequestions, and we do have a
bunch of questions.
I will say to start off, Expertin nothing, opinion in
everything.
Hey, listen that.
(02:25):
That's what we're all abouthere, right?
Yep?
Question number one All right,okay, how do you know when it's
time to make a big pivot in yourcareer or business, versus just
pushing through a tough season?
Speaker 2 (02:30):
Ooh, that's a good question.
There is no right or wronganswer here, but I think there's
kind of two ways to look at it.
How long have you had thatinkling or that feeling that you
want to change?
Have you had that inkling orthat feeling that you want to
change?
I think it was Steve Jobs,actually, that said if you wake
up more days in a row than notand say I need something
(02:50):
different, then it's time.
So I think you have to kind ofconstantly be checking in with
yourself Is this what I want, oram I ready to make a pivot?
The other way to think about itis far less inspirational and
far more tactical, and it'sasking yourself not just if
you're ready, but can you?
(03:11):
Everyone always says, like, liveyour dreams, chase the passion,
like that's great, but youcan't always do that right,
because we have a mortgage orrent or kids, and so if you want
to make a big pivot, one of thethings to do to figure out if
you're ready or if you can is tosit down and map it out.
Do I have the time to make thepivot?
Do I have the financialresources to make the pivot?
If the pivot is to another job,great.
What's the salary?
Is it commensurate to what I'mmaking now or am I making more
(03:32):
money?
If I want to start a company,what's my runway my personal
financial runway that I can quitmy job, not take a salary and
wait until I ramp up that newbusiness?
Because for most businesses, onday one you're not bringing in
the money.
And so when I started theRiveter, I left 10 years of a
career as a lawyer and at thetime my husband and I sat down
and we made a spreadsheet andthe question for us was how long
(03:55):
can we continue to affordfull-time childcare and maintain
the same standard of living,with me, amy, not making a
salary?
And I had 19 months and Idecided that that was enough of
a runway for me to go for it.
And I went for it, and I cantell you that at month 16, I had
completely replaced my salary.
But the fact that I had thatrunway and also that goal pushed
(04:19):
me toward it even more quickly,because I knew I wanted to get
there.
See, I was actually going tofollow up with?
Speaker 1 (04:25):
didn't you do a spreadsheet?
You fucking took that ball andyou just ran with it.
What's the biggest mind shiftwomen need to make before taking
a big risk in business?
Speaker 2 (04:34):
And a lot of people might hate this answer you need
to recognize that impostersyndrome doesn't even exist
anywhere but in your own mind.
I feel like we have talkedabout imposter syndrome so much
with women that we think it is areal thing.
It's completely made upbullshit, right Like, and I
think if we didn't think of sucha thing as it existing, we
(04:54):
wouldn't even have it.
But I think the biggest mindsetthat women need to have to take
a big risk to start a businessis to say I'm standing in this
space and I can do it Like.
It's a very simple thing to do,but for some reason we hold
ourselves back and we take fewerrisks and we have more
questions of like will I fail orcan I do this?
Then we see that men have sojust like, don't.
(05:17):
Don't think that way, do notallow yourself to think that way
.
Whenever I doubt myself and Ithink you know it's over some
idea or fear, I just tell myselfI'm not allowed to think that.
One other thing that I think isreally important is that I think
sometimes we think we are onlyallowed to try once and if we
(05:39):
fail it's over.
But that's not how the worldworks.
Everyone gets to try again andagain and again, like no one's
kicking you off of life stage.
You know there are so manyentrepreneurs that failed at
their first businesses.
Sam Altman, who is, you know,taking open AI on this rocket
ship, his first startup failedspectacularly right.
(05:59):
And what if then he'd said,okay, I'm done, I can't do this.
But we, as women, need to takethe same approach.
We can fail, we can begin again, it doesn't matter, there are
endless chances and there's roomfor all of us.
Speaker 1 (06:10):
You just answered the third question, which was how
do you deal with impostersyndrome when shifting into a
new industry or role?
Speaker 2 (06:17):
I mean I think like, if you want to say imposter
syndrome exists, or if you feelit, this is my best advice for
how to deal with it.
Say to yourself what would likea mediocre white man in this
role do.
Or what would I mean?
Pretend you're someone else,like if you have imposter
syndrome.
Pretend you are the person youfeel like, you're, like
(06:38):
pretending to be, and how wouldthey approach something?
Just do it that way.
It might sound crazy, but like Icame to that after I worked on
Wall Street for a decade and Iwas in these rooms with mostly
men and at a certain point Istarted looking around and I was
like these guys don't knowanything, or like they don't,
like they're not all, they'renot all that right, like they
don't know any more than I do,but they're just taking up the
(07:00):
space.
And so, although I feltslightly uncomfortable in the
moment, I just decided, like I'mtaking up the same space, no
one can stop me.
And like I honestly thinkthat's like how I ended up
pivoting to start a venture,backed business and raising $30
million and doing these things,because I just decided to take
up the space.
Damn girl.
And I'll say something I don'thave imposter syndrome, but I do
(07:22):
get scared, right, I get scaredof saying the wrong thing.
Or you know, or I am, you know.
I get scared of failing, butit's just like it's not a useful
emotion, but don't you?
Speaker 1 (07:33):
think that you, that was a muscle that you built
though.
So, even like you just sayingthat you had internal dialogue,
you did visual, like you didexercises, you talked yourself
through it.
