September 21, 2024
Do startups have a chance vs big tech in the age of AI? History says yes…in due time
The Cowboy Team
Aileen is the founder of Cowboy Ventures. She partners at the earliest stages with enterprise and consumer-oriented startup teams to build products customers love, and to help teams build aspirational companies. She has over two decades of experience 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 companies from series A through IPO 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, on the board of the Castilleja School, and a Henry Crown Fellow. She's also mom to 3 kids plus a dog and chickens, and wife to a startup co-founder/CTO.
Aileen is also known for the analysis that coined the business term “unicorn”, being named one of Time 100's most influential people, as well as being on the Forbes Midas List and top seed investor lists for multiple years.
Please note: she is not involved with any dedicated cryptocurrency fund or investment vehicle. Please report any parties representing her involvement in this way to appropriate authorities, including the IC3.
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 or watching 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 & 2023 was aan Aperol Sour or Aperol Spritz. 2024 is to be determined!