The Tim Ferriss Show Transcripts: Cindy Eckert (#314)

Please enjoy this transcript of my interview with Cindy Eckert (formerly Whitehead), an entrepreneur with $1.5 billion in exits who currently serves as the founder and CEO of The Pink Ceiling. Transcripts may contain a few typos—with some episodes lasting 2+ hours, it’s difficult to catch some minor errors. Enjoy!

Listen to the interview here or by selecting any of the options below.

Cindy Eckert — How to Sell Your Company For One Billion Dollars


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Tim Ferriss: Cindy, welcome to the show.

Cindy Whitehead: Thanks for having me.

Tim Ferriss: I am very excited to dig in. I thought we could start in medias res, as they say in novels where you start right in the middle of the action.

Cindy Whitehead: Okay.

Tim Ferriss: So, we’re going to bounce all over the place as I always do. JPMorgan Healthcare Conference – I’ve heard some murmurs about stories and getting attention or people to focus. Could you please describe for folks what happened?

Cindy Whitehead: 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 the 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 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 is 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, I went silent. 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.

Tim Ferriss: So, you let the silence do the work.

Cindy Whitehead: It was uncomfortable. I figured it was long enough for it to be uncomfortable for me, which was a fair trade for them having made me really uncomfortable as they started giggling and wouldn’t pay attention to me.

Tim Ferriss: Silence. Yeah. It’s so powerful. It’s so, so powerful. I remember advice I was given at one point – well, I was given that advice first by someone named Cal Fussman, who’s a master interviewer, when he was going over some transcripts from this podcast in the early days. He’s like, “No, you’re too fast. You don’t leave gaps. You don’t have to save people. Let the silence do the work.”

Cindy Whitehead: Sure.

Tim Ferriss: So, I love that story.

So, speaking of letting the silence do the work, I’m going to go silent really quick because I want to ask you two questions that might take a few minutes to answer, but I’m going to start with the short one. What is your favorite business and why?

Cindy Whitehead: My favorite business of all is Wegmans, which if anybody is from the Northeast, they appreciate this is a grocery store. How can you get excited about a grocery story? 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 the do?

So, it opened years later – I moved my whole life – it opened in the DC area. I went the first day that Wegmans opened in DC and I walked up and all of their employees were standing outside holding their hands above their head like a W because they have Wegmans pride, the Wegmans way.

I’ve got to tell you, that first day, anybody in the entire DC metro area who had 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.

Tim Ferriss: 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? How do they develop that?

Cindy Whitehead: 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. 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. There are all of these incentives to their employees to make them truly feel that appreciation from their employer and also, I think, be proud to work there. They go home and have pride in saying who they work for.

So, I started studying businesses I loved at a very young age.

Tim Ferriss: I had a conversation with Frank Blake, former CEO of Home Depot right here, sitting where you are. They developed this orange apron cult, as it was sometimes referred to. The dedication that some of these employees showed was incredible. His point was, “One of the systems I instilled was positive reinforcement by sharing stories on a very regular, scheduled basis of standout customer service.”

Cindy Whitehead: Incredible. Yeah.

Tim Ferriss: Yeah, it doesn’t have to be complicated.

Cindy Whitehead: I have to tell you, I sold my first business late. I sold it to a group that was private equity-backed. 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.” I think he said it with sort of one eyebrow raised, like, “Hmm…” And I said, “Why, thank you.”

Tim Ferriss: “Thank you for that.”

Cindy Whitehead: “That’s the nicest compliment I’ve ever received.”

Tim Ferriss: You mean in the Apple way, not the David Koresh way?

Perfect. I’ll take it.

Cindy Whitehead: Exactly.

Tim Ferriss: So, the next question, which will seem odd to people listening, but will soon make more sense, is not really a question. I’ll be polite and make it a question.

Cindy Whitehead: Okay.

Tim Ferriss: Could you please give me your three-minute commercial?

Cindy Whitehead: Okay.

Tim Ferriss: Tell me about yourself, soup to nuts.

Cindy Whitehead: Alright. I moved my entire childhood. So, every year from 4th to 12th grade, I was in a different school. So, I was the perpetual new kid. I think what that did was perfect my ability to stand on the outside of the room and look in and really listen, understand motivations, understand 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 they were doing differently.

Cindy Whitehead: And along that way, I 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. I called her up. I 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, I went to work for Merck. I started in pharma because it was Fortune’s Most Admired Company. That’s why I went there. I wanted to learn from the best. I thought I would actually take it elsewhere and apply it. I 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. I 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, and smaller until I ultimately was maybe crazy enough to start it for myself. I built two businesses, both in sexual health. People say, “Why?” I say, “Irish Catholic, of course.”

So, I built a business slate with the only long-acting testosterone for men. 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.

I 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.

Tim Ferriss: That was really good.

Cindy Whitehead: How many minutes?

Tim Ferriss: Now, I wasn’t watching the time, but if I had to use my spider sense…

Cindy Whitehead: Your listeners will know.

Tim Ferriss: If I had to use my spider sense, I think that was really, really close. So, I’m very impressed. 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?

Cindy Whitehead: 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.

Tim Ferriss: What would you look for? Were there any particular checkered flags, meaning fantastic, or red flags, meaning, “Maybe not a good person to pick?”

Cindy Whitehead: For me, 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.

I always laid my cards at 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.

Tim Ferriss: What did you study in undergrad?

Cindy Whitehead: Business.

Tim Ferriss: Business?

Cindy Whitehead: Yeah.

Tim Ferriss: What did your business professor do besides have you report back each week on your favorite business of the week?

Cindy Whitehead: 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. 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.” She really pushed back like it wasn’t such a sure thing.

So, she was constantly setting the bar for me.

Tim Ferriss: So, I don’t know if you had a chance to ask her, but did she genuinely think that you would have trouble getting the job or was it a Yoda trick to get you to stubbornly pursue it twice as hard?

Cindy Whitehead: 100 percent a stubborn trick. 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, “Go out there and prove it.” So, yeah, very clever.

Tim Ferriss: So, how does one start a pharma company without a pharma background?

Cindy Whitehead: Well, pharma background in that I’d been in the industry for a long time. So, I had the right contacts.

Tim Ferriss: You had the industry experience.

Cindy Whitehead: I had the industry experience, yes.

Tim Ferriss: You’re right. I didn’t word that very well – without the…

Cindy Whitehead: The scientific background.

Tim Ferriss: That’s right.

Cindy Whitehead: Surround yourself with an extraordinary scientific team. I feel like I’ve learned at the hands of some of the best in science.

I think I’ve always brought a lens to it of 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.

Tim Ferriss: How did you pick –

Cindy Whitehead: And I can play a doctor on TV now.

Tim Ferriss: You can?

Cindy Whitehead: Yes, or I at least think I can.

Tim Ferriss: Or via people’s earbuds if they may have them.

Cindy Whitehead: Yeah, that’s right.

Tim Ferriss: How did you end up choosing the – you said long-acting testosterone.

Cindy Whitehead: Testosterone.

Tim Ferriss: So, paint a picture of us.

Cindy Whitehead: Sure.

Tim Ferriss: We can certainly get into testosterone and like HPTA and all this fun stuff.

Cindy Whitehead: Sure.

Tim Ferriss: But I don’t want to bore some segment of my population of listeners to death, although I am fascinated by it. So, we probably will get into it. How did you end up choosing that? Did it start with finding the opportunity and then, “I want to start a company?”             

Cindy Whitehead: No.

Tim Ferriss: Or did you decide, “I want to start a company now. Let me try to find a product?”

Cindy Whitehead: That was it. Yeah. I wanted to start my own company. I felt like I had a hypothesis.

Tim Ferriss: If you don’t mind me asking, how old were you at the time or where were you in time?

Cindy Whitehead: I was in my early 30s at the time when I started it.

Tim Ferriss: Okay. Got it.

Cindy Whitehead: I had one career experience that was very informative. So, I had been at a company that was acquired. They had been gobbled up by somebody who had gobbled up a lot and then they had to integrate them. I got to be on that team. So, I got this put together of the perfect company. That was a great career moment for me. Then I got to go apply it doing my own.

The reason I did it is for that same reason. I love pharma for what it can do. At 3:00 a.m. 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. 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 my own terms? That was Slate. I named my company Slate on purpose – clean slate. We were going to do it our way. It was to go out and find a diamond in the rough, an asset that had been overlooked. I love the category. I love sexual medicine. I’m a card-carrying member of the Sexual Medicine Society. Who knew there was that? There is.

Tim Ferriss: Oh, there is?

Cindy Whitehead: It makes me popular at cocktail parties. I whip it out. No. There really is a society. It’s because actually, our understanding there has really come much more recently. It’s a relatively new field. Yet, we’re learning such interesting things. It’s in conditions that 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, I found this inventor who had the only FDA-approved long-acting testosterone.                

Tim Ferriss: How do you find someone like that? You would think in a world of pharma discovery that the bones would have been picked clean.

Cindy Whitehead: Yes. Okay. This is a great story. 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.”

Tim Ferriss: So, the inventor was looking for a way to commercialize?

Cindy Whitehead: It was a very fortuitous introduction. I 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 being indication. It was being used, interestingly, in women. So, my journey started very early in this use for libido.

Tim Ferriss: What’s the compound?

Cindy Whitehead: It was testosterone.

Tim Ferriss: What type of testosterone?

Cindy Whitehead: It was a pellet. So, it was long-acting, put under the surface of the skin, released testosterone over a four to six-month window.

Tim Ferriss: Wow. Okay.                 

Cindy Whitehead: So, here’s me looking at it going, “First of all, it should be used by urologists in men.” I did this crossover analyst. Only one urologist in the country was using it. So, I thought this would be a great business to build. 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. 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 be sunscreen on or rub something on. The most common applications for testosterone at the time were gels.

Tim Ferriss: Gel, right.

