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‘Where I got it wrong’: The Wing’s Audrey Gelman confronts the realities of rapid growth

For years, Gelman was the archetypal girlboss. But despite raising some $118 million and building a buzzy brand, there was more going on behind the scenes. “We prioritized business growth over cultural growth,” says Gelman, who explains why she’s committed to being more transparent. “The only way to make real progress is to change how the story gets told.”

‘Where I got it wrong’: The Wing’s Audrey Gelman confronts the realities of rapid growth
[Photo: Bryan Bedder/Getty Images for Equality Now]

Last fall, I was the first visibly pregnant CEO on the cover of a business magazine—a powerful symbol in a climate in which women-founded startups attracted less than 3% of venture dollars. (That number is even more dismal for women of color.) The accompanying Inc. profile celebrated the successes of The Wing, a network of spaces for women that I cofounded with Lauren Kassan. Off the page, we were having real challenges as a company. But I wasn’t talking about those.

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Instead, I was selling a new version of a decades-old fantasy that, as women, we can have it all: Be a young CEO, scale a fast-growing business, start a family. Not pictured were the brutal demands of growth, the overwhelming, uncharted waters of new motherhood, and the fear of failure that comes along with being a founder.

Off the page, we were having real challenges as a company. But I wasn’t talking about those.”

As a society, we decry the dismally low number of women who scale successful companies. The myth around female leadership is partly to blame. We’re still sold a dazzlingly unrealistic image of a superwoman—or in 2020, a girlboss. She raises capital without raising her voice. She has it all and does it all, without error. 

The myth doesn’t account for the reality that running a company is messy, terrifying, and often chaotic, especially in the early years.

When we started our company three years ago, it was to build a community where women could gather, connect, and feel safe and supported. We wanted to work with women to create something that could help women. We are proud of our successes—the covers and accolades, but more importantly, the connections, friendships, and businesses women have created and advanced within our spaces.

But what we’ve also learned is that when your product is community and the emotional and professional ecosystem that people create together, your work is inherently challenging. Failing to appreciate the complexity of creating a truly diverse and inclusive community—especially without the consistent self-interrogation of our own blind spots as white cis women—has led to serious stumbles and outright failures. The hardest part was that these failures led us to inadvertently replicate some of the very social hierarchies we’d set out to dismantle.

I’ve come to believe that growth as a leader requires that we understand that mistakes are fertile ground for learning. So, rather than tell you all the wins we racked up this past year, I’d like to pull back the curtain and talk about where I got it wrong:

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  1. While we were initially praised for a diverse membership and employee base, we believed we could scale and maintain that diversity without allocating the significant resources needed to make that mission a reality. We didn’t dedicate adequate attention to building inclusive recruiting practices. Employees were required to attend diversity and antibias trainings, but it was a one-time requirement and didn’t go deep enough. We also have realized that we weren’t explicit with our members about the expectations we had of their treatment of each other and of our staff. Incidents of micro and macro-aggressions within our spaces made it clear that we hadn’t created the conditions for safety, inclusion, and belonging for​ women of color. No matter how well-intentioned a company may be, there is no passive way to build an inclusive, anti-racist business.
  2. For the first time, employees we loved left because they didn’t see themselves growing at our company. In a fast-growing business with a mission of advancing women, we hired without properly defined career paths and growth opportunities for employees to advance within our company. In times of rapid expansion, it always feels easier to hire to fill immediate needs, but​ it is ​always better to hire for the future of your company and its employees.
  3. Rather than creating a healthy feedback loop and addressing with urgency the issues that members and employees identified, we prioritized business growth over cultural growth. There comes a time when your employees and customers know your business better than you do and when slowing down to listen becomes the smartest (and most strategic) thing you can do.

We went on a listening tour across all of our spaces to hear directly from both our members and staff about where changes needed to be made. Their comments are being incorporated into a formal Culture Code that we’re introducing to members this spring that explicitly addresses the behaviors and environment we want to create in our spaces. At the leadership level, I’m proud that our executive team is now 40% women of color. There’s more work to be done, of course, and we’ll be reflecting on our progress and course-correcting along the way.

Going forward, I’ve made a commitment to my team that I will be specific about where I need support in finding the answers. I’m admitting that we’re building something that’s new, and that mistakes and missteps are inevitable; our aspiration to build an inclusive, mission-driven culture while scaling a successful business is a complex balance that I’m constantly figuring out how to navigate. 

The reality of running a business is extraordinarily tough (and far less glamorous) than any magazine cover could show. It’s how the story gets told that needs to change in order for us to progress.

As more women, people of color, and other marginalized groups continue to step into positions of leadership, it seems necessary to project an image of flawlessness, knowing that we won’t be allowed to fail in the ways that our white, male, cisgender counterparts do—stupendously and repeatedly. But if we can normalize a more honest kind of leadership, one that doesn’t pretend to have all the answers or project an image of perfection—regardless of heightened scrutiny—then we might actually give ourselves the space we need: to listen to those around us, to ask embarrassing questions, to reflect openly about our shortcomings, to allow for the learning and unlearning that must occur to correct them, and to drive meaningful change within ourselves and our organizations.


Audrey Gelman is cofounder and CEO of The Wing, a network of work and community spaces designed for women with locations in New York, London, Washington D.C., Chicago, Los Angeles, Boston, and San Francisco. Prior to The Wing, Audrey worked in politics and public affairs. She has been recognized by Forbes 30 Under 30, Fast Company‘s “Most Creative People in Business,” and most recently as one of Bloomberg‘s “50 People Who Defined Global Business.”

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