Four Lessons from Women Remaking Entrepreneurship

In the wake of the #MeToo movement and persistent gender disparities in tech and venture capital, the past few years have brought a powerful new wave of organizing and action in the tech community. Since 2016, the Project Include organization has been combining data and advocacy to drive diversity and inclusion best practices in tech companies. In 2018, Aileen Lee of Cowboy Ventures and a group of likeminded female VCs founded All Raise, a nonprofit dedicated to increasing the representation of women in the VC-funded tech ecosystem. Meanwhile, investors like Freada Kapor Klein of Kapor Capital and Arlan Hamilton of Backstage Capital have started venture funds guided by investment theses that explicitly aim to support underrepresented communities and founders. 

During the recent fall 2019 session of our own Entrepreneurial Thought Leaders series, seven of the eight speakers were women, and they each brought unique insights about how they fulfilled their ambitions as female innovators. A few particularly memorable lessons: 

1. It’s time to retire the hacker bro stereotype. 

When Lever co-founder and CEO Sarah Nahm arrived at Stanford as an undergrad, she recalls, the stereotypical tech innovator was a “hacker in a hoodie”: a brash, hyper-confident (and probably male) coder. “As stewards of the technology community, we need to create a much richer and more diverse set of role models for leadership,” she says. Her own template for success has been very different from that persistent tech stereotype. She’s thrived, she says, by learning to reinvent herself and finding power through collaboration. 

2. Standing up for your values makes leadership meaningful. 

“As an entrepreneur, you have an opportunity to set the tone from the top and change the way companies are built and run,” observes PagerDuty CEO Jennifer Tejada. One of the most satisfying parts of leading PagerDuty to its April 2019 IPO, she says, was doing it with a particularly diverse and inclusive team, where the leadership team was gender balanced and more than 60% of employees were born outside the US. She urges entrepreneurs to create a culture that is bold and unapologetic about its values.

3. Dolphins can swim with the sharks.

At times, admits Cowboy Ventures founder and managing partner Aileen Lee, she thought she might not stay in the venture capital business. As a woman in a male-dominated space, she sometimes imagined herself as a guppy swimming among sharks. But during a seminar at The Aspen Institute, she came up with a powerful new image: She was a dolphin. “They have every right to be in the ocean, they just swim differently,” she observes. 

4. Underdogs have a unique kind of power.

One benefit of being a founder from an underrepresented background: You can see opportunities that others can’t. Backstage Capital founder and managing partner Arlan Hamilton points to the example of Delane Parnell, the founder and CEO of PlayVS, who saw an opportunity in the eSports space and raised almost $100 million in less than two years. “That’s your biggest competition coming for you,” she says, “and without any of this baggage about what they think they’re expected to be.” 

There’s definitely a long way to go. Arlan Hamilton referenced a particularly troubling statistic: Black women capture an estimated 0.2% of all venture capital money, despite making up about 8% of the US population. Still, as women and other underrepresented groups push Silicon Valley toward an equitable path, they’re setting the stage for technology innovation that welcomes a much more dynamic set of players.