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How These 8 Female Founders Get Customers to Have Uncomfortable Conversations

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This story appears in the
October 2019
issue of
Entrepreneur. Subscribe »

We asked eight of the entrepreneurs featured on our 100 Powerful Women list: How do you engage customers in uncomfortable conversations?

“We spend our days talking to directors of facilities about why menstrual products should be freely accessible in their bathrooms. To engage, we start with humor. Everyone has a period story. First there is blushing, then there is gushing with laughter and vulnerability. From there, we move to the facts, like offering menstrual products in schools increased girls’ attendance Related: This Female Founder Fought to Stay in the Game And She Just Raised $3 Million in Funding from Serena Williams, Mark Cuban and Arlan Hamilton

“Because I’m a Black female founder, these discussions often cover racial disparities in access to healthcare and the need for inclusive innovation in women’s health. In the past year, I’ve survived the traumatic stillbirth of my daughter and heard from people who have resorted to using socks because they couldn’t afford feminine care, so I’ve become a champion of making the ‘uncomfortable’ a comfortable part of the conversation.” — Arion Long; Founder and chief estrogen officer, Femly, a subscription service delivering monthly boxes of organic feminine care products

“People react to tone, and they naturally match the tone you use with them. So if we approach topics that might be awkward or uncomfortable in a calm and straightforward manner, people forget to be nervous. And then something magical happens—they want to talk about their sexual lives, as if they were waiting for you to ask.” — Janet Lieberman; CTO and cofounder (left, with Alexandra Fine, CEO, right), Dame Products, a women-focused sex toy company

“I always start off Related: This Founder Built a National Business By Helping Kids Get Into College

“So many brands in this space perpetuate the idea of ‘You can feel great on your period!’ or ‘Don’t be embarrassed to buy lube!’ and I think this is the wrong approach. When trying to get women to open up, we take a vulnerable and real approach, exposing the good, the bad, and the challenging when it comes to sex and periods.” — Meika Hollender; Cofounder and CEO, Sustain Natural, maker of natural condoms and feminine care products

“Historically, the sexual wellness industry has framed sex as something taboo or clinical, neither of which represents the reality of everyday sex. We launched to change that standard. To foster these conversations, we have a voice that doesn’t strip out the emotion of intimacy but is also matter-of-fact, friendly, and, most important, humorous, because that seems to disarm people the most and allows them to relate.” — Éva Goicochea; Founder and CEO, Maude, which creates sex essentials in a minimalist, ungendered design

“I created an adjacent editorial site where we tackle topics we know women aren’t talking about in polite conversation — periods, bladder leakage, mental health, sex, menopause and fertility, pregnancy loss, and abortion. I know now from the site that when women feel safe to talk about these experiences, they understand that they are not alone.” — Molly Hayward; Cofounder and chief brand officer, Cora, a women’s wellness company that provides products Related: Bobbi Brown’s Guide to Success: Go To Fewer Meetings, and Take More Action

“As the idea for our brand took shape and we connected with hundreds of consumers, we realized that people from all walks of life were actually eager to talk to us about these topics. So our goal is not to force uncomfortable conversations but to create a space that people can turn to, from our Instagram series around #FirstPeriodFridays to our ongoing dinner series. What we’ve learned is that women want to share their personal stories.” — Jordana Kier; Cofounder (right, with cofounder Alex Friedman, left), Lola, a brand of organic cotton period products sold Check out more stories from our October/November issue’s list of 100 Powerful Women.