Cindy Whitehead: So, this was like, “Hey, can you remember to show up three times a year to the doctor?”

Tim Ferriss: They’re like, “Sure, I can do that.”

Cindy Whitehead: Yeah.

Tim Ferriss: Alright. The inventor reaches out to your friend, the scientist, who says, “I can’t help you but maybe my friend can.”

Cindy Whitehead: Yeah.

Tim Ferriss: That’s how it starts. So, the pellet – I’m thinking of, for instance, like Trenbolone, which is used in cattle, in some cases, also popular with some power lifters and so on who do not use it in pellet form.

How is it administered or how is it put into the patient?

Cindy Whitehead: So, it’s put in 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…

Tim Ferriss: Off you go.

Cindy Whitehead: Yeah. For urologists or surgeons, this in-office procedure was very simple. The great news is it was half the price of anything on the market. So, everybody was winning in this equation.

Tim Ferriss: Why was it half the price?

Cindy Whitehead: On purpose for me.

Tim Ferriss: Because you set the pricing.

Cindy Whitehead: I did, yeah.

Tim Ferriss: Was it less costly because you were comparing it to other modes of administration which require more visits, hence it’s not – no. It was just the market positioning.

Cindy Whitehead: Just the cost of the drug. Yeah.

Tim Ferriss: Fascinating.

Cindy Whitehead: I have a belief system around that in pharma around drug pricing. So, it was important for me to do that. We were making great money, building a great business, and we were doing just fine at that cost.

Tim Ferriss: Right. You don’t need a 500 million-percent markup.

Cindy Whitehead: Exactly.

Tim Ferriss: Yes. As we may or may not talk about, some people get into a lot of trouble for that.

Cindy Whitehead: Rightfully so. Yeah.

Tim Ferriss: What other questions do you like to ask when you’re interviewing people? Are there any other questions that you find yield – or are worth the effort, that are particularly helpful or other approaches to hiring?

Cindy Whitehead: 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. I think I’m getting a lot of insights into who they are by doing that. I don’t think there are magical questions.

I think there are ways to tease out cultural fit. 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.

Tim Ferriss: So, culture can mean a lot of things to different people. In this particular case – you mentioned the adaptability, which in a small startup, especially, you’re going to be wearing a lot of hats and those hats may change. So, you need someone who’s adaptable. What else were you looking for and what did they mean to you?

Cindy Whitehead: Six things.

Tim Ferriss: Good. There we go.

Cindy Whitehead: Mine are pretty specific. Let me say – overarching, I’m looking for people who wake up every day and make deliberate choices. It’s all a choice how you go through life. My six were they had to choose to be an owner. They had to 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. It’s so important to watch what people do to learn every day. They had to choose to be family because we were going to be a small, tight-knit group. And they had to choose to be appreciative. I think that is how you go through life. What is your attitude? Do you marvel at the opportunity you have to make impact? So, those were my six choices I was looking for.

Tim Ferriss: How do you avoid false positives in the sense that if you say to them, “These are the six values…?”

Cindy Whitehead: Oh, I never, never – you’re listening to the story that, I think, exposes those values. But if you ask somebody that, like, “Do you choose to be quirky?” “Uh, sure.” You’re not going to get, I think, the right response. I think you have to know your core of who you are and who fits. Then I think you have to ask the questions.

I will say there is one other question I do always ask. I ask, “How is the very first way you ever made money?”

Tim Ferriss: I like that. That’s a really good one.

Cindy Whitehead: If they can’t tell me, “I put flyers in the mailboxes in the neighborhood and said, ‘Odd jobs, call me,’” or if they are like, “Well, my first job out of college was…” They’re out.

Tim Ferriss: Yeah.

Cindy Whitehead: They don’t have that sort of mentality that’s going to fit.

Tim Ferriss: One of my friends, Brian Johnson, who has done a whole host of very impressive things, he was the founder – I don’t think he had a cofounder – but let’s just say one of the founders, to be safe, of Braintree, which then sold for a whole lot of money. When entrepreneurs come to him, because he invests quite a lot now, and they say they want to start something, he’ll ask them, “Is that an itch or is it a burn?”

Cindy Whitehead: That’s cool.

Tim Ferriss: 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.

Cindy Whitehead: Can I tell you a quirky story?

Tim Ferriss: You can absolutely tell me a quirky story.

Cindy Whitehead: This is how it went in an interview.

Tim Ferriss: After you tell me one quirky story, I would like you to tell me a bold story from your personal experience.

Cindy Whitehead: Perfect. Okay. Here is my quirky – if I had asked for this, it wouldn’t have come out. But I am 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. Look, 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, 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 of recognition from 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

Tim Ferriss: I think it’s both.

Cindy Whitehead: It ultimately became her nickname in the office. We called her Duck Balls.

Tim Ferriss: Duck balls?

Cindy Whitehead: Yeah, because we had a whole other duck story.

Tim Ferriss: Wait, I’ll take the bait – what’s the duck?

Cindy Whitehead: We called her Ducky because she was always very calm on the surface, but like going like this a million miles an hour underneath.

Tim Ferriss: Okay. We’re going to come back to the bold story.

Cindy Whitehead: Yeah, that’s fair.

TIm Ferriss: 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.

Cindy Whitehead: Fair enough.

Tim Ferriss: And if you do and you don’t get hired, shame on you. In the course of doing some research, I believe – I don’t think I’m making this up – but you give everybody nicknames or a lot of your employees nicknames.

Cindy Whitehead: I do. Yeah.

Tim Ferriss: Why is that?

Cindy Whitehead: It is my quirk. I’ve had it my whole life. I know my mother by so many different names that I think people don’t know who I’m referring to half of the time that have known us for years. I did it because we love to story tell. We sit around the lunch table. We have a discipline of having lunch together every single day.

That was an effort to – you know, no death by meeting. How would we all be on the same page and still create this family spirit? People get to telling stories and of course, it’s the one you wish you hadn’t told that ultimately arrives at your nickname.

But the beauty of that is we have a whole ceremony – a caricature, you get a nickname. It’s basically handed over at the lunch table. You will never me known by your real name again.

Tim Ferriss: Wait a second – so, this is like the knighting by nickname.

Cindy Whitehead: It is.

Tim Ferriss: At what point does this happen? Is it like your first week on the job? Is it like, “On Friday, you’re going to be…?”

Cindy Whitehead: 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. The reason I did it – it was important to me that I was giving permission in my environments – permission to be yourself, to show who that was.

Especially when you’re building companies where a lot of your people are outside of the main office or salespeople or other, it was a way for us to get to know one another. It felt like, “Oh, I get it. I know who you are. I’ve heard your story.” I think it created this culture of locked arms, us against the world. We knew each other’s quirks. So, yeah, weird habit, but one that stays to today.

Tim Ferriss: Alright. If I may – this is going to lead somewhere, but I’m a little 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. I’m not going to give the whole joke because it’s kind of long, but this tourist goes to Scotland. He’s sitting in a bar. He’s hanging out.

There’s this old guy in the corner. He starts like yelling at this tourist every couple of minutes. He’d be like, “Hey, laddie, you see that pier out there? I built it with me own hands. What do they call me? Scotty the Pier Builder? No.” He keeps doing this. This guy’s like, “What the hell?” He goes on and on and on. He goes, “But laddie, I fuck one goat and what do they call me?” So, the point being do people have the ability to veto their nickname?

Cindy Whitehead: Absolutely not. Who gets to request their own nickname? That never works.

Tim Ferriss: That’s true. That’s not going to work. Just to give examples, you have Duck Balls.

Cindy Whitehead: I do.                

Tim Ferriss: What are some other examples?

Cindy Whitehead: 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 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. It was one of the other reps who came forward and said, “We’re going to do a virtual Get Well Spoon card.”

So, every single person in the company had the spoon hanging on the end of their nose and sent it out. It was their kids and it was their dogs and it was their family. I think that it didn’t come from me. That came from somebody else in the organization. That’s how as much as we teased him about it, in that really important moment, he knew we were all looking out for him.

Tim Ferriss: So, this makes me think of a few things.

 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.

Cindy Whitehead: Sure.

Tim Ferriss: I’ve also spoken with a controversial guy for a bunch of reasons, but Jim Watson, co-discoverer of the double helix. That story is also a little more complicated than we have time for right now. He talked about how these small groups – my words, not his, but like dick and fart jokes are actually really important 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?

Cindy Whitehead:  Fair. Yes.

Tim Ferriss: But that’s kind of why it works, right? So, my question is in today’s times where, yes, there are 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 do you – what would your advice be to people that are like, “Yeah, I want that, we need that,” but they’re afraid?

Cindy Whitehead: Well, look, I think you know – it’s that laying my cards on the table.

Tim Ferriss: Yeah.

Cindy Whitehead: When you first came in an interview with me, “Here’s who we are.”

Tim Ferriss: Right.

Cindy Whitehead: “You’ll hate us in six months if you don’t like this, this, and this.” I think that transparency from 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 gave us permission to have what I’ll call constructive irreverence.

Irreverence with me too – they gave me a nickname. We knew that we could have that comfortably inside of 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 to seriously, I think being self-deprecating – when I talk to a lot of female founders who are very frustrated by the injustices and this or that, I say, “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.

Tim Ferriss: Yeah, for sure.

Cindy Whitehead: It is the best way. 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. I think humor is really important.

Tim Ferriss: Yeah. It also gives – this is having spent a lot of time in Japan and China also, where in China, [inaudible] [00:29:58] is like to lose face.

You’re giving someone the chance to also kind of recover form a stumble instead of creating what could be a really longstanding, kind of awkwardness intention. Do you have a nickname?

Cindy Whitehead: I do. It’s HBIC.

Tim Ferriss: Were you allowed to come up with your own nickname?

Cindy Whitehead: Absolutely not. They tell me that the B stands for Betty, but I’m pretty sure they’re lying.

