The Tim Ferriss Show - #314: Cindy Eckert (formerly Whitehead) — How to Sell Your Company For One Billion Dollars
Episode Date: May 10, 2018Cindy Eckert (formerly Whitehead) (@cindypinkceo) is an entrepreneur with 1.5 billion dollars in exits who currently serves as the founder and CEO of The Pink Ceiling, an investment firm and ...consulting enterprise nicknamed the Pinkubator with a mission to invest in, launch, and build other women-led or focused businesses. She believes that access to good advice alone is not enough to change the ratio of men to women in business, and that is why she personally invested more than 15 million dollars in 2017 alone to support the development of nine portfolio companies.I should mention right off the bat that if you're a guy, don't let this bio turn you off in any way — in the sense that I wanted to have Cindy on the show because she is a good CEO and entrepreneur, very much irrespective of gender. The negotiating techniques, the approaches to deal-making, everything that we talk about applies to entrepreneurs, period, full stop.Earlier in her career, Cindy was the founder of Sprout Pharmaceuticals, home of Addyi, the first and only FDA-approved treatment for low sexual desire disorder in women, which was sold for one billion dollars and then reacquired in a crazy story with incredible terms that we will discuss in this conversation.Please enjoy this wide-ranging conversation with Cindy Eckert!This podcast is brought to you by Peloton, which has become a staple of my daily routine. I picked up this bike after seeing the success of my friend Kevin Rose, and I've been enjoying it more than I ever imagined. Peloton is an indoor cycling bike that brings live studio classes right to your home. 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Hello, boys and girls. This is Tim Ferriss, and welcome to another episode of The Tim Ferriss Show, where it is my job each and every episode to deconstruct world-class performers from
different fields, to tease out the habits, routines, life lessons, negotiating techniques,
favorite books, whatever it might be that I think think is tactical, practical, that you can apply to your own life.
And my guest this episode is Cindy Whitehead, at Cindy Pink CEO on Twitter, if you want to say
hello. She is an entrepreneur with $1.5 billion in exits, who currently serves as the founder and
CEO of The Pink Ceiling, an investment firm
and consulting enterprise nicknamed a Pinkubator with a mission to mentor, invest in, launch,
and build other women-led or focused businesses. She believes that access to good advice alone is
not enough to change the ratio of men to women in business. And that is why she has personally
invested more than $15 million in 2017 alone to support the development of nine
portfolio companies. I should mention just right off the bat that if you're a guy, don't let that
bio turn you off in any way in the sense that I wanted to have Cindy on the show because she is a
good CEO and entrepreneur, period, very much regardless or irrespective of gender. And the negotiating techniques,
the approaches to deal-making, everything that we talk about applies to entrepreneurs,
period, full stop, regardless of their genitalia. So I'll throw that out there because I really do
think that good advice is good advice. End of story. Now, Cindy is, before that, also the
founder of Sprout Pharmaceuticals, home of ADDY, that's A-D-D-Y-I, the first and only FDA-approved treatment for a low sexual desire disorder in women, which was sold for $1 billion and then reacquired in a crazy story with incredible terms that we will talk about in this conversation. So with all of that preamble, and without further ado,
as I always say, please enjoy this very wide ranging and what I found to be a very enjoyable
conversation with Cindy Whitehead. Cindy, welcome to the show.
Thanks for having me.
I am very excited to dig in. And I thought we could start in media risks, as they say in novels,
where you start right in the middle of the action. So we're going to bounce all over the place,
as I always do. JP Morgan Healthcare Conference. I've heard some sort of murmurs about stories
and getting attention or people to focus. Could you please describe for folks what happened?
Awesome. So biggest conference in all of healthcare.
I get invited in.
I have eight minutes, do or die.
So proud of this opportunity.
I get in front of the room.
You can imagine here's me in hot pink, head to toe.
I start to talk about women and sex and the whole room starts to giggle.
I can feel this giggle going off across the crowd, and I'm panicking, like watching the clock count down,
so I can remember reaching to my laptop,
fast-forwarding as fast as I can
to a slide that was just brain scan studies,
studies of women with this condition versus women without,
where in black and white we could see
there was a biological basis to women's lack of desire for sex.
So I put the slide up, I turned and pointed
long enough for it to be uncomfortable for everybody. So I put the slide up, I turned and pointed long enough for it to be uncomfortable
for everybody. I went silent. And when I did that, I said, are you looking at what I'm looking at?
Because I'm just here to talk about the biology of sex for women. It's an important lesson for
me of what I was going to have to do to make people focus. So you let the silence do the work.
It was uncomfortable. I figured it was long enough for it to be uncomfortable for me,
which was fair trade for them having made me really uncomfortable as they
started giggling and wouldn't pay attention to me.
Silence.
Yeah.
It's,
uh,
it's so powerful.
It's so,
so powerful.
And I remember advice I was given at one point while I was given that
advice first by someone named Cal Fussman,
his master interviewer,
when he was going over some
transcripts from this podcast in the early days. And he's like, no, you're too fast. Like you don't
leave gaps. And you don't have to save people, like let the silence do the work. So I just,
I love that story. And so speaking of letting the silence do the work, I'm going to go silent for a
bit because I want to ask you two questions that might take a few minutes to answer. I'm going to go silent for a bit because I want to ask you two questions that might take a few minutes to answer.
I'm going to start with a short one.
What is your favorite business and why?
My favorite business of all is Wegmans, which if anybody's from the Northeast, they appreciate this is a grocery store.
How can you get excited about a grocery store?
I'm excited because it's from my birthplace, Rochester, and I went there every Sunday as a little girl. Here's why I loved it. Because of
the incredible loyalty that they instilled. How do you get folks that are cashiers at the checkout
line with jobs that may seem relatively unexciting to show up every day with unbridled enthusiasm for what they do. So it opened years later.
I moved my whole life.
And it opened in the D.C. area.
And I went the first day that Wegmans opened in D.C.
And I walked up and all of their employees were standing outside
holding their hands above their head like a W.
Because they have a Wegmans pride, the Wegmans way.
And I got to tell you, that first day,
anybody in the entire D.C. metro area who'd ever been to a Wegmans pride, the Wegmans way. And I got to tell you, that first day, anybody in the entire
DC metro area who'd ever been to a Wegmans showed up and stood in line to walk through this store.
I love them for being a private, family-held business that has that kind of loyalty and
longevity of employees. How do they instill that? I mean, is it filtering for the right
employees who are prone to that to begin with? Is it something else? I mean, how do they develop? I think it is oh so simple. I think it is their
basic appreciation for the people who show up and work for them every day. And they reward them
through the right incentives. They reward them through the best benefits. They help develop them.
They encourage them when they lose weight. I mean, there are all of these incentives
to their employees that make them truly feel that appreciation from their employer. And also,
I think, you know, be proud to work there. They go home and have pride in saying who they work for.
Yeah.
So I started studying businesses I loved at a very young age.
I had a conversation with Frank Blake, former CEO of Home Depot, right here.
He's sitting where you are.
And they developed this orange apron cult, as it was sometimes referred to.
And the dedication that some of these employees showed was incredible.
And his point was one of the systems they instilled was positive reinforcement by sharing stories on a very regular scheduled basis of kind of standout customer
service. And yeah, it doesn't have to be complicated. I have to tell you when I sold
my first business slate, I sold it to a group that was private equity backed. And I ran into
one of those guys, one of the bankers years later, and he said, that group you had, they were almost cult-like. And I think he said
it with sort of one eyebrow raised, like, hmm. And I said, why, thank you. That's the nicest
compliment I've ever received. So yeah. You mean in the Apple way, not the David Koresh way?
Yes. Perfect. I'll take it. Exactly.
So the next question, which will seem odd to people listening but will soon make more sense, is, it's not really a question.
I'll be polite and make it a question.
Okay.
Could you please give me your three-minute commercial?
Okay.
Tell me about yourself.
Soup to nuts.
All right.
Moved my entire childhood.
So every year from fourth to twelfth grade, I was in a different school.
So I was the perpetual new kid. I think what that did is perfect my ability to stand on the outside
of the room and look in and really listen, understand motivations, understand sort of the
dynamic, which served me well later in life. At the time I went kicking and screaming.
I have a love that started very young in life for what makes
businesses great. So as I went through college, I was fortunate to have a great business professor
who really cultivated that in me. So I'd have to report to her every week what my favorite
business was, why, what were they doing differently, and along that way made a unilateral decision that
I was going to go work for Merck. So she thought I should probably broaden my options. It wasn't such a slam dunk. I told her, no, I'm going to work for Merck.
They weren't hiring when I got out of school, but eight months later they were, and I got the job.
Called her up, said, I got that job that you said I might not. And she said, great,
we're going out to dinner and you're buying. So went to work for Merck, started in pharma because
it was Fortune's most admired company. That's why I went there.
Wanted to learn from the best.
I thought I would actually take it elsewhere and apply it.
Didn't really think I was going to be so fascinated with the science.
Fell in love with the science and the innovation, what it could mean in people's lives.
Loved what pharma had the capacity to do.
Hated how they got it done in the bigger companies.
So I made the leap, went smaller,
smaller, smaller, smaller, until I ultimately was maybe crazy enough to start it for myself.
Built two businesses, both in sexual health. People say, why? I say, Irish Catholic, of course.
So built a business late with the only long-acting testosterone for men. And that made me on the path of watching this emergent science for women.
When this drug was put on the shelf by the company that invented it,
I made a decision to sell that off and take it on
and got the only ever drug approved for sexual desire in women.
Sold that business and now, as a pass-through,
do nothing but spend my time reaching my hand back
and trying to get female founders there to my kind of outcomes faster than I got there myself.
That was really good.
And I wasn't watching the time.
I wasn't watching the time.
But if I had to use my spider sense, I think that was really, really close.
So I'm very impressed.
And for people who are wondering, what the hell is Tim doing?
This is the oddest interview I've ever heard him attempt to give.
It is because, why?
What do the last two questions have in common?
Why did I ask those two questions?
You asked those two questions because I love to ask those questions of everybody I interview.
Because I think that if you'll just be quiet and listen, which you heard a little bit from my background,
people will tell you a lot about themselves and what their motivations are. So that was always probably my initial question
in interviewing and figuring out from people what they would tell me about themselves.
What would you look for? Or were there any particular sort of checkered flags,
meaning fantastic, or red flags, meaning maybe not a good person to pick for me you know it was discomfort
with change the lack of adaptability because in my environments they were not the same structure
that they might have been coming from they were going to have to be nimble have to move quickly
to keep pace or i i always laid my cards on the table at the end of interviews and said
here's who we are here's this culture um we both should lay our cards on the table at the end of interviews and said, here's who we are, here's this culture.
We both should lay our cards on the table because six months from now,
I don't want us to be unhappy with each other.
So I think I'm always listening for those cues that would indicate a fit for my environment.
And in it, I think I was finding the people with a love of businesses.
I often ask that question, what is the business that you most admire?
Because they've got to have that passion. I think particularly in small and startup, you have to have a real love affair with what it is that makes things tick. What did you study in undergrad?
Business. Business. Yeah. What did your business professor do besides have you
report back each week on your favorite business of the week?
You know, I think she just took a special interest.
I think she saw something there and cultivated it so that she was pushing me.
So not only did she push me with the assignment that was above and beyond what she was asking of everybody else,
but I think she also tortured me a little bit with the doubt to see if I would push through
it. You know, when I said to her, I'm going to go work for Merck, she's like, well, I don't know.
Your science grades aren't that good. I mean, she really sort of pushed back. Like it wasn't
such a sure thing. So she was constantly setting the bar for me. So did she now, I don't know if
you had a chance to ask her, but was, but did she genuinely think that you would have trouble getting the job,
or was it a Yoda trick to get you to stubbornly then pursue it twice as hard?
A hundred percent a stubborn trick.
And I think she knew that I have sort of a healthy chip on my shoulder of proving it.
So she was definitely pushing right at that button of, you know, go out there and prove it.
So, yeah, very clever.
So how does one start a pharma company without a pharma background?
Well, pharma background in that I'd been in the industry for a long time. So I had the right, you know, context. You had the industry experience. I had the industry experience. You're
right. I didn't learn that very well. Without the... Scientific background. That's right.
Surround yourself with an extraordinary scientific team. I feel like I've learned at the hands of
some of the best in science. And I think I've always brought a lens to it of, you know, what
would work in the market. We were sort of a magical pairing because many times in science,
you can get enamored in the lab with things
and not look outside to what's really going to work
in the mainstream.
