In this solo episode, Tyler breaks down the only six financial accounts you’ll ever truly need—and more importantly, how to actually use them. Whether you’re just getting started or managing a more complex portfolio, this is your streamlined, nonsense-free guide to designing a system that works.

No more chasing every new fintech app or wondering if you’re missing something. If you’ve ever felt overwhelmed by the alphabet soup of financial tools, Tyler’s here to cut through the noise and give you a clear path forward. These six accounts are enough to build wealth, protect your downside, and create long-term flexibility. And anything beyond them? Likely just extra complexity disguised as “optimization.”

What You’ll Learn:

• Why a regular checking account should be boring—and how to keep it that way
• How to think about a High-Yield Savings Account (HYSA): the “glovebox” for your cash—not your investment engine
• The power of a Roth IRA—and how it’s often misunderstood
• Why a pre-tax IRA or 401(k) still matters, even if retirement feels far away
• The secret weapon of the wealthy: the HSA (Health Savings Account) and how to use it for more than doctor’s visits
• How a taxable brokerage account unlocks true flexibility—and why you might want to use it before maxing everything else

Plus:

• A better metaphor than “bucket strategy”
• Why most emergencies aren’t emergencies at all (and what that means for where your cash lives)
• The order Tyler recommends for prioritizing contributions
• When not to use these accounts (because yes, even the Roth IRA can be misused)

Whether you're 25 and just opening your first Roth, or 55 and wondering how to consolidate accounts, this episode gives you a timeless roadmap to simplify your finances without oversimplifying your life. As always, Tyler brings the clarity, the nuance, and just enough humor to make talking about tax-advantaged accounts… well, weirdly fun.

Is Future Planning Ruining Your Future?

What if your financial advisor told you to spend your money now?
To give away your inheritance early?
To go on more vacations?
To prioritize experience over investment?

What if they told you the only inflation-protected asset is experience?

Bill Perkins is a hedge fund manager, poker player, and author of the bestseller Die With Zero. On this week’s episode, he breaks down why money is just a means — and experience is the end.

📚 What We Discuss with Bill Perkins:

🛤️ 02:40 — Early revelations and going the non-traditional route
 💡 05:10 — Borrowing from your poor self to give to your rich self
 📆 07:35 — “What experiences belong when?” — and why delayed gratification can go too far
 🤔 10:25 — What money can really buy — fulfillment vs. accumulation
 🎢 12:22 — Staple experiences worth the cost — collecting memories that stick
 🧠 13:35 — Memory dividends — the one return no market crash can erase
 👵 15:40 — Retirement planning — running out of money vs. running out of time
 🧘 17:50 — Letting go — why overplanning for the future can wreck the present
 🕰️ 20:25 — “Life is now, life is urgent” — estate planning and missed chances
 🏛️ 23:20 — When should inheritance be inherited? Challenging default thinking
 🎯 26:15 — Hindsight and financial regret — is gold-plated better than good enough?
 📖 28:20 — Learning from the past to make the most of what’s next
 💸 29:20 — What is your time worth? The hidden cost of chasing more income

💡 What You’ll Walk Away With

• Why deferring joy is often just fear in disguise
• A new way to think about saving, giving, and legacy
• How to measure value through memory, not money
• A framework for spending intentionally at different life stages
• How to plan for the end of life without missing the middle

🧾 Resources Mentioned

• Die With Zero by Bill Perkins → https://a.co/d/9KKHOzT
• Your Money or Your Life by Vicki Robin and Joe Dominguez → https://yourmoneyoryourlife.com

If you're still game to support the show, leaving a quick review really helps — even one sentence goes a long way to help others find the show.

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If you enjoyed this, check out episode 22 with Wendy Li — a former endowment CIO who managed billions for New York’s top institutions and shared how institutional investors evaluate risk, choose fund managers, and build resilient portfolios.

Let’s be honest: you’re not going to beat the stock market. And that’s not an insult — it’s a liberation. In this episode of Your Money Guide on the Side, Tyler Gardner unpacks one of the most misunderstood goals in investing: trying to “win” against the market.

Drawing on decades of investing experience (and more than a few Peloton mistakes), Tyler explains why comparing yourself to the S&P 500 is often irrelevant, how hedge funds and high-frequency traders have rigged the game against retail investors, and most importantly, why even when you do win, you often lose.

