APR 26, 2018

The Pink Ceiling’s Cindy Whitehead: Empathy Fuels Innovation

It’s no wonder Fortune magazine called Cindy Whitehead a “tireless force of nature.” She’s the entrepreneur behind the first-ever FDA approved drug to treat decreased libido in women, and she’s built two businesses from the ground up, selling them for over $1.5 billion. After securing FDA approval for ADDYI, dubbed “female Viagra” by numerous media outlets, Cindy founded The Pink Ceiling, an incubator and venture capital firm dedicated to helping women-focused businesses. In this episode, she and Spencer discuss the importance of empathy in product design, how the #MeToo movement will alter the venture capital landscape and why Cindy is an unapologetic proponent of the color pink.

Press Play to hear the full conversation or check out the transcript below. You can also subscribe to Office Hours on Apple Podcasts and PodcastOne.

Spencer Rascoff: Cindy, thanks a lot for sitting down with me. I’m excited for this conversation. Great to see you.

Cindy Whitehead: Good to see you too, Spencer. Thanks for having me.

Rascoff: So let’s take a step back. Before we jump into your accomplishments and to ADDYI and the other things you’ve created and the state of the venture capital industry and how you’re disrupting it, tell listeners a little bit about your background, sort of how did you get here, what did you do coming straight out of college, and what was the beginning part of your career like?

Whitehead: In no way in a straight line I guess I would say. So my background, I had an odd childhood. I moved every year from the fourth grade to my senior year of high school, which I think perfected my being the new kid on the block constantly and the outsider in the room.

Rascoff: A military family or what?

Whitehead: State Department, yeah. So I think I got very good at listening, which became an important and critical skill in my future career. In college, had a particular fascination with business, a curiosity of what made things that tick that was really fostered by an instrumental business professor. So I would have to report to her every week and of course about different businesses I had learned about, why they were great and because of that made the singular decision that I was gonna go work for Merck out of college. And the reason why, Merck at the time was Fortune’s most-admired company, so I wanted to go learn from the best, thought I would apply it anywhere. And what I think surprised me when I got that job is that I fell in love with the science, fell in love with what they did.

Rascoff: What type of role were you in initially at Merck?

Whitehead: Sales. So started in the field, worked my way up, loved pharma for what it could do, what it had the capacity to do for people’s lives. Didn’t love how they got it done, didn’t fit in a big environment, and so progressively went smaller, smaller until I was crazy enough to start it from scratch myself.

Rascoff: Always through the sales side or the science?

Whitehead: So I’m not a scientist. I’ve always been surrounded by what I think is a fantastic scientific team. At the time I went to Merck in fact, it was a time of great innovation when you know big pharmaceutical companies really celebrated their research and development. Today they mostly acquire it from small companies; that’s where a lot of the true innovation happens. But went from sales into management, into really a breakthrough opportunity when I went to a company that had not only gone out and acquired products and product lines to become more sophisticated but then got gobbled up by one of the bigs. And when they did, I had a chance to be on an integration taskforce overseeing how we would put the new business together, and it was a lesson in all those things you needed to know to build a business from scratch.

Rascoff: Now we’re gonna talk a little bit about mentorship and the importance of the Pink Ceiling and gender diversity. How important was it that that influential professor that clearly shaped your life you mentioned that it was a woman?

Whitehead: It was.

Rascoff: Actually, didn’t mention it was a woman but used a feminine pronoun, so I picked up on the fact that it was a woman.

Whitehead: Yes.

Rascoff: Was that important, and if it hadn’t been a woman, would you have been noticed?

Whitehead: That’s an excellent question. I think it was important that she saw something in me and fostered it. Would somebody else have seen it? No one else did. I was in a lot of business classes and I think she particularly saw that. Many times I think in a room I would be noticed for being the thing that doesn’t fit, right. This goes back to my childhood too, like which one of these is not like the other.

And so I think that over time you perfect how you get beyond that. But in her case, I think she embraced it and that meant a lot to me. when I got that job – I have to tell this story. Her name is Professor Feeney. She’s not with us anymore; she passed away. But when I got the job, I remember calling her so excitedly I got the position, and she said, “Great. We’re going out and you’re buying.” So she was the perfect blend of encouraging and tough on me and pushing me to be better.

Rascoff: It’s amazing how teachers at all levels, high school, college, and beyond, can have such a huge impact.

Whitehead: No question.

Rascoff: I’ve talked a lot about teachers who have impacted my career, mostly from high school, and I’m grateful to them every day. So tell us about ADDYI and how that happened.