So it's not like you're justgoing to wake up one day and be
like, ok, I don't have itanymore, but you have to make it
a priority to like think itthrough.
You figure that out.
Speaker 2 (07:52):
I mean you do like.
It is kind of like, if youthink about it, like you're not
going to become stronger if youdon't go lift weights Right,
like you have to make a decisionand do that.
And I think for me the practiceof getting over these things is
a practice of seeing it andframing it differently in my
mind.
So I used to shake before whenI had to public speak and it was
my right leg.
(08:12):
It would just shake, and itwould shake like if I was giving
a meat of honor toast or if Iwas public speaking for work,
and it would shake only if Ididn't have a podium.
It was like this very specificthing where I felt exposed.
If I had a podium, I was fine,no big deal.
And I remember when I startedthe Riveter I had to get up and
give a speech to like theChamber of Commerce in Seattle
(08:33):
and I was like, fuck, I'm goingto shake.
This is embarrassing.
And then I had this moment inmy head where I was like you
know what?
This is my job now, this ispart of my job and I either sink
or I swim and I better figureit out.
And then when I realized thatthis is part of my job.
I never my leg never shookagain.
I don't even know if it was.
I stopped being afraid, but Iwas like I have to do this.
(08:54):
This is my job.
Speaker 1 (08:55):
When you think about who you're speaking in front of,
like when there's a bunch ofeyes in front of you, of course
it's like, oh my God, everyone'slooking at me.
But you're like looking outthere.
You're like you're all justnormal human beings, they're all
just who cares?
Speaker 2 (09:08):
Yeah, and the other thing is, if I realized too,
when you're looking out at a seaof people you know most people
in this world do let fear stopthem from trying things where
they could fail, whether that'sgetting up on a stage and giving
a speech, starting a business,going for a promotion, and the
thing that most people arelooking at you for.
When you are the person on thestage or are the person going up
(09:29):
for the promotion, they'relooking at you and they're
thinking I wish I could do that.
I wish I could be that braveand like that's.
You're providing inspiration topeople and that's just not
something to be afraid of.
Speaker 1 (09:40):
I don't mean to beat up the mediocre white male out
there we afraid of.
I don't mean to beat up themediocre white male out there.
We love you, we love you, butit's okay, we can beat you up a
little bit, yeah, but working incorporate America and then
managing and being the director,every single person I was in
meetings with were men in suits,mostly white.
They're taking up the sameexact space, like look around,
(10:01):
compare, pretend.
Speaker 2 (10:02):
Like you said, I love that idea that visual, yeah, I
don't know.
I remember when you're playingsports as a kid you'd take stock
of the other team, right.
You look at them, you figureout who they are, what the
players are and then figure outhow you can contribute and win,
and I think that we lose sightof that in the world, but I
don't think that we should.
Speaker 1 (10:20):
What is one unconventional strategy for
making a bold career move thatmost people don't?
Speaker 2 (10:25):
talk about.
I think an unconventional movefor making a big pivot is to
spend time in the background,first planning the pivot, but
not over plan, but earlier.
Like make sure that you arefinancially set up to do it
(10:45):
yourself, plan your first stepsand also, I think, added to this
something that isunconventional and people are
afraid to do Ask everybody youknow to help you make that move.
Enlist your friends, enlistyour colleagues, because when
you make the move, it will bebigger and bolder if everyone
around you is on your supportingteam.
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Okay, this is from someone whohas spent a lot of time on a
(12:10):
personal brand and they want torebrand themselves.
Okay.
So the question is, how do yourebuild your personal brand when
you're pivoting into somethingcompletely new?
So you already are known forsomething, you have the brand,
but you're really looking tokind of shed that I love this
question because, first of all,we are allowed to change.
Speaker 2 (12:31):
Like you don't have to do the thing you did for 10
years.
You can change expertise, youcan change your jobs, you can
change your personal brand.
So my answer might be slightlyunconventional, but we live in a
world where people wantauthenticity.
Like if you look at socialmedia now, right, like gone are
the highly stylized reels Likewe just want you talking in
(12:52):
front of a camera and you knowand seeing what your life is
like.
And I think, to that end, Ithink there's something really
powerful, really vulnerable andreally authentic about taking
the community you have built onthe journey of your personal
rebrand.
And by that I mean tell yourcommunity you know I've spent X
years doing.
You know I've spent X yearstalking about sewing.
(13:14):
You all have been here with meas we did X, y and Z.
You know now we're going tolearn something new together and
explain, like, why you aretaking on this new project or
talking about this new expertiseand bring your people with you,
right.
I mean we want this, we want,we want change too.
As your community, we want tosee new things.
(13:35):
So we're here for it.
If you didn't do that and youjust one day, like rebranded
yourself with, like you know,say you were you know, sally,
who is an expert in criminallitigation, and then, all of a
sudden, the next day, yourwebsite is like I'm Sally, I
make pottery.
People would be like what thefuck just happened?
Right, and so take people withyou and they'll be there for it
(13:55):
and you will make new community.
Speaker 1 (13:57):
What are the OK?
What are some of the biggestmistakes women make when trying
to transition into a newbusiness or career path?
We ask for too little.
Speaker 2 (14:04):
If you are trying to get a promotion or get a new job
, the first salary offer is notthe best they have, right, like
it's an opening bid for anegotiation and you need to ask
for more.
You need to ask for the farm.
So I think that's the firstthing, right, like we just need
to ask for more.
