Aileen Lee

Aileen Lee

Founder/Managing Partner, Cowboy Ventures


Aileen is the founder of Cowboy Ventures. She loves partnering at the earliest stage with startup teams to build products customers love, and to help them scale to build aspirational companies. She works with both enterprise and consumer-oriented tech startups, starting at seed stage and staying involved for many years beyond.

Prior to Cowboy, she joined the venture firm Kleiner Perkins Caufield & Byers in 1999. At KPCB she worked hands-on with a range of consumer, enterprise and greentech companies including Bloom Energy (BE), Rent the Runway, Shopkick (acquired by SKPlanet), Tellme (acquired by MSFT), and Trendyol (acquired by Alibaba). During that time she was also founding CEO of KPCB-backed RMG Networks, a leading digital out-of-home media company. Aileen also held operating roles at Gap Inc. and started her career at Morgan Stanley.

She has degrees from MIT, HBS and MHS (Millburn High, in NJ). She's proudly the co-founder of All Raise, and on the boards of TimesUp and the Castilleja School. She also coined the business term "unicorn" and was named to Time's 100 most influential people. Most importantly, she's mom to 3 kids plus a dog and chickens, and wife to "WFHH", a startup co-founder/CTO.

What are some unusual jobs you’ve had in the past?
In high school, my 2 best friends and I worked various retail jobs at the Short Hills, NJ mall to make extra cash, with the dream of traveling. We also made and sold egg rolls at a street fair - our stand was called “Wok Out”, ha. We also made and sold tye-dye t-shirts in the hallways during high school, our company was called “Buy or Dye”.

What are you happiest doing when you’re not working?
Hanging out with my husband and our 3 kids, playing tennis or doing yoga, traveling when it’s safe to travel, gardening, cooking and eating, and catching up with my girlfriends.

If we went to happy hour, what would you order?
In 2019, my go to was the dark & stormy - dark rum with ginger beer. As of August 2020, that would be a “spicy sangria” - a ridiculously addictive drink made with spicy pepper infused vodka and wine.


Founder/Managing Partner

Cowboy Ventures

2012 - Present

Board Member

All Raise

2018 - Present

Board Member

Castilleja School

2018 - Present

Board Member


2019 - 2021

Associate, Principal, Partner, General Partner, & Senior Partner

Kleiner Perkins Caufield & Byers

1999 - 2012

Founding CEO

RMG Networks

2007 - 2009

Brand & Product Marketing


1999 - 1999

Special Assistant to CEO


1998 - 1999

Business Development


1997 - 1998

M&A Analyst

Morgan Stanley

1992 - 1994