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

This Week in Startups

Jason Calacanis

Technology

4.4 • 1.3K Ratings

🗓️ 15 October 2019

⏱️ 54 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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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0:47.6	minimum loan of $5,000.
0:51.9	We are really excited about our next guest. She's super busy. She's lived through about three of the cycles like me and she knows where the bodies are buried and how to make these companies scale.
1:05.4	She's seen it all and she doesn't really need an introduction.
1:09.0	Please join me in welcoming Aileen Lee from Cowboy Ventures.
1:13.0	So, you started in venture capital.
1:22.8	I think through what was the traditional route,
1:27.4	which was going to business school back in the day.
1:30.4	I know you went to MIT and then Harvard.
1:34.0	So obviously there's some kind of slacker, I guess, coming up.
1:36.7	Actually, you know, it's funny, I kind of was.
1:38.5	Not like, I'm not trying to say like I'm, I just,
1:41.0	I'm very lucky that, like, I think MIT had like a fluke in admissions that year where they were looking for people who were more well-rounded
1:48.4	Like they changed that policy after we graduated. What did you do at MIT? I actually was a Sloan undergrad.
1:54.3	Ah, what does that mean? Business? Yeah, I mean it's business. To be honest, I kind of, I
	...

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