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?