Whitehead: So my very first company that I built in pharma was with a male sexual health drug. So I was in a field that I love. Actually, sexual medicine is fascinating. A lot of our discovery is really new; the science is cool. It permeates effect on our life. And was really watching this science emerge in terms of our understanding of women and desire from the sidelines. There was a big company out of Germany that was innovating, and what I saw was that despite the fact that there was all this scientific discovery, company after company was walking away. And it made no sense to me. On the basis of the science, on the basis of the pathway that I had seen for the male drugs, it really became clear to me that it was on the basis of a societal narrative around women and sex. When that became clear, when I went out, when I spent a year, I talked to women with the condition, I made a decision to sell my business and take this on.

Rascoff: So was that a venture capitalist and pharma executive’s miss-sizing of the market, or there wasn’t enough gender diversity among decision makers and so they didn’t exhibit enough empathy to understand the issue that was facing these patients?

Whitehead: So 100 percent it wasn’t miss-sizing the market. The prevalence of this condition for women is the same as erectile dysfunction, so you get a picture of how big that market could be when you think of the Viagra and Cialis-like drugs. I think what it was was a reticence to take this on in a society that is stacked against taking women seriously when it comes to many different health conditions and, by god, for sure when it comes to sex. And if you look at the early commentary as this company was emerging with this science, all of the backlash for it I think they just made a decision it’s not who we’re gonna be, we’re gonna put it on the shelf, which is very atypical in pharma, right. If you have great scientific discovery, you put it out there, you shop it, in their case they were completely walking away.

Rascoff: So this company run by I’m kind of imagining like a caricature of kind of –

Whitehead: Classic pharma.

Rascoff: You know a lot of white men deciding how to proceed here.

Whitehead: Yeah.

Rascoff: They had a drug under their noses that had the potential to address women’s sexual interest.

Whitehead: First ever, yeah.

Rascoff: And yet they didn’t commercialize it. Now wouldn’t a decision-making apparatus like that want to ship a drug like that to stimulate this market, no pun intended?

Whitehead: You know it’s funny if you consider the fabric of companies and what happens. At the very beginning when I took this drug on, people were skeptical. Well if it was so great, why wouldn’t this huge company take it on? And I think you can never underestimate the personal sort of you know what we bring to the table personally are our philosophies and everything else that permeate those decisions. And I finally got to a place where I decided I have got to be able to explain this story more quickly and I said they said, “It’s sex. We’re German. We’re out.” So everybody would sort of laugh and go okay, I get it. But actually, what you were getting was truly a portrait of the company who was very conservative in a topic that was going to be taken on with not only curiosity but also controversy.

Rascoff: So this sort of orphaned drug was at this company that you were at or you saw?

Whitehead: No, I watched. I actually watched them present scientifically over and over again and was so impressed.

Rascoff: And then what?

Whitehead: So I watched this. They put it on the shelf. When they put it on the shelf, it was in a period of time when women were in open-label trials. That means they know they were on the drug. And one particular researcher who’s a visionary in the field learned that the company was gonna leave the space, put it on the shelf, and he said to the women who were in the trials, “Can I film this?” When he delivered the news that they were walking away, it was tearful.

Their hands were shaking as he gave the drug back and he showed that to me and said, “You need to do something about this.” And I think what he recognized is that it was gonna take a woman to listen to women, and once I did by god the rest of the world was going to as well.

Rascoff: And you raised venture capital money to acquire the drug?

Whitehead: No. Wouldn’t that be a nice and easy path?


Whitehead: It’s never been my path. So no, I actually had raised money from my first company Slate. I’d done that almost through high-net-worth individuals, angels who’d backed me because you know again my path was never gonna be the straight line. And when I decided to take this on, I sold that business off. I turned around to my shareholders and said, “Okay, give me some of that back, we’re going again.” And thankfully they’d watched me.

They knew who I was. They knew why this mission was so important to me that they all reinvested in me and we went for it.

Rascoff: You then as you acquired the drug ADDYI, did it have a brand name at the time?

Whitehead: No, it was named flibanserin.

Rascoff: Oh, that rolls of the tongue. [Laughter]

Whitehead: Yeah, I won’t share the old. The German name for it was even worse, the brand name. But yeah, it became ADDYI to us.

Rascoff: Okay. And then you still had to get FDA approval?

Whitehead: Yes.

Rascoff: And what was that process like and what can others learn from it?

