The Secret Strategies of Billion-Dollar Portfolios | Wendy Li

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answer the question, How Much Can I Spend in Retirement? 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 If you're game to support the show, leaving a quick review really helps — even one sentence goes a long way! You can also join thousands of others investment minded individuals in subscribing to my newsletter here. 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.