This Week in Startups 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
Oct 15, 2019
Aileen Lee, Founder and Managing Partner of Cowboy Ventures, has been a trailblazer in diversifying tech and VC. In this discussion, she shares her experiences confronting early gender bias in math and her journey from GAP to Silicon Valley. Aileen dives into the skewed funding landscape, highlighting the dangers of prioritizing growth over sustainability, particularly using WeWork as a case study. She offers insights from her investment in Dollar Shave Club and emphasizes the importance of diversity in the tech ecosystem, urging for stronger inclusion initiatives.
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MIT Admissions Fluke
- Aileen Lee was accepted into MIT due to a fluke in admissions, as they sought well-rounded individuals that year.
- She chose MIT to improve her procrastination habits and because she was inspired by an article about girls being discouraged in math and science.
Accused of Cheating
- After scoring highest on a math test in fifth grade, Aileen Lee was called to the principal's office.
- The principal questioned whether she cheated, reflecting the societal bias against girls excelling in math.
From Annoyance to Innovation
- Aileen Lee initially viewed internet enthusiasts as annoying during the dot-com boom.
- She later joined Gap's small internet team, facing challenges like customer acquisition and credit card hesitancy.