Business & Careers

Self-Made Billionaire Cindy Eckert on Fundraising, Risk Taking + Rocking the Odds

BY Team BossBabe

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Cindy Eckert is a serial entrepreneur, self-made billionaire, and visionary mind behind the groundbreaking “female Viagra” drug ADDYI. She's on a mission to nurture the next generation of female trailblazers, bringing more women entrepreneurs into the billion-dollar founders’ club — and she's doing it on her own terms; in head-to-toe hot pink with dazzling confidence to spare.

After blazing her way to the top of the male-dominated pharmaceutical industry — building and selling two companies that sold for over a cool billion dollars each — Cindy launched The Pink Ceiling, an early-stage investment fund run by a team of women. The Pink Ceiling’s in-house incubator, the Pinkubator, brings to market female-led innovations like a flushable pregnancy test and other revolutionary medical devices that will literally change the world.

Cindy is well versed in the challenges of being a female founder with bigger-than-life ideas, and her goal is to give more women the power to do the same; to have more of a voice, more autonomy and the confidence to crack the mold and make their own version of success.

With a front-row lesson in what it means for women to advocate not only for themselves but for each other, Cindy is the ultimate boss babe. Read on to discover the story behind the self-made billionaire's success and what she's learned about everything from fundraising to hiring teams…

What's the story of your entrepreneurial journey?

I wanted better. I wanted a better environment to work in, and I wanted better for my pocketbook. Frankly, I wanted to make the world a little better, too.

I was in the pharmaceutical industry and I was succeeding and moving up the ladder, company after company, but I was succeeding despite the fact that I was totally uninspired.

What I thought was, what if I got all of these individuals and gave them permission to really shine in their own way? What could they achieve together? That's why I started my first business. It was called Slate.

I was doing it on my own terms. I wrote down my principles on the paper towel like you're supposed to do as a good entrepreneur. My complete theory was, what if I got these incredible people, high performing out of environments where they were uninspired or overlooked, put them together, put ourselves against a project, what could we do? In four years, we built the second most prescribed medication among urologists.

There were a lot of bumps and twists and turns, but the motivation to keep going came from the culture we were creating.

I ended up selling that off to take on this incredible first for women: to create the world's first medication for sexual desire in women. That was such a moment of wanting that better in the world. I couldn't believe if they built a company with a male sexual health drug, there were 26 for men, not a single one for women.

You can't look at that disparity and not know that something is wrong with that picture and so I'm looking at this science that we've really discovered what it is that unlocks desire for women and every single person's running away, which was absolutely my signal to run in.
I sold off my profitable business in men that were finally flying and going well, went back to totally zero to start over, but that one was because I was not going to sleep until women were given equal consideration when it came to their sexual health.

What was the point where you really decided to launch?

I was at a medical conference where all this data is being presented on women, including brain scan images that showed that for many of us in our lifetime, something will go off biochemically that controls our desire in our brain. I'm looking at this in black and white and nobody's doing anything about it and for me, it wasn't on the basis of science. It was on the basis of really like a cultural narrative that was holding us back and that was really that fueled by injustice moment to go forward and go down that path.

I've got to tell you, it's not the easiest path to take on the government for women's sexual pleasure. It wasn't going to be a straight line. I like to call it the road less traveled, but really the ignition was how much I was fired up inside. I mean, every day I woke up just trail bound and determined to see that through.

What were the first steps in your launch process?

I think the first is the paper towel. Grab a towel or napkin and write down five to eight things that are absolute truths for what you want this to be. You need to be really clear on what that business is going to look like. I call it the paper towel moment. All entrepreneurs have, I still have a photo of mine from once upon a time, and I really lived by that, those truths.

I lived by them in terms of how I hired, how I fired, how I incentivized, all of those things. Now you know who you want to be. What do you do next? I call it preach. I didn't happen to have a rich uncle so I had to go find the money for this idea of what I wanted to build. I think you've got to be unabashed in telling people what you're trying to do. Many entrepreneurs are very secretive because they're worried that they tell anybody, they may do it. Don't worry about it. Most people are not going to take the time. They're not going to have your same vision.

