Aileen Lee
Born 1970 · Age 56
American venture capitalist, angel investor; founder & managing partner of Cowboy Ventures; coined the term “unicorn” in 2013; co-founder of All Raise; former partner at Kleiner Perkins.
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Life & Career Timeline
Graduated Millburn High School; senior class president
Served as senior class president and graduated Millburn High School (NJ).
Elected MIT class officer
Elected a class president role at MIT as a freshman/sophomore (reported during early MIT years).
Joined Morgan Stanley as financial analyst
Started career as a financial analyst (M&A / technology deals) at Morgan Stanley, ~2 years.
Graduated MIT Sloan (BS in Management)
Earned bachelor's degree from MIT Sloan School of Management.
Left Morgan Stanley (end of analyst stint)
Completed ~2 years at Morgan Stanley prior to business school.
Joined Gap Inc. — operating roles
Worked in operating roles at Gap Inc.; involved in supply chain and business development; became chief of staff to CEO in her second year.
Graduated Harvard Business School (MBA)
Earned an MBA from Harvard Business School.
Served as chief of staff to Gap CEO (approx.)
Held chief of staff responsibilities to CEO Mickey Drexler during tenure at Gap (reported as second-year role).
Joined Kleiner Perkins Caufield & Byers (KPCB)
Became an investor at Kleiner Perkins, beginning a 13-year tenure working hands-on with Series A+ companies.
Founding CEO of RMG Networks (within KPCB era)
Served as founding CEO of a KPCB-backed digital out-of-home media company (RMG Networks) while at Kleiner Perkins.
Hands-on investor at Kleiner Perkins (portfolio involvement)
Worked hands-on with multiple portfolio companies (consumer & enterprise) and refined early-stage investing expertise.
Worked on early investments (examples: Rent the Runway, Bloom Energy)
Credited with hands-on work with companies in KPCB portfolio including Rent the Runway and Bloom Energy during KPCB tenure.
Led Cowboy's first seed investments (example: Dollar Shave Club seed)
Cowboy invested at seed in companies including Dollar Shave Club (seed investment in 2012).
Announced departure from Kleiner Perkins
Left Kleiner Perkins after ~13 years to focus on seed-stage investing independently.
Founded Cowboy Ventures (first fund ~$40M announced)
Launched Cowboy Ventures, an early seed-stage VC firm; initial fund reported around $40 million (announcements in mid-2012).
Published 'Welcome To The Unicorn Club' (coined 'unicorn')
Wrote the TechCrunch analysis that coined the term 'unicorn' (privately held $1B+ startups); influential industry publication.
Spoke at Startup Grind Global Conference
Keynote / stage appearance at Startup Grind Global; public speaking on entrepreneurship and investing.
Cowboy Ventures raised second fund (~$55M)
Reported to be raising/closing a second Cowboy Ventures fund around $55 million (TechCrunch reporting Sept 2014).
Tally raised $15M (Cowboy investor)
Tally, a credit-card management app, raised $15M (Cowboy was an early backer).
Dollar Shave Club acquired by Unilever for $1B
Dollar Shave Club (Cowboy seed investment) acquired by Unilever for ~$1 billion; seed investors realized large multiples.
Product Hunt acquired by AngelList
Product Hunt (Cowboy-backed) was acquired by AngelList (Nov 2016); another portfolio exit.
Ted Wang joined Cowboy Ventures as general partner
Added Ted Wang to Cowboy as a general partner to expand firm capabilities.
August Home (Cowboy-backed) acquired by ASSA ABLOY
August smart lock company (Cowboy investment) was acquired by ASSA ABLOY (Oct 2017).
Spoke at Code Conference and GeekWire Summit
Keynote / panel appearances at Recode's Code Conference and GeekWire Summit (2018).
Co-founded All Raise (nonprofit to support women in VC/startups)
Launched All Raise with >30 venture capitalists to increase funding and support for women founders and investors.
Cowboy Ventures third fund closed (~$95M)
Cowboy announced/closed its third vehicle at approximately $95 million.
Spoke at Silicon Slopes Tech Summit
Appeared as a recognized speaker at the 2019 Silicon Slopes Tech Summit.
Named to Time 100 Most Influential People (2019)
Appeared on Time magazine's list of 100 Most Influential People in 2019.
Appeared on Forbes Midas List and Forbes' World's 100 Most Powerful Women
Listed on Forbes' Midas List (various years) and placed #97 on The World's 100 Most Powerful Women (2020).
Rent the Runway IPO (company she worked with at KPCB)
Rent the Runway (which she worked with during KPCB era) went public in 2021; notable portfolio public listing exposure.
Cowboy raised $260M across two funds (including opportunity fund)
Reported deployment of ~$260M across two new vehicles in 2023, expanding Cowboy's capital base.
Cowboy portfolio outcomes reported (as of 2023/2025 reporting)
Cowboy's portfolio reported multiple unicorns, dozens of acquisitions, and over 100 investments across years (metrics reported in firm materials through 2023–2025).
Public commentary: analysis of unicorn markdowns and market reset
Publicly analyzed unicorn markdowns/secondary market discounts and called 2024 a 'scarification' year for VC-backed startups.
Received NVCA Venture Vanguard Award
Awarded the National Venture Capital Association's Venture Vanguard Award in recognition of contributions to the VC ecosystem.
Continued public speaking and published insights (TechCrunch Disrupt 2025)
Spoke at major industry events (TechCrunch Disrupt 2025) and published thought leadership on AI and B2C comeback trends.
Cowboy performance summary reported (as of late 2025)
Public summaries around 2025 reported Cowboy-backed outcomes across >100 companies, multiple unicorns and >30 acquisitions; firm capital raised cumulatively ~$500M+ across vehicles.
Personal: Family & home life (public profile)
Publicly described as married with three children (twin daughters and a younger son nicknamed 'Cowboy' who inspired the firm name), board member of Castilleja School, Henry Crown Fellow, hobbies include tennis and cooking.
Maintained Cowboy public profile and team updates
Active managing partner at Cowboy Ventures; firm website and posts (2025) show ongoing hires, writings, and portfolio activity.
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