Tim Ferriss: What does the whole thing stand for.

Cindy Whitehead: Head Betty in Charge.

Tim Ferriss: Who gave you that?

Cindy Whitehead: There’s always a secret nicknaming committee. It’s never revealed.

Tim Ferriss: I see.

Cindy Whitehead: It just came to the table one day. It was written on my caricature.

Tim Ferriss: I’m just going all over the place, but that’s what I do. You mentioned new sales rep, Balls, 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. That’s six or seven. But the sales position is a really important position.

Cindy Whitehead: Really important position.

Tim Ferriss: It’s like everything is a whole lot of talk until something gets sold, ultimately, right?

Cindy Whitehead: Absolutely.

Tim Ferriss: How did you train? What were some of the techniques that worked really well for either of your products for selling?

Cindy Whitehead: Yeah. I think that the best approach was that I gave them permission to fire the D-list. 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 and frequency, reach and frequency.” 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. 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 the traditional pharma approach.

Tim Ferriss: How is first contact made? Is it walk in the door, brush the feet on the carpet, “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? What’s the right approach? What’s the right pitch?

Cindy Whitehead: Hit the front line of the office and you’re actually dealing with the receptionist that you need to talk to to see the physician, the nurse, etc. So, you’re going through all of those different steps to get to them. Our group was helping in an in-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, you’re just taking time in my day.”

Cindy Whitehead: I think they had enough confidence in what they were bringing that they didn’t accept that.

Tim Ferriss: Right. It wasn’t “Death of a Salesman.”

Cindy Whitehead: It wasn’t. Exactly. With that product, we had this incredible opportunity. So, what happens today? You get a drug. You get it filled at a pharmacy. 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?” I took my entire leadership team to Zappos and we learned from them. We were constantly looking outside of our industry for who was doing it great.

So, here’s a story. Our most important guide, sort of the top researcher in the country is from Harvard. 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.

Cindy Whitehead: We were 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 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 –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’d you think from a pharma company, huh?

Tim Ferriss: No, it’s not. What other companies did you borrow from or look at?

Cindy Whitehead: Wow. Big and small – I think that all of the people who worked for me were students of great businesses. They mimicked that behavior that my business professor probably taught me. At one time, we went to Seattle. I love Seattle. I used to live there. We went to the Pike Place Market, spent an hour, just went out and learned from those businesses. We were learning from Beecher’s, the cheese shop. What do they do exceptionally well? How do they invite people into the experience?

Cindy Whitehead: So, Zappos was probably our most formal – go together, learn from them. But constantly reading or picking those businesses that we loved, that was a constant conversation at the lunch table.

Tim Ferriss: If you were – this could be, let’s just say freshman year of high school, freshman year of college – teaching an entrepreneurship class, 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?

Cindy Whitehead: I would insist that they read “Purple Cow.”

Tim Ferriss: “Purple Cow?”

Cindy Whitehead: Yeah.

Tim Ferriss: Mr. Godin.

Cindy Whitehead: Right? Yeah. I would insist that they read it about how you stand out in a sea of sameness. That’s it. I think in terms of sales, for sure, or for entrepreneurship, how do you stand out? What is going to be your defining difference and how do you sort of attract remarkable to you if you’re doing something truly remarkable?

Cindy Whitehead: I don’t think it’s one-size-fits-all. That would be my ask. I think that I would tell every entrepreneur go sell something. If they’ve never sold anything, go learn from somebody. Go be in their sales organization and then take it back to your company.

Tim Ferriss: So, there’s a fellow Austinite here named Noah Kagan who recommends – one of his exercises that he suggests to everybody is the coffee challenge. The coffee challenge is just getting more comfortable with discomfort by for the next, say, week, every day, you have to go into a coffee shop – it doesn’t matter if it’s Starbucks, it doesn’t matter if it’s mom and pop – and asking for 10 percent off your coffee when you get to the checkout.

Cindy Whitehead: I love that.

Tim Ferriss: He’s the first one to say the outcome does not matter. You just have to ask.

Cindy Whitehead: Okay. I love that.

Tim Ferriss: 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.

Cindy Whitehead: Thank you, Noah. I’m going to be applying that now.

Tim Ferriss: It’s really valuable. I was trading texts with a friend of mine, younger guy, who is developing his own product and he’s working on the product in a startup, but it’s not at a point where he’s interacted with any customers yet.

I mentioned this to him and he’s like, “I don’t need that because I make myself uncomfortable in all of these following ways.” 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.”

He’s young enough that we have somewhat of a mentor/mentee relationship. He’s like, “That’s ridiculous. I don’t need to do that.” 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.

Cindy Whitehead: Sure.

Tim Ferriss: He’s like, “Okay, fine. I’ll do it just to make you happy.” He sends me a text a few days later. He’s like, “Oh my god, I had to walk around the block psyching myself up to do this. My palms were sweating.”

Cindy Whitehead: Really?

Tim Ferriss: “And I got 10 percent off, but it was so much harder – it brought up all of these emotions I didn’t expect to come up.” It’s like, “That’s right.

Cindy Whitehead: That’s awesome.

Tim Ferriss: You think it’s going to be easy. Let’s confirm.”

Cindy Whitehead:  I love it.

Tim Ferriss: This segues nicely to what I promised I would come back to, which is boldness. What are some events or inflection points for you, maybe – it doesn’t have to be – but any stories of you choosing boldness?

Cindy Whitehead: Well, I’ll tell you probably my boldest choice was when I made a decision to dispute the FDA. I was on this course – it’s pretty straightforward. You have a pre-specified endpoint. You go out and do the studies. You meet them with statistical significance. You get to an approval, provided there are no show-stoppers.

So, I had gone out. I’d gotten this drug from the company that first developed it. I had sat down with the FDA, “What do I need to do?” We had agreed. I had gone out. I had done the work. I had gotten the outcomes. We got rejected.

Tim Ferriss: What was the drug?

Cindy Whitehead: This was Addyi.

Tim Ferriss: A-D-D-Y-I.

Cindy Whitehead: 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. 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. People knew we were on this journey.

Tim Ferriss: Just for context for people listening, this is your second company.

Cindy Whitehead: It is, Sprout Pharmaceuticals.

Tim Ferriss: Dubbed by the media, the product, at least, as female Viagra, just for people who are trying to keep track. Okay. Please continue.

Cindy Whitehead: So, people knew that we were going down this path. 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 DC. I was in DC all the time.  I went to have a coffee with her. She walked into the room and this woman was in charge – type A, recognized her right away.

She walked over. She had her own business. She had raised two beautiful boys. She had what looked like the perfect marriage by all of 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 –

Tim Ferriss: Because of their sex life or lack thereof?

Cindy Whitehead: Yeah. She had no interest. She had been diagnosed with this condition.

Tim Ferriss: What is the condition?

Cindy Whitehead: It’s called hypoactive sexual desire disorder. HSDD is the moniker. Same prevalence as ED has for men – so, ED is the most common male sexual dysfunction. HSDD is women’s most common. It’s a lack of interest in having sex.

Tim Ferriss: Physiologically, how does that manifest?

Cindy Whitehead: 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. It’s how Addyi 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 with the normal ebb and flow of desire for sex, put them in an MRI, show them sexual cues, their brains light up, actually, totally differently.

Tim Ferriss: What are the chemicals?

Cindy Whitehead:  Dopamine and serotonin. So, our excitatory factors have a transient negative effect on serotonin, which is an inhibitor for your sexual response.

Tim Ferriss: Say that one more time?

Cindy Whitehead: Serotonin. So, dopamine is positive, excitement for sex. Serotonin is inhibition. The drug worked by this transient negative effect. So, a negative effect on a negative for sex equaled a pro-sexual effect.

Tim Ferriss: Got it.

Cindy Whitehead: Yeah.

Tim Ferriss: I’m just trying to think. Okay. So, it would be… Got it. So, serotonin has an inhibitory effect.

Cindy Whitehead: What do we know of the antidepressants? Their most common side effect is actually killing your sex drive.

Tim Ferriss: Right.

Cindy Whitehead: So, interestingly, as drugs are often discovered, this drug was looked at for its effect on depression. 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?” In this particular drug’s case, it all went the other direction. It had a pro-sexual effect.

Tim Ferriss: Oh, wow.

Cindy Whitehead: So, at that time, all of the study changed to look at this condition, specifically.

Tim Ferriss: I don’t know if this is due to the tracking. There’s some maybe folklore in this genesis story, but Viagra, same story.

Cindy Whitehead: Yeah, same. Absolutely. Blood pressure medication, low and behold, a very interesting side effect.

Tim Ferriss: So the folklore goes – I don’t know if it’s true – but the male subject would not give the medication back. They’re like, “Hey, this doesn’t work for blood pressure. Give us our supplies back.” They were like, “No, we want to keep them.”

Cindy Whitehead: Very interestingly, when I got to Addyi, I had built this great company for men. I was in this community. The company that innovated this drug originally was going to put it on the shelf.

They were going to walk away from it. One of the great researchers in the field went out to women who w ere in the trials and said, “I need you to come in and bring your medication with you. We’re going to have a normal meeting.”

He was actually delivering the news that they were killing it, that they were killing the development trial. He filmed it and the women were like this, giving their drug back – hands shaking, crying. He said, “You need to do something about this.”

Tim Ferriss: Two questions – why were they going to shelf it? When you say got the drug – there’s a good amount of discussion and deal making that goes into that. How does one get a drug? If you don’t mind discussing it, what does a typical deal structure look like for something like that?

Cindy Whitehead: Mine was very atypical.

Tim Ferriss: Well, then let’s talk about both typical and atypical.

Cindy Whitehead: Okay, happy. First, let me tell you just about how we got the drug. Lucky for me, I think I built 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. 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. 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.”

Tim Ferriss: Okay. So, was it a larger company developing multiple drugs?