You really need to get in the room, get in rooms with other entrepreneurs, angels, those people and they're in every one of our cities all over the country and start preaching what you're trying to do because really having not had a network or anybody in my contact book that was naturally going to write me a check, I needed to get in those rooms and when I met one person, I asked them to introduce me to two, I asked them to introduce me to four, I asked them to introduce me to six and it really is how I got all of my money to be able to do what I wanted to do.

So paper towel, preach and then I think the last part is picking wisely; that's how you are going to build your team. I read a book called Purple Cow by Seth Godin. It's about the notion that we're all so inundated that it would take a purple cow standing on the side of the road really to get our attention. For me, that resonated in terms of the business and the people. As I interview people, I was looking for… I call them pink cows. They were highly individual that I could put into an environment, give them permission to succeed and when I went from my first business to the second, really those steps are the same.

At what phase of the entrepreneurial process do you start bringing new people on board? Do you have any tips for vetting the right fit?

Entrepreneurship is really lonely. It's really lonely. So you better either find your network that you're going to regularly be in the room with. There's a lot of research done on really the dynamic duo and how teams are successful. Even just co-founder teams do better and I think it is because there's going to be such moments of low and high and you really need to be able to trade-off between somebody else. If you can find somebody to do it with you early, I actually encourage that. In terms of when you start to scale, not prematurely.

When I first started my company, people would call in to speak to the legal department. I would answer the phone “Slate Pharmaceuticals” and they would say, “Can I speak to legal?” and I put the phone down for a few seconds and I would pick back up and say “Hello, this is legal.” At some point, you wear all the hats and there's a moment in time where I actually think running lean and mean like that even with the partner is great, but the moment in which you can no longer be the only salesperson of it, if you will, that's the signal to start to scale. That you are actually limiting your growth by not moving forward.

What's the secret to hiring effectively?

You're really looking for that cultural fit. In fact, I almost don't give a damn about pedigree for who fits and would embrace the culture that we're creating. Willingness to learn is way more important to me, but I have basically six choices I say you have to make to work for me and I'm really clear about those.

You have to choose to be an owner. I'm looking for people with an ownership mindset. Ownership mindedness goes well beyond actually just having equity in a company. It's kind of how you show up in the world and accountability. Choose to be bold. I only hire people to make bold choices. Fortune favors the bold. I think that's certainly been our story of the companies that we've built. You've got to choose to be learning. What a boring day it would be if I woke up tomorrow and said, “Oh, know it all.” That is the characteristic I think of the most successful entrepreneurs that I know they are insatiably curious.

In my world, you have to choose to be quirky, which sounds so weird. I don't interview people and say, “are you quirky?”  I think I'm looking for again that individuality and that real authenticity that shows up that you really would show up at work and be truly who you are.

You kind of lock arms and go out there against the world and appreciative, which is a life choice for me as sort of walking around with an attitude of gratitude. You're going to hit some dark days as an entrepreneur. I've had some dark days and I think we've still, even in the moments when I never thought I would cross the finish line with this first-ever medication for women, I still marveled with appreciation at what we were trying to accomplish.

How did you get over mindset hurdles and propel yourself through tough moments as an entrepreneur?

I think you've got to shift fear. So you will have moments of paralyzing fear and the only way and for me to get beyond that is you have to move your mind from playing the short game of all the doom and gloom it feels like is immediate to looking to the long game. As soon as you do that, all of a sudden your fear is more, “What if I don't do it?” So that's a big, big piece for me of mindset is we often walk through life playing a very short game and if we could reframe it to the long game, we would take bigger risks and bigger swings.

What were the biggest risks you've had to take? 

It was taking a risk on this medication for women and then actually getting rejected by the FDA, who completely controlled my fate. My biggest risk of all is when I made the decision to dispute the FDA. Like I said, fighting the government for women's sexual pleasure is the road less traveled, and yet I did it because women deserve to be the center of the conversation.

We were making a societal judgment on whether or not it mattered and quite frankly in doing that we were ignoring the science. I just wanted to be data-driven. So taking that risk was a pretty epic one, but it paid off and it paid off not only for us as a company, but I think for the collective win scientifically in women's health, but I'll tell you a story. In the last moment of that, there's a big public meeting and it's hard to even imagine this, but the FDA assembles a big scientific panel, they choose who they are.

What is your particular zone of genius?

