With the unofficial tagline “Make other women really rich,” Cindy Whitehead, CEO of The Pink Ceiling, the business she founded in 2016 focused on mentoring and investing in female-focused startups, expects the pay it forward model to work. “Money is in many ways power,” Whitehead says. “And it’s a power women need for the next stage of the entire women’s movement.”  

Cindy Whitehead has spent 20+ years at the helm of companies. Most notably, her third venture, Sprout Pharmaceuticals was responsible for breaking through with the first FDA-approved drug for women with low libidos. This little pink pill, known to Whitehead as Addyi and to the media as “the female Viagra,” gave the entrepreneur “a front row lesson on what it means for women to advocate for themselves and each other.” It sold for a whopping $1 billion upfront payment. 

She’s a businesswoman. A force. And a breakthrough artist in the field of health tech. Though Addyi’s trajectory didn’t play out as Whitehead expected (that story can be found here) and she says there isn’t a day that goes by that she doesn’t think about the company, she took away an understanding of how to champion for others, the way many supporters have done for her along the way.

Having always built companies from scratch, many people expected her to jump into the next operating role. She surprised them. “What rips the sheets off in the morning for me is fighting injustices. It is an injustice that women get 2% of funding. It’s a ridiculous idea that half of the population only has 2% of the good ideas.” It’s also statistically incorrect--  and Whitehead likes data. She also likes pink. For her, these are not incongruous notions. “I like pink,” the CEO explains. “I like being a woman. I think women have unique strengths to bring to the table and by god nobody is going to make me lose my pink.”

"It’s a ridiculous idea that half of the population only has 2% of the good ideas.”

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When she says people use “pink” and the stereotype it conjures as a means to dismiss an idea, those are conversations she tends to run towards, as breaking preconceived notions is what will ultimately create change. “It’s why I showed up in blazing pink to the FDA. Every time. Unmistakably I was there to have a conversation about women because we weren’t listening to them.” She’s had her critics, sure. But thinks women embrace an unapologetic approach. “When I showed up [to the FDA] talking about sex in all pink, there was a healthy dose of underestimation. And then I’d surprise them with all the data I know.” This piggybacks on her favorite piece of advice: “Prepare to be underestimated. And then show up and kill them with competence. I say it over and over again because underestimation as a woman in business is inevitable. It is going to happen. That can either force you to retreat or you can harness it and surprise them.”

The Pink Ceiling is not a classic VC. It is Whitehead’s own investment post Sprout.

Inbound proposals abound and Whitehead and her team take an active role in the companies they choose to move forward with. “We make decisions based on bandwidth and our ability for real impact.” Can she help a woman in fashion tech as much as she could help someone in the health tech? With the fundamentals of business, yes.  With her rolodex, no. She thinks “below the belt for women” is an untapped area. “It is the last taboo in health. Even as women we don’t talk about the things we haven’t been ‘given permission’ to. If it’s below the belt it comes to me.” However, she says The Pink Ceiling teams works really hard with the companies that make it through the vetting process to find them a home. Admitting, “It’s not always with us. We have 11 companies that we actively work with every day. About another 4 that we’re about to go into. And we’ve taken 50 women through the 3-month mentorship program thus far.”

"Underestimation as a woman in business is inevitable. It is going to happen."

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The company’s battle against injustice is happening on two fronts. First, the lack of access to capital.“It requires an extra step and requires them [investors] to do their own homework with the audience that [the product] effects,” she says of why male investors aren’t funding female-focused companies or female founders. “My career has taught me the unconscious bias runs deep. I don’t think when [men] are sitting across the table that they’re intentionally thinking, ‘oh well this is for women I’m not going to fund it,’ but they’re sitting there not connecting to it.

She continues, “If I’m going to go up for investment dollars tomorrow, I have the highest probability that the entire table seated across from me will be men. And if I’m pitching an idea that is uniquely suited to women, I’m talking to an audience that fundamentally doesn’t relate. And I think the human nature component of that is that I’m less likely to invest in things that do not particularly impact me. Hopefully we’re catching up. But it’s why at the Pink Ceiling I equally look at men doing great work for women.”

To point: Undercover Colors, founded by four men. It is a nail polish intended help wearers detect the presence of date-rape drug. For Whitehead, that company is the sweet spot. “It’s not just a tool, it’s a conversation,” she says. “I’m always going to love health tech. I like the geeks that are innovating, creating a real tool-- one that creates a social conversation.” At the time we speak, she’s got at least one eye on Lauren Weiniger's “The Safe Sex” app. “We’re not yet invested, but I’m closely watching." SAFE let's you show your verified STD status on your phone, and know your partner's status.

The company is also fighting injustice with the “Pinkubator” program, The Pink Ceiling's way of addressing the lack of access to female mentors. It’s an integral part of the business that tackles the need for more straight-talk amongst female entrepreneurs. "The conversation that I’m going to have woman to woman is different," Whitehead says. "There’s nothing wrong with a climate of encouragement, I agree with that wholeheartedly. But we have to be careful that we balance that with candor,” she says.

And while she marks the powers of observation and empathy as a “superpower” of women, particularly when applied to business, she believes "data, in particular, is informed differently through the lens of empathy.” When combined the two have immense power and potential. Totally solo however, they might make for risky business.

“Oftentimes we’re delivering news that people don’t want to hear,” she explains. “But here’s my worry: If I’m a young woman coming out of college today and I know by the numbers that my chances aren’t as good in a classic corporate world and I have this idea of entrepreneurship from Shark Tank, which has given me the moxy to go out and start on my own, that’s great." The danger lies in blind encouragement. “If nobody talks about the scalability or sustainability of her business, here’s what’s going to happen: she’s going to fail. And when she fails, I fear that we are going to reinforce a narrative that women don’t have what it takes.”

Mentorship is so crucial to the process that it’s part of her team’s investment consideration. If you look at the numbers, she says, women are not only starting businesses faster than men, they're also often starting businesses alone. "One truly is the loneliest number in entrepreneurship. When we look at investments, I’m looking to see if they’ve been resourceful enough to find that network of other women who are going to help propel them.” She says resourcefulness is as easy as Google, where you can find conferences (*cough cough*), programs, accelerators, and the access to people who will push you. “Sometimes we have a paralyzing fear when it’s not going the way we expected that there’s no fallback. There’s always a fallback. And I hope that when women feel that way they can push through the moments of the deepest fear of entrepreneurship."

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