And I think that applies likewhen you are seeking a new job.
But it also applies like ifyou're starting a consulting
(14:25):
business or freelancing, likewhatever you think you should
set your prices at, you shouldprobably double it.
I mean, that might be a wildamount, but you know no one's
going to pay you more than youask for.
So ask for more, and if it'stoo much, you can negotiate down
.
Now I recently sent out aproposal and it was too much for
someone, and so we negotiateddown.
(14:45):
But like to their point, likeon the reverse side, my opening
bid was not the lowest amount Iwas willing to do it for, but I
was going to ask for as much asI thought I was worth, and then
I had the decision of whether Iwant to lower my rates depending
on the project, the person,whatever.
I have raised a lot of venturecapital and men receive 98
(15:06):
percent of venture capitaldollars, and I think one of the
reasons is that we, as women,just don't ask for as much.
So I think that's an importantthing.
The other thing I'll say aboutyou know what we need to do as
women when we're startingbusinesses or pivoting is, you
know, not everybody needs tobuild a $10 million business.
You can build an amazing, youknow, cash flowing lifestyle
(15:28):
business, and I think more andmore people are doing that, but
I think that we need to set ourexpectations and goals higher.
One of the reasons I thinkwomen raise less venture capital
is venture capital investorsare looking for a massive return
and I think, as women,sometimes we're like shit.
I cannot tell this person I'mgoing to build a hundred million
dollar business.
Well, yes, you can Right, likethere's no, there's no one
saying you can't do that.
You have to look at things asbig as you want them to be or
(15:52):
they could be, and then chasethat.
Speaker 1 (15:54):
When you started the Riveter and you had that moment
with your friend or that personwho was like, wait, why don't
you scale this?
And before that, you weren'teven thinking about that, nor
were you thinking about venturecapital or how can I do that?
However, you ended up raising$30 million.
So how did you go from thatperson planting the seed of
venture capital like what isthis VC you speak of to you
(16:17):
actually getting people to giveyou $30 million?
What was in?
Speaker 2 (16:20):
between that.
So I did a lot of research andI know that might sound
uninteresting or not sexy, buthere's the thing we talk
ourselves out of doing a lot ofthings because we're like I
don't know how to do it, it'stoo hard, I can't figure it out.
You can figure out anything inthe world.
I familiarized myself with thetype of capital, because VC
capital is just another sourceof capital.
It's one that's mythologized inAmerica but it shouldn't be,
(16:41):
because it's quite expensivecapital, actually in a lot of
different ways, because you'regiving up your business for it
or parts of your business.
But I familiarized myself withwhat it was and then I took
stock of the landscape who'sraising VC?
And at the time I was buildingco-working spaces and so I
looked over co-working spacefounders and like, once again,
it's like putting myself in thatroom in New York City where I
(17:02):
was layering and I was like, notthat business that I wanted to
build for that investment class,and by that I mean like if I
was applying for a you know, anSBA loan, the way I would have
told the story of my businesswould have been the way that you
tell it to the SBA, but I wasapplying for venture capital
(17:25):
funding, and so I needed to tellthe story of the business that
you know that they would want toinvest in, and then the last
thing that I did was I got theconnections that I needed.
I think this is the piece thatwe often overlook.
You know, you hear stories nowthat a job will get 10,000
resumes if you're just applyingto a random job online.
So what's the answer to that?
(17:45):
How do you stand out?
I don't think it's by writing abetter resume.
I think it's by finding warmconnections, and that is
something that anyone in theworld can do.
You know, I am a kid who grewup in Columbus Ohio my parents
are from Columbus Ohio and Iended up, you know, getting a
job at a top law firm in NewYork.
And how did I do it?
By building the rightconnections, and you know, here
(18:05):
are some ways that I did it.
With venture capital You'll besurprised, carrie I made a
spreadsheet, and in myspreadsheet I identified all of
the venture capital investors.
I did research and identifiedall of the VC investors who
invested in co working or inreal estate or, you know, in the
thing I was building.
And then I went on LinkedIn tofigure out if I had a direct
(18:28):
connection to someone who workedat that VC fund.
Now, that was very rare for mebecause I didn't know a lot of
people in the VC world.
So then what I did is usedLinkedIn's power of the second
connection and figured out whereI had an intermediate
connection that could connect meto someone at a VC fund.
After I'd done all the researchand had a list of like 100
(18:48):
investors I wanted to reach outto and I find warm connections
to like 75 through a middleman Ithen send emails to all of the
middlemen and ask them forcoffee or a phone call.
I didn't just send them anemail saying, hey, can you
connect me to Bob?
Because they'd be like whywould I connect you to Bob?
What's the point?
What are we doing here?
I needed to sell my intermediateconnection on my vision to get
(19:08):
them to use their social capitaland introduce me on my vision.
To get them to use their socialcapital and introduce me and
for them to make the rightintroduction and make it
powerful.
Yes, that took a ton of time,but I set myself up for the bold
move, I set myself up for thepivot so that by the time I was
asking for these introductions Ihad my story.
I was spending the time withthe intermediate person making
(19:29):
them realize.
I thought they were special.
I understood asking for thisintroduction was a big thing and
I treated it with care and assomething precious.
And the other thing when you dosomething like that and ask for
those connections say you'reasking Christy for a connection
to Roberta, at the end of theconversation with Christy, if
she's willing to introduce youto Roberta, you say to Christy,
(19:50):
is there anyone else you think Ishould meet?