So it was a lot about having just a great team.
How did you pick...
And I can play a doctor on TV now.
You can?
Or I at least think I can.
Yeah, yeah.
Or via people's earbuds that they may have.
Yeah, that's right.
How did you end up choosing the, you said, long-acting testosterone?
So paint a picture for us.
Sure.
Because we can certainly get into testosterone and like HPTA and all this fun stuff.
But I don't want to bore some segment of my population of listeners to
death, although I'm fascinated by it. So we probably will get into it. But how did you end
up choosing that? So you have, you want to start, did it start with finding the opportunity and
then I want to start a company or did you decide I want to start a company and now let me try to
find a product? That was it. Yep. I wanted to start my own company. So I felt like I had a hypothesis.
And if you don't mind me asking, how old were you at the time? Or where were you in time?
I know that. I was in my early 30s at the time when I started it. And I had one career experience
that was very informative. So I'd been at a company that was acquired. And they had been
gobbled up by somebody who'd gobbled up a and then they had to integrate them and I got to be on that team. So I got this sort of put
together of the perfect company. That was a great career moment for me. Um, and then I got to go
apply it and doing my own. And the reason I did it is that for that same reason, I love pharma for
what it can do at 3am in the morning. If you're sick, you love pharma. In the light of day, you probably don't.
And it's because it is an industry that has a certain reputation.
I thought there was a way to do it better.
And I had the hypothesis that here I am, driven and succeeding in these environments, but totally uninspired.
There have to be other people like me.
What if I got them together, gave them permission to do it on their own terms?
And that was Slate. I named my company Slate on purpose. Clean Slate. We were going to do it our
way. And it was to go out and find a diamond in the rough, an asset that had been overlooked.
I loved the category. I love sexual medicine. I'm a card-carrying member of the Sexual Medicine
Society. Who knew there was that? There is. Oh, there is.
Makes me popular at cocktail parties.
I'd whip it out. No, there really is a society. And it's because actually our understanding there
has really come much more recently. It's a relatively new field, and yet we're learning
such interesting things. And it's in conditions, you might not lose your life from them, but you will lose your life as you know it when you're affected by these dysfunctions.
So found this inventor who had the only FDA-approved long-acting testosterone.
And interestingly—
How do you find someone like that?
Because you would think that in a world of sort of pharma discovery, that the bones would have been picked clean.
Yes.
Okay, so this is a great story.
So a scientist that I knew from a previous company was quoted in an article.
This gentleman reached out to him.
He said, I don't know anything about this space,
but I know somebody who's really interested in it.
So the inventor was looking for a way to commercialize.
It was a very fortuitous sort of introduction
and couldn't believe that this had been overlooked.
The reason it had been overlooked is that almost all of this product
was being used off-label, meaning that not for its indication,
it was being used interestingly in women.
So my journey started very early in this use of libido.
What's the compound?
It was testosterone. What type of testosterone?
A pellet. So it was long-acting, put under the surface of the skin,
released testosterone over a four to six month window.
So here's me looking at it going, hmm, first of all it should be used by urologists in men. I did this
crossover analysis. Only one urologists in men. I did this crossover analysis.
Only one urologist in the country was using it.
So I thought this would be a great business to build.
And frankly, the delivery system is better than what's available on the market today if I thought of something that was custom-made for men.
They have to remember.
I have big brothers.
I'm used to being around guys.
They can be sitting on the beach burning bright red,
and they still won't put sunscreen
on or rub something on. And the most common application for testosterone at the time were
gels. So this was like, hey, can you remember to show up three times a year to the doctor?
I'm like, sure. I can do that. All right. So the inventor reaches out to your friend,
the scientist, who says, I can't help you, but maybe my friend can. And that's how it starts.
So the pellet, how do they, now I'm thinking of, for instance,
like Tremblone, which is used in cattle in some cases,
also popular with some powerlifters and so on,
who do not use it in pellet form.
But how is it administered?
Or how is it put into the patient?
So put in an in-office procedure.
At the end of it, it requires a Band-Aid.
So there's a device, a trocar. You go just under the surface of the skin,
set it underneath the skin, put a Band-Aid on. And for urologists who are surgeons, this
in-office procedure was very simple. And the great news is it was half the price of anything
on the market. So everybody was winning in this equation.
Why was it half the price?
Just because of the purpose for me,
because you set the pricing.
Now,
was it less costly because you are comparing it to other modes of administration,
which require more visits?
Hence it's not.
No,
it was just the market positioning.
Yeah.
Yeah.
Fascinating. What was the market positioning. Yeah, yeah. Fascinating.
I have sort of a belief system around that in pharma about drug pricing,
and so it was important to me to do that.
We were making great money, building a great business,
and we were doing just fine at that cost.
Right, right.
You don't need a 500 million percent markup.
Yes, exactly.
Yes, and as we may
or may not talk about, some people get into a lot of trouble
for that.
Rightfully so.
What other
questions do you like to ask when you're interviewing people?
Are there any other questions you find yield
or
are worth the effort that are particularly helpful
or other approaches to hiring?
I'm going to go back to silence. I'm going to go back to, I do more listening than asking.
I ask the one open-ended question and try to see where they'll take me. Because I think I'm
getting a lot of insights into who they are by doing that. So I don't think there are magical
questions. I think there's ways to tease out cultural fit. And that is so important. I care
much less about the resume. Everybody wants to come in and impress you. They haven't really
hit your doorstep unless they have the cred, I think, to be in there interviewing for the position.
So I feel like it's my job to really tease out that cultural fit so that we're both happy with
each other. So culture can mean a lot of things to different people.
In this particular case, and you mentioned the adaptability,
which in a small startup especially, I mean, you're going to be wearing a lot of hats
and those hats make change, so you need someone who's adaptable.
What else were you looking for and what did it mean to you?
Six things. So mine are,
mine are pretty specific looking for, well, let me say overarching. I'm looking for people who
wake up every day and make deliberate choices. It's all a choice, right? How you go through life.
And mine were, my six were, they had to choose to be an owner. They'd be highly motivated by that
ownership. They had to choose to be bold. We were going to make decisions a little differently. They had to choose to be quirky because I needed them to feel that permission to
be individual in my environment. Most of them were coming out of environments in which we
beat sameness into people and homogenize the whole group. They had to choose to be learning.
That's fundamental to me. Even as I invest today, so important to watch what people do to learn every day,
choose to be family, because we were going to be a small tight-knit group, and they had to choose to be appreciative. And I think that that is how you go through life. What is your attitude? Do you
sort of marvel at the opportunity you have to make impact? So those were my six choices I was looking
for. How do you avoid false positives in the sense that if you ask someone or if you lay out,
if you say to them, these are the six values.
Oh, I never, never.
Cause it doesn't, you're, you're listening to this story that shows that I think exposes
those values.
But if you ask somebody that, like, do you choose to be quirky?
Uh, sure.
I mean, you know, that's a, you're not going to get, I think, the right
response. I think you have to know to your core who you are and who fits. And then I think you
have to ask the questions. I will say there is one other question I do always ask. And I ask,
how was the very first way you ever made money? Oh, I like that. That's a really good one.
And if they can't tell me, you know, I put
like flyers in the mailboxes in the neighborhood and said, odd jobs call me. Or if they are like,
well, you know, my first job out of college was they're out. Yeah. Yeah. They, they don't have
that sort of mentality. That's going to fit. One of, uh, one of my friends, um, Brian Johnson,
who, uh, has done a whole host of very impressive things he was the
founder i don't think he had a co-founder but let's just say one of the founders to be safe
of braintree which then sold for a whole lot of money and uh when entrepreneurs come to him
because he invests quite a lot now yeah and they say they want to start something he'll ask them
is that an itch or is that a like is, is that an itch or is it a burn?
That's cool.
And then he'll take them down that discussion to assess, do you really have the stick-to-itiveness
and the stubbornness and just the, it can't be any other way with me to actually make
it through this?
Because it's not going to be all roses and kittens and sunshine.
Wait, can I tell you a quirky story? You can absolutely tell me a quirky story.
This is how it went in an interview. After you tell me one quirky story,
I would like you to tell me a bold story from your personal experience.
Perfect. Okay. So here's my quirky. If I had asked her this, it wouldn't have come out,
but I'm in an interview with a young woman who wants to come sell for me this testosterone product.
Her brother had a particular genetic condition that meant that he didn't go through puberty normally.
So they have to have testosterone replacement from a very young age.
Nobody was more passionate about our product.
She had witnessed what it did for his life, what it did for her family, but she'd never sold.
So I was taking a big chance.
And look, we are in young, no sales experience, going to be walking into urology offices,
having a pretty sensitive conversation about men's sexual health.
And I'm in the interview with her, and I'm going, well, you know, I'm just kind of worried about.
And I didn't so much as get it out as she looked at me and she said, balls.
I said, you're hired.
So there was no doubt a recognition for me
that this girl was quirky,
that she was not going to have fear in the office.
Maybe that's bold.
I don't know if it's bold or quirky.
I'm going to call it both.
I think it's both.
But it ultimately became her nickname in the office.
We called her Duck Balls.
Duck Balls?
Yeah, because we had a whole other duck story.
But we all had nicknames.
Wait, wait, wait.
All right.
I'll take the bait.
What's the duck?
Oh, we called her Ducky because she was always very, very calm on the surface, but going
like this a million miles an hour underneath.
Okay, so we're going to come back to the bold story.
Yeah, that's fair.
Well, first I should just, as a public service announcement,
say to those people out there who do not have common sense,
don't just jump up and shout balls in every job interview
because you think that's going to show how bold you are.
Fair enough.
Yeah.
And if you do and you don't get hired, shame on you.
Okay. enough. Yeah. So, and if you do and you don't get hired, shame on you. But, um, okay.
I, in the course of doing some research, uh, I believe, I don't think I'm making this up
that you give everybody nicknames or a lot of your employees nicknames. Why is that?
It is my quirk. I've had it my whole life. So I know my mother by so many different names that I think people who don't know who I'm referring to half of the time that have known us for years.
You know, I did it because we love to storytell.
We sit around the lunch table.
We have a discipline of having lunch together every single day.
And that was an effort to not, you know, no death by meeting.
How would we all be on the same page,
and still create this sort of family spirit.
And people get to telling stories,
and of course it's the one that you wish you hadn't told
that ultimately arrives at your nickname.
But the beauty of that is, you know,
we have a whole ceremony.
A caricature, you get a nickname,
and it's basically handed over at the lunch table,
and you will never be known by your real name again.
Just for a second.
So this is like the knighting by nickname.
And at what point does this happen?
Is it like your first week on the job?
It's like, all right, on Friday, you're going to be.
No, we need a little more time than that.
But probably a month in, it happens.
The caricature goes on the wall.
Your name is sort of never to be heard again other than your nickname. And the reason I did it is that it was important to me that I was giving permission in my environment,
permission to be yourself, to sort of show who that was.
And especially when you're building companies where a lot of your people are outside of the main office,
they're salespeople or other, it was a way for us to get to know one another.
There felt like, oh, I get it.
I know who you are.
I've heard your story.
And I think it created this culture of locked arms, us against the world.
We knew each other's quirks.
Yeah, yeah.
So, yeah, weird habit, but one that stays to today.
All right.
So if I may, I'm going to – all right, this is going to lead somewhere,
but I'm a little sleep-dep sleep deprived and on lots of caffeine.
So I'm just going to roll with it.
So a friend of mine told me a joke recently and I'm not going to give the
whole joke. It's kind of long, but this, this tourist goes to Scotland.
He's sitting in a bar, he's hanging out and there's this old guy in the corner
and he starts like yelling at this tourist every couple of minutes.
And he'd be like, Hey laddy, you see that the pier out there, you know,
and he like built it with me on hands. you see that pier out there you know and they're like built
it with my own hands but they call me you know scotty the pier builder no and he keeps doing
this and he's like what the hell and it goes on and on and on and then he goes he goes but laddy
and then i fuck one goat what do they call me the point being, do people have the ability to veto their nickname?
Absolutely not.
Who gets to request their own nickname?
That never works.
That's true.
That's not going to work.
Any other, just to give us some examples.
You have duck balls.
I do.
What are some other examples?
I have a guy named Spoon, which was born out of a story of this incredible bromance between him and another guy.
They're still great friends to this day.
They so loved each other in their sales training that we said that all that was missing was them spooning.
But look, this story, I'll give an example of how that story and that nickname stuck with the whole group.
