Your Money Guide on the Side

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

  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 withHow institutions manage risk — and how to apply it to your own investingWhy most retail investors misunderstand returnsHow to think long-term when markets are volatileWhat to ask before trusting a fund manager with your moneyHow to approach alternatives without insider accessThe core skills every smart investor needsIf 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.

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• Ep 21 - How Much Can I Spend in Retirement? Why the 4% Rule Gets it Wrong

  What if the most common retirement rule was never meant to be a rule at all?In this episode, we unpack the origins, flaws, and overlooked nuances of the 4% rule—and why it might not be the best way to plan your financial future. From its fear-based beginnings to its rigid application in a dynamic world, Tyler breaks down 5 key reasons to rethink the 4% rule altogether.You’ll learn:Where the 4% rule actually came from (hint: worst-case scenario thinking)What the Trinity Study really showed—and what most people ignoreHow sequence of returns risk can silently wreck your planWhy portfolio size and asset allocation matter far more than a static percentageSmarter, more dynamic strategies to adjust year-by-yearIf you’ve ever asked, "How much can I safely spend in retirement?"—this one’s for you.📝 Leave a review if you enjoy the episode or send your thoughts to [email protected]. This show is for you, and we want it to be as good as it can be.

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• Ep 20 - JL Collins - The Simple Path to F-You Money (And Why You Need to Ask Your Boss for a Paid Leave Today)

  Today’s guest is someone whose work has quietly and profoundly shaped how a generation thinks about money. JL Collins is the author of The Simple Path to Wealth, a personal finance classic that has empowered hundreds of thousands to think differently about investing, independence, and freedom.In this conversation, JL and I explore the real meaning behind financial independence — not retiring early, but reclaiming your ability to say no. We go back to the moments that shaped his life philosophy: the bold four-month leave he took just two years into his first job, the decision to convince his wife to leave her job while he wasn’t earning a paycheck, and the early desire to build what he calls FU money — not to quit work, but to buy back control.We revisit Black Monday in 1987 and how that shaped JL’s views on market volatility, risk, and emotional discipline. He shares how a humbling mistake helped hardwire the importance of staying the course, and how index investing eventually became the core of his life’s message: simplify.We also talk about the new edition of The Simple Path to Wealth, what’s changed, what hasn’t, and how his daughter went from being the reluctant listener to co-pilot on the updated edition.This is a conversation about money, yes — but more than that, it’s about living deliberately. JL reminds us that wealth isn’t about what we can afford — it’s about what we no longer have to worry about.You’ll hear about:How JL built his investing philosophy through trial and errorWhy VTSAX and chill remains his core guidanceWhat it means to live in a world where, eventually, everything is "free"Why simplicity is a radical act in a noisy, complex worldAnd why, if you get the money stuff right early, you can spend the rest of your life not thinking about it at all.

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• Ep 19 - The 10 Rules of Not Getting Screwed When Buying or Leasing a New Car

  Car buying has become one of the most financially dangerous consumer experiences in modern life. In today’s episode, we’re flipping the script.Whether you’re buying or leasing, trading in or paying cash, I’ll walk you through the 10 timeless rules you must follow if you want to avoid getting taken for a ride—financially and emotionally. No guilt trips. No boomer advice. Just strategy, leverage, and power dynamics decoded.And full disclosure: I love cars. I lease new ones every few years. I’m not here to shame your joy. I’m here to make sure that joy doesn’t cost you $9,000 more than it should.WHAT WE COVER:Why you should never walk into a dealership first—and what to do insteadThe email script that can save you thousands before you ever test driveWhy “What can you afford monthly?” is a trap—and how it costs you bigThe hidden revenue center called the “finance office” (and how to say no)The floor plan secret that gives you leverage when buying in stockHow to use pre-approved financing as bait to beat the dealer at their own gameReal math on depreciation—and why some “investments” are worth it anywayWhen leasing makes more sense than buying (and what to negotiate)How emotional timing ruins deals—and how to buy before you need toThe best days of the year to buy, based on actual dealer incentivesPlus, why your car purchase might be one of the biggest financial decisions of your next five years—whether you realize it or not.MENTIONED IN THIS EPISODE:Kelley Blue Book average car prices (2024): $47,000+CFPB, NADA, JD Power, Bankrate statistics on car loans, dealer profit centers, and interest rate gamesHow to calculate a lease “money factor” and negotiate like a proThe difference between buying a car and buying a feeling—and why that mattersJOIN THE CONVERSATION: Have a question, a rant, or a car-buying story that others need to hear? Shoot me a note at [email protected]. I read every message.And if this show is helping you feel more powerful and prepared, the best way to say thanks is with a quick review. It helps the show grow and lets me keep delivering practical, real-world financial guidance—without selling out.

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• Ep 18 - Mady Mills - Why Billionaires Panic, What Men Need to Hear, and the One Account that Buys Your Financial Freedom

  She’s been on Bloomberg. The New York Times. Yahoo Finance. But Mady’s real talent? Translating the chaos of markets and money into stories that make you feel seen. In this episode, we dive into everything from surviving the 2016 election newsroom to navigating the terrifyingly personal world of money and relationships. Mady opens up about growing up around volatility — both financial and emotional — and how it fuels her empathy-first approach to financial journalism today.We talk about:Why everyone, even billionaires, fears losing everythingHow to actually make money content more fun and accessibleWhat David Booth (yes, that billionaire) thinks you should do instead of stressing about a stock crashHow her background in political reporting shaped her calm, clear-eyed view of financial chaosThe most important account a woman can open (hint: it starts with “I” and ends with freedom)And the number one piece of advice for men in relationships—you’ll just have to listen and find out!This is one of those rare conversations that gets behind the curtain of financial media and your own money story — and leaves you feeling a little smarter, a little braver, and a lot more equipped to have the hard conversations.Interested in learning more about and/or following Mady Mills?Instagram: @madymillsTikTok: @madymills

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