And Christy will have like fiveother people you should meet.
She's now sold on your visionand she's going to connect you
to everybody else.
What I did there with venturecapital, you can do with finding
a job.
You can do with finding anykind of funding.
You can do with finding clientsright, like if you're starting
out as a freelancer or aconsultant.
You can do it with launching apodcast.
(20:11):
And that single piece offinding the right connections I
think is the most important one.
Speaker 1 (20:19):
You just hit it spot on in that it is the most
important way to navigateyourself through the intangible
network of getting where youneed to go, but so many people
don't understand it.
Speaker 2 (20:32):
This is a recommendation I would give to
any young person.
Or if you're older and haven'tput yourself in this position,
put yourself in a position whereyou are forced to ask people
for things and you're going tohear no a lot, because you have
to get comfortable with that asa life skill.
If you want to take risks anddo big things, you have to be so
used to hearing no that you'renot afraid of it, that you're
(20:54):
used to it, that you know how todeal with it, that you truly
understand that no today doesn'tmean no tomorrow.
I did work in politics and Iraised money or I door knocked,
you know, and I heard no overand over again and a lot of very
rude no's, I'll add, and I gotused to it and it became a very
unscary thing to me.
And I think that's superimportant because when you, when
(21:14):
you're learning the art ofconnection and to do big things,
you have to be able to embraceno and not be afraid of it, or
otherwise you won't.
You won't even try.
Speaker 1 (21:22):
So what this will also teach you a skill in is how
do I differentiate myself andhow do I win this person over
who's probably making $12 anhour might be.
You know, like whatever they'redoing, they could give a fuck.
How do I make them want to giveme information?
And so that too, you getcreative.
(21:43):
You make sure your looks aredialed in in terms of like don't
be wearing raggedy ass shoesand a stained ass coat, walking
in like you just rolled out fromlike some kind of hangover,
yeah.
Speaker 2 (21:53):
And also I think it's really important, in this like
very remote world we live in,learn how to do this shit in
person.
Like you aren't going to buildthese very deep relationships
online.
Some you will.
I mean you'll meet some peopleonline and become close and
build business relationships,but a lot of this is like earned
trust from face to face timeRight and people getting to know
(22:13):
you in person.
My good friend, susan McPherson, wrote this amazing book called
the Lost Art of Connection andit's so good.
She is one of the mostbrilliant authentic connectors
I've ever met in the world andshe's just so genuine and this
book is.
It's a great book to read tokind of get an overview more of
what we're talking about Lastquestion of the day.
Speaker 1 (22:36):
All right, if your pivot fails, how do you pick
yourself back up and reframe it?
Speaker 2 (22:42):
I always find inspiration in looking at other
people's failures.
I know that might soundterrible and I'm not looking at,
like the person on the corner,their failure.
I look at the stories of thegreats who failed right,
everything from you know thestory.
You hear that Michael Jordanused to tell he missed half or
more than half of his shotsright, but he's still the
(23:02):
greatest ever, or Kobe, or youknow, and so I think you know.
Looking at it from thatperspective, and then also I
mean sit down and make a list,not a spreadsheet, but a list of
what you learned, of what youdid a great job at, of what you
did a really bad job at, andlike what you liked and what you
didn't like.
You know the Riveter.
(23:24):
We started out by buildingco-working spaces and I took on
a lot of investment.
I had a lot of employees and wehad a black swan happen in
March of 2020 where we were nolonger allowed to legally
operate our spaces and so thatpart of my business it failed,
and I have since then, reallysat down and thought about what
(23:44):
I was good at, what I was bad at, what I liked, what I didn't
like, and I use that to informall of my next choices.
Like I don't want to manage ateam of 130 people ever again.
I'm not good at it.
I'm good at a lot of otherthings.
I'm not good at it Also.
I didn't like it and it's notsomething I want to learn how to
do.
Does that mean I would neverstart a company with 100 people?
(24:05):
No, but it means if I did, Iwould start it with a partner
who loved operations and peoplemanagement.
So you can take what youlearned and apply it to your
next endeavor.
And again, like always, go back.
There's Kobe.
There's like.
Abraham Lincoln lost everyelection ever until he became a
national politician, and if hehad quit after losing the first
(24:28):
one, what a loss for the rest ofus you are, just you know,
packed with inspiration, nobullshit, knowledge per usual.
Speaker 1 (24:35):
And sitting here for this first inaugural ask amy
just makes me that much morebullish about the fact that we
should be doing this.
It's fun, I love it if you'restill out there following your
girl.
Follow me on youtube, spotify,apple or wherever you get your
podcasts.
And until next time, ask amy isgoing to be a monthly drop.
It's a hour only.
We're eventually going to havea call-in option for you, but
until then, dm or email me atkerry, at the kerrycroftshowcom,
(24:57):
and ask your questions to Amyand keep moving, baby.
Hey there you beautiful badass.
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I'm your host, keri Croft,delivering you stories that get
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You're welcome.
You're really good at theseanswers.
No wonder we're doing Ask Amy.
My God, I'm like can I get mynotebook out?
Well, amy Nelson, we just Imean, we had to just draw you
right back in.
Here I am, how are you?
I'm good.
(01:32):
How are you?
I would say welcome to the KeriCroft Show, but this is Ask Amy
.
This is Amy Nelson's show.
It's the Keri Cro up, what youwere putting down, and so what
we're going to do now, we'regoing to do a spot every month,
30 minutes or less.