Actually, this guy got cancer, one of my reps, and a pretty dismal diagnosis. And it was one of the other reps
who came forward and said, we're going to do a virtual get well spoon card. And so every single
person in the company had the spoon hanging on the end of their nose and sent it out. And it was
their kids and it was their dogs and it was their family. And I think that it didn't come from me.
That came from somebody else in the organization.
And I,
that's how,
you know,
as much as we teased him about it in that really important moment,
he knew we were all looking out for him.
So this,
this makes me think of a few things and I really would love your thoughts on,
of course,
everything I'm asking you.
Otherwise,
why would I ask you in the first place?
But this type of joking around, I think, is a really, from what I've seen,
a really critical ingredient in almost any tight-knit group that does big things.
Sure.
And I've also spoken with a controversial guy for a bunch of reasons, but Jim Watson, all right, co-discoverer of the double helix.
I mean, that story is also a little more complicated than we have time for right now. important like for like letting the air out of the tires and to facilitate the endurance that people are going to need to get through the emotional
hurdles.
So my question is like duck balls,
clearly not the most politically correct nickname,
right?
But it's like,
that's why it's kind of why it works.
Right.
So my,
my question is in today's times where yes, there are like horrible things that do
happen in offices and terrible misbehavior at the same time, this type of nicknaming
and so on, I think is really helpful.
So how, how do you, what would your advice be to people who are like, yeah, like I want that.
We need that.
Yeah.
But they're afraid.
Well, look, I think, I think, you know, it's that laying my cards on the table.
Yeah.
When you first came in and interview with me, here's who we are.
Yeah.
Like you'll hate us in six months if you don't like this, this and this.
Right.
And I think that sort of transparency for me of who we were and what the environment was like. And look, we never were offensive. There was such an underlying affection
for one another. But it was this, it gave us permission to have what I'll call constructive
irreverence. Irreverence with me too. Like, you know, they give me a nickname and we knew that
we could have that comfortably inside our environment
and all be on the same page when we walked out into the world. I think it's really important.
I think that not taking yourself too seriously, I think being self-deprecating.
When I talked to a lot of female founders who are sort of very frustrated by the injustices
and this or that, I said, the best piece of advice I could have for you is perfect your sense of humor along the way. Because when it is something
that is offensive, the best way for you to cut through that is with humor. It is the best way.
And then actually the person on the other side might take a step back and think, oh God,
did I just do that? But you've given them room to sort of ask for forgiveness in that.
So I think humor is really important.
Yeah.
It also gives, I mean, this is having spent a lot of time in Japan and China also where,
you know, in China, like, is like to lose face, right?
So you're giving someone the chance to also kind of recover from a stumble instead of
creating what could be a really longstanding kind of awkwardness and stumble instead of creating what could be
a really longstanding kind of awkwardness and tension.
Do you have a nickname?
I do.
It's H-B-I-C.
Were you allowed to come up with your own nickname?
Absolutely not.
And they tell me that the B stands for Betty,
but I'm pretty sure they're lying.
What does the whole thing stand for?
Head Betty in charge.
Who gave you that?
There's always a secret nicknaming committee.
It's never revealed.
I see.
Yeah.
It just came to the table one day and was written on my caricature.
I'm just going all over the place, but that's what I do.
What makes, you mentioned new sales rep.
Yeah.
Balls, right?
Yeah.
And then henceforth, you will forever be known as Duck Balls.
We're not going to keep going on Duck Balls.
I just like saying it, so that's six or seven.
But the sales position, really important position.
Really important position.
Yep.
It's like, everything's a whole lot of talk until something gets sold.
Absolutely.
Right?
Yep.
How did you train? What were some of the techniques or
approaches that worked really well for either of your products for selling? Yeah. Uh, I think that
the best approach was that I gave them permission to fire the D list. Um, that, you know, we,
in sales, particularly in pharma sales, you get on this like every two weeks,
this is my routing, I'm going to go out, reach in frequency, reach in frequency.
And I think that it says to keep chasing your tail in situations
in which you're never going to pull it through.
So it's rare, I think, to say to a salesperson, you know what, scope it out.
If it's not, move on, fire them, wait until they call you back
and they're looking for the product, and really focus your energy on those who
are raising their hand quickly. So I think that was different,
at least in my industry.
I don't think that's counterintuitive at all to selling,
but it certainly is in sort of the traditional pharma approach.
How is first contact made? Is it walk in the door,
like brush the feet on the carpet? Hi, I'm here to see Dr.
So-and-so. Or is it an email? What does the first contact look like with a prospect? Who is the
prospect? And what's the right approach? What's the right pitch?
Prospect is the, you know, hit the front line of the office and you're actually dealing right now
with the receptionist
that you need to talk to to get back to see the physician, the nurse, et cetera. So you're going
through all of those different steps to get to them. Our group was helping in an office procedure.
I think they were highly valued for what they could do in the office. They walked in in scrubs.
It was different. They sort of walked right to the back of the room. So I think that it was them knowing that they're bringing something of value. I think in sales,
you can feel like the one that is the pain in the ass that people are saying, you go,
all right, you're just taking time in my day. And I think that they had enough confidence in
what they were bringing that they didn't accept that. Right. It wasn't death of a salesman. It wasn't. Yeah, exactly. And we had, you know, with that product, we had this incredible
opportunity. So what happens today? You get a drug, you go get it filled at a pharmacy. Like
you have no, you probably have no idea who the drug manufacturer is with that product because
it was done in office. We had this incredible opportunity to own that relationship with the
physician. So I looked
around and I'm like, okay, who in pharma does well with customer service? Oh, nobody. Okay. So what
are we going to do? And I took my entire leadership team to Zappos and we learned from them because we
were constantly looking outside of our industry for who is doing it great. And so here's a story.
Our most important guy, sort of the top researcher in the country, is from Harvard. And he did a lot of the
early days testosterone research. He did that research on lizards. When he would buy our product,
we'd put a plastic lizard in his box. Wouldn't say anything, just drop one in his box. You know,
we're trying to see what would happen. I went to visit him several months later. I walk in,
can't get more ivory tower. I'm in Harvard. He's got like this beautiful mahogany bookcase. Second shelf, all of our lizards. It made a difference. It was that quirky. So I think
our salespeople were always, they too, just like we listened to each other for what our stories
were. They really listened closely and celebrated that in the customer. Not what you think from a
pharma company, huh? No, it's not. I mean,
what other companies did you borrow from or look at? Wow. Big and small. I mean, I think that,
you know, all of the people who worked for me were students of great businesses.
They became sort of, they mimicked that behavior that my business professor probably taught me.
At one time we went to Seattle. Love Seattle.
I used to live there.
Went to the Pike Place Market, spent an hour,
just went out and learned from those businesses.
I mean, we were learning from Beecher's, you know, the cheese shop.
What do they do exceptionally well?
How do they invite people into the experience?
So I can't say Zappos was probably our most formal,
go together, learn from them,
but constantly like reading or picking those businesses that we loved.
That was a constant conversation at the lunch table.
If you were, this could be, let's just say, freshman year of high school, freshman year
of college, teaching an entrepreneurship class.
Yeah.
But the only way you could teach it is by recommending books and exercises or practices.
Are there any particular books that come to mind that you would insist they read or any particular
practices or exercises that you would have people do? I would insist that they read Purple Cow.
Purple Cow. think it's one size fits all. That would be my, uh, my ask. And I think that I would tell every
entrepreneur go sell something. If they've never sold anything, they better go, go learn from
somebody else, go be in their sales organization and then take it back to your company.
Mm-hmm. Uh, so there's a fellow Austinite here named Noah Kagan, who recommends, uh, one of,
one of his exercises that he suggests to everybody is the, what
does he call it?
The coffee challenge.
And the coffee challenge is just getting more comfortable with discomfort for the next,
say, week.
Every day you have to go into a coffee shop, doesn't matter if it's Starbucks, doesn't
matter if it's mom and pop, and asking for 10% off your coffee when you get to the checkout.
And he's the first one to say like the outcome does not matter.
Yeah.
You just have to ask.
Okay.
And you can't say you're doing an experiment.
You can't make them more comfortable with it.
You just have to ask for a discount.
Thank you, Noah.
I'm going to be applying that now.
It's really valuable.
And I was, I was, I was trading texts with a friend of mine uh younger guy who is uh
developing his own product and he's working on the product and startup but it's not at a point
where he's interacted with any customers yet and i mentioned this to him and he's like oh yeah well
it's like i don't need that because i make myself uncomfortable in all these following ways and i
was like well why don't you just do it? Send me a photograph of the receipt, whether you get a discount or not. And he's young enough that we have
somewhat of a mentor-mentee relationship. And he's like, that's ridiculous. I don't need to
do that. And I was like, well, prove it to me. If you don't need to do it, you're going to get
coffee or tea or water. It doesn't matter. Buy something. Ask for it. And he's like, okay,
fine. I'll do it just to make you happy. And he sends me a text a few days later. He's like, Oh my God. Like I had to walk around the block,
like psyching myself up to do this.
My palms are sweating and I got 10% off.
He's like,
but it was so much harder.
I brought up all of these emotions I didn't expect to come up.
And it's like,
that's right.
That's why you think it's going to be easy.
Let's confirm.
Love it.
Uh,
this segues nicely to what I promised I would come back to, which is boldness.
So what are some events or inflection points for you maybe?
It doesn't have to be, but any stories of you choosing boldness?
Well, I'll tell you probably my boldest choice was when I made a decision to dispute the FDA.
And I was on this course, you know, it's pretty straightforward. You have a pre-specified endpoints. You go out and
do the studies. You meet them with statistical significance. You get to an approval provided
there are no showstoppers. And so I had gone out, I'd gotten this drug from the company that first
developed it. I'd sat down with the FDA. What do I need to do? We'd agreed. I'd gone out, I'd gotten this drug from the company that first developed it.
I'd sat down with the FDA.
What do I need to do?
We'd agreed.
I'd gone out, I'd done the work, I'd gotten the outcomes.
We got rejected.
What was the drug?
This was Addi, which is-
A-D-D-Y-I.
So at that moment, it was crippling for my business.
We had done the work.
We had done all the right things scientifically, and yet we got to a no.
And I was faced with turning back to shareholders and saying,
this is going to be this many million more dollars.
At that time, I was lucky.
A woman reached out to me.
And people knew we were on this journey.
And just for context for people listening, this is your second company.
It is, yeah.
Sprout Pharmaceuticals.
Thought of or dubbed by the media, the product at least, as female Viagra.
Correct.
Just for people who are trying to keep track.
Okay, please continue.
So people knew that we were going down this path.
And I think that it was so fortuitous that she reached out to me at this moment and said,
don't give up.
I was on the drug in the research trials.
I want to share my story with you. She lived outside of D.C. I was on the drug and in the research trials. I want to share my story with
you. She lived outside of DC. I was in DC all the time. I went to have a coffee with her.
She walked into the room and you know, this woman was in charge, type a recognized it right away.
Um, you know, she walked over, she had her own business. She'd raised two beautiful boys.
She had what looked like the perfect marriage by all our normal standards.
She said, I have succeeded in every aspect of my life other than this. I'm waiting every day for
my husband to ask me for a divorce. And I'm looking at this woman and I thought-
Because of their sex life or lack thereof.
Yeah. She had no interest. So she had been diagnosed with this condition.
What is the condition?
It's called hypoactive sexual desire disorder. HSTD is the moniker.
Same prevalence as ED has for men.
So ED is the most common male sexual dysfunction.
HSTD is women's most common.
And it's a lack of interest in having sex.
Is it now physiologically, how does that manifest?
So in order to respond to sexual stimuli, you need the right balance of key chemicals in the brain.
Your excitement factors and your inhibition factors need to come into play.
For some subset of women, they go out of whack.
They become imbalanced.
That's how ADDIE works.
It works on the restoration of those key chemicals.
And we know it from these brain scan studies.
So a woman who has this condition versus a woman with the normal ebb and flow of desire, um, for sex, put them in a, an MRI, show them a sexual cues, their brains light up actually
totally differently. What are the, what are the, uh, chemicals, uh, dopamine and serotonin. So
our excitatory factors and we, it has a transient negative effect on serotonin, which is an inhibitor
for your sexual response. Say that one more time. Serotonin.
So dopamine is positive, excitement for sex.
Serotonin is inhibition.
And the drug worked by this transient negative effect.
So a negative effect on a negative for sex equal to pro-sexual effect.
Got it.
Yeah.
So I'm just trying to think.
Okay.
So it would be, got it.
But it was not, now we're not talking,
so serotonin has an inhibitory effect.
Yeah, mm-hmm.
