Your Money Guide on the Side

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.

And in case you missed it, check out last week's episode of Your Money Guide on the Side with JL Collins where we answer the question, How do I get F-You Money? 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 socialcapconnect@gmail.com. This show is for you, and we want it to be as good as it can be.

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question, How do I Buy a New Car Without Getting Screwed?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 error Why VTSAX and chill remains his core guidance What it means to live in a world where, eventually, everything is "free" Why simplicity is a radical act in a noisy, complex world And why, if you get the money stuff right early, you can spend the rest of your life not thinking about it at all.

Buying or leasing a car can feel like a financial minefield, but it doesn't have to be! Discover why you should never step into a dealership first and how an email script can save you thousands. Learn the pitfalls of focusing on monthly payments and how to leverage pre-approved financing against dealers. Understand the hidden costs like the finance office and dive into the best times to make your purchase. Plus, find out why your car choice could impact your finances for years to come!

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question, How Do I Invest $1,000,000?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 everything How to actually make money content more fun and accessible What David Booth (yes, that billionaire) thinks you should do instead of stressing about a stock crash How her background in political reporting shaped her calm, clear-eyed view of financial chaos The 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

And in case you missed it, check out last week's episode of Your Money Guide on the Side with Andrew Tobias where we answer the question, What is the easiest way to become wealthy?You've hit the million-dollar mark—now what?In this episode of Your Money Guide on the Side, we tackle the deceptively simple question: how should you invest a million dollars? This isn’t about theoretical asset allocation or textbook strategies. It’s about real lives, real goals, and real risk tolerance.We meet three investors—Chad, Nina, and Marge—each at very different life stages, each with a radically different approach to putting their wealth to work: Chad Slater, the thrill-seeking ex-startup bro who wants asymmetry, optionality, and upside. His portfolio is bold, volatile, and aggressive—global equities, venture capital, and yes, crypto. Nina Ellington, the grounded creative director turned Pilates instructor who wants growth without chaos. Her diversified, resilient mix of stocks, bonds, real estate, and alternatives prioritizes balance and autonomy over adrenaline. Marge Buttersworth, the sharp, independent retiree who wants reliability and peace of mind. Her income-focused portfolio features bond ladders, dividend stocks, and high-yield cash vehicles—designed to pay her, not stress her. These are not just asset allocations. They are reflections of who these people are, what they value, and what they need their money to do for them.💡 Along the way, we explore key questions: How soon will you need the money? How much risk can you stomach? Are you trying to grow, preserve, or withdraw from your portfolio? And if you stick around until the end, I share exactly how I invest my own money—no hype, no secrets—just a simple, transparent walk through my personal allocation and why I chose it.📌 In this episode, you’ll learn: 3 distinct investing strategies for $1M portfolios How risk tolerance, time horizon, and goals shape allocation The truth about fees, diversification, and asset class correlation Why your neighbor’s portfolio has nothing to do with yours How to evaluate your definition of enough 📬 Bonus: If this episode resonates, subscribe to my free weekly newsletter for deeper dives and personal stories at tylergardner.com 🎙️ Disclaimer: I’m not your financial advisor—I’m your guide on the side. Everything here is for educational purposes only. Always do your own research and consider working with a fiduciary advisor who understands your unique circumstances.

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answer the question, Should I Hire a Financial Advisor?What if the only investment guide you ever needed... actually was?This week, I sit down with personal finance legend Andrew Tobias—bestselling author, Harvard Business School grad, long-time political advocate, and the brilliant mind behind The Only Investment Guide You’ll Ever Need. His book was literally the first financial text I ever read, and it remains one of the few I return to over and over again—for its timeless principles, relatable tone, and surprising humor.In this conversation, we cover: The unlikely path from Slavic literature major to bestselling financial writer Why “don’t be boring” might be the best writing advice you’ll ever get The epic laundry list of startup investments that went very sideways (and what he learned from each) The true cost of chasing returns vs. chasing happiness Why retirement isn't a finish line—but a lifestyle with the right people His most embarrassing investing losses—and how they became his favorite teaching tools Andrew doesn’t just teach people how to manage money—he shows us how to think about it, with warmth, wit, and an honesty that’s rare in finance.🎧 If you’ve ever wondered what makes financial advice stick—or how to build a life rich in meaning as well as money—this episode is for you.🔗 Subscribe, rate, and share if it resonates. And thank you for joining me on Your Money Guide on the Side.

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question, How do I talk to Others About Money? This might be the most common money question I get, and maybe even the most important: Should I hire a financial advisor? And right behind it: If so, how do I find a good one?In today’s episode, I’m not giving you a yes or no answer (sorry, not sorry). Instead, I’m walking you through a three-part framework to decide if you need an advisor—skill, will, and time—and then I’m sharing seven real-world filters for choosing the right one if you do.Because the truth is: Working with a financial advisor might be one of the smartest moves you’ll ever make. Or it might be an expensive, unnecessary distraction. The difference lies in what you need and who you choose.We’ll talk about: The difference between CFP®, CFA®, CPA, and the rest of the alphabet soup What being a “fiduciary” really means (and doesn’t mean) The myth of market-beating promises (run from those) Fee models that make sense—and those that don’t Why credentials are clues, but not the whole story How investing is often more about behavior than brilliance The one question you must ask every advisor: “How do you invest your own money?” And yes, I even compare hiring a financial advisor to dating—because, honestly, it is. This episode won’t give you a rubber-stamped answer, but it will give you something far more valuable: a lens to look through so you can make the call yourself.🎧 Whether you’re DIY-ing your financial life or just trying to figure out if the grass really is greener with professional help—this one’s for you.If you enjoy the show, don’t forget to subscribe, leave a review, and share it with a friend who’s wondering if they should “talk to someone” about their money.📩 And as always, you can sign up for the free newsletter at tylergardner.com for more clear, action-oriented financial education. 

Dan Brigham, known as Dan the Budget Man, is a candid financial educator who transformed his life by paying off $100K in debt. He discusses the power of vulnerability over traditional financial 'expertise' and tackles societal defensiveness around money. The chat dives into the vibrant content creation scene in Austin and why community matters. Dan shares insights on financial habits, the challenge of public opinion, and highlights pivotal books that shaped his philosophy, proving that real financial literacy comes from authenticity and relatable experiences.

Debt isn’t just a burden; it can be a powerful tool for wealth creation. Learn to identify when to pay off debt versus invest, using a practical Debt Emergency Scale. Discover the psychological aspects of debt, from the stress it causes to how some thrive with it. Explore strategies like the avalanche and snowball methods tailored to your personality. Finally, understand how successful entrepreneurs leverage debt as part of their growth strategy, reshaping your view on financial responsibilities.