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 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:

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 ⁠⁠⁠⁠⁠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 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:

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 ⁠⁠⁠⁠⁠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 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 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 ⁠⁠⁠⁠⁠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!!

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:

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 ⁠⁠⁠⁠⁠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!!

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:

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.

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 assume the listed price is the real price.

It often isn't.

In this episode, Tyler shares a collection of practical money-saving strategies he's used himself — from negotiating internet bills to appealing property tax assessments — and explains why so many financial opportunities come down to one simple skill:

Asking.

Because companies routinely offer discounts, credits, and incentives that never appear on their websites.

In this episode, Tyler covers:

The common thread through all of these strategies is simple:

Most savings opportunities aren't hidden because they're complicated. They're hidden because most people never ask.

The companies know it.

The people who save money know it.

And now you do too.

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!!

Most investors spend their lives trying to beat the market.

The problem?

The market is already made up of millions of people trying to do the exact same thing.

In this episode, Tyler explores what he calls "the tyranny of the benchmark" — the idea that comparing ourselves to the S&P 500 often creates more anxiety, more mistakes, and worse outcomes than simply owning the market in the first place.

Because for most investors, matching the market isn't mediocrity. It's success.

In this episode, Tyler covers:

Tyler also explains why the greatest threat to most portfolios isn't Wall Street.

It's the person checking the portfolio.

The core idea:

The goal isn't to outsmart the market. It's to stop getting in your own way.

Own it cheaply.

Because the most remarkable investing outcomes often come from the most unremarkable investing stories.

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!!

We’ve been sold a very specific version of success:

Work for forty years.
Retire at sixty-five.
Finally enjoy your life.

But what if retirement, at least as we think about it, is the wrong goal entirely?

In this episode, Tyler makes the case that the wealthiest people don’t retire — they redesign work.

Because the real goal isn’t escaping your life.

It’s building one you don’t constantly want to escape from.

In this episode, Tyler covers:

Tyler also shares a more personal reflection on leaving a stable career to build something of his own — and why uncertainty, while uncomfortable, can be worth it.

The core idea:

Real wealth isn’t retiring from your life. It’s building one you don’t need to retire from.

Because the goal was never the finish line.

It was finding a game worth playing for a very long time.

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 now, on to the show notes!!

We’ve been taught that saving money is responsible:

But what if the way most people save is actually making them slightly poorer?

In this episode, Tyler challenges one of personal finance’s most sacred ideas: that keeping large amounts of money sitting in savings is the safest thing you can do.

Because safety and stagnation are not the same thing.

In this episode, Tyler covers:

Tyler also makes a more personal argument:

That many of us inherit financial beliefs built around scarcity, caution, and delayed gratification — even when we no longer need them.

The core idea:

Money is meant to support your life, not become the thing preventing you from living it.

Invest broadly.

And maybe, every once in a while…

Eat the shrimp instead of the mashed potatoes.

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!

The average American spends roughly $12,000 per year on their car.

For many people, that’s more than they invest.

In this episode, Tyler breaks down the real cost of car ownership — not just the sticker price, but the hidden financial drag of depreciation, financing, insurance, fuel, and maintenance.

Because most people buy cars emotionally… and only look at the math afterward.

In this episode, Tyler covers:

Tyler also explains why he believes people should stop optimizing every dollar purely for efficiency.

Because personal finance isn’t about removing joy from your life.

It’s about being intentional enough to know which things are genuinely worth spending on — and cutting ruthlessly everywhere else.

The episode ends with Tyler revealing the one category where he knowingly ignores his own financial advice:

A brand-new GMC Sierra Denali.

Not because it’s the best financial decision.

The core idea:

Don’t spend blindly. But don’t optimize the humanity out of your life either.

Know your “no’s.”

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.