John Quinn interviews Carolynn Levy, the Chief Legal Officer of Y Combinator, about her 13 years at the company. Carolynn describes Y Combinator's evolution from a small startup incubator to a major early-stage investment fund, detailing its structure, the selection process for startups, and the resources provided, including seed money, mentorship, and community. She shares insights into the challenges of her role, such as founder breakups and brand protection, and reflects on how her legal judgment has improved over time, emphasizing the importance of optimism and the qualities of successful entrepreneurs. Carolynn also recounts her professional background, from her early days in Big Law during the dot-com boom to her current position, highlighting the unique legal aspects of working with startups and the complexities of immigration for international founders.
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