Your Money Guide on the Side

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

And on to the show notes!!

Most of the biggest money questions aren’t really about what to buy. They’re about how to think when the answer isn’t obvious.

In this episode, Tyler answers the five questions listeners have asked most in 2026 — from pensions and politics to healthcare, market concentration, and long-term care — with an emphasis on what you can actually control.

You’ll learn:

The recurring lesson is that good planning rarely comes from predicting the future. It comes from understanding the whole picture, knowing what you own, and preparing for the decisions you can control.

If the show’s been helpful, please consider leaving a review on Apple or Spotify.

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:

And on to the show notes!!

Most people spend decades learning how to make and save money.

Far fewer learn how to spend it well.

In this episode, Tyler shares two very personal lists: five things he’ll happily overpay for, and five things he refuses to spend money on again.

Not because one list is objectively right.

Because the point is figuring out your own list.

In this episode, Tyler covers:

The core idea:

The money was never the finish line. It’s a tool for buying more of what you already value.

Spend generously where it meaningfully improves your life.

And stop paying for things you only thought you were supposed to want.

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:

And on to the show notes!!

Hiring a financial advisor can be genuinely valuable.

Hiring the wrong one can be extremely expensive.

In this episode, Tyler breaks down five red flags to watch for when choosing an advisor—or evaluating the one you already have.

Because the question isn’t whether financial advice has value.

It’s whether this advisor is worth what you’re paying them.

In this episode, Tyler covers:

The core idea:

Good financial advice can be worth paying for. But the price should reflect the service—not the size of your portfolio.

Look for transparent pricing, boring investments, real planning expertise, aligned incentives, and someone willing to tell you exactly how they get paid.

And remember: it’s your money, not theirs.

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

Hope this gives you something useful 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:

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:

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:

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:

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:

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:

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:

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:

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:

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:

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:

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:

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:

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:

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.