Lee describes growing up in an immigrant family, studying at MIT, and seeking out consumer businesses such as Odwalla and The North Face before joining Gap. She moved into venture capital at Kleiner Perkins, where she worked with John Doerr for 13 years, with a two-year break to lead digital media company RMG through the 2008 downturn.
A Conversation
Speakers
Aileen Lee, founder of Cowboy Ventures, talks with Y Combinator’s Geoff Ralston at Startup School about her career, startup leadership, fundraising, venture capital, and inclusion.
Lee says managing a company taught her that leadership requires adapting communication to different people and learning how to recruit them. She and Ralston emphasize qualifying sales leads: a customer should have a real, persistent problem and a reason to renew, or a company may end up chasing short-lived deals.
Lee recommends practicing a company story well before fundraising, using feedback from friendly listeners to refine it. She explains that institutional investors need a few very large outcomes: a $500 million to $800 million fund may need a multibillion-dollar winner, so founders should understand the return expectations behind investor questions.
Lee describes gender bias in fundraising, including a study where the same pitch raised twice as much when delivered in a male voice. She discusses All Raise and Founders for Change, then explains that her analysis of 39 billion-dollar companies found many founders started in their 30s and most had co-founders who already knew one another.
Lee suggests covering the founding team, problem and addressable market, product, competition, and financial plan in a pitch. In the Q&A, she advises nontraditional founders to show their insight and resourcefulness, recommends checking references on prospective investors, and says founders can pursue both warm introductions and cold outreach.
Takeaways
- Practice your fundraising pitch months ahead and use feedback to revise it.
- Qualify customers by checking whether their problem is urgent and likely to persist.
- Understand the fund size and return expectations of investors you approach.
- Reference-check investors before choosing long-term partners.
- Show how your background, insight, and resourcefulness prepare you to solve the problem.
Mentioned in this talk
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What was claimed 11
- foundedAileen Lee founded Cowboy Ventures
“the founder of Cowboy Ventures”
YouTube Unverified1 source· Talk
- role atAileen Lee is ran the online store at Gap
“My last job there was running the online store in 1999”
YouTube Unverified1 source· Talk
- previously atAileen Lee previously at Kleiner Perkins
“I wound up working for a partner there named John Doerr for four or five years”
YouTube Unverified1 source· Talk
- role atAileen Lee is partner at Kleiner Perkins
“I wound up staying 13 years”
YouTube Unverified1 source· Talk
- ceo ofAileen Lee CEO of RMGCEO
“That's what we were trying to build at RMG. I became CEO.”
YouTube Unverified1 source· Talk
- featureAileen Lee: Recommends practicing a fundraising pitch and getting feedback well before fundraising begins
“You want to start over the summer, practice, and get lots of feedback”
YouTube Unverified1 source· Talk
- featureAll Raise: A nonprofit aiming to accelerate success for women in the tech ecosystem
“All Raise is a nonprofit that aims to accelerate success for women in the tech ecosystem”
YouTube Unverified1 source· Talk
- featureFounders for Change: Founders publicly commit to inclusion and diversity on their team, board, and cap table when they have choices
“publicly commit to inclusion and diversity on your team, your board, and your cap table”
YouTube Unverified1 source· Talk





