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

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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.

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.