We explore:

• The real origin of the “beat the market” mindset — and why it was never about helping you
• Why the S&P 500 isn’t a fair benchmark for most people
• Market efficiency theory explained without Greek letters (but with plenty of sarcasm)
• Behavioral biases that will ruin your returns: overconfidence, recency bias, loss aversion, confirmation bias, and more
• How even the pros struggle — and why surviving your own brain is the real edge
• When paying a 1% advisor fee might actually be a bargain
• Why boring, automated, diversified investing is the best strategy no one wants to hear about

Whether you're new to investing or already deep in the weeds of candlestick charts and YouTube stock tips, this episode will reframe what success really looks like. Because real wealth isn’t built by outsmarting others — it’s built by staying in the game.

 📬 Subscribe to the newsletter for 3 financial insights every Sunday
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 📈 Want to support the show? A quick review or share goes a long way.

Wendy Li managed billions for New York’s top institutions — here’s what she thinks individual investors can (and should) steal from the pros.

After leading portfolios for the Met Museum, UJA-Federation, and the Mother Cabrini Health Foundation, Wendy now serves as CIO at Ivy Invest. She’s spent decades on the inside — and in this episode she’s walking us through how institutional investors actually make decisions, where regular people go wrong, and what it means to manage risk.

📚What We Discuss with Wendy: 

 🧠 02:17 — Institutions vs. individuals: why the ultra-wealthy play a different investing game
 📉 06:28 — Risk vs. return: are you really being paid for the risk you’re taking?
 📚 08:34 — Invest in what you know: learning by doing (and surviving your mistakes)
 🪤 11:48 — Career course-corrections: mistakes, pivots, and staying in the game
 🤝 15:28 — Trust but verify: what good investor relationships actually look like
 💰 18:00 — The luxury of investing: identifying the how and the when to invest
🧾 20:32 — Portfolio allocation: managing your capital with intention
🚪 25:46 — Alternatives and access: knowing your place in a complex market
🕵️ 30:06 — Fund managers: who and how to choose
🛠️ 33:32 — Investing skills: humility, curiosity, and flexibility in the face of risk
🔍 36:58 — Where to learn: insider investment resources
🧰 42:18 — Practical takeaways: frameworks and tools you can use today

💡 What you’ll walk away with

• How institutions manage risk — and how to apply it to your own investing
• Why most retail investors misunderstand returns
• How to think long-term when markets are volatile
• What to ask before trusting a fund manager with your money
• How to approach alternatives without insider access
• The core skills every smart investor needs

If you're game to support the show, leaving a quick review really helps — even one sentence goes a long way!

You can also join thousands of others investment minded individuals in subscribing to my newsletter here.

If this episode resonated with you, be sure to check out Episode 15, where Tyler breaks down the 7 steps to identifying your needs for a financial advisor.

What if the most common retirement rule was never meant to be a rule at all?

In this episode, we unpack the origins, flaws, and overlooked nuances of the 4% rule—and why it might not be the best way to plan your financial future. From its fear-based beginnings to its rigid application in a dynamic world, Tyler breaks down 5 key reasons to rethink the 4% rule altogether.

You’ll learn:

Where the 4% rule actually came from (hint: worst-case scenario thinking)

What the Trinity Study really showed—and what most people ignore

How sequence of returns risk can silently wreck your plan

Why portfolio size and asset allocation matter far more than a static percentage

Smarter, more dynamic strategies to adjust year-by-year

If you’ve ever asked, "How much can I safely spend in retirement?"—this one’s for you.

📝 Leave a review if you enjoy the episode or send your thoughts to [email protected]. This show is for you, and we want it to be as good as it can be.

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.

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 everything
• How to actually make money content more fun and accessible
• What David Booth (yes, that billionaire) thinks you should do instead of stressing about a stock crash
• How her background in political reporting shaped her calm, clear-eyed view of financial chaos
• The 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: @madymills

TikTok: @madymills

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 portfolios
• How risk tolerance, time horizon, and goals shape allocation
• The truth about fees, diversification, and asset class correlation
• Why your neighbor’s portfolio has nothing to do with yours
• How 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 writer
• Why “don’t be boring” might be the best writing advice you’ll ever get
• The epic laundry list of startup investments that went very sideways (and what he learned from each)
• The true cost of chasing returns vs. chasing happiness
• Why retirement isn't a finish line—but a lifestyle with the right people
• His most embarrassing investing losses—and how they became his favorite teaching tools

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.