Cindy Whitehead: Large German. I like to tease. I said, “It’s sex. We’re German. We’re out.” That helps actually promote the understanding. But you have to appreciate cultures inside of companies, certain categories that they’re in.

This would have been paving a new frontier for them.

Tim Ferriss: How did you find this?

Cindy Whitehead: I was watching all of this research being presented at the scientific meetings I went to at the 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.” Then they walked away. 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. 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 upfront. They won. I win, they win. 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. I think they bet on me.

Tim Ferriss: How did you convince them?

Cindy Whitehead: 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. 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 judgements on whether or not they needed it or the worthiness of treatment, but just purely the science had spoken and we needed to listen. I think they knew that was my definition of success. I wasn’t in this to create the next blockbuster drug. I was in it to make sure to make sure that women had access. Then they got to choose for themselves.

Tim Ferriss: Did you first deliver that message via email, in person?

Cindy Whitehead: In person.

Tim Ferriss: How did you get them in person for it, a conference?

Cindy Whitehead: Again, thankfully, this kind of key researcher reached out to them and said, “You need to meet with her.”

Cindy Whitehead: “I think she can get this done.”

Tim Ferriss: Got it.

Cindy Whitehead:  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. He would have to tell this story, but in my mind, the story goes he did that and he was like, “Okay, fixed, guys, moving on to women.” He’s actually spent almost all of his years since then just working on women and researching.

Tim Ferriss: No kidding. What’s his name?

Cindy Whitehead: Dr. Irwin Goldstein.

Tim Ferriss: Irwin Goldstein. Good for Dr. Goldstein.

Cindy Whitehead: I know.

Tim Ferriss: If you don’t mind me asking, if we can’t get into the particulars, it’s fine, but I’m just so fascinated by this stuff – in publishing, for instance, books, my world, typical royalties would range from, say, 12 to 15 percent for a hardcover. Keeping in mind we’re talking about books. So, the margins are very different, I’m sure.

Then there are fairly typical advance ranges for certain types of books, advance on royalties than there are typical royalty rates. 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.

Cindy Whitehead: 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 key areas of focus,” or whatever, you’d put it out there to auction, people would bid. They would be buying it on the basis or sort of a projected ultimate kind of peak sales.

So, ours was so different I don’t think the royalties look all too different than as you describe, but it was really a very unusual deal. Usually, you’re buying it for a healthy upfront that is anticipating peak sales.

Tim Ferriss: Got it. Is that an advance on royalties, just like books, where you’re getting pre-paid for the anticipated sales?

Cindy Whitehead: That’s making a big bet. That’s somebody coming in and betting on that future for it. So, I buy it. You go away. It’s mine now to further the development.

So, we had interesting – I can’t say it was a partnership. They just ultimately got a check if I was successful. Maybe I even surprised them.

Tim Ferriss: How did you get it through the FDA?

Cindy Whitehead: Well, I was talking about that moment of boldness of the rejection and that decision to fight them. I was fighting them because I had 11,000 women worth of data. That’s why I was fighting them. I knew that the science had spoken.

Tim Ferriss: It’s also a large sample size compared to, I’m sure, a lot of the other 26.

Cindy Whitehead: Extraordinary. So, we’re talking in the 700 to 800 patient range, vis-à-vis ours.  Viagra were big trials, 4,000, but we were several factors higher than that and a very different path. So, I think ultimately, I won on the science.

But what had to happen is we had to listen to women. I think in categories where we have natural 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 is a show-stopper in there. But otherwise, it is to turn that decision over to patients and the providers.

Because of, again, I think all of the 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.” 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. If it breaks down in the bedroom, it is breaking down over the breakfast table.

Tim Ferriss: Yeah, absolutely.

I might be butchering this, but I’ve read you quoted as saying something along the lines of 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. Not we, but most people. You certainly don’t, but many people in society do.

Cindy Whitehead: In society at large, for sure, we absolutely do. We sort of pat them on the shoulder. When is at with this woman outside of DC and she told me she 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.’”

When I saw that, I said to her, “Hey, mind if I show you something?” I popped open by MacBook, I started showing her, geeking out showing these brain scans. I turned to her and she’s crying. 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.” That really was a defining moment for when I said, “I’m going to fight the FDA.”

Tim Ferriss: So, tactically speaking, now you have the motivation.

Cindy Whitehead: Yeah. How do you do it?

Tim Ferriss: What do you do?

Cindy Whitehead: It is, actually, a path available to drug manufacturers. I like to call it the road less traveled to take them on. 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 they could have a better understanding for impact, for how they would define success. 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.

Tim Ferriss: Is there a name for this alternative path?

Cindy Whitehead: It’s a dispute resolution path. Then there’s something called an advisory committee, which is the FDA can go out, assemble experts. You almost go on trial. They read all of your data. They get to ask you, the company, questions.

Cindy Whitehead: They get to ask the FDA questions. Then the public gets to speak at the microphone. On that day, by the press of a button they vote. Would they approve it or not based on everything? I 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.

Tim Ferriss: 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.

Cindy Whitehead: 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. 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 had 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 and letting them make the decision for themselves.

Tim Ferriss: So, part of the reason that I’m asking, we definitely don’t need to get into this right now. Even though it’s called the Tim Ferriss show, it’s not me being interviewed, so I’ll try not to be long-winded. Part of the reason I’m so fascinated by this is I am in the process of doing my best to help get both MDMA and [inaudible] [00:54:40] through phase II trials.

Cindy Whitehead: Oh, yeah.

Tim Ferriss: Very much top of mind to me. Fortunately, MDMA was recently designated or received breakthrough therapy designation.

Cindy Whitehead: Awesome.

Tim Ferriss: Which is fantastic. The results with PTSD are truly astonishing. The magnitude of effect is just so incredible.

It’s like 22 percent efficacy psychotherapy alone, 72 percent efficacy – of course, you have to look at how that’s measured, but with the aid of just a handful of sessions. In any case, that’s part of the reason why I’m digging so much. It’s very much of great interest.

Okay. Where to go next? So, you’ve sold two companies, at least.

Cindy Whitehead: Yes, I have.

Tim Ferriss: To an entrepreneur who is someday thinking of selling a company or in the midst of maybe on the cusp of trying to sell a company, what advice would you give them?

Cindy Whitehead: The first is be prepared that if you sell it, it is both exhilarating and excruciating. I think you don’t anticipate that. It’s the, “Isn’t there the billion-dollar happy ending?” 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. Have a real sense of, “This is my baby,” but in the hands of an adoptive parent, it’s going to go to the next level. When you do that deal, make sure you have safeguards that they really will raise that child you want them to.

I’ll tell you a lesson learned for me. I sold my first company. Typically, when you sell a company, it’s structured transaction. You get an upfront payment and then hopefully, you participate in the success down the road. Certainly, that’s good for your shareholders. The first time I sold, it was a best efforts clause. Best efforts can hide a multitude of sins.

Tim Ferriss: Describe a best efforts clause. This is really important. So, everybody should listen very, very closely.

Cindy Whitehead: If you’re going to participate together downstream, you don’t want somebody to 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 sales people on the product. So, lesson learned. When I went in to 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’ll make this commitment in terms of disease state education.

What that ultimately meant for me is the opportunity when they didn’t do it to get the product back.

Tim Ferriss: Okay. We’ll definitely get to that. This best efforts is really important. I want to just emphasize it. It’s certainly been said that the man and woman who acts as their own lawyer has an idiot for a client, something like that. So, unless you’re trained as a lawyer, get proper legal advice, please.

Cindy Whitehead: Absolutely. On that point, don’t worry as much about the bank. People are always saying, “Who did you use? What is the bank?” Worry about your transaction attorneys because of how you write these contracts. In any structured transaction, they are your most important asset.

Tim Ferriss: Absolutely. 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 – publishing, television. If you are a product developer or inventor and you want to license something for a royalty, you only get a percentage of what is sold and what happens if they decide it’s not a priority? Do you have an out?

Cindy Whitehead: Well, how scary is it to think that somebody might take it on and kill it? Competitors wanting to own the market – often, you’re bought by somebody who has products in the category. What if they’re buying you and they’re going to kill your product?

Tim Ferriss: Absolutely. Or doing a fishing expedition to determine how they can kills you or steal your employees – super common.

Cindy Whitehead: Yeah.

Tim Ferriss: 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?

Cindy Whitehead:  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 count on, “Hey, this really needs to be in the hand of somebody who could march it across the globe.” I needed the plan of going it alone if they never showed up.

Tim Ferriss: What do you mean by that?

Cindy Whitehead: Meaning I had the 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.

In fact, if you want to command the highest price, you better have that ability to say, “Bye. I’m doing it myself. See you. I know you want it. I’m going to do it myself.” I think people sometimes mess that piece up.

Tim Ferriss: Yeah, for sure.

Cindy Whitehead: They go in on skids.

Tim Ferriss: Yeah. 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.

Cindy Whitehead: Yeah.

Tim Ferriss: Could you pull some Jedi mind trick? Yeah, maybe. I was given advice a long time ago because I’ve just negotiated so many types of deals. I’ll come back to why that doesn’t actually conflict with lawyer advice that I just gave.

But the piece of advice that comes to mind that I was given at one point was this expert, master negotiator, done a lot of business development and bought and sold companies, just dozens and dozens of times, he said to me, “He who cares the least wins.”

Cindy Whitehead: Yeah. Absolutely.

Tim Ferriss: It’s like the person who has like, “Take it or leave it.”

Cindy Whitehead: Absolutely. That’s true.

Tim Ferriss: I think some advice that I remember in the fundraising world, which is slightly different – but actually, we should talk about fundraising too – it was, “If you want money, ask for advice. If you want advice, ask for money.”

Cindy Whitehead: Yeah.