Which is why, what do we know of the antidepressants?
Their most common side effect is actually killing your sex drive.
Right.
So interestingly, as drugs are often discovered,
this drug was looked at for its effect on depression.
And what you do when you're testing those drugs is you actually have to administer a scale to see how much am I killing their sex
drive? Well, in this particular drug's case, it all went the other direction. It had a prosexual
effect. So at that time, all of the study changed to look at this condition specifically.
Curiously, quite similar. I don't know if this is due to the tracking. I mean,
there's some maybe folklore in this Genesis story, Viagra. Yeah. Same story. Yeah,
absolutely. Blood pressure medication, lo and behold, a really very interesting side effect.
Yeah. I mean, so the, so the, the folklore goes, I don't know if it's true, but that the male
subject would not give the medication back. Right. They're like, Hey, this doesn't work
for blood pressure. Hey, give us our supplies back. And they're like, no, we want to keep them.
It's like, wait, what? So very interestingly,
when I got to Addy, I
built this great company for men.
I was in this community. And the company
that innovated this drug originally
was going to put it on the shelf.
They were going to walk away from it. And one of the great
researchers in the field went out
to women who were in the trials
and said like,
I need you to come in and bring your medication with you.
We're going to have just a normal meeting.
And he was actually delivering the news that they were killing it,
that they were killing the development trial.
And he filmed it.
And the women were like this,
giving their drug back,
handshaking,
crying.
And he said,
you need to do something about this.
Why,
why were they two questions?
So why were they going to shelf it?
And when you say got the drug, right?
So there's a good deal, a good amount of discussion and deal making,
I imagine that goes into that.
How does one get a drug?
Like what is the, if you don't mind discussing,
what does a typical deal structure look like for something like that?
Oh, mine was very atypical.
Oh, well then let's talk about both typical and atypical. Okay, happy. So first,
let me tell you just about how did we get the drug?
Lucky for me, I think I'd build a reputation in this field
that the key researchers in it knew that
I cared deeply about women having access to medicine. At the time,
there were 26 FDA-approved
drugs for some form of male sexual dysfunction and not a single one for women. And you asked
why that company would put it on the shelf. It was very clear to me that it wasn't on the basis
of science. Actually, the scientific understanding is spectacular. We've come a long way recently in
terms of this understanding. It was on the basis of the societal narrative.
Boy, if you say women and sex, people have an opinion. It's not like developing a diabetes medication. Unless you're diabetic, you probably don't care. Develop something for sex, we all
have a point of view. And I think that it was a conservative company. They said, we're not getting
into this. We're not going to get into this entire discussion. Okay. So was it a larger company developing multiple drugs?
Large German. I like to tease. I said, it's sex for German. We're out.
That helps actually promote the understanding, but you have to appreciate like cultures inside
of companies, certain, you know, categories that they're in. This would have been paving a new
frontier for them. How did you find this?
So it was, I was watching all of this research being presented at the scientific meetings I went to,
at these sexual medicine society meetings, and really just cheering it on from the sidelines
as a woman, like, finally, we're going to have one for women. And then they walked away. And I
watched a clinical community go from all of this excitement to this true sadness in delivering this message to women.
So I spent a year just listening to women.
After I did that, I sold off my company for men and took this on.
But when I did that, I went to this company,
and I think it was with thanks to the fact that the clinical community,
the experts in the field were so supportive of me that they gave me the shot.
So they gave me the drug.
I didn't pay for it up front.
They won.
I win, they win.
So they had a royalty in the case that I finally got it to market
and in a success scenario.
But it was a bold move for them.
They'd never done a deal like this before.
And I think they bet on me.
How did you convince them?
I don't know that I convinced them as much as those who had watched me build Slate
and saw who I was and what I really cared about.
And, you know, I really cared about women having access to this.
Women with a medical condition deserved access to a medical treatment.
Not any of our value judgments on whether or not they needed it
or the worthiness of treatment, but just purely the science had spoken and we needed to listen.
And I think they knew that that was my definition of success.
I wasn't in this to create the next blockbuster drug.
I was in it to make sure that women have access.
And then they got to choose for themselves.
Did you first deliver that message via email, in person?
In person.
In person.
Yeah, in person.
How did you get them in person for it?
Again, thankfully, this kind of a key researcher reached out to them and said,
you need to meet with her.
I think she can get this done.
And he wanted me to get it done, I think, for women.
He was, by the way, the principal investigator
on the Viagra trials. So he got Viagra approved for men. And I tease, he would have to tell
this story. But in my mind, the story goes, he did that and he was like, okay, fix guys.
Moving on to women. And he's actually spent almost all of his years since then just working
on women.
No kidding.
Yeah, and researching.
What's his name?
Dr. Erwin Goldstein.
Erwin Goldstein. Good for Dr. Goldstein.
I know.
If you don't mind me asking, and we can't get into the particulars, it's fine, but I'm just so fascinated by this stuff.
So in publishing, for instance, books, my world, typical royalties would range from, say, 12% to 15% for hardcover.
Keeping in mind, we're talking about books, right?
So the margins are very different, I'm sure. But then there are fairly typical advance ranges for certain types of books,
advance on royalties, and then there are fairly typical royalty rates. I mean,
there's very little deviation in the traditional deals, which are still very,
very common and certainly predominant. What does that look like in pharma,
broadly speaking? We don't have to talk about your deals necessarily,
but you know,
it's in pharma.
Typically,
if you had this type of discovery,
you would go out and shop it.
If you,
as an organization decided not a fit,
not a fit in our,
you know,
key areas of focus or whatever,
you'd put it out there to auction.
People would bid,
they would be,
you know,
buying it on the basis of sort of a projected,
uh, you know, a projected ultimate peak sales. And so ours was so different. I don't think the royalties look all too different
than as you described, but it was really a very unusual deal.
Usually you're buying it for a hefty upfront that is anticipating peak sales.
Got it. And is that an advance on royalties, just like books? I mean, where you're getting sort of prepaid
for the anticipated sales?
That's making a big bet.
Like, that's somebody coming in and betting
on that future for it.
So, you know, I buy it, you go away,
it's mine now to further the development.
So we had an interesting,
I can't say it was a partnership,
they just ultimately got a check if I was successful. And maybe I even surprised them.
So how did you get it through the FDA?
Well, I'm telling you, I was talking about that moment of boldness of the rejection.
Yeah.
And that decision to fight them. And I was fighting them because I had 11,000 women worth
of data. That's why I was fighting them. Because I knew that the science had spoken.
It's also a large sample size compared to, I'm sure,
a lot of the other 26.
Extraordinary. So we're talking
in the 700 to 800 patient range
vis-a-vis ours. I mean, Viagra were big trials,
4,000. But we were
several factors
higher than that. And
a very different path. So I think ultimately,
look, ultimately I went
on the science, but what had to happen is we had to listen to women. And I think in categories where
we have, we have natural bias, unconscious bias, we'll call it unconscious, conscious, unconscious
bias. You really do have to spend time with the people who are affected by it. So even if you look at things like AIDS, it took the patient voice for us to really appreciate what needed to happen.
Our job as a drug company is to characterize the benefits and the risks with great rigor in trials.
Ultimately, the FDA's job is to protect patient safety if there's a showstopper in there,
but otherwise, it is to turn that decision over to patients and the providers.
And because of, again, I think all of that feelings we have about sex,
I was told all the time, I said this earlier,
Cindy, why are you such a crusader in this?
Nobody's going to lose their life from this.
And what I said is, go spend time with these women.
They're losing their life as they know it.
It's breaking up their marriages.
It's affecting how they feel about themselves. Our sex is a lot of how we show up in the world, our moxie. And if it breaks down in the bedroom, it is breaking down over the
breakfast table. Yeah, absolutely. And I might be butchering this, but I've read you quoted as saying something along the lines of,
you know, in sexual dysfunction in males, we assume it's biological and in sexual dysfunction
in women, we assume it's psychological or not we, but most people, you certainly don't,
but many people, society does.
For sure. We absolutely do. We sort of pat them on the shoulder. When I sat with this woman
outside of DC and she told me that she'd
succeeded in every aspect of her life other than this, I saw the portrait of a woman who turned
on herself like, oh, if only I bought sexier lingerie, if only I read 50 Shades of Grey.
And when I saw that, I said to her, hey, mind if I show you something? Popped open my MacBook,
I started showing her geeking out, showing these brain scans. And I turned to her and she's crying.
And I thought, this is why I'm going to do it.
It's the validation that this is real.
It's not just in her head.
And that really was a defining moment for when I said,
I'm going to fight the FDA.
So tactically speaking, so now you have the motivation.
Yeah.
How do you do it?
What do you do? It is actually a path available to,
um, drug manufacturers. I like to call it the road, less traveled to take them on. Um, but it
was a path in which to their credit, what happened was a lot of public conversation. So they opened
their doors, they invited in women who have the condition, they asked them a number of questions
so that they could have a better understanding, I think, for impact, for how they would define success. And then ultimately,
they asked us to do additional work along the way, and they assembled a body of scientific
experts to vote. Yes or no? It's an incredible process. So talk about the nerves in the room.
I went in this day. It was a panel of 24. Is there a name for this alternative path?
It's called, so it's a dispute resolution path. I see. And then there's
something called an advisory committee, which is the FDA can go out, assemble
experts. You almost go on trial. They get to read all of your data. They get to ask
you the company questions. They get to ask the FDA questions. And then the public actually gets
to speak at the microphone. And on that day, by a press of a button,
they vote. Would they approve it or not, based on microphone. And on that day, by a press of a button, they vote. Would they approve
it or not based on everything? And so I can remember looking at the screen and my hand
shaking with my phone and they overwhelmingly voted to approve it. Again, science won.
It had always given us the answer, but we just had to listen to women to, I think,
listen to what the data was telling us. What were their objections with the initial rocky territory that you then had to overcome
via the dispute resolution?
You don't have to get into it.
I'm just curious.
No, I think it was just additional study, additional study.
We are very protective of women in the process.
I think what we have to be careful of is that we don't become
paternalistic in terms of being so protective of women that we are not allowing them to have
choice. And here's why I say it. 26 times we had looked at data sets for men that had benefits and
risks. Make no mistake, all drugs have benefits and risks. And we had said,
okay. And we turned over the decision to the guy and his provider.
We were being protective to the point of not just characterizing those benefits and those risks,
giving women that information, letting them make the decision for themselves.
So part of the reason that I'm asking, we definitely don't need to get into this right now, because even though it's called the Tim Ferriss Show,
it's not me being interviewed, so I'll try not to be long-winded.
But part of the reason I'm so fascinated by this
is that I'm in the process of doing my best
to help get both MDMA and psilocybin through facelift trials.
Oh, yeah.
So very much top of mind for me.
Yeah.
And fortunately, MDMA was recently designated, uh, or received
breakthrough therapy designation, which is fantastic. And the results with PTSD are truly
astonishing. I mean, the magnitude of effect is, is just so incredible. It's like sort of 22%
efficacy psychotherapy alone, 72% efficacy. And of course you have to look at how that's measured,
but with the aid of just a handful of sessions to look at how that's measured, but with
the aid of just a handful of sessions in any case, that's why part of the reason why I'm digging so
much. It's very much of great interest. Uh, okay. Where to go next? Uh, so you've sold two companies,
right? At least two to an entrepreneur who is someday thinking of selling a company,
uh,
or in the midst of maybe,
uh,
on the cusp of about trying to sell a company.
Yeah.
What advice would you give them?
Oh,
okay.
Um,
the first is,
uh,
be prepared that if you sell it,
it is both exhilarating and excruciating.
I think you don't anticipate that.
You know, it's the, isn't there the billion-dollar happy ending?
And I think you lose a big piece of who you are in that moment,
and that's something you're going to have to wrestle with.
So that's in a success scenario.
But as you prepare for it, I think only do it if you believe it makes good
on the mission that you hold dear.
Like, have a real sense sense of this is my baby, but in the hands of an adoptive parent,
it's going to go to the next level.
And when you do that deal, make sure you have safeguards
that they really will raise that child you want them to.
So I'll tell you a lesson learned from me.
I sold my first company.
And typically when you sell a company, it's a structured transaction.
You get an upfront payment, and then hopefully you participate in the success down the
road. And certainly that's good for your shareholders. And in the first time I sold,
it was a best efforts clause. Best efforts can hide a multitude of sins.
Yeah, describe a best efforts clause, because this is really important.
So everybody should listen very, very closely.