People can call in, they can DM, they can write us and this is
(01:55):
a very highly concentrated,dialed in show about women
pivoting in business Men you'rewelcome.
You're welcome to come.
Speaker 2 (02:01):
Anyone's welcome.
Men can be here, it's fine, butthis is just.
Speaker 1 (02:03):
You know the riveter has been.
That's what it is right Womenpivoting in business.
So I'm telling you, when youhave her here in the hot seat,
you better be ringing in thequestions, and we do have a
bunch of questions.
I will say to start off, Expertin nothing, opinion in
everything.
Hey, listen that.
(02:25):
That's what we're all abouthere, right?
Yep?
Question number one All right,okay, how do you know when it's
time to make a big pivot in yourcareer or business, versus just
pushing through a tough season?
Speaker 2 (02:30):
Ooh, that's a good question.
There is no right or wronganswer here, but I think there's
kind of two ways to look at it.
How long have you had thatinkling or that feeling that you
want to change?
Have you had that inkling orthat feeling that you want to
change?
I think it was Steve Jobs,actually, that said if you wake
up more days in a row than notand say I need something
(02:50):
different, then it's time.
So I think you have to kind ofconstantly be checking in with
yourself Is this what I want, oram I ready to make a pivot?
The other way to think about itis far less inspirational and
far more tactical, and it'sasking yourself not just if
you're ready, but can you?
(03:11):
Everyone always says, like, liveyour dreams, chase the passion,
like that's great, but youcan't always do that right,
because we have a mortgage orrent or kids, and so if you want
to make a big pivot, one of thethings to do to figure out if
you're ready or if you can is tosit down and map it out.
Do I have the time to make thepivot?
Do I have the financialresources to make the pivot?
If the pivot is to another job,great.
What's the salary?
Is it commensurate to what I'mmaking now or am I making more
(03:32):
money?
If I want to start a company,what's my runway my personal
financial runway that I can quitmy job, not take a salary and
wait until I ramp up that newbusiness?
Because for most businesses, onday one you're not bringing in
the money.
And so when I started theRiveter, I left 10 years of a
career as a lawyer and at thetime my husband and I sat down
and we made a spreadsheet andthe question for us was how long
(03:55):
can we continue to affordfull-time childcare and maintain
the same standard of living,with me, amy, not making a
salary?
And I had 19 months and Idecided that that was enough of
a runway for me to go for it.
And I went for it, and I cantell you that at month 16, I had
completely replaced my salary.
But the fact that I had thatrunway and also that goal pushed
(04:19):
me toward it even more quickly,because I knew I wanted to get
there.
See, I was actually going tofollow up with?
Speaker 1 (04:25):
didn't you do a spreadsheet?
You fucking took that ball andyou just ran with it.
What's the biggest mind shiftwomen need to make before taking
a big risk in business?
Speaker 2 (04:34):
And a lot of people might hate this answer you need
to recognize that impostersyndrome doesn't even exist
anywhere but in your own mind.
I feel like we have talkedabout imposter syndrome so much
with women that we think it is areal thing.
It's completely made upbullshit, right Like, and I
think if we didn't think of sucha thing as it existing, we
(04:54):
wouldn't even have it.
But I think the biggest mindsetthat women need to have to take
a big risk to start a businessis to say I'm standing in this
space and I can do it Like.
It's a very simple thing to do,but for some reason we hold
ourselves back and we take fewerrisks and we have more
questions of like will I fail orcan I do this?
Then we see that men have sojust like, don't.
(05:17):
Don't think that way, do notallow yourself to think that way
.
Whenever I doubt myself and Ithink you know it's over some
idea or fear, I just tell myselfI'm not allowed to think that.
One other thing that I think isreally important is that I think
sometimes we think we are onlyallowed to try once and if we
(05:39):
fail it's over.
But that's not how the worldworks.
Everyone gets to try again andagain and again, like no one's
kicking you off of life stage.
You know there are so manyentrepreneurs that failed at
their first businesses.
Sam Altman, who is, you know,taking open AI on this rocket
ship, his first startup failedspectacularly right.
(05:59):
And what if then he'd said,okay, I'm done, I can't do this.
But we, as women, need to takethe same approach.
We can fail, we can begin again, it doesn't matter, there are
endless chances and there's roomfor all of us.
Speaker 1 (06:10):
You just answered the third question, which was how
do you deal with impostersyndrome when shifting into a
new industry or role?
Speaker 2 (06:17):
I mean I think like, if you want to say imposter
syndrome exists, or if you feelit, this is my best advice for
how to deal with it.
Say to yourself what would likea mediocre white man in this
role do.
Or what would I mean?
Pretend you're someone else,like if you have imposter
syndrome.
Pretend you are the person youfeel like, you're, like
(06:38):
pretending to be, and how wouldthey approach something?
Just do it that way.
It might sound crazy, but like Icame to that after I worked on
Wall Street for a decade and Iwas in these rooms with mostly
men and at a certain point Istarted looking around and I was
like these guys don't knowanything, or like they don't,
like they're not all, they'renot all that right, like they
don't know any more than I do,but they're just taking up the
(07:00):
space.
And so, although I feltslightly uncomfortable in the
moment, I just decided, like I'mtaking up the same space, no
one can stop me.
And like I honestly thinkthat's like how I ended up
pivoting to start a venture,backed business and raising $30
million and doing these things,because I just decided to take
up the space.
