Your Money Guide on the Side – Details, episodes & analysis

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.

Car buying has become one of the most financially dangerous consumer experiences in modern life. In today’s episode, we’re flipping the script.

Whether you’re buying or leasing, trading in or paying cash, I’ll walk you through the 10 timeless rules you must follow if you want to avoid getting taken for a ride—financially and emotionally. No guilt trips. No boomer advice. Just strategy, leverage, and power dynamics decoded.

And full disclosure: I love cars. I lease new ones every few years. I’m not here to shame your joy. I’m here to make sure that joy doesn’t cost you $9,000 more than it should.

WHAT WE COVER:

• Why you should never walk into a dealership first—and what to do instead
• The email script that can save you thousands before you ever test drive
• Why “What can you afford monthly?” is a trap—and how it costs you big
• The hidden revenue center called the “finance office” (and how to say no)
• The floor plan secret that gives you leverage when buying in stock
• How to use pre-approved financing as bait to beat the dealer at their own game
• Real math on depreciation—and why some “investments” are worth it anyway
• When leasing makes more sense than buying (and what to negotiate)
• How emotional timing ruins deals—and how to buy before you need to
• The best days of the year to buy, based on actual dealer incentives

Plus, why your car purchase might be one of the biggest financial decisions of your next five years—whether you realize it or not.

MENTIONED IN THIS EPISODE:

• Kelley Blue Book average car prices (2024): $47,000+
• CFPB, NADA, JD Power, Bankrate statistics on car loans, dealer profit centers, and interest rate games
• How to calculate a lease “money factor” and negotiate like a pro
• The difference between buying a car and buying a feeling—and why that matters

JOIN THE CONVERSATION:
Have a question, a rant, or a car-buying story that others need to hear? Shoot me a note at [email protected]. I read every message.

And if this show is helping you feel more powerful and prepared, the best way to say thanks is with a quick review. It helps the show grow and lets me keep delivering practical, real-world financial guidance—without selling out.

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.

In this week's episode, we explore our common tendency to react emotionally to political elections and their perceived impact on the stock market. I argue that changing investing habits based on external "noise," and it is noise to me, is nonsense; I only change investing habits when my own life or financial needs have changed. Emphasizing and drawing upon historical data, the show explores the market's long term patterns of growth, regardless of who is in office. In short, the market transcends our politics (in a way). Additionally, we explore the pitfalls of trying to time the markets based on politics, business cycles, or consumer sentiment. Finally, as always, we remember that it's normal to feel this way, and the moment of empathy comes form knowing that we all feel this way at times and need to remind one another to take a breath and focus on the long term plan. 

My guest this week, Patrick Wetherille, shares a little bit about his experience with optimizing life, managing empathy through start-up culture, and taking advantage of every opportunity to learn from and alongside business minds at every level. As the episode progresses, Patrick shares his thoughts on the importance of being able to work from anywhere and how that very freedom can often bring teams together and create optimized work cultures and production.

In this episode, I explore the power of diversifying communication channels, income streams, and the irony of many people knowing they should diversify and yet their not quite being able to walk the same walk. When the TikTok "ban" occurred, I was left wondering why so many creators, all of whom discuss the power and importance of diversification on a daily basis, had not diversified their digital assets, as well, and considered their content as part of their overall portfolio.