Well, look, if you're going to participate together downstream, you don't want somebody to just say, hey, I'm going to make my best effort to have this work. You better have some
definition around that. I did that the first time and I had pain when they were deprioritizing it,
when they didn't have enough salespeople on the product. And so lesson learned when I went into selling Sprout, I had real rigor around the definition
of performance obligations.
You will have this many salespeople.
You will spend this much money on marketing.
You will make this commitment in terms of disease state education.
And what that ultimately meant for me is the opportunity when they didn't do it to get
the product back.
Okay. Well, we'll definitely get to that. And this, this best efforts is really important.
I want to just emphasize it. Don't, I mean, it's, it's certainly been said that, you know,
the man or woman who acts as their own lawyer has an idiot for a client. So unless you're
trained as a lawyer, get proper legal advice, please. But on that point, don't worry as much about the bank.
People are always saying, well, who did you use?
What does the bank?
Worry about your transaction attorneys because of how you write these contracts.
In any structured transaction, they are your most important asset.
Absolutely.
And this is important in so many different types of contracts.
Whether, for instance, I've run into this quite a lot in many of my contracts, right?
Publishing, television.
If you are a product developer or inventor and you want to license something for a royalty,
well, you only get a percentage of what is sold.
And what happens if they decide it's just not a priority absolutely do you have an out how scary is it to think that somebody might take it on and kill it yeah totally i mean competitors wanting to sort of own the market like often you're bought
by somebody who has products in the category what if they're just buying you and they're
going to kill your product yeah absolutely yeah yeah or doing a fishing expedition to determine how they can kill you or steal your employees.
It's super common.
So you talked about the second company.
What are some other pieces of advice for people thinking of selling a company
or in the process of selling a company?
Well, I was selling it early.
So from that point, at least in my case, it was actually
having the full plan to go it alone. I couldn't go out and just couldn't count on, hey, this really
needs to be in the hand of somebody who can march it across the globe. I needed the plan of going it
alone if they never showed up. What do you mean by that? Meaning, so I had the whole plan to launch
it myself, the ability to hire. I was capitalized to do all of those things,
like never go into a negotiation running out of money in the bank
because you think you're going to sell this grand idea
that could be realized in the hands of somebody bigger than you.
I think that's a huge mistake.
I watch a lot of people do that, thinking they're going to sell it then.
And in fact, if you want to command the highest price,
you better have that ability to say, Bye, I'm doing it myself. See ya. I if you want to command the highest price, you better have that ability to say,
bye, I'm doing it myself.
See ya.
I know you want it.
I'm going to do it myself.
I mean, and I think people sometimes mess that piece up.
Yeah, for sure.
They go in on skids.
Yeah.
I mean, if you don't have alternatives, it does not matter how great a wordsmith you are with your negotiating.
If the other side knows that you are shit out of luck, you are fucked.
I mean, look, could you pull some Jedi mind trick?
Yeah, maybe.
But remember, I was given advice a long time ago because I've just negotiated so many different types of deals.
I'll come back to why that doesn't actually conflict with the lawyer advice that I just gave.
But the piece of advice that comes to mind that I was given at one point was an expert,
like master negotiator, done a lot of business development and bought and sold mean, just dozens and dozens of times. And he said to me,
he who cares the least wins.
Yep.
Absolutely.
And it's like the person who has like,
eh,
take it or leave it.
Absolutely.
That's true.
And,
um,
I think,
you know,
also some,
uh,
some advice that I remember in the fundraising world,
which is slightly different,
but,
and we'll actually talk about fundraising too.
It was,
you know,
if you want money,
ask for advice. If you want advice, ask for money. Uh, so they're all these,
but they're actually accurate. The reason I said just for people listening that the
negotiating deals does not conflict with the get a good lawyer is that, and I'd love to hear your
thoughts on this, but lawyers are really, really, really, really, really critically important. I work with a ton of lawyers for a ton of different things.
However, you have to recognize, like really study the, and certainly cheaper to spec out the basic terms of engagement. And maybe along the lines, it doesn't have to be a
letter of intent, but to have the basic, at least range of what numbers could look like
so that you can disqualify a deal before you pay lawyers to put 20 hours in at $1,500 an hour.
I totally agree with that.
So the second company, all right, so Sprout.
Yeah.
Hoorah, hoorah, you get the FDA approval.
Yes.
Well, before I get to my real question, I'll give another question, which I guess is just small.
What did you guys do to celebrate?
Did you do anything to celebrate?
And how did you feel?
Button, button, button, button, holy shit.
How did you feel?
In that moment, when you first realized what had happened, how did you feel?
So I have to tell you, it wasn't at the moment of sale.
It's at the moment when we won that advisory committee.
And what we did was, my team had, they were blood, sweat, and tears,
true to the cause.
They'd prepared so hard for this day.
I actually threw a victory party the night before.
And I can remember the chairman of my board came up and said,
wow, Cindy.
Hold on a second.
The night before you got the news on the advisory committee?
Oh, yeah.
Because I thought.
Because you were waiting, you were like, all right,
we're going to get the results tomorrow.
Yes. And I thought, win or, you were waiting, you were like, all right, we're going to get the results tomorrow. Yes. And I thought win or lose, we will have
given this all like we will have taken it to the mat and I needed the team to go in with that.
They had won, they had won the night before, before we ever got to the outcome. And I can
remember the chairman, I board came over and he said, he's a Brit like Cindy. Like, I'm not sure
I've ever seen this before, but I'm questioning this one right now, but I a Brit, like, Cindy. I'm not sure I've ever seen this before. I'm
questioning this one right now, but I'm going to go with it. And I think that was really important.
We celebrated the victory of having gotten it to there and really having cared. When we sold
the company, I think that was the whirlwind of, there's a lot of emotion with it. I woke up the
next day, I'm the same person. Nothing's different. I still got to go to work. I still got to get it done.
I think people think there's some kind of remarkable transformation from one day to the next.
And I think it's actually often a little bit of sadness.
Oh, yeah.
Yeah, I mean, having spent time with a lot of people who just have more money than they could ever spend,
or even in some cases give away before they die,
it rarely fixes as many things as you would hope it to. No question.
The day of the approval, I will say, we waited.
So what we knew is that the day we won at the adcom
just informs the FDA decision.
So it wasn't the day that we got the approval.
So they take their information in, they get to go back, deliberate,
and ultimately the FDA comes forward with their decision.
And you wait.
They actually send it to you late in the day.
So I flew the entire company was in.
We were all standing around, pink balloons everywhere, waiting for a victory.
And what was actually so sweet about this is that all the other companies on the same floor,
we were on the 10th floor of a building.
He used to say we could almost entirely fit in an elevator and we were going to change the conversation about women and sex forever.
They waited too.
They stayed.
And I can remember them showing up and it was 7 o'clock at night and they're like,
oh my God, how are you guys doing?
Is it okay?
Are you not going to get the approval?
And so that was fun that so many people, I was so lucky that as small as we were, we
had this extraordinary
group cheering us on. We had this incredible bench. So as, as the fearless later. Yeah.
So you didn't know what the verdict was going to be. I mean, you had high hopes, but what,
did you have anything prepared? What were you going to do if it came back a no?
Celebrate that we did it all. Okay. What were you going to do if it came back a no? Celebrate that we did it all.
Okay.
What were you going to say to the troops?
Or if you had to imagine, if you can't remember, what you would have said.
Did you even think about it, really?
I mean, what would you have said?
I didn't imagine a scenario in which we wouldn't win.
And the reason is that I really thought that at the end of the day,
we all had the capacity to get out of our own way,
get beyond our own bias, and look at the data. And I think that in particular, look, I think that
part of the characteristic of female leaders that I love is a certain empathy. And I felt like
that data informed through a lens of empathy, of having walked a mile in the shoes of these women. And now we having all, we have all listened to them. I just, I believed we would get there.
I really did. Um, so I don't know what, what I would have said to the team had we lost is I would
have said, you know, I'm, I'm proud of you. I'm proud of you for putting it all in and for carrying
that deeply to see it all the way through. Cause it was grueling work and long hours and a lot of punches in the
face on the way to get there. Welcome to entrepreneurship.
Exactly. That's right.
Oh, you're going to conquer the world, huh?
Yeah.
Okay.
I will tell you, I have to go back to-
Do you have a mouth guard? Good, because you're going to need that.
All right. I'm going back to your story for the people thinking about selling. I think there is
be a little bit reluctant to give it up. It's your point about who, like, you know, he who cares, he or she who cares the least in the room.
When we went into our first negotiation with the company that ultimately bought it,
we went into the room, they made an offer. They said, we're going to walk out of the room.
Wait, I'm sorry, say this one more time.
So the company that was offering to purchase us, we went to this room.
This is the second company.
This is for Sprout, yes.
For Sprout, yeah.
So we go into the room.
A company has come courting.
They want to buy us.
And they throw an offer down.
And they said, we're going to let you guys think about that and leave the room.
One of the things I had done is I had prepared binders of all of our data, of all of our research. And it was huge. We brought them into the room and set them down
for effect. And they left the room and I looked around at my team and I said, okay, when they
walk back in, within five minutes, we're going to all be out of our chairs and we're going to
walk out of the room. They were like, what? So they come back in the room and I said,
thank you so much. We're very flattered by that offer.
We're going to do it on our own.
And as we got up, a woman who worked for me, she had all these binders sitting next to her.
And she's looking at me like, should I take the binders?
I'm like, leave them, leave them, leave them.
And so we walk out of the room.
And sure enough, I knew that they would call me back to get those binders.
So they had a reason to reengage, which was, of course, the, you know, hey, Cindy, we have those binders. So they had a reason to re-engage, which was, of course, the, you know,
hey, Cindy, we have these binders. I said, no, no, those are for you. You can keep them.
But they called back a little while later and said, hey, we still have those binders. We have
to give back. So the conversation continued. I mean, that's negotiation, right? But it was a
fun story. That's so, for people listening who listening who are like oh that's one in a million no
this shit works
and
I mean it's
yeah so a couple
of thoughts for people listening
okay number one
is
so there is a book called Getting DS Harvard Negotiation
Project etc I think Getting Past
No which is another book written by one of the original co-authors,
is actually a little more realistic.
But they talk about the BATNA, the best alternative to negotiated agreement.
You really need to think this through.
Negotiation rewards those who come in prepared.
And I remember at one point, I learned so much.
I mentioned I lived in China for a while and it was in China where I really learned
the flinch, right?
So the, and realized, wow, like you can actually improve so many deals just by letting someone
negotiate against themselves.
It's not like you're making a counter offer.
And it's like, if you try to buy anything at the time, I guess it was, uh, I think it was just called silk alley
in Beijing where you could buy, you know, like counterfeit Jordan shoes and all this stuff.
Right. And it, they would always start off like 10 X with any rational person who they've lived
in China. And then you would counter and they go, ah, ah, like you've just, you know, offended their dog or something.
I mean, they like the emotion that come pouring out is so exaggerated.
And you would see these foreign exchange students immediately capitulate or
reverse me.
Oh no, I'm so sorry.
Like I don't mean to offend you.
And then they'd walk off and you just see these people laughing.
And so it's like the, you know, kind of the flinch or silence, letting the silence do the work.
And the one that I encourage people to use, and look, read the room, know the person across the table.
But it's just before you counter with anything, if you're not going to use silence, just saying something like, is this the best offer you guys can make?
You know, is this the best you guys can do?
And don't be condescending about it, but just be like, okay, just so I'm clear, is this
the best you guys can offer?
Yeah, sure.
And I would say, depending on who you're dealing with, but the vast majority of the time, if
it's not someone who's paid to negotiate, you're going to get something.
But you have to be comfortable sitting in that silence. So once approved, so my homework says it could be inaccurate, three competing offers?
Yes.
Is that right?
Okay.
Were those forthcoming?
Were they inbound or did you?
They were inbound.
Okay, they were.
They were inbound. Okay. They were, they were. And so to walk me through then,
how you in a competition slash auction environment, how do you make the most of that?
Well, for me, I think the winner emerged, um, not on the basis of the price, but on the basis
of willingness to keep my team. That's funny. That was actually, uh, and that had been important to
me when I sold my previous company. So in both of my companies, it was really important what happened to the people
who came to work for me. So that became one of the differentiators for me in the room. But no
question when people know that others are interested, right? You do want that competitiveness
because definitely it drives up the price and everything else. But that's how I reached my
final decision. What were some of the most important terms?
For me, it was that we were going to go to the distance together,
that it was still going to be realized, I think, on our terms,
and that there was a real commitment to making it broadly, affordably accessible to women,
that they were going to march it across the globe,
because I can pull this data, this incidence data, out of the U.S., out of Brazil,
out of the U.K., wherever it may be.