I think that I have a really clear vision of what I want to see and that helps me. Seeing sort of beyond the critics, the doubt, the self, all of that is really that I can get uber calm in a moment in which there is a lot of conflict, a lot of things coming at you because I really am very clear about how this is going to play out three steps from now and that's been really helpful for me.

When you take on things that no one's ever done and this is true for all female entrepreneurs that are paving new paths completely, people are going to tell you that you can't do it. You don't have the background. You don't have the education. You don't have the money. You don't have the blah, blah, blah, blah. If you're really clear about what that's going to be, it's going to allow you to take in constructive information along the way, but tune out all of the noise that's getting in the way of your vision.

What should more female entrepreneurs know about fundraising?

The fact that we're celebrating the 2.7% last year went to female founders is outrageous. It was 2.1% I believe, maybe it was 2.4% the year before. The fact that we go, “Oh yay, it's up” is alarming. Less than 3% of funding, venture funding goes to half of the population. We think half the population is 2% of the good ideas. Ridiculous.

Here's the truth, eyes wide open, the odds are stacked against you. There are two things you can do about that. One is if you're going to go into a traditional VC, then they and you have any product that is female-focused, which is my world, they are going to position it as if it's a niche product. I will take a product that addresses half of the world's population any day.

Don't get hung up in the fact that they're being biased against your idea. Consider the human factor that people invest in those things they can relate to. So now how do I work around that? I say to them, “I need you to have somebody in the room who would be a user of this product to get their perspective.” You have every right to make an ask to your choosing who gets a piece of your company. We often forget when we're looking for money that we're choosing too. So that's a piece of it and gets me the room and I'm going to turn it around on me. So if somebody came to me tomorrow and said, “Cindy, I have the best invention in golf.” I'm not a golfer. I'm like, “Eh, I don't care.”

If you're going to VC path, I want you to think about your absolute right to ask for people in the room because again by the numbers is going to be a bunch of guys in blue and gray suits sitting across the table from you.

The other option is to find your money in a different way. I never raised any VC money. I raised $100 million through private individuals, none of whom I knew when I started. So that is a path available. Angel money in my mind is a very different kind of money for female founders and well, your curse becomes your blessing.

Aa you can imagine, I need to raise a lot of money. Pharma is very capital intensive and it was so frustrating to me and yet that curse became the blessing because I had this unbelievable network now of people across the country. The way that they bet on me was they really bought into the vision, the big vision and in all those moments of hiccups, I had when I got turned down when I'd have to go back and ask for 10 million more dollars, et cetera. They hung with me all the way through and had I had venture money, I suspect they would have walked much sooner.

They say that we are the sum of the five people we spend the most time with. Who do you surround yourself with and why?

I spend so much time working, so it's going to be my team. I need to put my fiancé in there as well. I'll tell you a common thread: they're all quirky. I really do invite sort of quirkiness into my life. These people are true characters to the core. All of them, very individual, very different backgrounds, walks of life, but the common thread is optimism.

I have people around me who always see possibility where others see limitations, that kind of thing energy every day. Now they're also irreverent as hell. So they also believe they can do the things that other people can't do and that's healthy too. I call it constructive irreverence and even with me, they're constantly pushing me.

Who are some female trailblazers that you admire? 

I'm a 100% biased, I will confess, but the women in my Pinkubater are remarkable. Take Bethany has invented the first-ever biodegradable pregnancy test. It's flushable. Only a woman would've thought of that, right?

This is an example of an idea that the traditional VCs would never get, but it's an extraordinary disruption from our mother's pregnancy tests which by the way also happens to be 80% plastic and it doesn't need to be. This is an example of somebody you might not have heard of, but she's about to disrupt a market in a major way and she's in her thirties and she's just getting started.

I also have Jessica from Texas. She'll reinvent the spinal tap. She's basically created what I call a stud finder for the spine. I don't know if she likes it when I say that, but that's the idea. Today, we basically feel around and put a needle in and 60% of the time we get it wrong. She's created such a simple device and yet what she will do is so remarkable and here's what I love.

The way that I think about these female trailblazers is not only that they're bringing these revolutionary firsts into this world, but they're changing our minds about what the next billion-dollar founder looks like.

What is your definition of a boss babe?

My definition of a boss babe is really simple: It is the woman who has shifted underestimated to unapologetic.


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