Navigating Challenges and Transformations in E-Commerce

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The chapter delves into the early days of the internet boom in the late '90s, discussing the speaker's transition from conventional retail practices to e-commerce. It highlights the skepticism and challenges faced in integrating online sales, focusing on infrastructure, customer concerns, and operational complexities. The narrative also explores the transformation of societal attitudes towards online shopping and the career journey of a research analyst supporting Amazon during turbulent times.

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?