It's the same for women worldwide.
So that and that factor of what became so attractive to me
in this one company that came forward who bought us was Valiant.
Sure.
So when Valiant bought us, it was that they did this deliberately.
So they had acquired a lot.
They were highly acquisitive.
They were a company with a lot of McKinsey folks
and maybe fewer traditional operators.
And their greatest criticism at that time, it has changed,
but at that time was really no organic growth.
And so I think they saw this product that had a lot of interest
and an ability to prove it,
to prove it from scratch
that they could grow it inside.
And they saw in me an operator
who'd been there, done that.
And so that deal structure was such
that here I could go out, run.
I had all of their resources,
the ability to do it at a much bigger scale
than I could have on my own. And I got to keep the team who cared so deeply that they got it to the finish
line of approval. And you had deliverables and measurables instead of best efforts.
Absolutely. We'll do our best. Handshake.
It was absolutely how many salespeople are going to have.
Thanks for that handshake, but my mama told me get it in right.
That's right. Exactly. And pretty. And it wasn't extraordinary.
These weren't extraordinary.
They were sort of market standard for what is brand new category drug launch 101.
So there were reasonable expectations.
So let's fast forward.
Maybe we could spend a lot of time on any segment of your story.
This is just so amazing.
And I've seen this is not as as it's, it's rare,
but it does happen. Like this kind of thing does happen.
And it's happened to a few of my friends in tech actually have had the
opportunity to take,
then take back their company or product or whatever it is that they've sold.
So what the hell happened?
Well, what happened is,
first of all, so if,, so if you're comfortable,
I mean, I think it's public at this point.
So how much did Sprout sell for?
A billion dollars up front.
A billion dollars.
And we had a pretty impressive kind of structured transaction on the back end.
Like earn out slash royalty thing, right?
And so Trace Comus for you Silicon Valley fans.
And then what unfolds? I mean, I couldn't have written it for a movie.
I really couldn't have. So we got the drug approved in August. Everybody had come courting
after that advisory committee meeting. We announced our intention to sell, and then it
takes time for a deal to close. So in that interim time, I'm just running. I'm building a sales force. I'm getting ready for launch. And the deal is coming to full closure. 11 days into our deal closing,
the world basically went sideways for Valiant. And if you follow pharma, you certainly know they
were at about 260 a share the day they bought us. They've traded as low as eight in the last two
years. And it was just- For those people who don't know, why did that happen?
Accusation around drug pricing issues
and also a nondisclosure of a pharmacy relationship
that they had that they hadn't disclosed.
So it really just went kaboom.
And it was so sad for me for all of these salespeople
who'd come to work for me.
I mean, they weren't in the field a week before this happened. And me being who I am, here's my baby. We've just gone
out. The world is sort of collapsing higher up. I'm not getting information and I'm screaming
quite wildly. And I think that just didn't fit for them at that moment. They had enough
distraction. They did not need Cindy Whitehead screaming as well. Hey lady, we have enough
stress. So I was invited to leave. I actually, they called me and they said, it's clear you no
longer want to be here, to which I'm pretty sure my answer was like hell. And they said, well,
as it turns out, you are no longer going to be here. And so, um, you know, and I have to tell you at that moment
for me, like a founder, sometimes you have to go, you know what? Like I'm the founder and maybe
there will be a personality conflict. This is their, you know, they've taken my baby,
they've paid good money. Um, and so in an effort, I think to sort of check myself,
I thought I need to step to the sidelines and cheer everybody on.
And I need to be positive about this and optimistic that maybe with me removed, it will be championed inside of the organization.
And certainly I wanted to protect all of my people who were still there.
I think if I have one regret, it's that I didn't speak up then because what happened after I was gone is that they surely, I can't even say slowly, but surely pretty rapidly dismantled my whole organization and then everybody was gone.
Now there's more to the story. of those important performance obligations, I had an opportunity when they weren't meeting
those to go back and open a different discussion with them that ultimately became the basis
of a lawsuit.
And in this time, they changed CEOs.
We've had a really positive.
It became clear to me this was not going to be an area of focus.
Again, remember, they had bought it very intentionally,
but it was an outlier. It was different than what they had normally done. And they didn't quite have
the infrastructure inside to put that focus into it. And so I think what was started off as a
lawsuit to be able to get through the noise of everything they were going through ultimately
became a discussion in what's the win-win here? Nobody's winning. We're not winning.
You're not winning.
Women aren't winning.
And I think in exchange for dropping that lawsuit,
they decided to give me the drug back.
Okay, so a few things.
So in exchange for dropping the lawsuit,
they decided to give you the drug back.
So they did not charge you for the drug.
Correct.
They gave me a loan.
They gave you a $25 million loan to help you get started.
Yes, they did.
And did you and other people who had equity in your company when it sold have to give back the billion dollars?
We did not.
That's a good deal.
It's a good deal.
Yeah.
We're pretty happy with it.
But let me tell you, for my shareholders, I do think this speaks volumes to them.
We could have stayed the course.
We had a pretty explicit contract in terms of a lawsuit.
Not a single one of my – this had to be approved by my shareholders to do this transaction.
Not a single one of them voted against it.
Even though they could stare down...
Now, just to clarify, did it have to be,
you're saying by all of your shareholders
or majority or board of directors?
So it was, no, no, all of my shareholders voted.
It had to be by a majority,
but not a single one voted against it.
Not a single one.
And that speaks volumes, I think,
to who funded me, what they really cared about.
Because an easier path to money was probably just staying on the path that we were on with the lawsuit.
This is the path of getting it right.
And this is about it always having been about the women and really defining success the way we want to.
We had a great outcome for a company.
And now we have the ability, I think, to just do it in a different way in a way that we're all proud of. So what's,
I mean, I've, I've plenty of questions, but what's, what's next then for that particular
drug? Uh, what's next is one Oh one it's access that women have access to the product. It's
education that we remove some of the myth
and misconception, I think that surrounds quote female Viagra and the condition itself. Um, and
then I think it is marching across the globe. We have a lot of work in front of us. Okay. So you're
going to, you're, are you going to be at the helm? Absolutely. All right. Okay. So, so many, so many questions. And all right. So let's talk about rules for a second. All right. So there are, I think you've drawn this distinction. There are a lot of rules out there and there, there's some that you're generally better off following as they might.
The rules of law and order.
The rules of law and order.
Regulatory.
Yes.
Right.
And then there are unwritten rules or just socially reinforced rules.
So what are some of the rules that you have broken or routinely break as just a matter of personal best practices?
I embrace underestimation as an opportunity to surprise people.
And I think that I break rules in terms of it's frustrating to me when people say, yeah, but nobody does it that way.
And I'm saying, okay, nobody does it that way. Show me a
rule in which I cannot do it that way. And if they don't have an answer to that, be they a lawyer,
a consultant, whoever they may be, that's an unacceptable answer. I think they just haven't
dreamed up a new way to do something or a better way to do something. I think that for particularly
women in business, I think women are bound by many more unwritten rules.
And this TEDx talk I gave was about this, like what's the DNA of a female rule breaker?
Because I think that it takes this extraordinary sort of injustice and the empathy that surrounds
that for them to really break a rule. And that certainly is my story of fueled by the injustice, really informed by
listening. Why would I move forward with something that nobody else was willing to do? And I think
there's rules about, do you talk about money? I like to say in the Pinkubator, I want my goals
to make women really rich. That elicits a certain response. I do these pajama parties in the Pinkubator.
Eighth grade girls.
The Pinkubator, and we're going to come back to this,
but could you just give us a sentence or two on what that is?
Then we're going to come back to it.
Yeah, so as part of the Pink Ceiling,
I make early bets on Breakthrough First,
either by or for women,
and they all become part of my pinky baiter.
So got 10 different companies in there right now, all with a female lens.
Yeah.
How are you going to balance that with?
Having a great team.
Yeah.
Having a great team.
It's just, you know, it's certainly not all me.
I didn't get to here without having had the most incredible people surround me.
Many of them do today. I didn't get to here without having had the most incredible people surround me.
Many of them do today.
I mean, I'm with people who know all of my stories because they've been on the ride with me for 13 plus years through the startups.
And so it's always about the other people you surround yourself with.
So let's, I mean, so far we've talked about, not necessarily the highlight reel, but we've talked about a bunch of huge successes.
I'd love for you to talk about, so this is from a bit of my homework also.
So I read, and you correct me if this is wrong,
and I'd really love to dig in very briefly.
So for people who are listening,
this isn't going to be all startup finance for the next 30 minutes. So just sit tight. Uh, this,
this will apply more broadly. Um, but I read that one mistake that you'd made at one point
in your business was taking money from someone you either didn't know very well or didn't trust.
Um, can you talk about what you learned from that and to the extent that you can disclose
whatever you're comfortable disclosing and then how that informed later decisions or approaches.
My biggest fail. So really and truly early days of Slate, um, you know, was fortunate that
this drug was adopted by sort of the top tier and they were out at medical conferences talking
about it. And all of a sudden I'm getting phone calls in from other people like, Hey, I write testosterone. Why has nobody come by to see me?
So I, I really didn't have the capital to build a sales organization on my own.
So I went out with a company that would build a sales organization around it.
And, you know, did the deal, all the right intentions seemingly couldn't have departed
more,
more radically in terms of our philosophy on how you compensate people on how you treat people.
And so because you didn't have the money,
you paid them in equity.
I,
I,
so they,
yes,
they had a seat on my board.
Um,
they came into this company,
had this partnership with them.
And it was that inexperience.
I think in my first company of going, God, I need money.
God, I need this partner.
Like, I need this for scale.
And not being discriminating enough in terms of really who they were.
And so it was painful because we really didn't get along.
And it had the ability to cripple a company.
And at that moment that I could cut the deal, I had swallowed hard, hired as many
people as I could. Our eight people were outselling their 40. Cut the deal and-
Cut meaning ended.
Ended it and went off to the races. But it taught me the lesson of-
How long did it take you to cut the deal?
A year. I had a year agreement with them. And it, it took years off my life. Like it didn't feel like a year felt like a lot longer
than that, but it was a lesson of who I was going to raise money from going forward. So I had to buy
this is the perfect sort of segue to it. I had to buy out their position. I needed them the hell
off my board because they couldn't, they could have stayed on the board even with that deal gone.
So I had people coming in to try to buy it out.
And actually one guy came in, VC, and he came to our table.
One of the things I want to do is I spent time with them,
and then they came out to the glass table where we have our lunch together every day.
And he was hideous to one of my sales reps.
Just like the attitude, how he treated them.
And I thought, absolutely not.
Like, I'm not doing it.
I've seen how this movie turns out.
Let's not do that.
The next group came in.
It was a family office.
Also came, sat with my table, wanted them to be there.
They said nothing.
I was like, oh my God, I'm not going to get the money. we're going under. It was so important. I needed to get this group out.
And they called me back and they said, we're going to invest for what we saw at the table.
So they were the right person. And I now started to understand I have to have people
who care about who we are and our mission. So I raised actually almost all of my money through
basically angels or family offices.
Very unconventional in pharma.
How much funding?
$100 million.
All right, so $100 million through angels.
I'm guessing we're not talking like $25,000 checks.
Correct.
Okay.
Yeah.
So how many of these people did you know in advance
before raising the money?
Or it doesn't need to be an exact number.
Like roughly what percentage of the people you raised money from did you know beforehand?
Three.
Okay.
And how, roughly how many were there?
We were at a little over a hundred in the end.
So how the hell do you do that without it becoming your full-time job for six plus months?
It grew in, you know, It grew through word of mouth.
I was fortunate that they introduced me to a group
or they introduced me to a group.
So I had sort of pockets of investors
that I treated almost like they were units.
I have an incredible group of investors in Fort Worth, Texas.
I'd love to go visit them.
But it was so flattering, I think, that they helped me get there. I came from
no background where I had access to this kind of privilege, right? I didn't know these high
net worth individuals, but I was fortunate that once one of them came in, they introduced me to
others. And I don't know, you know, the joy, I actually was a great joy in communicating with
them. I didn't see it as a full-time job.
I actually saw it as this opportunity for an incredible network who today come in on a lot of my companies as well and invest in them.
How did you choose people?
How did you vet them?
Because I know companies with, let's just say in contrast, right?
You could certainly have, say, a VC, a venture capitalist, or somebody who comes in, writes
a huge check, and they say, all right, number one, I need 10, 20% of the company, and I
want at least one seat on the board.
