It's Time to Reinvent the "Girlboss"
Free Book Preview: Unstoppable
Most headlines would lead you to believe that being a female founder today is all about breaking glass ceilings, shattering fundraising records, or spectacular rise-and-fall sagas. Emily Weiss is obsessively lauded as the Teen Vogue intern who rose to the helm of Glossier’s billion-dollar beauty empire. Ty Haney’s recent departure from Outdoor Voices was scrutinized down to the granular level of her Instagram stories. But what about everyone in between? What do these headlines mean for women entrepreneurs going forward?
To find out, I asked the Rad Ladies.
I never meant to start a pseudo-club for female founders, but over the short course of five years as an early-stage investor, the message was clear: Women tend to build, present, execute, and problem-solve differently than men. Women also tend to have shallower networks supporting what they are building. So I made it my responsibility to informally connect those I thought could help each other — and Rad Ladies was born.
Our first meeting involved 10 founders, 10 bottles of wine (yep), and three pizzas, and took place in a dark office in downtown Manhattan in 2017. The format was simple: Drink, eat, and let your guard down to talk honestly about what isn’t going well for you or your business — unsexy, non-headline-worthy material. The conversation, when framed this way, was unstoppable.
Rad Ladies has grown organically through supportive referrals over the years, today consisting of around 100 founders. We meet monthly (nowadays by Zoom) to confront all manner of business issues. We have a dedicated Slack channel with threads for cobranding, recruiting, fundraising, and more.
I asked some of the Rad Ladies what they thought about the recent resignations of Haney and other high-profile founders, including Sophia Amoruso of Girlboss and Audrey Gelman of The Wing, to name a few. The founders I spoke with were empathetic to the unknown challenges these founders may have faced, hesitant to blindly accept headlines, and mindful of the work still to be done to level the playing field. As one member put it: “The first wave of successful female founders proved that women could start and run businesses. The second wave should create visibility around all the things that are preventing us from doing it over and over.”
Many Rad Ladies felt strongly that looking ahead, it will be critical to take a cooperative versus cutthroat approach. They stressed adopting an abundance mentality, which involves reorienting roadblocks and reframing rejection as opportunity.
“It is the singular most important skill I’ve learned as a female founder,” Nu Dao, founder of Allies, told the group at one point. “When you hear a ‘no’ or face some obstacle, tackling it from an abundance mindset will radically change the results you’ll get. Women are generally not socially conditioned in a way where that mentality comes naturally to us.”
The prevailing hyperbolic narrative of the fallen founder fails to acknowledge the death-by-a-thousand-cuts truth about being a female entrepreneur today. A new playbook needs to be drafted based on honest conversations about how we confront challenges that sit behind the headlines, how we face the daily grind, and how we create abundance out of scarcity.
Rad Ladies itself speaks to the power of forming motivated, supportive networks. VC referrals originated internally have generated millions of investment dollars, and there have been countless brand partnerships forged, promoting audience cross-pollination. If the facade of glamour has helped propel female entrepreneurship in the past few years, going forward, the key will be in building collective strength to conquer the everyday.