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
Aileen Lee, Founder of Cowboy Ventures, discusses diversifying tech & VC, early e-commerce innovation, dangers of prioritized growth, lessons from Dollar Shave Club, & challenges for women in VC. Insights on SoftBank valuations, WeWork, & diversity in tech.
Read more
AI Summary
AI Chapters
Episode notes
auto_awesome
Podcast summary created with Snipd AI
Quick takeaways
Aileen Lee emphasized the importance of focusing on sustainable growth over prioritized expansion in tech startups.
Aileen Lee discussed the challenges faced by underrepresented groups in the venture capital industry and advocated for diversity and inclusion initiatives.
Aileen Lee shared insights on the evolving funding landscape in tech, highlighting the skewed market dynamics that tend to reward rapid growth.
Deep dives
Aileen Lee's Venture Capital Journey
Aileen Lee, from Cowboy Ventures, shares her venture capital journey starting from her background with a traditional route through business school at MIT and Harvard. She reflects on her experiences as a first-generation immigrant and her motivation to pursue math and sciences, highlighting the societal biases faced by women in these fields.
Transition to Tech and Internet
Aileen Lee discusses her shift to tech, recalling her late adoption of the internet around 1997 after graduating from business school. She shares her experience at a startup selling books on the internet, presenting the transition from traditional business models to e-commerce and the challenges faced during the dot-com era.
Venture Capital Fundraising Challenges
Aileen Lee dives into the complexities of fundraising for Cowboy Ventures, detailing her strategic approach to target investors experienced in seed funding. She recalls the hurdles faced as a first-time fund manager and emphasizes the importance of focusing on prospective investors' knowledge and interest in early-stage investing.
Diversity and Inclusion in Venture Capital
Aileen Lee advocates for diversity and inclusion in the venture capital industry, sharing insights from AllRaise's efforts to accelerate success for women in the tech ecosystem. She discusses the challenges faced by underrepresented groups, emphasizing the need for a supportive network and opportunities for advancement.
Promoting Social Change in Tech
Aileen Lee highlights the need for a movement towards social change in tech, drawing parallels with societal movements like acceptance towards gay marriage. She stresses the necessity of creating a positive impact and leading by example to drive progress in diversity, inclusion, and culture within the industry.
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?
Get the Snipd podcast app
Unlock the knowledge in podcasts with the podcast player of the future.
AI-powered podcast player
Listen to all your favourite podcasts with AI-powered features
Discover highlights
Listen to the best highlights from the podcasts you love and dive into the full episode
Save any moment
Hear something you like? Tap your headphones to save it with AI-generated key takeaways
Share & Export
Send highlights to Twitter, WhatsApp or export them to Notion, Readwise & more
AI-powered podcast player
Listen to all your favourite podcasts with AI-powered features
Discover highlights
Listen to the best highlights from the podcasts you love and dive into the full episode