That has its potential pitfalls.
I've also seen situations where startups that are super lean, right?
Yeah.
And a small company have a ton of people on their cap table.
Yeah.
So they're taking a ton of investors.
And all of a sudden, they're getting the hug of death, basically.
Because even if the investor is trying to be helpful, they're managing communications with 100 people.
So how did you think about avoiding that?
I mean, family offices are kind of a unique animal, but how did you, how did you think about avoiding that potential problem?
I actually think it, I was hyper communicative myself. I was like, I went on the, um, the offense
on that. I was, you know, they were part of this with me. Like they were part of the ride. I was
going to turn around to them and say, how are you going to help me? You can introduce me to
what am I, what am I not thinking of here?
I mean, these are very impressive people.
So I think I didn't wait for that to choke me.
If anything, they would tell you, like, I communicated a lot.
I expected a lot of them.
Because I felt like they were part of it.
They were owners in this.
And they had to perform not unlike the owners of my employees.
All right, so I promised we'd come back to the pinky better.
Yeah.
So what is the pink ceiling?
So the pink ceiling is investment firm meets hell of a great place for mentorship,
where we make bets on early-stage companies, buyer for women, mostly all health tech.
Um,
and not only I think disruptive first,
but often products that can be catalyst and social conversations we care about.
What would be some examples of products or companies?
So a company with a technology that detects state rape drugs and drinks,
how does it detect your color change?
So put your finger,
dip your finger in a drink, touch your finger to the decal,
changes colors if there's a date rape drug.
I mean, I have two nieces in college.
It's sad that we need a product like this, but we need to put power in the hands of women.
Great company.
It's sort of the quintessential fit for who we are.
Love the tech, first of its kind, patented,
but also just love the social conversation it promotes.
Flushable pregnancy test coming out, great female founder.
I think only a woman would have thought of that.
It's not your mother's pregnancy test, right?
And in so many ways, not only in the eco way,
but I think also because we have this belief that all women want a certain outcome when they take a pregnancy test.
And some women want to get rid of the evidence, including women just who are going through infertility and don't want a daily reminder.
That's a product. a great young female founder who has a biometric sensor, um, to recognize deviate deviations in
in movement for athletes. Um, so they could start to signal when you're moving differently and may
injure in the future, you know, and she's such a story. I mean, um, mother was a Russian mail
order bride, wanted to move herself and her daughter to a better life, came over to
the U.S. in a pretty poor neighborhood.
She thought my only way out is if I get a scholarship in athletics.
Became a nationally ranked soccer player, injured.
Yeah, soccer's brutal.
Decided, okay, I still have upper body strength.
Became a rower, got a full ride to Duke.
Oh, my God.
And then invented this tech.
What a beast.
Lover.
So, I mean, that's, you know, I'm betting on that.
When Ivana walked in the room, I will tell you, when she walked in the room, I was buying no matter what she was selling.
She didn't have to yell balls for you.
No, she did not.
I'm telling you, she had no, I didn't tell her this at the moment.
But I was investing because even if this wasn't her deal, the next one was going to be.
And so it's fun because I get to bet on these great people doing, I think, really interesting things.
Where is it based?
We're in Raleigh, North Carolina, where I've built all my companies.
What should people know about Raleigh?
People should know that Raleigh is number two in the country in terms of exits.
I think that surprises people.
I didn't know that.
You would expect me to know that.
So yeah, PitchBookData, in terms of the multiples,
we get out of companies.
So the next billion-dollar company will come from Raleigh.
How about?
Just like, who knew the birthplace of female Viagra
was Raleigh, North Carolina?
Great startup scene, wonderful talent in that area.
So I'm going to read a quote and it may be off,
but I liked it. And so I thought maybe I could ask you to elaborate on it.
I'm not sure where I found this, but I think it's yours.
We talk all the time about how women need a voice. We don't need a voice. We need power.
Money is power.
Please explain, or please tell me where that comes from.
I think we just, you know, we're constantly in the discussion around women talking about needing a voice.
What really changes is when women have power.
The power that comes with money is to sit on the other side of the table and make the
decisions.
2% of VC funding goes to women. 2%. It means we think
half the population have 2% of the good ideas. It's ridiculous. If you consider it, what we need
to do is get women to outcomes like mine so they get to sit on the table, sit at the other side of
the table, and pick those things that they really care about, not pass over a product for women
thinking it's a niche brand. And I think it's also just this comfort with the conversation around money.
I started talking about these pajama parties in the Pinkubator.
We have eighth grade girls come through.
We do all these drills.
They're setting their sights for the C-suite.
And the first group we ever had come in, one of their teachers came and she said,
oh, Cindy, when they were coming over here, they wanted to ask you about money,
but we told them they shouldn't do that. I said, oh, no, no, have them ask me.
And the young girl who was asking me all the questions and getting to the real data,
that girl is going to create a big company. And that's OK to have that conversation.
Even as a woman, those are some of the unwritten rules. When I first got an opportunity to go out and speak on these stages to rising star female
entrepreneurs or women in business, a woman came up to me and said, I love that you don't
ever say that you sold your company for over a billion dollars.
Next time I got up on stage, I said, hi, I'm Cindy Whitehead.
I sold my last company for a billion dollars because I was clear that, oh, my God, I'm doing it.
And I think that there is – here's why I say it happily, because women will pay it back.
They'll give it back to other women.
They'll give it back into their community.
There's plenty of data sources on that.
And what I love to see, and my greatest pride, has been the ripple effect of ownership.
Everyone who came to work for me got skin in the game. And to watch our outcomes and what it has meant for them in
terms of freedom, and I don't really mean financial freedom. Like if you're in it just for the money,
you're never going to be successful. But it affords them not only financial freedom, but
freedom to do the things they really care about. And I'm watching them either start their own companies or fund their children's companies.
And that's what I'd love to see is a sort of army of pink ladies coming out of the Pinkubator who
are sponsoring the next group to do it. Well, I love that you also caught yourself,
or even if you didn't have that as a subconscious behavior made it a
point to get up and say what you might have not been saying.
And I think this underscores something really critical,
which is we,
and this is not gender specific,
anyone,
we often think of the,
the external opponents,
right?
And how we might be restricted by someone else,
which could very well be the case and is the case very often.
However, when you're looking for unwritten rules,
it's important not to just look at unwritten rules
that are being imposed on you externally,
but to look at the unwritten rules you are following.
And I remember talking to, I'm not going to name her
because I don't have her permission, but very, very super successful entrepreneur. And I asked her what she, what, what the, some of the main challenges were that she thought women were facing. And she said, well, she, she mentioned quite a few, which you're very familiar with. And, but one that I didn't expect was she said, uh, women need to learn how to ask for raises and negotiate.
They just, a lot of them just don't ask. And it's, it's a, I don't know exactly why that is,
but I was like, Oh fuck. And when I think about my, you know, the female founders that I've
invested in, whether it's, uh, Leah TaskRabbit, which was acquired not too long ago by Ikea or, uh, Tracy Denunzio or any,
any number of these women,
like they are all so good at negotiating.
It didn't even kind of cross my mind that I was like,
Oh shit.
I mean,
it's certainly true for a lot of men as well,
but the point being like,
be really cognizant of,
and this definitely goes for everybody,
not just women,
but where you are following rules that are really just enforced in your own mind.
You can certainly experiment with bending and breaking.
I think a lack of asking for raises is also that discomfort or that don't brag.
It's sort of not ladylike to talk about money or be capitalistic, if you will.
And I think that has an incredible effect that maybe we're not so conscious of.
Yeah, totally.
If you were going to teach a freshman class, I'll come back to the freshman class again, or a class.
If you were going to teach a seminar,
it could be any age range.
You could pick your audience.
It could be female only.
It could be mixed gender.
It doesn't matter.
What would you teach?
What would the seminar look like?
It's like once a week, two or three hours a week.
You could pick as many.
You have as many weeks as you want.
But what would you teach?
This doesn't have to be anything we've talked about. Um, what would I teach? Um,
I think I would, I would teach how you, I would push people around how you're going to make
choices and in life. I think that my, my teaching would be, you know, how do you set out there and sort of remove all of those confinements in thinking?
I, I am lucky, I think, having grown up in such a mobile childhood, um, that I think
what it taught me is you can imagine I was always physically mobile.
Yes.
Physically mobile.
Your dad's state department.
State department.
Yeah.
In that I, I was the perpetual new kid and always having to have that agony of what was going to happen.
And it turned out nothing bad happened.
Yeah.
Right?
In retrospect, nothing.
But I went in anticipating that.
And I think that really helped me.
I don't know if that's a course.
Is that a course?
Can I teach a course in sort of losing the fear?
Yeah.
What's the worst that can happen?
Yeah.
And helping folks go through that.
Yeah. You could just have case study after case study after case study.
I think when I do the Pinkubator, I'm teaching a course and really at its core confidence
for these girls and its confidence in the choices that they make and the,
you know, going all in when they're going to do it.
Well, and I'd love to actually hear you elaborate on that
because looking through my many, many, many notes,
one of the things that I highlighted where I was like,
yes, please, thank you for that.
Okay.
Let's see here.
This is for Fortune.
The question was,
what advice would you give early stage founders?
And it was embrace the workhorse to become the unicorn.
I'm so tired of all the grandiose startup speak.
The founders should declare their genius before they ever even execute it.
So what I tell founders is, don't tell me you're going to change the world.
Put your head down, do the work, and show me.
Okay, so assuming that's somewhat accurate,
I'm asked all the time, how do I build my confidence?
Or how can I become confident?
And the best answer I've been able to come up with,
and this is just my perspective,
is you have to actually believe in yourself.
The way you develop that belief is by actually getting onto the playing field
and taking your lumps,
but proving to yourself that you have certain competencies.
It's not about like Stuart Smalley sitting in front of a mirror,
telling yourself how awesome you are and believing that and then going out and
getting your face ripped off by the real world. Like, no,
you actually have to put in the time to earn the confidence that you then
carry.
What has your experience been,
or how do you think of that with the startup founders?
Yeah.
I think, well, look, I'm particularly focused on women.
And I think that just by virtue of the numbers,
they tend to be unexpected in the room.
I feel like my whole career is a game.
What do you mean by that?
They're unexpected. I mean, by the numbers, we're not be unexpected in the room. I feel like my whole career is- What do you mean by that?
They're unexpected. I mean, by the numbers, we're not expecting them to walk through the room and ask for the money. They're not likely to get the funding, all of that. And I think that's
certainly been the course of my career. When you say pharmaceutical CEO who sold her, don't give a
name, who sold the last business for a billion dollars. Nobody imagines me showing up in hot pink.
I don't look the part.
I'm not your classic in any way.
And I think that's been sort of the story of my career in terms of places I've gone
or products I've taken on have been unexpected.
And so as a result of being unexpected, I think it's underestimated.
And so my kind of key piece of advice is underestimation, you got two choices.
I think you can either reel back in frustration and self-doubt, you can let that eat away at you, or how they reframe the frustrations, the setbacks,
the kicks in the teeth to this opportunity to go forward and surprise.
What do you say to women?
I don't know if you get this question.
Yeah.
What do you, what do you say to women who, uh, and I don't get this question cause I'm
not a woman, but I've certainly, um, with some of my founders, they get this question a lot from other founders, which is a long, or the belief, it might not even be a question, that women should dial back their woman-ness, femininity.
Oh my God, did you hear my reaction?
I did hear that.
I choked.
I did hear the choke.
But this seems to be a very common belief, not just among women, but certainly advice that maybe
men would give to women. It's very prevalent. The worst.
Yes. What do you think of that? The worst advice. And it's given. And it's given
woman to woman. Yeah, all the time. For sure. Men, whatever it may be.
I absolutely, part of the reason I wear pink, so I wear pink all the time.
And you should see my closet. But when I went through the process with the, quote, female Viagra, it was called the little pink pill.
And people all but, like, patted me on the shoulder and said, that's cute. Like it was so the little
pink pill was so dismissive that I realized, my God, this is the conversation we need to be having.
So I started showing up in blazing pink to the FDA. Hi, we're going to talk about this. And I
think what it taught me is like in gender stereotypes or that underestimation, like you,
you run away from it. And I guess if you'reation, you run away from it.
And I guess if you're me, you run right toward it.
And the idea that there isn't something valuable and unique that a woman brings to the table,
and in owning her femininity.
Pink for me is about owning it as a woman, unapologetically pink.
I like pink.
I'm going to wear it, and we're going to have this conversation.