Tim Ferriss: Actually, the reason I said, just for people listening, that the negotiating deals does not conflict with the get a good lawyer is that – I’d love to hear your thoughts on this, but lawyers are 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 incentives and how lawyers are rewarded and how they are punished. If you want to be very business-forward and not play defense, it is often times very, very helpful 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 have the basic range of what numbers could look like so that you can disqualify a deal before you pay lawyers to put 20 hours in at $1,500.00 an hour.

Cindy Whitehead: No question. I totally agree with that.

Tim Ferriss: So, the second company, Sprout – hurrah, hurrah, you get the FDA approval. Before I get to my real question, I’ll give a real question, which I guess I just smaller – what did you guys do to celebrate? Did you do anything to celebrate? How did you feel? Button, button, button, button, holy shit. In that moment, when you first realized what had happened, how did you feel?

Cindy Whitehead: So, I have to tell you, it wasn’t at the moment of sale. It was the moment we won that advisory committee. What we did was – my team, they were blood, sweat, and tears true to the cause. They prepared so hard for this day. I actually threw a victory party the night before. I can remember the chairman of my board came up and said, “Wow, Cindy.”

Tim Ferriss: Hold on a second – the night before you got the news on the advisory committee?

Cindy Whitehead: Oh, yeah, because I thought –

Tim Ferriss: Because you were waiting – you were like, “Alright, we’re going to get the results tomorrow?”

Cindy Whitehead: Yes. I thought, “Win or lose, we will have given this all. We will have taken it to the mat.” I needed the team to go in with that. They had won the night before, before we ever got to the outcome.

Tim Ferriss: That’s really smart.

Cindy Whitehead: I can remember the chairman of my board came over and he said – he’s a Brit – like, “Cindy, I’m not sure I’ve ever seen this before, but I’m questioning this one right now, but I’m going to go with it.” 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. There was a lot of emotion with it. I woke up the next day. I’m the same person. I’ve still go to go to work. I’ve still got to get it done. I think people think they’re some kind of remarkable transformation from one day to the next and I think, actually, it’s often a little bit of sadness.

Tim Ferriss: Oh, yeah.

Cindy Whitehead: 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.

Cindy Whitehead: No question. The day of the approval, I will say we waited. What we knew is that the day we wanted the outcome just informs the FDA decision. So, it wasn’t the day that we got the approval.

Tim Ferriss: I see.

Cindy Whitehead: So, they take their information in.

Tim Ferriss: That’s one factor. Okay.

Cindy Whitehead: 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, the entire company was in. We were all standing around, pink balloons everywhere waiting for a victory.

What was actually so sweet about this is that all the other companies on the same floor – we were on the tenth floor of a building – I 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.

I can remember them showing up and it was 7:00 at night and they were like, “Oh, my god, how are you guys doing? Is it okay? Are you not going to get the approval?”

Cindy Whitehead: 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.

Tim Ferriss: So, as the fearless leader, you didn’t know what the verdict was going to be. You had high hopes.

Cindy Whitehead: Sure.

Tim Ferriss: Did you have anything prepared – what were you going to do if it came back a no?

Cindy Whitehead: Celebrate that we did it all.

Tim Ferriss: 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? What would you have said?

Cindy Whitehead: I didn’t imagine a scenario in which we wouldn’t win. The reason is 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. I think that in particular – look, I think that part of the characteristic of female leaders I love is a certain empathy.

I felt like that data informed through a lens of empathy of having like walked a mile in the shoes of these women and now, we have all listened to them. I believed we would get there. I really did. What I would have said to the team had we lost is I would have said, “I’m proud of you for putting it all in and for caring that deeply to see it all the way through.” It was grueling work and long hours and a lot of punches in the face to get there.

Tim Ferriss: Welcome to entrepreneurship.

Cindy Whitehead: Exactly. That’s right.

Tim Ferriss: You’re going to conquer the world, huh?

Cindy Whitehead: I will tell you, I have to go back to –

Tim Ferriss: Do you have a mouthguard? Good. You’re going to need that.

Cindy Whitehead: I’m going back to your story for the people thinking about selling. Be a little bit reluctant to give it up. It’s your point about who – he or she who cares the least –

Tim Ferriss: He who cares the least wins, yeah.

Cindy Whitehead: When we went into our first negotiation with the company that ultimately bought it, we went into the room. They made an offer.

Cindy Whitehead: They said, “Were going to walk out of the room.”

Tim Ferriss: I’m sorry. Say this one more time.

Cindy Whitehead: So, the company that was offering to purchase us, we went to this room. They were very excited.

Tim Ferriss: This is the second company.

Cindy Whitehead: This is for Sprout. Yes.

Tim Ferriss: We go into the room. Companies come courting. They want to buy us. They throw an offer down. 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 him into the room and sat them down for effect. They left the room and I looked around at my team and I said, “Okay, when I 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. She’s looking at me like, “Should I take the binders?” I’m like, “Leave them.”

So, we walk out of the room. Sure enough, I knew they would call me back to get those binders. So, they had a reason to reengage, which is, of course, “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 want to give back.” So, the conversation continued. That’s negotiation, right?

Tim Ferriss: Yeah.

Cindy Whitehead: But it was a fun story.

Tim Ferriss: So, for people listening who are like, “Oh, that’s one in a million,” no. This shit works.

Cindy Whitehead: Yeah.

Tim Ferriss: Yeah. A couple of thoughts for people listening – number one is there is a book called “Getting to Yes,” “Harvard Negotiation Project,” etc. I think “Getting Past No,” which is another book written by one of the original coauthors is actually a little more realistic, where 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. I remember at one point, I learned so much. I mentioned I lived in China for a while. It was in China where I really learned the flinch and realized, “Wow, you can actually improve so many deals just by letting someone negotiate against themselves.” It’s not like you’re making a counter-offer.

If you try to buy anything, at the time I think it was just called Silk Ally in Beijing, where you could by all the counterfeit Jordan shoes and all this stuff, they would always start off like 10X what any rational person would pay if they ever lived in China. Then you would counter and they go… Like you’ve just –

Cindy Whitehead: Offended them.

Tim Ferriss: You’ve clubbed their dog or something. The emotion would come pouring out so exaggerated. You would see these foreign exchange students immediately capitulate or reverse and be like, “I’m so sorry. I don’t mean to offend you.”

And then they’d walk off and you’d just see these people laughing. It’s like the flinch or silence, letting the silence doing the work.

One that I encourage people to use – read the room, know the person across the table – but 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? Is this the best you guys can do?” Don’t be condescending about it, but just be like, “Just so I’m clear, is this the best you guys can offer?”

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, my homework says – it could be inaccurate – three competing offers, is that right?

Cindy Whitehead: Yes.

Tim Ferriss: Were those forthcoming?

Were they inbound?

Cindy Whitehead: They were inbound.

Tim Ferriss: Okay. They were.

Cindy Whitehead: They were.

Tim Ferriss: Walk me through, then, how you, in a competition/auction environment, how do you make the most of that?

Cindy Whitehead: Well, for me, I think the winner emerged not on the basis of the price but on the basis of willingness to keep my team. That had been important to me when I sold my previous companies. 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, you do want that competitiveness because definitely it drives up the price and everything else. That’s how I reached my final decision.

Tim Ferriss: What were some of the most important terms?

Cindy Whitehead: For me? It was that we were going to go 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.

I can pull this incidence data out of the US, out of Brazil, out of the UK, wherever it may be, it’s the same for women worldwide. That factor of what became so attractive to me in this one company that came forward who bought us –

Tim Ferriss: Can you…?

Cindy Whitehead: It was Valeant. Sure. So, when Valeant bought us, it was that they did this deliberately. So, they had acquired a lot. They were highly inquisitive. They were a company with a lot of McKinsey folks and maybe fewer traditional operators. Their greatest criticism at that time – it has changed – but at that time it was really no organic growth.

So, I think they saw this product that had a lot of interest and an ability to prove it from scratch that they could grow it inside and they saw in me an operator who had been there, done that.

So, that deal structure was such that here, I could go out and 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.

Tim Ferriss: And you had deliverables and measurables instead of best efforts.

Cindy Whitehead: Absolutely.

Tim Ferriss: “We’ll do our best.” Handshake.

Cindy Whitehead: Absolutely. How many salespeople are we going to have?

Tim Ferriss: Thanks for the handshake, but my mama told me put it in writing.

Cindy Whitehead: That’s right. Exactly. These weren’t extraordinary. They were sort of market standard for what is brand new category drug launch 101. So, they were reasonable expectations.

Tim Ferriss: So, let’s fast-forward – we can spend a lot of time on any segment of your story. It’s just so amazing. This is not as – 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, who have the opportunity to then take back their company or product or whatever it is that they’ve sold.

So, what the hell happened?

Cindy Whitehead: Well, what happened is…

Tim Ferriss: First of all, if you’re comfortable, I think it’s public at this point – how much did Sprout sell for?

Cindy Whitehead: $1 billion upfront.

Tim Ferriss: $1 billion.

Cindy Whitehead: And we had a pretty impressive structure transaction on the backend.

Tim Ferriss: Like earnout/royalties.

Cindy Whitehead: Correct.

Tim Ferriss: So, tres commas, for you Silicon Valley fans. Then what unfolds?

Cindy Whitehead: 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 salesforce. I’m getting ready for launch. The deal is closing to full closure.

Eleven days into our deal closing, the world basically went sideways for Valeant. If you follow pharma, you certainly know they were at about $260.00 a share the day they bought us.

They’ve traded as low as $8.00 in the last two years. It was just…

Tim Ferriss: For those people who don’t know, why did that happen?

Cindy Whitehead: Accusation around drug pricing issues and also a non-disclosure of a pharmacy relationship that they hadn’t disclosed. So, it really just – it went kaboom. It was so sad for me for all of these salespeople who had come to work for me. They weren’t in the field a week before this happened. Me being who I am, here’s my baby. We’ve just gone out. The world is collapsing higher up. I’m not getting information and I’m screaming quite loudly.

