Your Money Guide on the Side

Pre-order Tyler's book, Real Wealth, at tyler.gardner.com/book

And as always, a MASSIVE thank you to this week's sponsors:


Fabric: → ⁠meetfabric.com/tyler⁠ because if you have dependents, and you don't have term life, getting term life insurance is the financial step you need to take right now.


Gelt: ⁠→ ⁠joingelt.com/tyler because Q2 is where strategic businesses make game-changing tax moves


LMNT: → ⁠drinklmnt.com/tyler⁠ Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way.


Facet: → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! And see for yourself why I've partnered with Facet for almost TWO YEARS!

And now on with the show notes!

What if the most important investing conversation you’ve ever had… never got recorded?

That’s what happened here.

In this episode, Tyler reconstructs a lost interview with Burton Malkiel, author of A Random Walk Down Wall Street, and uses it to tell a bigger story — one about index investing, behavior, and why the simplest strategy is still the hardest to follow.

Because this isn’t just about theory.
It’s about what actually works in real life — and why people still struggle to stick with it.

In this episode, Tyler walks through:

The origin of index investing — and why Wall Street fought it for decades

Why most active managers fail to beat the market after fees

The role of academics like Markowitz, Fama, and Samuelson in shaping modern investing

How fear and behavior — not knowledge — derail most investors

Why trying to time the market (even when you’re right) can still cost you returns

The risk of concentration in modern index funds — and why it’s not a new problem

Malkiel’s core principle: you will never consistently outguess the market

Tyler also shares one of the most important takeaways from the conversation:

Even Burton Malkiel feels fear. He just doesn’t act on it.

And that’s the difference.

The core idea:

Investing isn’t about being right. It’s about staying consistent when it’s hardest to do so.

The episode closes with a broader reflection on retirement — not just how to invest, but how to live.

Because according to Malkiel, the goal isn’t to stop working.

It’s to stay engaged — with ideas, with learning, and with life itself.

If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps.

Hope this gives you something to think about this week.

As always, a MASSIVE thank you to this week's sponsors!


LMNT⁠: → ⁠drinklmnt.com/tyler⁠ Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way.


⁠Bilt⁠: → ⁠joinbilt.com/tyler⁠ to get rewarded for your biggest annual expense!


⁠Copilot Money⁠: → ⁠try.copilot.money/tyler⁠ and use code TYLER2 for two free months.


⁠Gelt⁠: → ⁠joingelt.com/tyler and see if you can get your business tax planning to the next level in 2026 and beyond!

And now, on with the show notes!

Most retirement withdrawal conversations focus on one number:

4%? 5%? 6%?

But that misses a much bigger variable:

Taxes.

In this episode, Tyler revisits his $2 million retirement portfolio framework and explains why the real issue isn’t just how much you withdraw — it’s how much you keep after taxes.

Because two retirees can withdraw the exact same amount and end up with very different lifestyles depending on how their accounts are structured.

In this episode, Tyler covers:

Why after-tax returns matter more than headline portfolio returns

The hidden cost of relying too heavily on traditional IRAs and 401(k)s

How Roth conversions can reduce future tax pain

Why taxable brokerage accounts are one of the most underrated retirement tools

How the 0% capital gains bracket can legally lower taxes in retirement

Why withdrawal order matters: taxable, pre-tax, and Roth accounts each play different roles

How poor tax planning can quietly reduce spending power for decades

Tyler also explains why the classic withdrawal-rate debate often misses the point entirely.

A 6% withdrawal with poor tax planning may feel like 4.75%.

A well-structured 6% withdrawal may feel like…6%.

The core idea:

The goal was never to withdraw less. The goal was always to keep more.

This episode isn’t about tax gimmicks or loopholes.

It’s about understanding the rules well enough to make smarter decisions with the money you’ve already built.

If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps.

Hope this gives you something to think about this week.

As always, a MASSIVE thank you to this week's sponsors!


Momentous: → ⁠livemomentous.com Use code Tyler for 35% off your first order!


Thrive Market: → ⁠thrivemarket.com/tyler $20 off your first three orders plus you’ll get a FREE $60 gift!


Facet: → ⁠facet.com/tyler for an exclusive $550 kickstart offer!


Anthropic: → ⁠claude.ai/tyler if you're looking for the best business and thought partner I have EVER had.

And on to the show notes!

Most financial advice focuses on optimization.

This episode is about something else entirely: alignment.

In this more personal episode, Tyler shares five lessons from spending two months “snowbirding” in Sedona — and what the experience revealed about money, time, and the life we think we want.

Because sometimes the biggest financial insights don’t come from spreadsheets.
They come from living differently long enough to notice what actually matters.

