Aileen Lee is one of Silicon Valley’s top female venture capitalists known as the co-founder of Cowboy Ventures.

By Balthazar Malevolent


Aileen Lee (born 1970) is a U.S. seed investor. A venture capital investor, she is the founder of Cowboy Ventures.

Lee coined the often-used Silicon Valley term unicorn in a TechCrunch article "Welcome To The Unicorn Club: Learning from Billion-Dollar Startups" as profiled in The New York Times. A unicorn is generally defined as a privately held startup that has a $1 billion valuation or more – something rare (like a unicorn).

Lee earned her bachelor's degree from the MIT Sloan School of Management in 1992. After MIT, she worked as a financial analyst for two years at Morgan Stanley. She earned her MBA from Harvard Business School in 1997.

Lee joined Kleiner Perkins (KPCB) in 1999 and was the founding CEO of RMG Networks, a company backed by KPCB. Lee worked at Kleiner Perkins for 13 years and left in 2012.

In 2012, she left KPCB to start seed-stage venture firm Cowboy Ventures. In 2017, Lee added Ted Wang to the firm as a general partner.

Cowboy Ventures is one of the first female-led venture capital firms. Over the past six years, Cowboy Ventures has received three large funds, the most recent reaching $95 million.

Through Cowboy Ventures, Lee has made investments in many early-stage companies, including August, Dollar Shave Club, Accompany and Tally Technologies. She is a public advocate of increasing the number of female founders and investors in the Silicon Valley.

In 2018, Lee co-founded All Raise, a nonprofit organization which seeks to increase the amount of funding that female investors receive. The organization was founded as a collective by more than 30 venture capitalists who advocate for increasing the presence of women in venture capital. Lee described the organization's importance in saying “We believe that by improving the success of women in the venture-backed tech ecosystem, we can build a more accessible community that reflects the diversity of the world around us.”

What's your advice for entrepreneurial women who want to get into an area like cryptocurrency, but don't have a deep expertise on the topic?

Nowadays, to be honest, it really depends on what kind of a company they want to create. If it’s a robotics company, finding someone who has a technical background in robotics is helpful. But if I look at Rent The Runway, founders Jenn Hyman and Jenny Fleiss were both not technical. There are so many great contractors and people who have experience who want to help be a part of building something. As a founder, one of your most important skills is as a recruiter, as an identifier of talent and a curator of talent. If you hire the wrong developer or you hire the wrong UX person, you could run out of time and make a product that nobody likes to use. So it’s really about attracting a lot with very little resources.

There’s a saying that the definition of "entrepreneur" is being able to do more than anyone thought possible with less than anyone thought possible. That’s the ticket. You do not have to have a Ph.D. from MIT. It's about what can you get done with the little you scrap together. Jenn and Jenny are a great example of that. I’m so proud of what they’ve built. It’s such a game-changing and visionary product. And that was the key. They had the insight to create something that would delight customers.

Jenn Hyman has said in the past that, when pitching their ideas to investors, women need to assume their market is huge, that they're tapping into a billion-dollar opportunity.

She’s right, you know? It’s been quantitatively proven that women are judged more harshly when raising money than men, and that’s part of the reason why they only get two percent of the money and men get 98 percent.

Women who are looking to raise money need to have a big vision. Don’t play small ball. Communicate that you are trying to develop something big and important.

And when I was growing up, I was not taught to talk about money or to talk about making money, or to think that trying to make money was cool. Like it was distasteful for women to talk about money. That’s super wrong. Women should take control of their financial futures and feel confident and comfortable talking about money. And wanting to make money.

Aileen Lee

In other news, Rick Owens Fall 2021 fashion show. On the subject of underthings, the pentagram briefs from the January men’s show reappeared here wrapped around evening clutches, the implication being that these alien females had handled the “unhinged male aggression” that those briefs signified.

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