Damn girl.
And I'll say something I don'thave imposter syndrome, but I do
(07:22):
get scared, right, I get scaredof saying the wrong thing.
Or you know, or I am, you know.
I get scared of failing, butit's just like it's not a useful
emotion, but don't you?
Speaker 1 (07:33):
think that you, that was a muscle that you built
though.
So, even like you just sayingthat you had internal dialogue,
you did visual, like you didexercises, you talked yourself
through it.
So it's not like you're justgoing to wake up one day and be
like, ok, I don't have itanymore, but you have to make it
a priority to like think itthrough.
You figure that out.
Speaker 2 (07:52):
I mean you do like.
It is kind of like, if youthink about it, like you're not
going to become stronger if youdon't go lift weights Right,
like you have to make a decisionand do that.
And I think for me the practiceof getting over these things is
a practice of seeing it andframing it differently in my
mind.
So I used to shake before whenI had to public speak and it was
my right leg.
(08:12):
It would just shake, and itwould shake like if I was giving
a meat of honor toast or if Iwas public speaking for work,
and it would shake only if Ididn't have a podium.
It was like this very specificthing where I felt exposed.
If I had a podium, I was fine,no big deal.
And I remember when I startedthe Riveter I had to get up and
give a speech to like theChamber of Commerce in Seattle
(08:33):
and I was like, fuck, I'm goingto shake.
This is embarrassing.
And then I had this moment inmy head where I was like you
know what?
This is my job now, this ispart of my job and I either sink
or I swim and I better figureit out.
And then when I realized thatthis is part of my job.
I never my leg never shookagain.
I don't even know if it was.
I stopped being afraid, but Iwas like I have to do this.
(08:54):
This is my job.
Speaker 1 (08:55):
When you think about who you're speaking in front of,
like when there's a bunch ofeyes in front of you, of course
it's like, oh my God, everyone'slooking at me.
But you're like looking outthere.
You're like you're all justnormal human beings, they're all
just who cares?
Speaker 2 (09:08):
Yeah, and the other thing is, if I realized too,
when you're looking out at a seaof people you know most people
in this world do let fear stopthem from trying things where
they could fail, whether that'sgetting up on a stage and giving
a speech, starting a business,going for a promotion, and the
thing that most people arelooking at you for.
When you are the person on thestage or are the person going up
(09:29):
for the promotion, they'relooking at you and they're
thinking I wish I could do that.
I wish I could be that braveand like that's.
You're providing inspiration topeople and that's just not
something to be afraid of.
Speaker 1 (09:40):
I don't mean to beat up the mediocre white male out
there we afraid of.
I don't mean to beat up themediocre white male out there.
We love you, we love you, butit's okay, we can beat you up a
little bit, yeah, but working incorporate America and then
managing and being the director,every single person I was in
meetings with were men in suits,mostly white.
They're taking up the sameexact space, like look around,
(10:01):
compare, pretend.
Speaker 2 (10:02):
Like you said, I love that idea that visual, yeah, I
don't know.
I remember when you're playingsports as a kid you'd take stock
of the other team, right.
You look at them, you figureout who they are, what the
players are and then figure outhow you can contribute and win,
and I think that we lose sightof that in the world, but I
don't think that we should.
Speaker 1 (10:20):
What is one unconventional strategy for
making a bold career move thatmost people don't?
Speaker 2 (10:25):
talk about.
I think an unconventional movefor making a big pivot is to
spend time in the background,first planning the pivot, but
not over plan, but earlier.
Like make sure that you arefinancially set up to do it
(10:45):
yourself, plan your first stepsand also, I think, added to this
something that isunconventional and people are
afraid to do Ask everybody youknow to help you make that move.
Enlist your friends, enlistyour colleagues, because when
you make the move, it will bebigger and bolder if everyone
around you is on your supportingteam.
Speaker 3 (11:07):
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Okay, this is from someone whohas spent a lot of time on a
(12:10):
personal brand and they want torebrand themselves.
Okay.
So the question is, how do yourebuild your personal brand when
you're pivoting into somethingcompletely new?
So you already are known forsomething, you have the brand,
but you're really looking tokind of shed that I love this
question because, first of all,we are allowed to change.
Speaker 2 (12:31):
Like you don't have to do the thing you did for 10
years.
You can change expertise, youcan change your jobs, you can
change your personal brand.
So my answer might be slightlyunconventional, but we live in a
world where people wantauthenticity.
Like if you look at socialmedia now, right, like gone are
the highly stylized reels Likewe just want you talking in
(12:52):
front of a camera and you knowand seeing what your life is
like.
And I think, to that end, Ithink there's something really
powerful, really vulnerable andreally authentic about taking
the community you have built onthe journey of your personal
rebrand.
And by that I mean tell yourcommunity you know I've spent X
years doing.
You know I've spent X yearstalking about sewing.
(13:14):
You all have been here with meas we did X, y and Z.
You know now we're going tolearn something new together and
explain, like, why you aretaking on this new project or
talking about this new expertiseand bring your people with you,
right.
I mean we want this, we want,we want change too.
As your community, we want tosee new things.
(13:35):
So we're here for it.
If you didn't do that and youjust one day, like rebranded
yourself with, like you know,say you were you know, sally,
who is an expert in criminallitigation, and then, all of a
sudden, the next day, yourwebsite is like I'm Sally, I
make pottery.