So I think that's the way to go.
Never leave.
I tell women all the time, if you are in an environment in which you need to not wear makeup, pull your hair back, not be you.
And I'd listen.
I was at a table, I won't name the conference, where we were giving advice to younger women across the table.
And a woman, very accomplished, sitting to my right, told a woman, you're too pretty.
You need to pull your hair back and not wear any makeup. And I said, absolutely not. And
if you're in an environment in which you need to do that move. Yeah. So, uh, I love the reason for
the pink and it makes me think of a conversation I had with Amanda Palmer, the musician on this podcast.
Yeah.
And she's amazing.
She's a hell of a character.
Certainly has her fair share of controversy,
but I don't know how this came up exactly,
but I,
I,
I heard her referring to herself or her friends calling her Amanda fucking
Palmer AFP. And at
some point I was like, what is the story with this Amanda fucking Palmer? And it turns out,
so she, it turns out that one of her like frenemies or, or just straight up enemies,
like somebody who hated her always referred to her as Amanda fucking Palmer. And instead of
letting it bother her,
the way she put it to me was,
you know,
take that pain and wear it as a shirt basically.
And I might be,
I'm paraphrasing,
but I love the fact that she took this like barb or something that was thrown
at her and turned it around and like co-opted it and used it in such a way
that she found empowering and maybe,
maybe just funny to start with,
but yeah,
disarmed it in that way.
I thought it was just fantastic.
Awesome.
I love it.
Uh,
so I think we should probably just do a round two at some point or an
extension.
So I'm not going to ask all of my rapid fire questions,
but I do want to ask,
uh,
two or three of them.
Okay.
All right.
So let's see. The first is what book or books have you gifted the most
to other people? Purple cow. The purple cow. Yeah. I have to everybody who's worked for me.
What books besides that have you reread yourself the most, if any come to mind?
I won't name one of yours cause that seems too flattering.
No, no, no. More, more, more. No, no, no. More, more, more.
No, no, no.
More, more, more.
What else have I read that I love?
Other books.
If none come to mind, that's fine too.
Yeah.
Pat Linceone.
Pat Linceone, these books.
I love that.
What is it?
Like The Five Dysfunctions of a Teen?
Five Temptations of a CEO.
Yeah.
Yeah.
And I think it was about what do you prioritize?
Yep.
What do you prioritize?
What do you let go?
You know, I thought that was actually a great book.
Maybe they're the simple reads that I need to on the airplane.
What is the last time that you cried tears of joy?
This is a new one.
Oh, tears of joy.
Or the time that comes to mind.
I rescued a pig.
You rescued a pig?
I cried tears of joy for taking this animal out of a terrible situation.
I love animals.
So I went across the state and rescued a pig in a Porsche.
How did you find a pig needing rescuing?
I was worried that my car was never going to smell the same.
Just through a network, knowing that.
The pig called a scientist and he said, I can't help you, but I know that you can.
I cried tears of joy for making a better life. Hold on a second. This is a full-grown pig?
Yeah. Like hundreds of pounds of pig? Not a hog, like a potbelly,
but still big.
Are you now the caretaker of some pig?
I think it's important to have
in my daily routine, I still got to
scrape the shit off my boots.
Wow, so you have a pet pig.
Amazing.
That's incredible.
The most impressive, I hope I'm getting
this right, I'm a little low on caffeine
right now, but Jesse Graff, who's an incredible phenom in the American Ninja Warrior world.
Okay, yeah.
The most impressive hand strength maybe of anyone I've ever seen.
Certainly any woman.
I mean, she's just probably 30 times stronger than I am.
Wow.
At least, which maybe isn't saying a lot, but like a thousand times stronger.
Incredible athlete. And she has a pet pig as well.
That's cool. Jesse, call me and tell me what to do.
Jesse, if you're listening, let her know. Best practices.
Best pig practices.
What is an unusual habit or an absurd thing that you love or love doing and i'll give you an example
just to buy some time so give you some time to think uh when i asked cheryl strayed this question
who wrote wild and has done many many many other things and written many other books
she said well i like to rearrange my sandwiches so the first thing I do when I get a sandwich is I rearrange the inside
so that with every bite you get an everything bite.
It's very important that the avocado or the tomatoes or so on are evenly distributed.
And she will also do this for, I think, her husband's sandwiches.
She'll open his sandwich and rearrange.
That's pretty odd.
That is pretty weird, yeah.
There are a lot of weird things that everybody does.
So what is one of yours?
God, I was going to say nickname people, but that seems so vanilla now.
What is the most absurd thing I like to do?
I climb and sit in the sink to put my makeup on, which is really weird.
That's unusual.
It's kind of weird.
Do you have any superstitions?
Not really.
No, I grew up, you know, when I was a little girl, I was in the Fiji Islands.
All right.
And so I had a very unusual childhood where there was a lot of superstition.
So I think that being exposed to that young made me lose them later in life.
Not so sure they were true.
Not so sure they were worth buying into at that age.
They created a lot of fear unnecessarily.
Do you have any examples?
Oh, I mean, in that culture, everything was very superstitious about if you didn't see the fish first,
you didn't get in the water.
Yeah, and I think that at a young and impressionable age,
they probably had an effect where I decided,
no, I'm not going to worry about this going forward.
If you had to give a TED Talk on something no one would expect, so it can't be the pharma
stuff, can't be the company building stuff.
TED Talk on something people wouldn't expect.
Growing up in a third world country.
I don't know.
Can I do that one or what lessons learned?
You can do that.
What if you had,
all right,
what if you had six months to prepare for a TED talk,
but it had to be on a new skill?
What would you focus on?
Oh my God.
I would,
I would learn how to fiddle.
Fiddle. Totally.
Fiddle like Irish bar music fiddle. Yeah, for sure. I would learn how to do that. And I teach
something you just came up with, or is this something you've thought about? Like one day
I should learn the fiddle. Yes. I would love to learn how to fiddle. Like I feel,
I don't have any musical talent. It sucks. Like I would like to be able to do that.
That's a good party trick. I need a better party trick than my sexual medicine card.
It's not good enough.
It's not taking me far enough.
I need to like play music or inspire through that.
Well, I will tell you as someone who, who has been, uh, fantasizing about and simultaneously
putting off, uh, voice lessons for probably a decade.
I just started about a month, a month ago, I want to say,
or six weeks ago. That's awesome. One of the best things I've ever done. That's cool. Yeah.
It's really been empowering and also worth doing in terms of fiddle, just so that you
listen to music differently. Yeah. That's cool. I hear things totally different. Oh,
that's cool. Which is very cool. Okay. Next time I come on, I'm going to fiddle at the
beginning of it. Please. Yes. That can be, some people hate my intro music,
so perhaps I could license for a reasonable fee or fiddle.
Uh,
what do you do when you feel overwhelmed or unfocused?
What do you do to get back on track or to let some pressure out of the tires?
I usually call my big brothers.
I mean,
I think that they're very,
they're like the exact right balance of kicking me in the ass and encouraging me.
So when I'm feeling overwhelmed or anything else,
nothing like my family to be totally unimpressed with my problems
and kick me in the ass.
So I think that's what I do.
I probably call my big brothers.
They've been hugely influential in my life.
Can you think of an example of them kicking you in the ass
or what they would say to you to be like, really?
Yeah, I think it's just generally.
What do they do professionally, if you don't mind me asking?
Sure.
So one is a lawyer who actually has an operating role in a big construction company,
and the other one was a startup guy who's head of sales and marketing for a company,
and he's grown through a lot of stuff.
He was a big part of why I went smaller when I left my big company career.
When you left Merck?
Merck, yeah.
He said, go smaller, push yourself, challenge yourself.
And I knew I didn't fit in a big environment, so he was important in that.
But listen, I can call my brothers, same thing, overwhelmed or even overly enthused about myself.
Like, hey, did you see I was just talking with Tim Ferriss?
Like, yeah, whatever.
Don't take yourself.
Don't be too proud of yourself.
So I don't know.
They're just classic big brothers.
Tim who?
That shiny gnome with the big head?
Yeah.
Not impressed.
They like a lot of mockery.
Yeah.
Well, they've also both spent quite a bit of time in the trenches.
They have.
I mean, they've played full contact sports.
No doubt.
That's always very helpful.
If you could have a word, a message, a quote, anything on a billboard,
a message to get out to millions, billions, whatever,
metaphorically speaking, a lot of people, right?
Yeah.
What would you put on it?
Can I put it in the valley?
Sure.
I'd put, fuck the unicorn, be the workhorse.
I'd like that to get out to millions of people in the valley.
Yes.
It would make me super happy.
This is my distaste for all, uh, all the grandiose speak
and startup. And, and I think the lack of attention on the fundamentals. Yeah. Show,
don't tell friend, get it done. Uh, how has a, a failure or an apparent failure, uh, set you up
or led to later success contributed to later success.
So, I mean, one potential example would be, you know, the decision to take that money from
someone who's your spider sense told you shouldn't take money from. Are there any other examples that
that come to mind? Um, I, you know, professionally that's certainly, uh, been the worst. I think that I'm thinking of, you know, huge personal failures of mine that have taught me lessons along the way.
I probably crashed and burned a lot going through childhood of, you know, trying to figure out how to fit in in new environments and, you know, sort of playing to the popular thought and it not working because it wasn't authentically who I am.
And I think at some point I became comfortable that I might just be the outlier.
Well, what's funny about being the outlier is you tend to attract other outliers.
And then it kind of works out.
It does work. I love it. The band of misfits.
The band of misfits. I was just going to say that exact thing.
Wow, I've never said that before. That's crazy.
Band of misfits.
Well, I think at this point I would just say,
where can people find you? Where can people say hello?
Where can people see what you're up to?
Where would you like people to wave a hand on the internet?
Oh, I'd love for people to find me online on Twitter.
I'm at Cindy Pink CEO that are on Insta.
I'd love for people to find me there
considering I'm so late to the social media party.
Being in a regulated industry with my point of view,
my lawyers are pretty sure I should not be on social media.
So it's been a pretty fun journey in these last two years.
I've got a lot to say.
So I'd love for them to find me there and say something back.
Cool.
And I'll put those in the show notes as well for folks.
Do you have any final parting words,
advice, and ask of the audience,
something they should consider,
try themselves, anything?
Look, I'm going to play to my group
that I'm looking out for,
which is female founders.
I'm just going to ask you to share
the stories. Share the stories
of success. I think it matters that
we do that. If I looked just
recently, I learned that only 17%
of those profiled on Wikipedia
are women.
More than that deserve to be profiled.
And I think they're stories. So I thank you
too for having me on today for that reason.
Of course. My pleasure.
And you know,
for what it's worth and maybe this,
this could be taken the wrong way by some people,
but hopefully not like I didn't,
didn't invite you on because you're a woman.
Yeah,
I get it.
But you on because you're good on there.
Thank you.
I appreciate that.
And if that also gets more women on the show,
fantastic.
Yeah.
You know,
because they are out there.
Uh,
and I'm really glad you took the time. So thank you for being on the show. Fantastic. Yeah. You know, because they are out there. Uh, and I'm really glad you took the time.
So thank you for being on the show.
I think it's a,
your question to say,
what's the worst that could happen?
I do think people should ask themselves that.
Yeah.
Yeah,
absolutely.
And,
uh,
it's,
that is one of the most empowering questions,
but you have to spend some time on it.
You do.
Because if it's just a big,
scary shadow,
it's going to continue to be a big, scary shadow.
You have to shine light on it.
Yeah.
And for people who want to explore that,
you can just check out my TED Talk,
tim.blog.com forward slash TED.
But this has been really fun.
Really fun.
Thank you for taking the time.
And we have so many other questions we could explore,
but I'll let you get back to your evening. Thank you for taking the time. And we have so many other questions we could explore,
but I'll let you get back to your evening.
And for everybody listening or watching, hi.
As always, you can find links to everything we've discussed,
books, resources, at Cindy Pink, CEO, on Twitter, Instagram,
all of the places in the show notes at Tim.blog forward slash podcast for this episode and every other. And until next time, thank you for listening.
Hey guys, this is Tim again, just a few more things before you take off. Number one,
this is five bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun for the weekend? That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do.
It could include favorite articles that I've read and that I've shared with my close friends, for instance.
And it's very short.
It's just a little tiny bite of goodness before you head off for the weekend.
So if you want to receive that,
check it out. Just go to 4hourworkweek.com. That's 4hourworkweek.com all spelled out and
just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it.
This episode is brought to you by LegalZoom, which more than 2 million Americans have used
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