Your Money Guide on the Side

Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.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:

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

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.

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

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

And on to the show notes!!

In Pursuit of the Perfect Portfolio, Part 1

Is there such a thing as the perfect portfolio?

Yes.

And no.

In this episode, Tyler steps back from his own investing philosophy and looks at how five of the most influential thinkers in modern finance approached the same question.

Drawing from In Pursuit of the Perfect Portfolio, Tyler explores where their ideas overlap, where they disagree, and what individual investors can actually use.

In this episode, Tyler covers:

Harry Markowitz and why correlation and diversification changed investing forever

William Sharpe on balancing market risk with safer assets

Eugene Fama and the case for efficient markets, broad indexing, and factor tilts

Jack Bogle’s obsession with low costs, simplicity, and staying invested

Myron Scholes on tail risk, market concentration, and the limits of passive investing

Why risk tolerance, taxes, time horizon, and life stage matter more than finding a universal allocation

The common ground is surprisingly simple:

Diversify. Keep costs low. Understand the risks you can actually tolerate. And don’t add complexity unless it solves a real problem.

There may not be one perfect portfolio for everyone.

But there are a handful of principles that keep appearing whenever serious people study the question.

Next week, Tyler looks at five more investing thinkers before bringing all ten together into a practical framework.

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 ⁠⁠⁠⁠⁠⁠tylergardner.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:

Factor → factormeals.com/tylerg50off and use code tylerg50off to get 50% off and one free breakfast item per box for one year while supplies last until 10/31/2026.

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!!

Personal finance is usually very good at answering how.

How to invest.How to save.How to retire.

The harder question is what any of it is actually for.

In this episode, Tyler steps away from the technical side of money to share four lessons that have shaped how he thinks about work, time, happiness, and wealth.

In this episode, Tyler explores:

Why having more free time means little if you don’t know what to do with it

Why work itself isn’t the enemy—the wrong work, people, and structure are

The myth of the “heroic week,” and why meaningful progress is built on ordinary weekdays

Why money really can buy happiness—if you spend it on what genuinely matters to you

How to use your own spending as data through the Path Dividend

Why the financial plan should always serve the life, not become the life

The core idea:

Money is a means, not an end.

The goal isn’t simply more wealth, more freedom, or more time.

It’s knowing what kind of days, work, people, and experiences you actually want those things to make possible.

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 ⁠⁠⁠⁠⁠⁠tylergardner.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!

Gelt → ⁠⁠joingelt.com/tyler⁠ because Q3 is where strategic businesses make game-changing tax moves. If you're a business or a high-net worth individual, time to make moves.

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.

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

And on to the show notes!!

You can have enough money and still be afraid to spend it.

That’s the final problem.

In Part 5 of the Art of Decumulation series, Tyler moves beyond withdrawal rates, tax brackets, and portfolio mechanics to the harder question:

How do you actually become a spender after spending forty years becoming a saver?

Because the transition isn’t really financial.

It’s an identity shift.

In this episode, Tyler covers:

Why saving becomes part of your identity—not just a behavior

The real cost of oversaving in retirement

Why permission to spend has to come from you

How to front-load experiences whose value declines with age

Why retirees should explicitly define what the money is for

The case for giving money away while you’re still alive to see what it changes

Why real wealth is ultimately about control over your time

The core idea:

The portfolio exists to fund the life. The life does not exist to preserve the portfolio.

Spend on the experiences that won’t wait.

Give while you can witness the impact.

And use the money to buy back the hours you actually care about.

This is Part 5 and the final episode of the Art of Decumulation series.

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 ⁠⁠⁠⁠⁠tylergardner.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.

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

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

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!!

A market crash doesn’t usually destroy a retirement.

Panic does.

In Part 4 of the Art of Decumulation series, Tyler explores how retirees can survive market downturns without turning temporary losses into permanent ones.

Because the financial news reports the weather.

Your retirement plan needs to be built for the climate.

In this episode, Tyler covers:

Why the first five years of retirement carry the greatest sequence-of-returns risk

How a larger cash buffer can prevent forced selling during downturns

Why a rising equity glide path may make more sense than becoming increasingly conservative with age

How the Guyton-Klinger guardrails adjust spending in good and bad markets

Why modest spending cuts can support a higher sustainable withdrawal rate

The behavioral cost of panic selling—and why knowledge alone rarely prevents it

How writing a decision plan in advance can protect you when markets turn

Why almost every apparent catastrophe eventually proves to be ordinary market weather

The core idea:

The most valuable skill in retirement investing is often the ability to do nothing.

Use the cash buffer.Adjust spending when the guardrails require it.Trust the plan you made while thinking clearly.

Then let the storm pass.

This is Part 4 of the Art of Decumulation series. Next week, the final episode: how to move from saver to spender and give yourself permission to enjoy what you 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.

Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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:

Gelt → ⁠⁠joingelt.com/tyler⁠ because Q3 is where strategic businesses make game-changing tax moves. If you're a business owner or a high-net worth individual, time to make moves!

Facet → ⁠⁠⁠facet.com/tyler⁠⁠ for an exclusive $550 kickstart offer! Schedule your intro call today!

Fabric → ⁠⁠meetfabric.com/tyler⁠⁠ because if someone depends on your income, term life insurance is the next item on your financial agenda!

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

And On To the Show Notes!

A traditional IRA can look like your money.

But part of it belongs to the IRS.

In Part 3 of the Art of Decumulation series, Tyler tackles three of the most important—and expensive—pieces of retirement tax planning:

Roth conversions, RMDs, and IRMAA.

Because the goal isn’t to avoid taxes entirely.

It’s to control when you pay them and at what rate.

In this episode, Tyler covers:

Why the years between retirement and RMDs can be your biggest tax-planning opportunity

How Roth conversions work—and when they can save significant money

Why filling lower tax brackets deliberately can matter more than minimizing income

How required minimum distributions (RMDs) can push retirees into higher brackets later

Why IRMAA is a cliff, not a normal marginal tax bracket

The importance of planning for the widow’s penalty

Why retirement tax planning should become an annual practice, not a one-time decision

The core idea:

Your traditional IRA is a future tax bill. The question is whether you choose when to pay it—or let the IRS choose for you.

This is Part 3 of the Art of Decumulation series. Next week: market downturns, sequence-of-returns risk, and when to actually change the plan.

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.