Whitehead: Well you know what they can learn is that the world is truly a tale of two genders, and I say that because I built a company with one of the male sexual health drugs. And I knew what those requirements were and what those hurdles were, and they were fundamentally different. So sat down with the FDA, bought this drug, what is the path, what do we need to do. We went out, followed that path. We met all of our objectives with statistical significances end points that the FDA lays out, and we got turned down. And I was in that moment faced with this decision, small company, a lot of money for me to go out, do this additional work the FDA was asking for. So I made the decision to dispute the

FDA, and I did it because I had 11,000 women worth of data in which we’d met our end points.

Rascoff: Now they turn it down because of efficacy or side effects or both?

Whitehead: So they asked for more work, and we followed that path. We did more work, but what was hard for me is – let me give an example. So just for context, most people don’t know what drug discovery is. The average new drug approval has a little bit less than 1,000 patients. We had 11,000 women worth of patients. If you look at the male drugs, a big drug like Viagra, we had three times as many women in our trials that they had in theirs.

Rascoff: So you felt you were being held to a different standard than male sexual dysfunction drugs?

Whitehead: At this point, we were six years in. It took them in the process six months to get approved because Viagra in fact was fast tracked because it met such an important medical need. For sure we have a different lens when we look at female sexuality than male.

Rascoff: Eventually you got FDA approval.

Whitehead: I did.

Rascoff: Many “no”s later.

Whitehead: Yeah.

Rascoff: What was that feeling like?

Whitehead: It was incredible to watch the impact of science actually, science won. Science won the day, but then women won in turn. And it only won because we listened. Once we started listening to women, we understood what it was like to live with this condition, what it meant in their lives and marriages in many cases, relationships. Then we opened our mind to the science. Science had given us the answer from the get-go, so just to watch what that process is and what it means for women to not only advocate for themselves but for each other was game changing for me.

Rascoff: So that product empathy of being as an innovator, whether you’re an entrepreneur or a founder or I guess in your case an acquirer of another piece of science, empathy is being able to walk in someone else’s shoes. And yeah, there’s a great section in Emily Chang’s book Brotopia where she discusses how the lack of gender diversity in Silicon Valley and therefore the lack of empathy for users has caused a lot of product missteps. And she talks about Twitter for example and social media in general about the problem of trolling, of trolls and hateful speech and election hacking I suppose by extension that if there had been more women in the room when these social networks were being hatched, things like the mute feature, the block feature, other verified accounts, things that Twitter has raced to build later, might have been upfront.

Whitehead: Afterthoughts, of course.

Rascoff: So I mean does that resonate with you?

Whitehead: Listen, I gave a TEDx talk about the DNA of a rule breaker and specifically what do I believe the DNA of a female rule breaker? And I think it’s completely driven by empathy. I think there are all of these rules in society, you know rules of law and order that we all need to live by, but then there are a ton of unwritten rules. And I think women in particular are subjected to these, and it takes absolute frustration for them to then go and break it. And I think it’s that empathy I see time and again with the female founders of problem solving either for themselves or for each other. It is empathy. Empathy informs data differently. We had the same data set that won the day. We further characterized through study, etcetera, along the way, but actually when a committee got in front of it and just looked at the nuts and bolts, the black and white of the data, they voted three to one to approve it.

Rascoff: So you received FDA approval.

Whitehead: Yes.

Rascoff: When was that? What year?

Whitehead: 2015, August of 2015.

Rascoff: And then you sold the company?

Whitehead: I did.

Rascoff: Before commercializing the drug?

Whitehead: Yes.

Rascoff: So why did you make that decision?

Whitehead: It was the entrepreneur’s dream come true. Here we were this small company. I used to tease we could entirely fit in an elevator, a freight elevator maybe by the end of it, but you know that set out to change the conversation on women in sex. And what we did was to get it to the finish line so that women had a treatment option.

The ability to have somebody come in and march that across the globe and make it affordable and accessible to women, that was the extension of the dream. So it was really this opportunity to partner with a large multinational who’s gonna do that for us.

Rascoff: And when you sold it, you surely thought it would be on drug store shelves within months, a year, two years, soon?

Whitehead: Immediately. I’d already had the salesforce ready to go literally to pull the trigger in the event of a success scenario, in event of approval.

Rascoff: Unfortunately, that’s not what happened.

Whitehead: No. [Laughs]

Rascoff: So complete the story.

Whitehead: Yeah, it isn’t. In fact, it wasn’t a billion-dollar dream come true. It was disheartening for all of us who blood, sweat and tears that got it to the finish line. The company that we sold it to went through their own complete turmoil.

