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:

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:

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:

📬 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:

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:

The difference lies in what you need and who you choose.

We’ll talk about:

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. 

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 Beat Debt and Use Debt? 

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:

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.

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 do I afford college for my kid?!?

Is All Debt Bad? What the Wealthy Know That Most People Don’t

Debt doesn’t have to be your enemy—and in this solo episode, Tyler Gardner breaks down how to make smarter decisions about debt, ditch shame, and leverage it as a tool for long-term wealth.

Whether you’re currently drowning in high-interest credit cards, juggling student loans, or just debating whether to pay off your 3% mortgage early, this episode is your new north star for how to think clearly about debt. You’ll learn how to:

✅ Decide whether to pay off debt or invest
✅ Use a practical ranking system to tackle your debt (hello, Debt Emergency Scale!)
✅ Think about opportunity cost like an investor
✅ Understand the psychological weight of debt—and why some people sleep soundly with it while others spiral
✅ Use the avalanche or snowball method depending on your own wiring
✅ Flip the script: how leverage (yes, debt!) can be used strategically to build wealth the way entrepreneurs and investors do every day

Plus, Tyler shares a vulnerable reminder that debt isn't a moral failing—it's a part of modern life. The goal isn’t perfection. It’s clarity, action, and momentum.

This one is personal. And powerful. And might just change the way you think about debt forever.

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 do I solve any Financial Problem?

What happens when a former English teacher becomes a CFO—and decides to teach everyone around him how money actually works?

In this episode, Tyler sits down with longtime friend and campmate Andy Schneider, a career educator and current CFO at an independent school, for a wide-ranging and deeply honest conversation about what we teach (and don’t teach) about money.

Andy has worn a lot of hats—boarding school English teacher, PWC consultant, MBA grad, educational administrator—and he brings a rare combo of humility, humor, and clarity to the messy overlap between education, money, and life purpose.

You’ll hear:

🎙️ Plus:

This one’s for anyone navigating careers, family, and the growing pressure of financial decision-making in a world that feels increasingly complex and expensive. Whether you're saving for college or trying to explain your 401(k) to your teenager, this episode helps add clarity, confidence, and maybe even some joy to the process.

📚 Education, meet real-world finance.

🐶 Also: Tyler’s dogs make a guest appearance with some strong opinions on college tuition.

🔍 Highlights & Resources:

📬 Subscribe to Tyler’s newsletter for 3 weekly money insights: tylergardner.com
🎧 More episodes at 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, Is Budgeting Worth It? 

Have you ever said, “I’m just bad with money”?

Yeah—me too. But what if the real issue isn’t your spending or saving or investing strategy... but your ability to name the actual problem in the first place?

This solo episode is a follow-up to last week’s conversation with CFP® Victoria Ferguson, and it’s all about creating a personal framework that helps you stop spinning your wheels and finally make meaningful progress in your financial life.

You’ll learn:

🔍 Whether you’re overwhelmed by credit card debt, unsure how to retire, or simply tired of feeling like you’re doing everything but getting nowhere, this episode gives you the tools to:

✅ Name the problem
 ✅ Prioritize the problem
 ✅ Solve the problem—without getting lost in the noise

Plus:

If you want clarity, confidence, and a simple way to move forward in your financial life—this episode is for you.

🎯 Don’t just solve problems. Solve the right one.

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question, What is Risk and How do I optimize it? 

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:

Victoria 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 advice

Connect with Victoria
@financiallyvictoria | TikTok & Instagram
 

Mentioned in the show:

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🧠 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

And in case you missed it, check out last week's episode of Your Money Guide on the Side with Jess Inskip where we answer the question, How do I fight against misinformation? 

Most people spend their lives trying not to lose. The wealthy? They play to win.

In this solo episode, Tyler Gardner breaks down the asymmetry of opportunity—why one big win can outweigh dozens of small failures, and how our fear of loss keeps us from seeing the upside that could change everything.

Tyler takes you from Disney’s acquisition of Pixar to Jeff Bezos’ “regret minimization framework,” unpacks the psychology of loss aversion, and explains why Monte Carlo simulations, the Kelly Criterion, and even barbell investing can help you make better decisions in life and money.

You’ll also learn:

Whether you’re building a business, investing for your future, or just trying to get out of your own way, this episode will help you rewire your decision-making process and start playing for upside.

🧠 It’s not about taking reckless risks—it’s about taking the right ones.
📈 Learn how to structure your decisions like a builder, not a hedger.

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For more insights, visit tylergardner.com, and subscribe to Tyler’s weekly newsletter for 3 actionable financial ideas every Sunday.

Follow Tyler on all platforms @socialcapofficial (IG + YT) and @socialcap (TT)

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 invest in bonds?

This week on Your Money Guide on the Side, I’m joined by the incredible Jessica Inskip—one of the sharpest, most grounded voices in modern investing. Jessica was the first female on Fidelity’s active trader desk, and you may have seen her breaking down complex strategies alongside Jim Cramer, or offering sharp, accessible takes on CNBC, Fox Business, Schwab Network, and Yahoo Finance.

In this episode, we unpack her journey from nearly becoming an engineer to becoming a nationally recognized voice in financial education—and why she made the bold decision to give up her professional licenses in order to educate people where they’re actually learning: on TikTok, Instagram, and her #1-ranked personal finance podcast, Market MakeHer.

Jessica shares the powerful story of how she pivoted careers after realizing that the people who needed the most help—young investors learning from unverified sources—weren’t being reached due to compliance constraints. The tragic case of Alex Kearns, and the inability for licensed professionals to correct misinformation in real-time, was a tipping point. From that moment on, Jessica committed to bridging the gap between Wall Street and the everyday investor, even if it meant leaving behind the traditional career path.

We talk about how she built a media presence without compromising her authenticity, how she measures impact over virality, and why she believes good education, not flashy trends, is the antidote to financial misinformation online. She shares her approach to making complex topics like credit markets and macroeconomics accessible—and the surprising (and sometimes frustrating) viral moments that have shaped her platform.

We also dive into:

Jessica also reflects on what success really means in a digital world that rewards metrics over meaning. Her answer? It’s not about the followers. It’s about the impact—the emails, the DMs, the women who now feel confident speaking about bonds, credit markets, and earnings reports because someone took the time to meet them where they are.

We wrap by talking about her work with Jim Cramer, the power of representation in finance, and how she’s planning a book that will finally explain the domino effect of markets—from interest rates to consumer behavior—in a way that actually makes sense.

Whether you’re an active investor, a new creator, or just someone trying to be smarter with your money, Jessica offers a masterclass in clarity, commitment, and courage. This conversation is packed with insights, humility, and heart.

🎙️ Take a listen—you won’t just learn about markets. You’ll learn why voice, vision, and values matter more than ever in today’s financial landscape.