Cowboy Ventures' Aileen Lee on pioneering diversity in tech & VC, lessons from backing winners | E988

Jason Calacanis chats with Aileen Lee about her journey from MIT to San Francisco, her experience at GAP during the internet's early days, and working under Mary Meeker. They discuss the appeal of WeWork to early investors, the market's growth bias, and SoftBank's role in increasing valuations. Aileen shares her involvement with Dollar Shave Club, her time at Kleiner Perkins, and the launch of Cowboy Ventures. They also touch on the diversity issue in tech and All Raise's current projects.

Speakers

AI Chat

Unidentified

Jason Calacanis

Host • 41%

Aileen Lee

Guest • 57%

Chapters

0:00	Opening
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?

Transcript

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