Rascoff: Unrelated to the acquisition of ADDYI?

Whitehead: Totally. Just you know and literally it was 11 days into our deal that things went sideways. And I couldn’t have written it as a movie in terms of how dramatic it was. And very shortly thereafter, I was gone. My entire team was gone, and the drug in essence was put back on the shelf.

Rascoff: But the check cleared?

Whitehead: It did.

Rascoff: The billion-plus-dollar check.

Whitehead: But that’s not what it was about you know.

Rascoff: Right. So what was that feeling like, right? You’ve got this incredible exit for investors and yourself, but what you’d been working on for so long never saw the light of day.

Whitehead: Heartbreaking, heartbreaking, heartbreaking. I think you know not only for me but for all of my team, for all of those who had surrounded us, you know advocates for women’s health and women’s rights. It just was heartbreaking to watch that happen when it was you know a victory so hard fought and won. And it took a while for me to sort of settle with that. I mean there isn’t a day that I don’t wake up and think about ADDYI; it really became part of who I am.

Rascoff: And at what point what did you regret? The sale? ‘Cause if you’d held on to it and maybe tried to raise money at that point to productionalize it you could have shipped it.

Whitehead: I think that given all the same information at the same time, it would’ve been the same decision. Knowing what I know now, for sure it would’ve been a different path, and I think that’s been my work in the interim is changing that path.

Rascoff: And so the story will hopefully have a happy ending.

Whitehead: Yes. [Laughs]

Rascoff: A second happy ending.

Whitehead: That’s right.

Rascoff: So you bought it back.

Whitehead: Got it back. Got it back for nothing, yes.

Rascoff: For nothing, okay. And what is the status today as we sit here in the spring of 2018?

Whitehead: Working on it. So the status is stay tuned. This story is not yet over. And I think finally women are going to have access to the treatment. That was always the definition of success for me. The definition of success was women with a medical condition deserved access to a medical treatment. Take it, don’t take it, that’s your choice, but I wanted them to have that choice.

Rascoff: Now I saw you on I think the CBS Early Show where you explained this medical condition and how it’s different from just plain-old too-tired to be intimate.

Whitehead: Totally.

Rascoff: So can you elaborate on that?

Whitehead: Litmus test. If it is no time, no energy, no privacy and that’s leading to honey, not tonight, normal. Desire ebbs and flows for women. But what we have learned and we’ve learned this even though brain scan studies is it takes a certain balance of key chemicals in the brain to be receptive to sexual cues. For some women, those get disrupted. And for those women, not only did they have a desire they were once happy with and it’s gone, but it’s been persistently gone and it’s causing them great distress. That definition really is what is a biological basis to a lack of desire to sex, called HSDD.

Rascoff: And when it’s commercialized will be the first available treatment for it?

Whitehead: Yeah, first-ever treatment. We’ve known about this condition too for four decades. It’s been in the medical literature. It’s been in our diagnostic manual. We just haven’t had anything to treat it until now.

Rascoff: So one of the reasons we haven’t had anything to treat it is because there’s been a lack of female entrepreneurs and female pharma executives and female venture capitalists to show enough empathy to create and fund these types of initiatives.

Whitehead: We got to 26 drugs for men before we got to one for women, just for the record. [Laughs]

Rascoff: So the Pink Ceiling is gonna change all that of course.

Whitehead: Well in every way the Pink Ceiling is a passthrough of all of my lessons learned on my way of the journey of Sprout. And we are an investment firm meets Pinkubator where we pick businesses disruptive first by or for women. So I love the first. I love the things that will be catalyst and important social conversations, and we’re making early bets on them. You know if I look down the road and define success of the Pink Ceiling, I’m gonna make other women really rich. I can do that unabashedly because I know by all the data if I do that they will pay it forward to other women and into their communities as well. And you know we talk a lot. Right now, we’re talking all about women need a voice. What women need is power, and money is power. We really start to change things when women sit on the other side of the table and they get to make decisions on what gets invested in, what products get to market, and that’s what we have the luxury of doing at the Pink Ceiling. So hopefully in our own small way we’re making a difference.

Rascoff: So what are a couple companies that have been either incubated in and/or funded by Pink Ceiling that you’re particularly excited about?

Whitehead: So one that has received FDA clearance that’s about to launch is a flushable pregnancy test. The company is called Leah Diagnostics. Great CEO, Bethany. I think only a woman would have in fact invented that solution to a problem. So not only is there an environmental solution but in every way this is not your mother’s pregnancy test, nor should the conversation be the same.

