E988: Aileen Lee, Founder & Managing Partner of Cowboy Ventures, pioneered actionable change to diversify tech & VC, shares early days innovating in e-commerce, insights on current funding landscape, dangers of prioritized growth over sustainability, & lessons learned from backing winners like Dolla

0:51 Jason intros Aileen Lee
1:36 Aileen on her time at MIT, early bias against women in math
5:56 What brought Aileen to San Francisco & working at GAP in the early days of the Internet
9:40 Aileen on working for Mary Meeker & what makes her special
10:25 “All companies that leverage technology are not the same.”
13:10 What made WeWork attractive to investors in the early days?
17:54 How the market is skewed to reward growth
22:35 Thoughts on SoftBank increasing valuations
28:24 How Aileen got involved with Dollar Shave Club
31:07 Jason’s experience with Dollar Shave Club
32:07 “Crushing it” culture in tech
35:12 Aileen’s history at Kleiner Perkins
36:27 Being a woman in VC in the 2000s
41:12 Starting Cowboy Ventures
43:46 Diversity in tech
48:38 What are they working on at All Raise?