Your Money Guide on the Side

• Ep 24 - Bill Perkins - How to Die With Zero (and Actually Live First)

  Is Future Planning Ruining Your Future?What if your financial advisor told you to spend your money now? To give away your inheritance early? To go on more vacations? To prioritize experience over investment?What if they told you the only inflation-protected asset is experience?Bill Perkins is a hedge fund manager, poker player, and author of the bestseller Die With Zero. On this week’s episode, he breaks down why money is just a means — and experience is the end.📚 What We Discuss with Bill Perkins:🛤️ 02:40 — Early revelations and going the non-traditional route 💡 05:10 — Borrowing from your poor self to give to your rich self 📆 07:35 — “What experiences belong when?” — and why delayed gratification can go too far 🤔 10:25 — What money can really buy — fulfillment vs. accumulation 🎢 12:22 — Staple experiences worth the cost — collecting memories that stick 🧠 13:35 — Memory dividends — the one return no market crash can erase 👵 15:40 — Retirement planning — running out of money vs. running out of time 🧘 17:50 — Letting go — why overplanning for the future can wreck the present 🕰️ 20:25 — “Life is now, life is urgent” — estate planning and missed chances 🏛️ 23:20 — When should inheritance be inherited? Challenging default thinking 🎯 26:15 — Hindsight and financial regret — is gold-plated better than good enough? 📖 28:20 — Learning from the past to make the most of what’s next 💸 29:20 — What is your time worth? The hidden cost of chasing more income💡 What You’ll Walk Away WithWhy deferring joy is often just fear in disguiseA new way to think about saving, giving, and legacyHow to measure value through memory, not moneyA framework for spending intentionally at different life stagesHow to plan for the end of life without missing the middle🧾 Resources MentionedDie With Zero by Bill Perkins → https://a.co/d/9KKHOzTYour Money or Your Life by Vicki Robin and Joe Dominguez → https://yourmoneyoryourlife.comIf you're still game to support the show, leaving a quick review really helps — even one sentence goes a long way to help others find the show.You can also join thousands of other investing-minded folks by subscribing to the newsletter: www.tylergardner.comIf you enjoyed this, check out episode 22 with Wendy Li — a former endowment CIO who managed billions for New York’s top institutions and shared how institutional investors evaluate risk, choose fund managers, and build resilient portfolios.

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• Ep 23 - The 3 Reasons You’ll Never Beat the Market (And Why That’s Okay)

  Let’s be honest: you’re not going to beat the stock market. And that’s not an insult — it’s a liberation. In this episode of Your Money Guide on the Side, Tyler Gardner unpacks one of the most misunderstood goals in investing: trying to “win” against the market.Drawing on decades of investing experience (and more than a few Peloton mistakes), Tyler explains why comparing yourself to the S&P 500 is often irrelevant, how hedge funds and high-frequency traders have rigged the game against retail investors, and most importantly, why even when you do win, you often lose.We explore:The real origin of the “beat the market” mindset — and why it was never about helping youWhy the S&P 500 isn’t a fair benchmark for most peopleMarket efficiency theory explained without Greek letters (but with plenty of sarcasm)Behavioral biases that will ruin your returns: overconfidence, recency bias, loss aversion, confirmation bias, and moreHow even the pros struggle — and why surviving your own brain is the real edgeWhen paying a 1% advisor fee might actually be a bargainWhy boring, automated, diversified investing is the best strategy no one wants to hear aboutWhether you're new to investing or already deep in the weeds of candlestick charts and YouTube stock tips, this episode will reframe what success really looks like. Because real wealth isn’t built by outsmarting others — it’s built by staying in the game. 📬 Subscribe to the newsletter for 3 financial insights every Sunday 📲 Follow Tyler on IG/TikTok: @socialcapofficial 📈 Want to support the show? A quick review or share goes a long way.

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• 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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