31 Female CEOs Who Mean Business

The common theme is badass”

Katie Couric
Oct 17 · 5 min read
Sara Blakely is the founder of Spanx

LLast month, Forbes released its list of “America’s Most Innovative Leaders” — which included 99 men… and only one woman. Forbes received criticism for overlooking so many remarkable female innovators, and its chief content officer later reflected on the missed opportunity. But when it comes to a roundup of amazing female movers and shakers in the business world, look no further than journalist Diana Kapp’s new book, Girls Who Run the World. We chatted with Diana about the 31 amazing women featured in her new book — and why the world needs to pay attention to the many women business leaders crushing it on a daily basis.


Katie Couric: Your book Girls Who Run the World came out just a month after Forbes was criticized for the lack of women on its “Most Innovative Leaders” list. Why do you think this sort of thing is still happening?

Diana Kapp: The rooms of power are still almost all male. They hire, appoint, choose for the list people who look like them. It’s called “pattern matching,” and it’s a common phenomenon. We assume that the person who succeeded in the role in the past is what works and what we are looking for. A huge problem is the lack of women in venture capital. The decisions about who and what ideas merit funding are being made by men, and as a result, just 2% of female-led companies get financed. It makes no sense since the majority of purchasing decisions are made by females.

What’s a common theme you saw while interviewing these 31 phenomenal women?

The common theme is badass. These women don’t know the word “no.” When Jennifer Hyman was driving to meet Diane Von Furstenberg for a much-anticipated meeting, Diane’s assistant reached her in the car ten minutes outside Manhattan to say, “Sorry the meeting is cancelled.” Jennifer had the cojones to say, “What? What? I don’t hear you. My signal is breaking up. I’ll be right there in five.” And she just showed up. And the meeting happened.

These women aren’t waiting to get permission. They steamroll through problems. They are solutions-oriented. They are also relentlessly resourceful, figuring things out on the fly, whether that’s learning to arrange flowers on YouTube or perfecting their email subject lines so they are sure click-bait. What does resourceful look like? Natasha Case at Coolhaus wanted to launch her first ice cream food truck at Coachella. She could only afford an old mail truck with no engine. But, she remembered that her AAA membership came with one free 200-mile tow. So, she told AAA to tow her truck to Coachella. Coolhaus launched there, all the hipsters went wild for her chicken and waffles ice cream, and the rest is history. They expect and live with uncertainty, which is the only way, because a start-up definitely doesn’t have a manual.

In your book, you outline the ultimate business survival kit for women in the business world. What’s crucial for any up-and-coming female entrepreneur to know if they’re starting a business?

The advice Jessica O. Matthews at Uncharted Power would give her 13-year-old self is the same essential I’d give, “Make sure to wear extra padding.” Starting a venture and just being a woman in the business world is really hard. Hold tight to your conviction about your idea, your smarts and instincts, and ignore the naysayers — they are always out there.

Katrina Lake had her professor tell her Stitch Fix would be “an inventory nightmare.” We all know where that story ended up. Don’t wait to get everything figured out — the only way to figure things out is by getting started, running experiments and pilots. The fundraising is going to be a challenge, so set yourself up to succeed by using all the resources available to you and finding early champions.

What can women do to defy these statistics and level the playing field?

Women need to stop underestimating themselves and underselling their ideas. Female entrepreneurs need to train themselves, using coaches and learning about bias, to sell the massive upside potential rather than take the bait and go down the rabbit hole of all potential risks. They need to know going into the pitch meeting that men are more likely to ask female founders about downside risk. They need to overcompensate and sell themselves and their vision boldly. Brag! Tout! Beam! Women also need to develop mentors and relationships to make sure that they have always men in the room who have their back.

The biggest roadblock for female entrepreneurs is funding, particularly past seed and Series A. Groups like All Raise, started by VC’s Aileen Lee and Jenny Lefcourt, to double the number of female VCs in a decade and significantly increase funding for female entrepreneurs, are providing powerful tools to help overcome this. They are providing “office hours” with entrepreneurs and VC mentors, one-one-one coaching. Women need to take advantage of these offerings. Also, the obvious steps we all know matter, like closing the gender pay gap, addressing workplace harassment, reevaluating job specs for senior management, and giving women bottom-line/revenue responsibility because that is the track to leadership. Finally, women who can, ought to fund other female entrepreneurs.

And what about men?

Men need to step up and sponsor women, vying for them, funding them (especially VC men) and moving them into higher and higher leadership positions. They need to boldly commit to hiring half women when bringing in their new associate class. They need to remake the hiring process. Tracy Young, CEO of PlanGrid, figured out that using the word ninja for the nimble, kickass engineers they were looking to hire, signaled male. When the company changed the wording of the posting, its pool filled with female candidates. Once more women are in the decision-making process — whether making funding decisions or hiring decisions — we will start to see a new business world.

These women gives tons of tips in your book. Spanx founder and CEO Sara Blakely says to carry a pocket-sized notebook and Glossier’s Emily Weiss encourages readers to be “self-starting.” So, what’s a tip you would give to female entrepreneurs?

Candy and coffee can fix most any problem. Seriously — my secret weapon is my 5:45 a.m. daily running gang called the EMC (early morning crew). Ten of us have been meeting most mornings for 15 years, and we are an everyday support network. Our motto is just show up, and we all do show up for each other in every way in running shoes and out. Get yourself an EMC, whatever that looks like.

You ask these women for one piece of advice they would share with their 13-year-old self. What about you, Diana?

I was a girl who picked cake decorating and hairdressing as the workshops to attend at my elementary school career fair. I’d tell that girl to aim high always, that she is powerful and all is possible if she believes that. Also have her own opinions and to learn to express them.

This interview has been edited and condensed.

This originally appeared in the October 17, 2019 edition of Katie Couric’s Wake-Up Call newsletter. Subscribe here.

Katie Couric

Written by

Founder, Katie Couric Media. Newscaster: Wake-Up Call. Podcaster: Next Question. Doc filmmaker. @SU2C founder.

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Katie Couric and friends talk career, culture, politics, wellness, love, and money

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