Aileen Lee
Born 1970 · Age 55
U.S. venture capitalist, angel investor, co-founder and managing partner of Cowboy Ventures; coined the term “unicorn” (privately held $1B+ startups); co-founder of All Raise; former Kleiner Perkins partner.
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Life & Career Timeline
Born in New York City (Staten Island)
Aileen Lee was born in New York City; sources reference Staten Island as her place of birth. Daughter of Chinese immigrants.
High-school entrepreneurship: 'Buy or Dye' and 'Wok Out'
As a teenager in Millburn, NJ, Lee and friends ran small businesses in high school: tie-dye shirts ('Buy or Dye') and an egg-roll stand ('Wok Out').
Graduated Millburn High School; senior class president
Graduated Millburn High School in New Jersey and served as senior class president.
Elected class president at MIT (incoming sophomore class)
Newspaper item notes she was elected president of the incoming sophomore class / served as freshman class president at MIT.
Started as financial analyst at Morgan Stanley
Began career as a financial analyst at Morgan Stanley in technology M&A/finance after MIT.
Graduated MIT Sloan (Bachelor's)
Earned a bachelor's degree from MIT Sloan School of Management (Course 15/management).
Left Morgan Stanley (after two years)
Completed roughly two years at Morgan Stanley before pursuing MBA and operating roles.
Enrolled at Harvard Business School (MBA)
Entered Harvard Business School MBA program (typical two-year program culminating in 1997).
Worked in operating roles at Gap Inc.
Held various operating roles at Gap Inc. between HBS and joining Kleiner Perkins; role specifics not fully detailed in sources.
Earned MBA from Harvard Business School
Completed Harvard Business School, strengthening credentials for operating and VC roles.
Joined Kleiner Perkins Caufield & Byers (KPCB)
Began a long tenure (13 years) at Kleiner Perkins, working hands-on with series A-through-IPO companies.
Founding CEO of RMG Networks (KPCB-backed)
Served as founding CEO of RMG Networks, a digital media company backed by KPCB. (Exact founding year not specified in source; placed in Kleiner tenure.)
Worked hands-on with suppliers/portfolio companies at Kleiner
During KPCB tenure worked closely with companies including Bloom Energy, Rent the Runway, Trendyol, One Kings Lane and Tellme (dates span her Kleiner years).
Became one of the first female-led VC firm founders
By founding Cowboy Ventures in 2012, Lee became one of the earlier female-led venture capital firm founders in Silicon Valley.
Left Kleiner Perkins after 13 years
Departed Kleiner Perkins in 2012 after a 13-year tenure to start her own seed-stage VC firm.
Founded Cowboy Ventures (seed-stage VC)
Left KPCB to found Cowboy Ventures, a seed-stage venture capital firm focused on Life 2.0 companies.
Cowboy Ventures initial fund nearly $40M
Media reported Lee was almost done raising an approximately $40 million seed fund for Cowboy Ventures.
Public advocacy and articles on tech and gender (various essays)
Authored and spoke about topics including 'Why Women Rule the Internet' and 'Social Proof is the New Marketing' (dates span her public commentary period; exact publication dates vary).
Published 'Welcome To The Unicorn Club' (coined 'unicorn')
Wrote the widely-cited TechCrunch post 'Welcome To The Unicorn Club: Learning From Billion-Dollar Startups', popularizing the term 'unicorn' for $1B private startups.
Raised Cowboy Ventures Fund II (~$55M)
Cowboy Ventures raised a second fund reported at approximately $55 million (TechCrunch reported fund-raise activity in Sept 2014).
Spoke at Startup Grind Global Conference
Took the stage at the 2014 Startup Grind Global Conference and shared insights on seed investing and entrepreneurship.
Continued active seed-stage investing (approx. 12 investments/year)
Reported that Cowboy invested at a rate of about one company per month (~12 per year) and wrote about preferred check sizes ($100k–$1M; sweet spot $500k–$800k).
Listed as an angel investor on AngelList and active seed investor
Publicly listed as an angel investor; active in early-stage rounds across consumer and enterprise startups.
Tally raises $15M (portfolio company)
Tally, a credit-card management app that Cowboy Ventures invested in, raised $15 million in May 2016 (Lee listed as an investor through Cowboy).
Named a Henry Crown Fellow (Aspen Institute) (acknowledged)
Listed as a Henry Crown Fellow on Cowboy Ventures and other profiles (exact fellowship year not specified in provided sources).
Hired Ted Wang as Cowboy general partner
Added Ted Wang to Cowboy Ventures as a general partner to expand the firm's team and capabilities.
Appointed to board of the Castilleja School (board role)
Listed as a board member of the Castilleja School (source: Cowboy Ventures team biography). Exact appointment date not specified; event dated as an ongoing role.
Named to Forbes Midas List (2018) – #97
Included on Forbes' Midas List of top investors in 2018 at position #97.
Co-founded All Raise (nonprofit to support women in VC and startups)
Co-founded All Raise with more than 30 venture capitalists to increase funding and support for female founders and investors.
Spoke at Recode's Code Conference (2018)
Invited speaker at Recode's Code Conference in 2018, discussing venture capital and tech trends.
Cowboy Ventures Fund III: $95M
Cowboy raised its third fund, reported at $95 million, marking the firm's largest to date in its first six years.
Spoke at GeekWire Summit
Spoke at the 2018 GeekWire Summit offering advice on equitable technology and investing.
Named to Time 100 Most Influential People
Recognized by Time magazine as one of the 100 Most Influential People in 2019.
Named to Forbes Midas List (2019) – #82
Appeared on the 2019 Midas List at position #82 for notable investing performance.
Spoke at Silicon Slopes Tech Summit (2019)
Presented at the Silicon Slopes Tech Summit, discussing startup and investment trends.
Named to Forbes Midas List (2020) – #80
Included on the 2020 Midas List at position #80.
Appeared on Forbes' The World's 100 Most Powerful Women (2020) – #97
Listed by Forbes among the World's 100 Most Powerful Women at #97 (2020).
Profiled by MIT Technology Review
Featured in MIT Technology Review story about her career and influence on startups and women in VC (Feb 26, 2020).
Ongoing portfolio activity and public advocacy for women founders
Continued to invest through Cowboy Ventures in companies such as August, Dollar Shave Club, Textio, Accompany and others; continued public advocacy for female founders and investors.
Published 'Do startups have a chance vs big tech in the age of AI?' (Cowboy blog)
Authored an insights post on the Cowboy Ventures website reflecting on startups and big tech in the era of AI (Sept 21, 2024).
Published 'Welcoming Caroline Duffy to Team Cowboy!' (Cowboy blog)
Authored a Cowboy Ventures team announcement welcoming Caroline Duffy (Jan 9, 2025).
Published 'Welcoming Tyrone Anderson to Team Cowboy!' (Cowboy blog)
Authored a Cowboy Ventures team announcement welcoming Tyrone Anderson (Feb 7, 2025).
Key Achievement Ages
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