Ep 22 - Wendy Li - The Secret Strategies of Billion-Dollar Portfolios

Your Money Guide on the Side

Wendy Li managed billions for New York’s top institutions — here’s what she thinks individual investors can (and should) steal from the pros.

After leading portfolios for the Met Museum, UJA-Federation, and the Mother Cabrini Health Foundation, Wendy now serves as CIO at Ivy Invest. She’s spent decades on the inside — and in this episode she’s walking us through how institutional investors actually make decisions, where regular people go wrong, and what it means to manage risk.

📚What We Discuss with Wendy:

🧠 02:17 — Institutions vs. individuals: why the ultra-wealthy play a different investing game
📉 06:28 — Risk vs. return: are you really being paid for the risk you’re taking?
📚 08:34 — Invest in what you know: learning by doing (and surviving your mistakes)
🪤 11:48 — Career course-corrections: mistakes, pivots, and staying in the game
🤝 15:28 — Trust but verify: what good investor relationships actually look like
💰 18:00 — The luxury of investing: identifying the how and the when to invest
🧾 20:32 — Portfolio allocation: managing your capital with intention
🚪 25:46 — Alternatives and access: knowing your place in a complex market
🕵️ 30:06 — Fund managers: who and how to choose
🛠️ 33:32 — Investing skills: humility, curiosity, and flexibility in the face of risk
🔍 36:58 — Where to learn: insider investment resources
🧰 42:18 — Practical takeaways: frameworks and tools you can use today

💡 What you’ll walk away with

• How institutions manage risk — and how to apply it to your own investing
• Why most retail investors misunderstand returns
• How to think long-term when markets are volatile
• What to ask before trusting a fund manager with your money
• How to approach alternatives without insider access
• The core skills every smart investor needs

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If this episode resonated with you, be sure to check out Episode 15, where Tyler breaks down the 7 steps to identifying your needs for a financial advisor.