People would be like what thefuck just happened?
Right, and so take people withyou and they'll be there for it
(13:55):
and you will make new community.
Speaker 1 (13:57):
What are the OK?
What are some of the biggestmistakes women make when trying
to transition into a newbusiness or career path?
We ask for too little.
Speaker 2 (14:04):
If you are trying to get a promotion or get a new job
, the first salary offer is notthe best they have, right, like
it's an opening bid for anegotiation and you need to ask
for more.
You need to ask for the farm.
So I think that's the firstthing, right, like we just need
to ask for more.
And I think that applies likewhen you are seeking a new job.
But it also applies like ifyou're starting a consulting
(14:25):
business or freelancing, likewhatever you think you should
set your prices at, you shouldprobably double it.
I mean, that might be a wildamount, but you know no one's
going to pay you more than youask for.
So ask for more, and if it'stoo much, you can negotiate down
.
Now I recently sent out aproposal and it was too much for
someone, and so we negotiateddown.
(14:45):
But like to their point, likeon the reverse side, my opening
bid was not the lowest amount Iwas willing to do it for, but I
was going to ask for as much asI thought I was worth, and then
I had the decision of whether Iwant to lower my rates depending
on the project, the person,whatever.
I have raised a lot of venturecapital and men receive 98
(15:06):
percent of venture capitaldollars, and I think one of the
reasons is that we, as women,just don't ask for as much.
So I think that's an importantthing.
The other thing I'll say aboutyou know what we need to do as
women when we're startingbusinesses or pivoting is, you
know, not everybody needs tobuild a $10 million business.
You can build an amazing, youknow, cash flowing lifestyle
(15:28):
business, and I think more andmore people are doing that, but
I think that we need to set ourexpectations and goals higher.
One of the reasons I thinkwomen raise less venture capital
is venture capital investorsare looking for a massive return
and I think, as women,sometimes we're like shit.
I cannot tell this person I'mgoing to build a hundred million
dollar business.
Well, yes, you can Right, likethere's no, there's no one
saying you can't do that.
You have to look at things asbig as you want them to be or
(15:52):
they could be, and then chasethat.
Speaker 1 (15:54):
When you started the Riveter and you had that moment
with your friend or that personwho was like, wait, why don't
you scale this?
And before that, you weren'teven thinking about that, nor
were you thinking about venturecapital or how can I do that?
However, you ended up raising$30 million.
So how did you go from thatperson planting the seed of
venture capital like what isthis VC you speak of to you
(16:17):
actually getting people to giveyou $30 million?
What was in?
Speaker 2 (16:20):
between that.
So I did a lot of research andI know that might sound
uninteresting or not sexy, buthere's the thing we talk
ourselves out of doing a lot ofthings because we're like I
don't know how to do it, it'stoo hard, I can't figure it out.
You can figure out anything inthe world.
I familiarized myself with thetype of capital, because VC
capital is just another sourceof capital.
It's one that's mythologized inAmerica but it shouldn't be,
(16:41):
because it's quite expensivecapital, actually in a lot of
different ways, because you'regiving up your business for it
or parts of your business.
But I familiarized myself withwhat it was and then I took
stock of the landscape who'sraising VC?
And at the time I was buildingco-working spaces and so I
looked over co-working spacefounders and like, once again,
it's like putting myself in thatroom in New York City where I
(17:02):
was layering and I was like, notthat business that I wanted to
build for that investment class,and by that I mean like if I
was applying for a you know, anSBA loan, the way I would have
told the story of my businesswould have been the way that you
tell it to the SBA, but I wasapplying for venture capital
(17:25):
funding, and so I needed to tellthe story of the business that
you know that they would want toinvest in, and then the last
thing that I did was I got theconnections that I needed.
I think this is the piece thatwe often overlook.
You know, you hear stories nowthat a job will get 10,000
resumes if you're just applyingto a random job online.
So what's the answer to that?
(17:45):
How do you stand out?
I don't think it's by writing abetter resume.
I think it's by finding warmconnections, and that is
something that anyone in theworld can do.
You know, I am a kid who grewup in Columbus Ohio my parents
are from Columbus Ohio and Iended up, you know, getting a
job at a top law firm in NewYork.
And how did I do it?
By building the rightconnections, and you know, here
(18:05):
are some ways that I did it.
With venture capital You'll besurprised, carrie I made a
spreadsheet, and in myspreadsheet I identified all of
the venture capital investors.
I did research and identifiedall of the VC investors who
invested in co working or inreal estate or, you know, in the
thing I was building.
And then I went on LinkedIn tofigure out if I had a direct
(18:28):
connection to someone who workedat that VC fund.
Now, that was very rare for mebecause I didn't know a lot of
people in the VC world.
So then what I did is usedLinkedIn's power of the second
connection and figured out whereI had an intermediate
connection that could connect meto someone at a VC fund.
After I'd done all the researchand had a list of like 100
(18:48):
investors I wanted to reach outto and I find warm connections
to like 75 through a middleman Ithen send emails to all of the
middlemen and ask them forcoffee or a phone call.
I didn't just send them anemail saying, hey, can you
connect me to Bob?
Because they'd be like whywould I connect you to Bob?
What's the point?
What are we doing here?
I needed to sell my intermediateconnection on my vision to get
(19:08):
them to use their social capitaland introduce me on my vision.
To get them to use their socialcapital and introduce me and
for them to make the rightintroduction and make it
powerful.