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.

Tim Ferriss: “Hey, lady. We have enough stress.”

Cindy Whitehead: I was invited to leave. 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.”

They said, “Well, as it turns out, you are no longer going to be here.” I have to tell you, at that moment, for me, founder, sometimes you have to go, “You know what? I’m the founder and maybe there will be a personality conflict. They’ve taken my baby. They’ve paid good money.”

So, in an effort, I think, to check myself, I thought, “I need to step to the sidelines and cheer everybody on. I need to be positive about this and optimistic that maybe with me removed it will be championed inside of the organization.”

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.

Tim Ferriss: Now, there’s more to the story.

There is. Because 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. 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.

So, I think what was starting off as a lawsuit to be able to get through the noise of everything they were going to 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.” I think in exchange for dropping that lawsuit, they decided to give me the drug back.

Tim Ferriss: A few things – so, in exchange for dropping the lawsuit, they decided to give you the drug back. They did not charge you for the drug.

Cindy Whitehead: Correct. They gave me a loan.

Tim Ferriss: They gave you a $25 million loan to help you get started.

Cindy Whitehead: Yes, they did.

Tim Ferriss: And did you and other people who had equity in your company when it sold have to give back the $1 billion?

Cindy Whitehead: We did not.

Tim Ferriss: That’s a good deal.

Cindy Whitehead: It’s a good deal. 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.

Tim Ferriss: Just to clarify, you’re saying by all of your shareholders or a majority or board of directors?

Cindy Whitehead: 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. That speaks volumes, I think, to who funded me, what they really cared about. An easier path to money was probably just staying on the path that we were on. This is the path of getting it right. 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 to just do it in a different way, in a way that we’re all proud of.

Tim Ferriss: I have plenty of questions, but what’s next, then, for that particular drug?

Cindy Whitehead: What’s next is 101. It’s access, that women have access to the product. It’s education, that we remove some of the myth and misconception that surrounds female Viagra and the condition itself, and then I think it is marching across the globe. We’ve got a lot of work in front of us.

Tim Ferriss: Are you going to be at the helm?

Cindy Whitehead: Absolutely.

Tim Ferriss: Okay. So many questions… Let’s talk about rules for a second.

Cindy Whitehead: Okay.

Tim Ferriss: I think you’ve drawn this distinction. There are a lot of rules out there. There are some that you’re generally better off following.

Cindy Whitehead: The rules of law and order.

Tim Ferriss: The rules of law and order, regulatory, 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 a matter of personal best practices?

Cindy Whitehead: I embrace under-estimation as an opportunity to surprise people.

I think that I break rules in terms of it’s frustrating to me when people say, “Yeah, but nobody does it that way.” I’m saying, “Okay, nobody does it that way, like show me a rule in which I cannot do it that way.” 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 particularly women in business, I think women are bound by many more unwritten rules. This TEDx Talk I gave was about this, like what’s the DNA of a female rulebreaker because I think that it takes this extraordinary injustice and the empathy that surrounds that for them to really break a rule. That certainly is my story – fueled by the injustice, really informed by listening. Why would I move forward with something that nobody else was willing to do? I think there are rules about, “Do you talk about money?”

I like to say in the Pinkubator, my goal is to make women really rich. That elicits a certain response. I do these pajama parties in the Pinkubator, eighth grade girls –

Tim Ferriss: The Pinkubator – we’re going to come back to this, but could you give us a sense or two on what that is?

Cindy Whitehead: Sure. As part of the pink ceiling, I make early bets on breakthrough first either buyer for women and they all become part of my Pinkubator. So, I’ve got ten different companies in there right now, all with a female lens.

Tim Ferriss: How are you going to balance that with…?

Cindy Whitehead: Having a great team.

Tim Ferriss: Yeah.

Cindy Whitehead: Having a great team. 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’m with people who know all of my stories because they’ve been on the ride with me for 13+ years through the startups. So, it’s always about the other people you surround yourself with.

Tim Ferriss: 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 – this is from a bit of my homework also. Correct me if this is wrong and I’d really love to dig in very briefly – for people listening, this isn’t going to be all startup, finance for the next 30 minutes, so just sit tight. This will apply more broadly.

But I read that one mistake that you made at one point in your business was taking money from someone you either didn’t know very well or didn’t trust. Can you talk about what you learned from that to the extent that you can disclose whatever you’re comfortable disclosing and then how that informed later decisions or approaches?

Cindy Whitehead: My biggest fail, really and truly. Early days of Slate, I was fortunate that this drug was adopted by the top-tier.

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?” 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. I did the deal, all the right intentions, seemingly. It couldn’t have departed more radically in terms of our philosophy on how you compensate people, on how you treat people.

Tim Ferriss: And because you didn’t have the money, you paid them in equity?

Cindy Whitehead: Yes. They had a seat on my board. They came into this company, had this partnership with them. It was that inexperience, I think, in my first company of going, “God, I need money. God, I need this partner. I need this for scale,” and not being discriminating enough in terms of really who they were.” So, it was painful because we really didn’t get along.

It had the ability to cripple the company. At that moment that I could cut the deal, I had swallowed hard, hired as many people as I could. Our eight people were out sell their 40, cut the deal and –

Tim Ferriss: Cut meaning ended.

Cindy Whitehead: Ended it and went off to the races. But it taught me the lesson of –

Tim Ferriss: How long did it take you to cut the deal?

Cindy Whitehead: A year. I had a year agreement with them. It took years off my life. It didn’t feel like a year. It felt like a longer than that. But it was a lesson of who I was going to raise money from going forward.

This is the perfect segue to it. I had to buy out their position. I needed them the hell of my board. They could have stayed on the board even with that deal gone. I had people coming in to try to buy it out. Actually, one guy came in, a VC, and he came to our table.

One of the things I want to do is I spent time with him and he came out to the glass table, where we have our lunch together every day. He was hideous to one of my sales reps, just like the attitude, how he treated them. I thought, “Absolutely not. I am not doing it.”

Tim Ferriss: “I’ve seen how this move turns out. Let’s not do that.”

Cindy Whitehead: 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, we’re not going to get the money. We’re going under.” It was so important. I needed to get this group out. 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. I now started to understand I have to have people who care about who we are in our mission. So, I raised, actually, almost all of my money through basically angels or family offices, very unconventional in pharma.

Tim Ferriss: How much funding?

Cindy Whitehead: $100 million.

Tim Ferriss: Alright. So, $100 million through angels – I’m guessing we’re not talking like $25,000.00 checks.

Cindy Whitehead: Correct.

Tim Ferriss: How many of these people did you know in advance before raising the money? It doesn’t need to be an exact number. What percentage of the people you raised money from did you know before hand?

Cindy Whitehead: Three.

Tim Ferriss: Okay. Roughly how many were there?

Cindy Whitehead:  We were at a little over 100 in the end.

Tim Ferriss: How they hell do you do that without it becoming your full-time job for six-plus months?

Cindy Whitehead: 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 pockets of investors that I treated almost like they were units. I have an incredible group of investors in Fort Worth, Texas. I 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. 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.

There actually was great joy in communicating with them. I didn’t see it as a full-time job. I actually saw it as an opportunity for this incredible network, who today come in on a lot of my companies as well and invest in them.

Tim Ferriss: How did you choose people? How did you vet them? I know companies with – let’s just say in contrast. You could certainly have, say, a VC, venture capitalist, or somebody who comes in, writes a huge check and they say, “Number one, I need 10, 20 percent of the company and I want at least one seat on the board.”

Cindy Whitehead: Sure.

Tim Ferriss: That has its potential pitfalls. I’ve also seen situations where startups that are super lean and have a small company have a ton of people on their cap table. They’ve taken a ton of investors. All of a sudden, they’re getting the hug of death, basically, because even if the investors are trying to be helpful, they’re managing communications with 100 people.

So, how did you think about avoiding that? Family offices are kind of a unique animal, but how did you think about avoiding that potential problem?


Cindy Whitehead: I actually think I was hyper-communicative myself. I went on the offense on that. They were part of this with me. They were part of the ride. I was going to turn around to them and say, “How are you going to help me? Who are you going to introduce me to? What am I not thinking of here?” 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. 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.

Tim Ferriss: I promised we’d come back to the Pinkubator. So, what is The Pink Ceiling?

Cindy Whitehead: So, The Pink Ceiling is investment firm meets hell of a great place for mentorship, where we make bets on early stage companies by or for women.

Mostly all health tech and not only, I think, disruptive first, but often products that can be catalysts in social conversations we care about.

Tim Ferriss: What would be some examples of products or companies?

Cindy Whitehead: So, a company with a technology that detects date rape drugs in drinks.

Tim Ferriss: How does it detect?

Cindy Whitehead: Through color change. So, dip your finger in a drink, touch your finger to the decal. It changes colors if there’s a date rape drug. 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 were. 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? 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. Some women want to get rid of the evidence, including women who are going through infertility and don’t want a daily reminder. That’s a product.

I have a great young female founder who has a biometric sensor to recognize deviations in movement for athletes so they can start to signal when you’re moving differently and may injure in the future.

She’s such a story – mother was a Russian mail order bride, wanted to move herself and her daughter to a better life, came over to the US 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.

Tim Ferriss: Yeah, soccer is brutal.               

Cindy Whitehead: She decided, “Okay, I still have upper body strength, became a rower, got a full ride to Duke, and then invented this tech.

Tim Ferriss: Oh my god, what a beast.

Cindy Whitehead: Love her. 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.

Tim Ferriss: She didn’t have to yell, “Balls,” for you.

Cindy Whitehead: No, she did not. 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. So, it’s fun because I get to bet on these great people, doing, I think, really interesting things.

Tim Ferriss: Where is it based?

Cindy Whitehead: We’re in Raleigh, North Carolina, where I’ve built all my companies.

Tim Ferriss: What should people know about Raleigh?

