Your Money Guide on the Side

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.

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.

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. 

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.

Andy Schneider, a career educator and current CFO at an independent school, shares his insightful journey from teacher to financial leader. He discusses the misconceptions about money in education and stresses the need for financial literacy. Andy reveals the driving factors behind soaring college costs and advocates for a hands-on approach to learning. He challenges the myth of the 'money expert' and highlights the importance of mentorship. Plus, he shares why 'The Psychology of Money' could be a game-changer for anyone navigating finances.

Feeling lost with money? Discover a three-step framework to tackle your financial issues by naming, prioritizing, and solving the right problems. Learn how vague advice can mislead you and why the origin of the word 'priority' might surprise you. Dive into Warren Buffett’s 25-5 Rule, and understand why financial clarity is crucial. With personal stories and practical tips, this guide aims to empower you to break free from the overwhelming noise and make real progress with your finances.

What do you get when you combine a financial planner with the heart of a teacher and the boldness of a creator? You get Victoria Ferguson—today’s guest and a true money guide for the modern world.Victoria is a CERTIFIED FINANCIAL PLANNER® who left a traditional finance career to create educational content full-time. Why? Because she knew more people needed clear, honest money guidance—and that trust is built through storytelling, not spreadsheets.In this episode, we talk about:Why budgets are like diets—and why most don’t workWhat really makes someone a financial “expert”The emotional side of money most advisors ignoreHow to interview a financial advisor (with the questions that matter)Why money shame exists at every income levelAnd how to define your own goals before chasing anyone else’s tacticsVictoria shares her best insights from years of working with high-net-worth clients, her decision to walk away from a stable paycheck, and what it really means to feel secure with money—regardless of your bank balance.Whether you’re looking for a financial planner, trying to navigate online money advice, or just curious what it means to live in alignment with your values… this episode is for you.🎧 Listen now to learn: ✅ How to find a CFP® who’s a true fit for you ✅ Why understanding your values changes your money game ✅ The exact framework to use when you're overwhelmed by financial adviceConnect with Victoria @financiallyvictoria | TikTok & Instagram Mentioned in the show:Fee-only fiduciaries (what that really means)Why where do you summer? is the wildest financial flexAnd why first principles matter for financial planning—🧠 Want more episodes like this? Subscribe to Your Money Guide on the Side wherever you get your podcasts and join Tyler’s weekly newsletter at tylergardner.com

Discover how the wealthy thrive by focusing on opportunities rather than fearing losses. Tyler Gardner explores the concept of asymmetric opportunities, illustrating how one significant win can far outweigh numerous failures. Delve into Disney's purchase of Pixar and Jeff Bezos' regret minimization strategy. Learn about effective decision-making frameworks and the investment barbell approach that balances risk and reward. Rewire your mindset to embrace uncertainty and make choices that lead to substantial gains in life and finances.

Jessica Inskip, the first female on Fidelity’s active trader desk and a respected voice in financial education, shares her inspiring journey from aspiring engineer to finance expert. She discusses her bold decision to leave behind traditional licensing to reach young investors on platforms like TikTok. Jessica highlights the urgent need to combat financial misinformation, particularly in light of tragic cases like Alex Kearns. She emphasizes the importance of authentic education over viral trends and shares insights on balancing active and passive investment strategies.