The Cowboy Team

Aileen Lee

Founder & Managing partner

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 has over two decades of experience working with both enterprise and consumer-oriented tech startups, starting at seed stage and staying involved for many years beyond.

Prior to Cowboy, Aileen spent over a decade with the venture firm Kleiner Perkins Caufield & Byers. At KPCB she worked hands-on with a range of companies including Bloom Energy (BE), Rent the Runway (RENT), and Trendyol (acquired by Alibaba). During that time she was also founding CEO of KPCB-backed RMG Networks, a digital media company. Aileen previously 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 board of the Castilleja School. Most importantly, she's mom to 3 kids plus a dog and chickens, and wife to "WFHH", a startup co-founder/CTO.

Aileen coined the business term “unicorn”, has been named to Time 100 most influential people, as well as to the Forbes Midas List in multiple years.

Partners with

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 kids, playing tennis, loafing, 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. In 2020 and 2021, a “spicy sangria”, and 2022 an Aperol Sour or Aperol Spritz. 2023 is to be determined!