Yes, that took a ton of time,but I set myself up for the bold
move, I set myself up for thepivot so that by the time I was
asking for these introductions Ihad my story.
I was spending the time withthe intermediate person making
(19:29):
them realize.
I thought they were special.
I understood asking for thisintroduction was a big thing and
I treated it with care and assomething precious.
And the other thing when you dosomething like that and ask for
those connections say you'reasking Christy for a connection
to Roberta, at the end of theconversation with Christy, if
she's willing to introduce youto Roberta, you say to Christy,
(19:50):
is there anyone else you think Ishould meet?
And Christy will have like fiveother people you should meet.
She's now sold on your visionand she's going to connect you
to everybody else.
What I did there with venturecapital, you can do with finding
a job.
You can do with finding anykind of funding.
You can do with finding clientsright, like if you're starting
out as a freelancer or aconsultant.
You can do it with launching apodcast.
(20:11):
And that single piece offinding the right connections I
think is the most important one.
Speaker 1 (20:19):
You just hit it spot on in that it is the most
important way to navigateyourself through the intangible
network of getting where youneed to go, but so many people
don't understand it.
Speaker 2 (20:32):
This is a recommendation I would give to
any young person.
Or if you're older and haven'tput yourself in this position,
put yourself in a position whereyou are forced to ask people
for things and you're going tohear no a lot, because you have
to get comfortable with that asa life skill.
If you want to take risks anddo big things, you have to be so
used to hearing no that you'renot afraid of it, that you're
(20:54):
used to it, that you know how todeal with it, that you truly
understand that no today doesn'tmean no tomorrow.
I did work in politics and Iraised money or I door knocked,
you know, and I heard no overand over again and a lot of very
rude no's, I'll add, and I gotused to it and it became a very
unscary thing to me.
And I think that's superimportant because when you, when
(21:14):
you're learning the art ofconnection and to do big things,
you have to be able to embraceno and not be afraid of it, or
otherwise you won't.
You won't even try.
Speaker 1 (21:22):
So what this will also teach you a skill in is how
do I differentiate myself andhow do I win this person over
who's probably making $12 anhour might be.
You know, like whatever they'redoing, they could give a fuck.
How do I make them want to giveme information?
And so that too, you getcreative.
(21:43):
You make sure your looks aredialed in in terms of like don't
be wearing raggedy ass shoesand a stained ass coat, walking
in like you just rolled out fromlike some kind of hangover,
yeah.
Speaker 2 (21:53):
And also I think it's really important, in this like
very remote world we live in,learn how to do this shit in
person.
Like you aren't going to buildthese very deep relationships
online.
Some you will.
I mean you'll meet some peopleonline and become close and
build business relationships,but a lot of this is like earned
trust from face to face timeRight and people getting to know
(22:13):
you in person.
My good friend, susan McPherson, wrote this amazing book called
the Lost Art of Connection andit's so good.
She is one of the mostbrilliant authentic connectors
I've ever met in the world andshe's just so genuine and this
book is.
It's a great book to read tokind of get an overview more of
what we're talking about Lastquestion of the day.
Speaker 1 (22:36):
All right, if your pivot fails, how do you pick
yourself back up and reframe it?
Speaker 2 (22:42):
I always find inspiration in looking at other
people's failures.
I know that might soundterrible and I'm not looking at,
like the person on the corner,their failure.
I look at the stories of thegreats who failed right,
everything from you know thestory.
You hear that Michael Jordanused to tell he missed half or
more than half of his shotsright, but he's still the
(23:02):
greatest ever, or Kobe, or youknow, and so I think you know.
Looking at it from thatperspective, and then also I
mean sit down and make a list,not a spreadsheet, but a list of
what you learned, of what youdid a great job at, of what you
did a really bad job at, andlike what you liked and what you
didn't like.
You know the Riveter.
(23:24):
We started out by buildingco-working spaces and I took on
a lot of investment.
I had a lot of employees and wehad a black swan happen in
March of 2020 where we were nolonger allowed to legally
operate our spaces and so thatpart of my business it failed,
and I have since then, reallysat down and thought about what
(23:44):
I was good at, what I was bad at, what I liked, what I didn't
like, and I use that to informall of my next choices.
Like I don't want to manage ateam of 130 people ever again.
I'm not good at it.
I'm good at a lot of otherthings.
I'm not good at it Also.
I didn't like it and it's notsomething I want to learn how to
do.
Does that mean I would neverstart a company with 100 people?
(24:05):
No, but it means if I did, Iwould start it with a partner
who loved operations and peoplemanagement.
So you can take what youlearned and apply it to your
next endeavor.
And again, like always, go back.
There's Kobe.
There's like.
Abraham Lincoln lost everyelection ever until he became a
national politician, and if hehad quit after losing the first
(24:28):
one, what a loss for the rest ofus you are, just you know,
packed with inspiration, nobullshit, knowledge per usual.
Speaker 1 (24:35):
And sitting here for this first inaugural ask amy
just makes me that much morebullish about the fact that we
should be doing this.
It's fun, I love it if you'restill out there following your
girl.
Follow me on youtube, spotify,apple or wherever you get your
podcasts.
And until next time, ask amy isgoing to be a monthly drop.
It's a hour only.
We're eventually going to havea call-in option for you, but
until then, dm or email me atkerry, at the kerrycroftshowcom,
(24:57):
and ask your questions to Amyand keep moving, baby.
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