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:

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.

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The best financial advisor Tyler has ever worked with charges almost nothing, never calls during dinner, and automatically fires its own losers.

It’s the S&P 500.

In this episode, Tyler revisits the case for simple index investing—and tackles the arguments that usually come next:

What about concentration?What about international diversification?What about investor behavior?And what exactly are you paying an advisor to do?

In this episode, Tyler covers:

How the S&P 500’s profitability and inclusion rules create a built-in quality filter

Why the index automatically removes declining companies and replaces them with stronger ones

The case that large U.S. companies already provide meaningful international exposure

Why today’s market concentration is a real risk—but not necessarily a reason to abandon the index

The enormous long-term advantage of low fees and tax efficiency

Tyler’s three-bucket framework for matching investment risk to when you actually need the money

Whether behavioral coaching really justifies a 1% advisory fee

How AI, primary-source verification, and hourly or flat-fee professionals can handle more complex planning questions

The core idea:

You don’t necessarily need someone continuously managing your investments. You need a simple structure you understand, enough friction to stop yourself panicking, and targeted expertise when the problem actually requires it.

The S&P 500 won’t hold your hand.

But for the job of growing long-term savings cheaply and automatically, it’s remarkably difficult to beat.

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:

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!

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

⁠⁠⁠⁠⁠⁠⁠⁠⁠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!!

There is no single perfect portfolio.

There is only the portfolio that is right for you.

In Part 2, Tyler looks at five more of the greatest investing thinkers of the last century before pulling all ten together into a practical framework for building a portfolio that can actually survive real life.

In this episode, Tyler covers:

Robert Merton on building around the income you actually need

Martin Leibowitz and why your capacity for risk matters more than a questionnaire

Robert Shiller on valuations, behavioral finance, and global diversification

Charles Ellis on winning by avoiding mistakes, not making brilliant moves

Jeremy Siegel on stocks, long time horizons, and dollar-cost averaging

Why TIPS repeatedly appear as the preferred long-term risk-off asset

The five principles that emerge when all ten thinkers are compared

The conclusions are surprisingly simple:

Keep costs low. Know yourself. Diversify broadly. Protect against inflation. And stay the course.

The perfect portfolio isn’t the one with the cleverest allocation.

It’s the one built around your life, your risk tolerance, and your goals—and simple enough that you won’t abandon it when markets get ugly.

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:

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.