Cindy Whitehead: People should know that Raleigh is number two in the country in terms of exits. I think that surprises people.

Tim Ferriss: I didn’t know that.

Cindy Whitehead: There you go.

Tim Ferriss: You would expect me to know that and I didn’t. Shame on me.

Cindy Whitehead: Pitchbook did the terms of the multiples we get out of companies. So, the next billion-dollar company will come from Raleigh, just like who knew the birthplace of female Viagra was Raleigh, North Carolina?

Great startup scene, wonderful talent in that area.

Tim Ferriss: I’m going to read a quote and it may be off, but I liked it. 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.

Cindy Whitehead: I think we just – 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 percent of VC funding goes to women, 2 percent.

That means we think have the population have 2 percent 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 they really care about.

Not pass over a product for women thinking it’s a niche brand. I think it’s also just this comfort with the conversation around money. I started talking about these pajamas parties in the Pinkubator. We have eighth-grade girls come through. We do all these drills or setting their sites for the C-suite.

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 you shouldn’t do that.” I said, “Oh, no, no, have them ask me.” 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. That’s okay 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 $1 billion.”

The next time I got up on stage, I said, “Hi, I’m Cindy Whitehead. I sold my last company for $1 billion,” because I was clear that, “Oh my god, I’m doing it.” 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.

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. To watch our outcomes and what it has meant for them in terms of freedom – I don’t really mean financial freedom. 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. I’m watching them start their own companies or fund their children’s companies. That’s what I love to see as an army pink ladies coming out of the Pinkubator who are sponsoring the next group to do it.

Tim Ferriss: 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. I think this underscores something really critical, which is we – and this is not gender-specific, anyone – we often think of the external opponents and how we might be restricted by someone else, which could very well be the case and is the case very often.

Cindy Whitehead: Yeah.

Tim Ferriss: 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 were following.

Cindy Whitehead: Absolutely.

Tim Ferriss: I remember talking to – I’m not going to name her because I don’t have her permission – but super successful female entrepreneur and I asked her what some of the main challenges were she thought women were facing.

She mentioned quite a few, which you’re very familiar with. But one that I didn’t expect was she said women need to learn how to ask for raises and negotiate. A lot of them just don’t ask. I don’t know exactly why that is, but I was like, “Oh, fuck.”

When I think about the female founders I’ve invested in, whether it’s Leah at TaskRabbit, which was acquired not too long ago by Ikea, or Tracy DiNunzio or any number of these women, they are all so good at negotiating. It didn’t even cross my mind that I was like, “Oh, shit.” It’s certainly true for a lot of men as well.

The point being be really cognizant of – 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.                

Cindy Whitehead:  I think a lack of asking for raises is also that discomfort or that don’t brag. It’s sort of not lady-like to talk about money or be capitalistic, if you will. I think that has an incredible effect that maybe we’re not so conscious of.

Tim Ferriss: Yeah, totally. If you were going to teach, say, 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 have as many weeks as you want. What would you teach? It doesn’t have to be anything we talked about.

Cindy Whitehead: What would I teach?

I would push people around how you’re going to make choices in life. I think that my teaching would be how do you set out there and sort of remove all of those confinements in thinking. I am lucky, I think, having grown up in such a mobile childhood. I think what it taught me is you can imagine I was always –

Tim Ferriss: Mobile, physically mobile.

Cindy Whitehead: Physically mobile.

Tim Ferriss: Was your dad State Department?

Cindy Whitehead: State Department, yeah. I was the perpetual new kid and always having to have that agony of what was going to happen. It turned out nothing bad happened, right? In retrospect, I went in anticipating that. 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 losing the fear? What’s the worst that can happen and helping folks go through that?

Tim Ferriss: Yeah. You can just have case study after case study after case study.

Cindy Whitehead: I think when I do the Pinkubator, I’m teaching a course in, really at its core, confidence for these girls.

It’s confidence in the choices that they make and going all in when they’re going to do it.

Tim Ferriss: I’d love to actually hear you elaborate on that. I’m looking through my many, many, many notes. One of the things I highlighted where I was like, “Yes, please, thank you for that,” 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 who 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.”

So, assuming that’s somewhat accurate, I’m asked all the time, “How do I build my confidence?” or, “How can I become confident?” 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. 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?

Cindy Whitehead: Yeah. 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.

Tim Ferriss: What do you mean by that?

Cindy Whitehead: They’re unexpected. 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. I think that’s certainly been the course of my career.

When you say pharmaceutical CEO who sold the last business for $1 billion, 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. So, as a result of being unexpected, I think it’s underestimated.

So, my key piece of advice is underestimation, you have two choices – you can either reel back in frustration and self-doubt, you can let that eat away at you, or you can gamify it as this opportunity to surprise people with your competence. So, I think that for founders, I’m looking at how they reframe the frustrations, the setbacks, the kicks in the teeth to this opportunity to go forward and surprise.

Tim Ferriss: What do you say to women – I don’t know if you get this question –

Cindy Whitehead: That’s confidence.

Tim Ferriss: Yeah.

What do you say to women – I don’t get this question because I’m not a woman, but I’ve certainly, with some of my founders, they get this question a lot from other founders, which is the belief – it might not even be a question that women should dial back their womenness, femininity –

Cindy Whitehead: Did you hear my reaction?

Tim Ferriss: I did hear that.

Cindy Whitehead: I choked.

Tim Ferriss: I did hear the choke. This seems to be a very common belief, not just among women, but certainly advice that men would give to women. It’s very prevalent.

Cindy Whitehead: The worst.

Tim Ferriss: What do you think of that?

Cindy Whitehead: The worst advice. It’s given and it’s given woman to woman, for sure. Whatever it may be, I absolutely – part of the reason I wear pink – so, I wear pink all the time. You should see my closet. But when I went through the process with the “female Viagra,” it was called the little pink pill.

People all but patted me on the shoulder and said, “That’s cute.” The little pink pill was so dismissive that I realized, “My god, this is a conversation we need to be having.” I started showing up in blazing pink to the FDA. “Hi, we’re going to talk about this.”

I think what it taught me is like in gender stereotypes or that underestimation, you run away from it. I guess, if you’re me, you run right toward it. The idea that there isn’t something valuable and unique that a woman brings to the table and in owning her femininity – you know, pink for me is about owning it as a woman, unapologetically pink. I like pink. I’m going to wear it. We’re going to have this conversation.

So, I think that’s the way to go. 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…” Listen, I was at a table – I won’t name the  conference – where were giving advice to younger women across the table.

A woman very accomplished sitting to might right told a woman, “You’re too pretty. You need to pull your hair back and not wear any makeup.” I said, “Absolutely not. If you’re in an environment in which you need to do that, move.”

Tim Ferriss: Yeah. So, I love the reason for the pink. It makes me think of a conversation I had with Amanda Palmer, the musician, on this podcast. She’s amazing. She’s a hell of a character, certainly has her fair share of controversy. I don’t know how this came up exactly, but I heard her referring to herself or her friends calling her Amanda Fucking Palmer, AFP. At some point, I was like, “What is the story with this Amanda Fucking Palmer?”

It turns out that one of her frenemies or just straight up enemies or somebody who hated her always referred to her as Amanda Fucking Palmer. Instead of letting it bother her, the way she put it to me was take that pain and wear it as a shirt, basically. I’m paraphrasing.

I love the fact that she took this barb or something that was thrown at her and turned it around and like co-opted it in and used it in such a way that she found empowering and maybe just funny to start with, but disarmed it in that way.

Cindy Whitehead: Yes.

Tim Ferriss: I thought it was just fantastic.

Cindy Whitehead: That’s awesome. I love it.

Tim Ferriss: I think we should just do a round two at some point or an extension. I’m not going to ask all of my rapid fire questions, but I do want to ask two or three of them.

Cindy Whitehead: Okay.

Tim Ferriss: So, the first is what book or books have you gifted the most to other people?

Cindy Whitehead: “Purple Cow.”

Tim Ferriss: “The Purple Cow?”

Cindy Whitehead: Yeah, I have to everybody who’s worked for me.

Tim Ferriss: What books besides that have you reread yourself the most, if any come to mind?

Cindy Whitehead: I won’t name one of yours because that seems too flattering.

Tim Ferriss: No, no, no, more, more, more.

Cindy Whitehead: What else have I read that I love?

Tim Ferriss: If none come to mind, that’s fine too.

Cindy Whitehead: Yeah. Pat Lencioni’s books – I love that.

Tim Ferriss: What is it, like “The Five Dysfunctions of a Team?”

Cindy Whitehead: “Five Temptations of a CEO.” Yeah. I think it was about what do you prioritize, what do you let go – I thought that was actually a great book. Maybe they’re simple reads that I need on the airplane.

Tim Ferriss: What is the last time that you cried tears of joy? This is a new one. Or the time that comes to mind…

Cindy Whitehead: I rescued a pig.

Tim Ferriss: You rescued a pig?

Cindy Whitehead: 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.

Tim Ferriss: How do you find a pig needing rescuing?

Cindy Whitehead: I was worried that my car was never going to smell the same. Just through a network, like knowing that, but I cried tears –

Tim Ferriss: The pig called a scientist and he said, “I can’t help you, but I know a lady who can.”

Cindy Whitehead: I cried tears of joy for making a better life.

Tim Ferriss: Hold on a second – this is a full-grown pig?

Cindy Whitehead: Yeah.

Tim Ferriss: Like hundreds of pounds pig?

Cindy Whitehead: Not a hog, like a pot-belly, but still big.

Tim Ferriss: Are you now the caretaker of said pig?

Cindy Whitehead: Yeah. I think it’s important to have – sort of in my daily routine, I’ve still got to scrape the shit off my boots.

