Uncompensated Risks in VC | Wendy Li | Superclusters | S5E12

“It’s not the probability; it’s the consequence. It’s not the probability when something goes wrong. It’s the consequence when it goes wrong.” – Wendy LiWendy Li is the co-founder and Chief Investment Officer at Ivy Invest, a fintech investment platform bringing an endowment-style portfolio to everyday investors.Before Ivy Invest, Wendy was Managing Director of Investments at the Mother Cabrini Health Foundation, where she built the Investment Office from the ground up and managed a $4 billion portfolio. Prior to Mother Cabrini Health Foundation, Wendy was Director of Investments at UJA-Federation, investing across a broad range of asset classes. Wendy began her career in the Investment Office at the Metropolitan Museum of Art. She has a Bachelor of Arts degree from Columbia University and is a CFA charterholder.You can find Wendy on her socials here:LinkedIn: https://www.linkedin.com/in/wendy-li-cfa/X / Twitter: https://x.com/askwendyliOUTLINE:[00:00] Intro[02:29] Wendy's family's history with Columbia University[07:55] The importance of understanding family history[11:09] Why Wendy chose to work at The Met[15:16] How did Wendy know in the interview that Lauren would be her mentor?[19:18] Specialist vs generalist in 2006[22:58] Pros and cons of using AI as an LP[29:02] The 80-20 rule for how an LP thinks[29:29] The one mistake EVERY SINGLE LP makes[33:27] What is the Takahashi-Alexander model?[39:38] Who do you learn from when your LP institution is so small?[41:22] The wisdom of an open-sourced LP reading list[45:34] What is headline risk?[47:09] What does 'uncompensated risk' mean?[50:20] Why now for 'endowment-in-a-box'[55:07] Wendy's proudest dish from her mom's recipe book[57:09] Wendy's last piece of adviceFollow David Zhou for more Superclusters content:For podcast show notes: https://cupofzhou.com/superclustersFollow David Zhou's blog: https://cupofzhou.comFollow Superclusters on X: https://x.com/SuperclustersLP