Your Money Guide on the Side

Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st!

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

Caldera+ Lab⁠: → If you've been meaning to take better care of your skin, head to CalderaLab.com/TYLER and use code TYLER for 20% off your first order. This has been a game-changer for me.

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

⁠⁠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.

And On to the Show Notes!

Most retirement advice gives you a simple withdrawal order:

Taxable.Traditional.Roth.

Useful? Yes.

Always right? Not even close.

In Part 2 of the Art of Decumulation series, Tyler digs into what actually determines where your retirement income should come from each year — taxes, healthcare, market conditions, account type, and the life you’re trying to fund.

Because retirement withdrawals aren’t a problem you solve once.

They’re a decision you revisit every year.

In this episode, Tyler covers:

Why the “taxable → traditional → Roth” rule is only a starting point

How to use low tax brackets strategically instead of simply minimizing withdrawals

Why asset location matters just as much as asset allocation

How sequence-of-returns risk changes the early years of retirement

Monthly vs. annual withdrawals — and why the mathematically “best” answer may not be the best life answer

When ACA subsidies and Roth conversions should override the usual withdrawal order

Why the Roth is often best preserved for last

The core idea:

The best withdrawal strategy changes with the year in front of you.

Do the math carefully.

But remember what the math is for.

This is Part 2 of the Art of Decumulation series. Next week: Roth conversions, RMDs, and IRMAA.

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 book, Real Wealth, at ⁠⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st!

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

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠DeleteMe⁠ → joindeleteme.com/tyler20⁠ Use code Tyler20 for up to 20% off!

Caldera+ Lab⁠ → CalderaLab.com/TYLER and use code TYLER for 20% off your first order.

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

Gelt → ⁠⁠joingelt.com/tyler⁠ because having the right tax strategist changes the game entirely. If you're a business or a high-net worth individual, you might want to check this one out today.

And on to the show notes!!

Most financial advice is about building wealth.

Far less is about what comes next.

In this episode, Tyler kicks off a five-part series on the art of decumulation—the transition from saving for retirement to confidently spending what you've spent decades building.

Because retirement isn't just a financial shift.

It's a life shift.

In this episode, Tyler covers:

Why the first year of retirement is often the most emotionally challenging

How to build a 12–24 month cash buffer before leaving work

What to do with your 401(k) when you retire

How to think about Social Security and the healthcare gap before Medicare

Why every retiree should review beneficiaries and prepare their spouse to manage the finances

How to reposition your portfolio before retirement—not after

The core idea:

A successful retirement starts long before your last day at work.

The more decisions you make in advance, the less likely you'll be forced into emotional ones later.

This is Part 1 of Tyler's five-part series on retirement spending. Next week, he dives into one of the biggest decisions retirees face: which accounts to withdraw from first—and why the order matters.

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 book, Real Wealth, at ⁠⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st!

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

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fabric⁠ → ⁠meetfabric.com/tyler⁠ Made for busy parents like you; all online, on your schedule, right from your couch. You could be covered in under 10 minutes, often with no health exam required.

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.

⁠⁠⁠Copilot Money → ⁠⁠www.copilot.money/tyler⁠⁠ — use code TYLER2 for two free months.⁠

⁠Bilt⁠ → ⁠joinbilt.com/tyler⁠ So you can choose the card that fits your lifestyle without missing out on points and exclusive benefits.

And on to the show notes!!

Most investors think a better portfolio is a more complicated portfolio.

It usually isn't.

In this episode, Tyler revisits his retirement portfolio framework and answers one of the most common questions he's received:

How many funds do you actually need?

From a simple two-fund portfolio to more complex five-fund allocations, Tyler explains where diversification adds real value—and where it simply adds complexity.

In this episode, Tyler covers:

The differences between two-, three-, and five-fund portfolios

Why simplicity often outperforms complexity over the long run

The difference between bond funds and money market funds

Whether international stocks are actually necessary

When adding more funds becomes an active bet, not diversification

Why rebalancing once a year is usually enough

The behavioral advantage of owning a portfolio you can actually stick with

The core idea:

The best portfolio isn't the most sophisticated. It's the one you'll hold through the next bear market.

Because long-term investing isn't won by finding the perfect allocation.

It's won by keeping costs low, staying invested, and resisting the urge to tinker.

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 book, Real Wealth, at ⁠⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st!

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


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

⁠Gelt: → ⁠⁠⁠joingelt.com/tyler⁠⁠ because Q3 is where strategic businesses make game-changing tax moves before the yearis over. If you're a business or a high-net worth individual, check out Gelt today.


Anthropic⁠: → ⁠⁠claude.ai/tyler ⁠to experience AI for minds that don't stop at good enough.


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

And on to the show notes!!

We spend a lot of our lives chasing financial milestones.

A six-figure salary. Coast FIRE. Retirement. The next big achievement.

But what if those milestones were never meant to make us feel complete?

In this episode, Tyler steps away from spreadsheets and investment strategies to explore what literature can teach us about money, ambition, and the illusion that one more milestone will finally make everything click.

Drawing on works by C.P. Cavafy, Samuel Johnson, Kazuo Ishiguro, and David Foster Wallace, Tyler reflects on why so many financial goals feel strangely empty once we reach them—and what that means for how we should build our lives.

In this episode, Tyler explores:

Why a six-figure salary often changes less than we expect

What Coast FIRE really gives us—and what it doesn't

The hidden myth at the heart of retirement planning

Why major achievements rarely deliver lasting fulfillment

The importance of always having another "Ithaca" on the horizon

The one financial milestone that genuinely does transform people's lives: getting out of high-interest debt

The core idea:

Financial milestones matter—but not because they complete us.

They give us direction.

The real value isn't in arriving.

It's in the person you become on the way there.

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 book, Real Wealth, at ⁠⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st!

And 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.


Wispr Flow: → wisprflow.ai/tyler for one free month of Wispr Flow Pro free!


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

⁠⁠Fabric⁠⁠: → ⁠⁠meetfabric.com/tyler⁠⁠ because if someone depends on your income, term life insurance is the next step you should take today.

And on to the show notes!!

Inflation doesn't usually destroy wealth overnight.

It does it slowly.

A little bit each year.

A little less purchasing power.

A little more expensive to maintain the same lifestyle.

And over a long retirement, those small changes add up.

In this episode, Tyler breaks down how investors can build portfolios that are designed to keep pace with inflation, rather than slowly fall behind it.

Because protecting your money isn't just about growing it.

It's about preserving what it can actually buy.

In this episode, Tyler covers:

Why inflation is one of the biggest long-term risks retirees face

The asset classes that have historically done the best job of outpacing rising prices

Why stocks remain the most powerful long-term inflation hedge

How TIPS (Treasury Inflation-Protected Securities) work

The role of real estate and infrastructure in an inflation-resistant portfolio

Why traditional bond-heavy portfolios can struggle when inflation rises

The hidden cost of holding too much cash

How overreacting to inflation headlines can hurt returns more than inflation itself

Tyler also walks through three increasingly sophisticated portfolio approaches, ranging from a simple stock-and-TIPS allocation to a more diversified strategy incorporating real assets.

The core idea:

Inflation isn't a market event. It's a permanent feature of the system.

The goal isn't to predict it.

The goal is to build a portfolio that's prepared for 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.