Tim Ferriss: 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 Jessie Graff, who’s an incredible phenom in the “American Ninja Warrior” world, the most impressive hand strength maybe of anyone I’ve ever seen, certainly any woman. She’s probably 30 times stronger than I am, at least, which maybe isn’t saying a lot, but like 1,000 times stronger.

Incredible athlete. She has a pet pig as well, for those interested.

Cindy Whitehead: That’s cool.

Tim Ferriss: Okay.

Cindy Whitehead: Jessie, call me and tell me what to do.

Tim Ferriss: Jessie, 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? I’ll give you an example just to buy some time. I’ll give you some time to think.

When I asked Cheryl Strayed this question, who wrote “Wild” and has done 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 and the tomatoes and so on are very evenly distributed.”

She will also do this for, I think, her husband’s sandwich and rearrange it. That’s pretty odd.

Cindy Whitehead: That is pretty weird, yeah.

Tim Ferriss: There are a lot of weird things that everybody does.

Cindy Whitehead: I like it.

Tim Ferriss: What is one of yours?

Cindy Whitehead: 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.

Tim Ferriss: That’s unusual.

Cindy Whitehead: It’s kind of weird.

Tim Ferriss: Do you have any superstitions?

Cindy Whitehead: When I was a little girl, I was in the Fiji Islands. So, I had a very unusual childhood where there was a lot of superstition. So, I think being exposed to that young made me lose that 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.

Tim Ferriss: Do you have any examples?

Cindy Whitehead: In that culture, everything was very superstitious that if you didn’t see the fish first, you didn’t get in the water.

Tim Ferriss: Good omen, bad omen.

Cindy Whitehead: Yeah. I think at a young and impressionable age, they probably had an effect where I decided, “I’m not going to worry about this going forward.

Tim Ferriss: If you had to give a TED Talk on something no one would expect – it can’t be the pharma stuff, it can’t be the company building stuff…

Cindy Whitehead: A TED Talk on something people wouldn’t expect… Growing up in a third-world country? I don’t know. Could I do that one? Lessons learned?

Tim Ferriss: What I you had six months to prepare for a TED Talk but it had to be on a new skill. What would you focus on?

Cindy Whitehead: Oh my god, I would learn how to fiddle.

Tim Ferriss: Fiddle?

Cindy Whitehead: Totally.

Tim Ferriss: Fiddle like Irish bar music fiddle?

Cindy Whitehead: Yeah, for sure. I would learn how to do that and I would teach everybody else.

Tim Ferriss: Is this something you just came up with or is this something you thought about, like, “One day, I should learn the fiddle.”

Cindy Whitehead: Yes, I would love to learn how to fiddle. I feel I don’t have any music talent. It sucks.

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. I need to play music or inspire through that.

Tim Ferriss: Well, I will tell you, as someone who has been fantasizing about and simultaneously putting off voice lessons for probably a decade – I just started about a month ago, I want to say, or six weeks ago.

Cindy Whitehead: That’s awesome.

Tim Ferriss: One of the best things I’ve ever done.

Cindy Whitehead: That’s cool.

Tim Ferriss: It’s really been empowering and also worth doing, in terms of the fiddle, just so that you listen to music differently. Now I hear things totally differently, which is totally cool.

Cindy Whitehead: Next time I come on, I’m going to fiddle at the beginning.

Tim Ferriss: You don’t have to get good. Please, yes. Some people hate my intro music. So, perhaps I can license for a reasonable fee your fiddle. What do you do when you feel overwhelmed or unfocused? What do you do to get back on track or let some pressure out of the tires?                 

Cindy Whitehead: I usually call my big brothers. 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 like overwhelmed or anything else, nothing like my family to be totally unimpressed with my problems and kick me in the ass. I think that’s what I do. I probably call my big brothers. They’ve been hugely influential in my life.

Tim Ferriss: Can you think of an example of them kicking you in the ass or what they would say to you to be like, “Really?”

Cindy Whitehead: Yeah. I think it’s just generally…

Tim Ferriss: What do they do professionally, if you don’t mind me asking?

Cindy Whitehead: 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. He was a big part of why I went smaller when I left my big company career.

Tim Ferriss: When you left Merck?

Cindy Whitehead: Yeah. He said, “Go smaller, push yourself, challenge yourself.”

I knew I didn’t fit in big environments. So, he was important in that. But I can call my brothers, same thing, overwhelmed or overly enthused about myself, like, “Hey, did you see that I was just on with Tim Ferriss,” like, “Yeah, whatever.”

Tim Ferriss: That’s great.

Cindy Whitehead: Don’t be too proud of yourself. So, I don’t know. They’re classic big brothers.

Tim Ferriss: “Tim who, that shiny gnome with a big head?”

Cindy Whitehead: Yeah.

Tim Ferriss: “Not impressed.”

Cindy Whitehead: They like a lot of mockery.

Tim Ferriss: Well, they’ve also both spent quite a bit of time in the trenches.

Cindy Whitehead: They have.

Tim Ferriss: They’ve played full-contact sports. So, that’s always very helpful. If you could have a word, a message, a quote on a billboard to get out to millions, billions, metaphorically speaking, a lot of people, what would you put on it?

Cindy Whitehead: Can I put it in the Valley?

Tim Ferriss: Sure.

Cindy Whitehead: I’d put, “Fuck the Unicorn, Be the Workhorse.”

I’d like that to get out to millions of people in the Valley.

Tim Ferriss: Yes.

Cindy Whitehead: It would make me super happy. This is my distaste for all the grandiose speak in step and I think the lack of attention on the fundamentals.

Tim Ferriss: Show, don’t tell, friend. Get it done. How has a failure or an apparent failure set you up or led to later success, contributed to later success? I mean one potential example would be the decision to take that money from someone who your spider sense told you you shouldn’t take money from, right?

Cindy Whitehead: Yeah.

Tim Ferriss: Are there any other examples that come to mind?

Cindy Whitehead: Professionally, that’s certainly been the worst. I’m thinking of huge personal failures of mine that have taught me lessons along the way. I’ve probably crashed and burned a lot going through childhood of trying to figure out how to fit in in new environments and playing to the popular thought and it not working because it wasn’t authentically who I am.

I think at some point, I became comfortable that I might just be the outlier.

Tim Ferriss: What’s funny about being the outlier is you tend to attract other outliers. Then it kind of works out.

Cindy Whitehead: It does work. I love it, the band of misfits.

Tim Ferriss: 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 internets?

Cindy Whitehead: I’d love for people to find me online. On Twitter, I’m @CindyPinkCEO, that or 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.

Tim Ferriss: Cool. I will put those in the show notes as well for folks. Do you have any final parting words, advice, an ask of the audience, something they should consider, anything?

Cindy Whitehead: 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.

Tim Ferriss: I agree.

Cindy Whitehead: Just recently, I learned that only 17 percent of those profiled on Wikipedia are women. More than that deserve to be profiled with their stories. I thank you too for having me on today for that reason.

Tim Ferriss: Of course. My pleasure. For what it’s worth – this could be taken the wrong way by some people, but hopefully not – I didn’t invite you on because you’re a woman.

Cindy Whitehead: I get it.

Tim Ferriss: I invited you on because you’re a good entrepreneur.

Cindy Whitehead: Thank you. I appreciate that.

Tim Ferriss: If that also gets more women on the show, fantastic. They are out there. I’m really glad you took the time. Thank you for being on the show.

Cindy Whitehead: I think it’s your question to say, “What’s the worst that can happen?” I do think people should ask themselves that.

Tim Ferriss: Yeah. Absolutely. That is one of the most empowering questions. You have to spend some time on it. 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. For people who want to explore that, you can just check out my TED Talk, This has been really fun.

Cindy Whitehead: Really fun.

Tim Ferriss: Thank you for taking the time. We have so many other questions we could explore, but I’ll let you get back to your evening. For everybody listening or watching, hi, as always, you can find links to everything we’ve discussed, books, resources, @CindyPinkCEO on Twitter, Instagram, all of the places in the show notes, for this episode and every other.

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 before the weekend?

Five-Bullet Friday is a very short email where I share the coolest things I’ve found or I’ve been pondering over the week. That could include favorite new albums 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.

It’s very short. It’s just a little tiny bite of goodness before you head off for the weekend. If you want to receive that, check it out. Just go to That’s all spelled out and just drop in your email and you will get the very next one. If you sign up, I hope you enjoy it.

This episode is brought to you by I love WordPress. I have used it for so many years. It’s my go-to platform for blogging and creating websites. I use for everything every day. My site, is built on it. The websites for my books, including “Tools of Titans,” “Tribe of Mentors,” all on

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This episode is brought to you by Four Sigmatic. If you’re a long-time listener of the show or brand new to the podcast, my favorite Finnish entrepreneurs who founded this company – of course, I don’t know that many Finnish entrepreneurs, but they may be my favorites – have something new that I’ve been loving.

Some of you are familiar with Four Sigmatic. I’ve used their products for years now. They were introduced to me by an acrobat of all folks and they tend to mix different types of medicinal mushrooms into their products. I have recently started using their matcha, which is a green tea, which is designed as a coffee alternative.

If you’re trying to cut back on caffeine, as I am these days, the matcha is a great option and one that I originally learned to love in Japan. It has a very smooth texture to it. Their matcha blend in particular includes the amino acid L-theanine, which helps to provides a balance-boosted energy without the jitters.

It also includes the adaptogen astragalus, if I ‘m pronouncing that correctly, which may help with overall stress tolerance. For those of you that are wondering, no, the products don’t taste like mushrooms.

If they say mushroom coffee, for instance, another product I use, it doesn’t taste like mushrooms. It tastes like coffee. But you get the nutritional benefits of some of these special ingredients. So, the products don’t taste like mushrooms and are enjoyable. I offer them to my houseguests and use them myself and I don’t particularly want to drink anything that tastes like mushrooms.

So, moving on – the folks at Four Sigmatic have designed a few special deals for you guys, my listeners, which include many of my favorite products of theirs.

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The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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