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. 

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 money
• Why so many creators struggle with relevance and comparison
• How to stay grounded (literally and spiritually) when the work feels heavy
• The reality behind Austin’s finance/media scene
• And 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.

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.

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:

• Why Andy left the classroom—and why he came back
• How business was “demystified” for him in the least expected way
• What actually drives the cost of college (and why some schools won’t survive)
• The myth of the “money expert”—and how to choose who you trust
• What a CFO wishes more teachers asked him (but never do)

🎙️ Plus:

• The uncomfortable truth about health insurance, school budgeting, and stock-picking competitions in high schools
• Why college needs a Julliard-style reset for the modern world
• And why Psychology of Money by Morgan Housel just might be the most important book you’ll ever read

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:

• Book: The Psychology of Money by Morgan Housel
• Concept: Education vs. College (yes, there’s a difference)
• Tool: Why every good CFO keeps a whiteboard in their office
• Framework: You don’t need to be a teacher to teach

📬 Subscribe to Tyler’s newsletter for 3 weekly money insights: tylergardner.com
🎧 More episodes at Your Money Guide on the Side

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:

• Why most people never get past step one in solving their money problems
• How to stop drowning in to-do lists and prioritize the right thing
• A new lens for filtering financial advice (and spotting BS in a sea of influencers)

🔍 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:

• What Warren Buffett’s 25-5 Rule has to do with your finances
• The Latin origin of the word “priority” (spoiler: it was never meant to be plural)
• Why vague financial advice is like shopping at Costco while hungry
• And how smoke alarms at 2 a.m. taught me more about problem-solving than any spreadsheet ever did

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.

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 work
• What really makes someone a financial “expert”
• The emotional side of money most advisors ignore
• How to interview a financial advisor (with the questions that matter)
• Why money shame exists at every income level
• And how to define your own goals before chasing anyone else’s tactics

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:

• Fee-only fiduciaries (what that really means)
• Why where do you summer? is the wildest financial flex
• And why first principles matter for financial planning

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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

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:

• Why we overweight risk and underweight opportunity
• How only 4% of public companies have driven all net market gains (ASU study)
• What venture capital teaches us about failure and power laws
• Why the S&P 500 has never lost money over any rolling 20-year period (Fama/French)
• The exact 3-question framework the wealthy use to evaluate high-stakes decisions

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)

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:

• How she transitioned from Merrill to full-time educator and creator
• The emotional and professional weight of giving up her Series licenses
• The difference between being a financial expert and simply playing one on social media
• Why compliance rules continue to keep great educators out of the creator economy
• How she balances family life, media work, and her growing personal brand
• Her podcast, Market MakeHer, and how it became a trusted resource for tens of thousands

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.

Bonds have been a staple in portfolios for decades, often hailed as the “safe” investment that brings stability and protects wealth. But what if I told you that this belief is outdated, and in many cases, dangerously misleading?

In today’s episode, I take a hard look at why bonds are overrated, the risks most investors overlook, and whether they deserve a spot in your portfolio at all. While bonds can serve a purpose, blindly following the 60/40 portfolio mantra without questioning its effectiveness can be a costly mistake.

We’ll break down the three biggest risks of bonds and why they may not be as “safe” as you think:
✅ Interest Rate Risk – When rates go up, your bond values drop. It’s that simple, and 2022 proved it when the Bloomberg U.S. Aggregate Bond Index suffered its worst year in history.
✅ Inflation Risk – Your 3% return isn’t a real 3% return if inflation is running at 4-5%. That’s a recipe for losing purchasing power over time.
✅ Opportunity Cost – For every dollar you park in bonds, you’re missing out on investments with real growth potential—whether that’s stocks, real estate, or other wealth-building assets.

Many investors believe bonds guarantee stability, but I argue that true long-term financial security comes from growth, not just preservation. The reality? A well-diversified stock index fund has statistically near-zero risk of going to zero, while bonds can quietly eat away at your purchasing power.

So, do bonds ever make sense? Maybe—if you’re already financially set and just want to protect what you have. But for most investors, the classic advice to shift heavily into bonds at retirement may be one of the biggest financial missteps.

This episode isn’t about hating bonds—it’s about thinking critically before defaulting to outdated strategies. Are you actually protecting your wealth? Or are you unknowingly holding yourself back?

👉 Tune in now, challenge conventional wisdom, and decide for yourself.

Back in 2003, I met Mike Taormina at the London School of Economics, never expecting we'd stay in touch—let alone spend decades debating finance and traveling together. Fast forward, and Mike has become a powerhouse in fintech, co-founding Vault, CommonBond, and Alluvial, with a Wharton MBA and a CFA to back it up.

But credentials aside, what sets Mike apart is his ability to break down complex crypto and finance topics into something actually useful. In this episode, we dive into decentralized finance, separating the noise from real opportunities, and why blockchain tech is transforming financial transparency.

We also discuss personal investing, risk tolerance, debt, and why even a seasoned finance pro like Mike trusts a robo-advisor over DIY trading. Whether you're deep into crypto or just trying to make smarter financial moves, this conversation is packed with insights.