Rascoff: Because there’s more privacy if it’s flushable?

Whitehead: Absolutely. You know the discretion of it we have an image that with every pregnancy test it’s a smiley face and happy, happy.

That’s not always the outcome that’s wanted, and so I think that she’ll have an interesting conversation around it as well.

Rascoff: That is a good idea.

Whitehead: Isn’t that cool? It’s coming. You know and if you think of it even in the compassion of women who are struggling with infertility, actually seeing a pregnancy test sitting on top of the waste bin is a painful everyday reminder.

Rascoff: For sure.

Whitehead: So there’s just so many reasons why this invention is the right one and I’m excited to be invested in that. We have a wearable technology that detects date rape drugs in drinks. I have two nieces in college, this can’t come to market fast enough. These are the kind of things we love.

Rascoff: This is amazing. You told me about this when we first met, so can you just describe how this works.

Whitehead: Sure. So we’re figuring out the ideal application for women. We think it will sit actually on the back of your phone now, and you will be able to dip it in a drink or touch your finger from a drink to it, and it will change color in the presence of date rape drugs.

When you look at the epidemic we have on college campuses and campus assault, this is just a phenomenal product to come to market.

Rascoff: That’s fascinating. I think it was a nail polish adhesive when we first met.

Whitehead: Originally, yes. You know this is really incredible technology, and the art to reduce it to the size of a fingernail and think through the application and touching food and drink has been really an impressive scientific process that I think will have a number of applications in fact you know even beyond the detection of date rape drugs in drinks.

Rascoff: And so these are companies that entrepreneurs are finding you, pitching to you, you’re investing in and advising all the time of course. What is the structure here?

Whitehead: So I’ll tell you the structure. We make early bets. The companies typically are coming to market in a 12 to we’ll say 36-month time horizon. And I have some of my team with me who’ve been with me building two different businesses who surround them. So we typically have engineers or scientists, often the folks that were the entrepreneur that we’re investing in and we surround them with business acumen to bring them to launch. So we’re very hands on. We do about ten companies a year is our target and very actively involved everyday sleeves rolled up.

Rascoff: And I mean there are a number of, not enough, but there are a number of prominent women VCs that let’s call them traditional venture capital firms.

Whitehead: Yes.

Rascoff: Are they deal flow for you and back forth?

Whitehead: Absolutely.

Rascoff: How do you interact with the rest of the venture community?

Whitehead: So part of what you know when I decided to go out and do this, part of what was on me is to go out and meet all the others who are working to fix this problem as well, because you know if it’s the next cupcake shop, it’s not for the Pinkubator. Doesn’t mean it’s not an investable idea, couldn’t be great, but we work really hard to refer them out to somebody else who can help them. Similarly, I think they see things in health tech that they refer into us.

Rascoff: So one of the things that is fascinating about you is how you’ve masterfully built a personal brand about women empowerment, wealth, entrepreneurialism, and ADDYI is the perfect — let’s call it platform, I guess — on which to really build that brand, and now Pink Ceiling is part of it. One of the things you’ve done is you’ve branded this color. You’re wearing this hot pink kind of magenta-y color, and every time I’ve ever seen you in person or on the media this is your color.

Whitehead: Yeah.

Rascoff: So what’s your –

Whitehead: You should see my closet.

Rascoff: Yeah.


Rascoff: So when did you start doing that, and obviously it’s intentional but explain this decision.

Whitehead: Sure. So in the process with Sprout –

Rascoff: Sorry, Sprout was the company that created ADDYI?

Whitehead: Sprout was the company with ADDYI. People refer to ADDYI as the little pink pill, and all that was missing was a dismissive pat on the shoulder. Like the way that it came out was very telling to me about the conversation we needed to be having, and I think in those you have two decisions, right. You can either lean back from it, reel in frustration or doubt, or perhaps if you have my personality you go right for it, because that is what we need to be talking about. So I started showing up in hot pink to FDA meetings with the media at scientific conferences because we were going to have this conversation, and we were gonna have it on the merits of the science. But it took that to get people to pay attention and it stuck. I think underneath it is probably a healthy irreverence and an idea that why is it bad. Why do we apologize for those things that are feminine and make us I think have unique things to offer in the C suite or in the boardroom, wherever it may be. So unapologetically pink.

Rascoff: Well, good for you. It’s awesome. Thanks a lot, Cindy.

Congratulations. Good luck commercializing ADDYI and good luck with the Pink Ceiling.

Whitehead: Appreciate it. Thanks for having me on.