WhoBuilt

A Conversation

Sep 21, 2018· 1 h 1 min· 21K views·Watch on YouTube

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.

A winding path into venture

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.

Leading teams and choosing customers

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.

Fundraising as storytelling and venture math

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.

Bias, inclusion, and the unicorn analysis

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.

Pitch structure and founder questions

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.

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