In this episode, Tyler reflects on:

Why buying back time only works if you know what to do with it

The idea of a “path dividend” — testing lifestyles before committing to them

How lifestyle upgrades quickly become your new normal (and lose their impact)

Why major life changes require understanding what you’re leaving, not just gaining

The illusion that a new place will create a new version of you

Along the way, Tyler connects everyday moments — cooking dinner, staying in Airbnbs, almost buying a house — to deeper financial decisions around spending, relocation, and retirement.

The core idea:

Wherever you go, there you are.

Money can change your environment.
It doesn’t automatically change you.

This episode isn’t about maximizing efficiency.

It’s about building a life that actually fits — before you build the plan to fund it.

If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps.

Hope this gives you something to think about this week.

Pre-Order Tyler's First Book, Real Wealth, ⁠⁠here⁠⁠ & be immediately eligible for exclusive bonuses between now and December 1st!

April Bonus: Free two-hour digital live event on Wednesday, May 6th from 7-9pm EDT, where Tyler will answer the most commonly asked questions and walk through what you can expect from the book!

And as always, a MASSIVE thank you to this week's sponsors:

LMNT just dropped a limited-time Pink Lemonade flavor — exclusively for LMNT INSIDERs, which means you need to order the INSIDER Bundle (four boxes for the price of three) to get it. If you like your electrolytes without the sugar and your hydration without the regret, this one's for you:

→ drinklmnt.com/tyler

Fabric: ten minutes online, no health exam, no phone calls, a million dollars in coverage for less than a dollar a day — and if you're young and healthy, there's no better window to lock this in than right now.

→ meetfabric.com/tyler

Copilot Money tracks your spending, net worth, investments, subscriptions, and savings goals in one place — and it's the only personal finance app to win an Apple Editor's Choice Award, with a 4.8-star rating from over 25,000 reviews.

→ try.copilot.money/tyler — use code TYLER2 for two free months.

And on to the show notes!

Most people think investing is about finding the next big thing.

The reality is much less exciting — and far more effective.

In this episode, Tyler sits down with Chris Hill, longtime host of Motley Fool Money, to talk about what actually drives long-term success in investing — and why so many people get distracted along the way.

From launching a podcast during the 2008 financial crisis to interviewing some of the biggest names in business and finance, Chris shares lessons from decades inside one of the most influential investing platforms.

In this conversation, Tyler and Chris discuss:

How Motley Fool Money started during a crisis — and why simplicity won

Why investors obsess over “hot stocks” and excitement (and why that hurts returns)

The importance of time in the market — and not interrupting compounding

Why the best companies are often the ones everyone already knows

The balance between simple index investing vs. active stock picking

Chris also reflects on what makes a great investor over time — and it’s not intelligence or access.

It’s patience.

Discipline.

And the ability to ignore noise when it matters most.

The core idea:

Investing isn’t about being clever. It’s about staying consistent long enough for compounding to do its job.

If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps.

Hope this gives you something to think about this week.

Pre-Order Tyler's First Book, Real Wealth, ⁠here⁠ & be immediately eligible for exclusive bonuses between now and December 1st!

April Bonus: Free two-hour digital live event on Wednesday, May 6th from 7-9pm EST, where Tyler will answer the most commonly asked questions and walk through what you can expect from the book!

And as always, a MASSIVE thank you to this week's sponsors:

Thrive Market: Get $20 off your first three orders plus a FREE

$60 gift if you order at thrivemarket.com/tyler today.

Facet: find out why I have been endorsing Facet for over 18 months now by checking out ⁠facet.com/tyler⁠. They are a one-stop shop for financial planning, investment management, tax strategy, and retirement planning. And best part: it's all for one flat annual membership fee.

And on to the show notes!

No one wants to think about long-term care.

Which is exactly why most people don’t plan for it.

In this episode, Tyler tackles one of the most uncomfortable — and most overlooked — parts of financial planning: what happens if you live long enough to need care.

Because longevity is a gift.
And financially, it’s also a risk.

In this episode, Tyler covers:

The reality that ~70% of people over 65 will need some form of long-term care

What long-term care actually means (it’s not just nursing homes)

The real costs — from home care to assisted living to memory care

Why long-term care is separate from normal retirement planning

The four ways to pay for it: self-insuring, Medicaid, traditional insurance, and hybrid policies

Why Medicare doesn’t cover what most people think it does

How to estimate your true long-term care exposure (and why it can reach seven figures)

The biggest mistakes people make — including relying on kids or “figuring it out later”

Tyler also lays out a clear, practical framework:

Understand your numbers.
Decide who pays.
And make the decision before you need it.

The core idea:

A retirement plan isn’t complete until it answers one question — what happens if care is required?

Because this isn’t just a financial decision.

It’s a decision that affects your spouse, your kids, and how the last chapter of your life actually plays out.

If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps.

Hope this gives you something to think about this week.