Your Money Guide on the Side

• 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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• Ep 17 - How I Would Invest $1,000,000 - 3 Approaches, 3 Stories, and 1 Question to Simplify Your Life

  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 portfoliosHow risk tolerance, time horizon, and goals shape allocationThe truth about fees, diversification, and asset class correlationWhy your neighbor’s portfolio has nothing to do with yoursHow 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.

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• Ep 16 - Andrew Tobias - The Only Investment Interview You Will Ever Need (And How Money CAN Buy Happiness)

  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 writerWhy “don’t be boring” might be the best writing advice you’ll ever getThe epic laundry list of startup investments that went very sideways (and what he learned from each)The true cost of chasing returns vs. chasing happinessWhy retirement isn't a finish line—but a lifestyle with the right peopleHis most embarrassing investing losses—and how they became his favorite teaching toolsAndrew 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.

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• Ep 15 - Should You Hire a Financial Advisor? (And 7 Things to Look For If You Do)

  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 soupWhat 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’tWhy credentials are clues, but not the whole storyHow investing is often more about behavior than brillianceThe 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. 

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• Ep 14 - Dan Brigham - On Faith, Finance, and First Principles

  He paid off $100K in debt and isn’t trying to sell you a thing — meet Dan the Budget Man.In a financial world cluttered with gurus, grifters, and gatekeepers, Dan Brigham (@budgeters_anonymous) is a breath of fresh air. No paywalls. No “six-figure side hustle” webinars. Just brutally honest content, bite-sized math on notecards, and a contagious belief that you can take control of your money — excuses not included.In this episode of Your Money Guide on the Side, we dive into the moments that shaped Dan’s mission, including his two-year journey out of over $100,000 in debt and why vulnerability—not credentials—is his currency of trust. We talk about his viral “Smart Guy vs. Dumb Guy” series, the backlash he gets over car payments (you’ve been warned), and why he thinks showing integrity is far more important than performing expertise.You’ll also hear us unpack:What makes people defensive about moneyWhy so many creators struggle with relevance and comparisonHow to stay grounded (literally and spiritually) when the work feels heavyThe reality behind Austin’s finance/media sceneAnd the books that actually changed our lives (spoiler: one’s still in print after 2,000 years)If you’re tired of being yelled at by the financial internet or just want to hear two humans wrestle with what it means to help others and still help themselves—this one’s for you.Listen wherever you get your podcasts. And don’t forget to subscribe if you’re into financial literacy, big questions, and small wins.

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