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Aileen Lee

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Aileen Lee was born in 1970 in Staten Island, New York, the child of Chinese immigrants. She is the founder of Cowboy Ventures, a seed-stage venture fund focused on backing technology innovations in the way we live and work. It’s an extension of her work at well-respected Silicon Valley venture capital firm Kleiner Perkins Caufield & Byers, where she’s focused on consumer-oriented digital companies since she joined in 1999. Unlike KPCB, however, Cowboy Ventures focuses on smaller, seed-stage projects that imagine what they call “Life 2.0,” the ever-changing way we live our day-to-day in the digital age. In March 2014, Cowboy Ventures boasted the highest growth rate on Mattermark’s list of active venture capital firms.

Lee had an interest in entrepreneurship from an early age, forming start-ups with friends in junior high and high school, including a tie-dye t-shirt company called Buy or Dye and take-out egg roll stand called Wok Out. This interest carried her to MIT’s Sloan School of Management, where she earned her BA and served as president of her class for three years. She went on to Harvard Business School, where she graduated with an MBA in 1997. She also spent some time at Fudan University in Shanghai, studying Mandarin Chinese and teaching English from 1994-1995. She earned a bachelors degree from the Sloan School of Management at MIT, serving as president of her class for three years, and earned an MBA from Harvard Business School in 1997.

While her career began as a financial analyst at Morgan Stanley, Lee also spent time on the corporate level in several consumer products companies. Before joining KPCB, she held numerous operating roles at Gap Inc., including involvement in Business Development and Strategy, Gap Online, and as Special Assistant to the CEO. She also worked in brand and product marketing for Odwalla and The North Face. Her projects at KPCB include Callaway Digital Arts, Offermatic, One Kings Lane, Plum District, Rent the Runway, Trendyol, Dollar Shave Club, Storenvy and RMG Networks (formerly Danoo), where she served as the founding CEO for two years. She also worked closely with Blue Nile, Bloom Energy, Friendster, Good Technology, Shopkick and Tellme. Lee remains a partner at KPCB, but has shifted her attention to Cowboy Ventures full-time; she is the first KPCB partner to start their own fund.

Lee’s Cowboy Ventures is perhaps best known for the results of its “Learning Project,” an ongoing project centered on a dataset of U.S.-based tech companies started since 2003 and most recently value at $1 billion by private or public markets. Those valued at more than $1 billion were termed the “Unicorn Club,” with a few valued over $100 billion earning the designation “super unicorns.” Trends in the information they acquired could lead to smarter investment choices.

One of the key trends for Lee, however, is that there is very little diversity among founders in the Unicorn Club. While a record number of companies are valued at this high level, this growth isn’t reflected in the number of women involved in those top-valued tech businesses. Lee is passionate about fostering more gender diversity in the tech world, calling herself “a huge believer in power of women on the web.”

Lee is married to a Series A-stage co-founder/CTO, and they have three children, a dog, chickens, and bees.

Companies and Investments

Cowboy Ventures (Founder and Partner), Kleiner Perkins Caufield & Byres (Partner), RMG Networks (Founding CEO and Chairman Board Member), MiaSole (Team Member)

The Aspen Institute (Henry Crown Fello), Gap (Brand and Product Marketing, Gap Online), Morgan Stanley (M&A Analyst)

StyleSeat (Investor), Dollar Shave Club (Investor), Massdrop (Investor), NuOrder (Investor), JOYRIDE Auto Community (Investor), nWay (Investor), Brit + Co (Investor), True&Co (Investor), Locality (Investor), Librato (Investor), August (Investor)

shopkick (Board Director), Trendyol (Board Member), Rent the Runway (Board Member), Bloom Energy (Board Observer), Plum District (Board Member), Offermatic (Board Member), One Kings Lane (Board Member), Callaway Digital Arts (Board Member)

Lessons Learned

Follow your interests: Lee’s interest in entrepreneurship and start-ups didn’t start with her career or when choosing her degree. It began much earlier than that; she describes herself as “one of those geeks who used to read Inc. magazine” in high school. Her fascination with starting businesses led her to create businesses with her friends throughout junior high and high school, including a Buy or Dye (a tie-dye t-shirt company) and Wok Out (a take-out egg roll stand.) When you’re doing work that incorporates your interests beyond financial gain, you’re likely to be more engaged in your efforts, a key ingredient in the recipe for success. In fact, Lee recommends that start-up founders explain why their passionate about the businesses they’re creating in their pitches. She doesn’t just want to know if the company will make money, but why you’re doing it. As she put it, she wants to know if you’re visionary or mercenary when she decides whether or not to invest.

Overnight success is the exception, not the rule: Cowboy Venture’s research revealed that most of the companies in the “Unicorn Club” (companies valued at $1 billion or more) were founded by experienced teams in the their 30s who had worked together in the past and/or were college friends. The popular image of the wildly successful start-up founded by fresh-out-of-college 20-somethings is actually an outlier. The message here seems to be that there’s huge value in experience and the cultivation of strong working relationships.

Find a need and meet it: Cowboy Venture’s was born out of the realization that venture capital funds weren’t suited to the needs of the new, smaller generation of tech start-ups. Lee saw an unmet need for venture capital investing in start-ups that required smaller investments and more personal, boutique approach. She created Cowboy Ventures to meet that need, and its success is partially attributable to the fact that she saw and filled an existing gap.

Inspiring Quotes

Aileen Lee's Quotes

By adding new blood to the boardroom, these companies are getting a four-fer, or more: 1) gender diversity, and in most cases, age diversity around the table; 2) better understanding of core customers; 3) Social-Mobile-Local expertise and insight into digital platforms like Facebook, Google, Apple, Amazon, Twitter, Path, Square, Flipboard and Pinterest that are fundamentally changing business; and 4) hyper growth and rapid innovation DNA.

Aileen Lee

I think it’s a really important part of the life-cycle of these companies, more so than ever before. I like to be part of the trusted pit crew they are looking to for guidance. I look at the companies I am working with now, and I wish that I’d been all of their seed investor.

Aileen Lee

There’s an opportunity to make your board, and your company, smarter by adding diversity, especially of gender. And if you’re at a smaller company, there’s a greater likelihood that your board lacks diversity – and that’s an opportunity to seize, especially if your company counts on females as key users. Savvy companies are quietly changing up their boards of directors and teams, and this is giving them better collective intelligence, more community admiration, and better financial results.

Aileen Lee

It’s really hard, and highly unlikely, to build or invest in a billion dollar company. The tech news may make it seem like there’s a winner being born every minute — but the reality is, the odds are somewhere between catching a foul ball at an MLB game and being struck by lightning in one’s lifetime. Or, more than 100x harder than getting into Stanford.

Aileen Lee

I’m a huge believer in power of women on the web. I understand the role and importance of females in companies can make a big difference.

Aileen Lee

Influential Books