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Latest Episodes:

5 Things I Will Never Spend Money On as a Multimillionaire (And 5 That Are Worth Every Penny) Sep 28, 2026

Show notes

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:

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

Gelt → ⁠⁠joingelt.com/tyler⁠ because Q2 is where strategic businesses make game-changing tax moves. If you're a business or a high-net worth individual, you might want to check this one out today.

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.

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:

Why many well-funded retirees still struggle to give themselves permission to spend
Five things Tyler believes are genuinely worth the money, from generous tipping to buying back time
Why a capsule wardrobe, books, house cleaning, and even leasing a car can make sense when they solve the right problem
Five purchases he’s done with—including short-haul first class, expensive wine, and other versions of “luxury” that don’t actually improve his life
Why outsourcing tasks you hate can increase happiness—but outsourcing things you enjoy can do the opposite
How to separate spending that buys time, health, peace, or connection from spending that mostly buys an audience
The exercise of building your own “worth it” and “never again” lists

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.

The 5 Biggest Red Flags of Financial Advising Sep 21, 2026

Show notes

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 Get a free 8-count Sample Pack of LMNT’s most popular drink mix flavors with any purchase at drinklmnt.com/tyler.

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

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

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:

Why the traditional 1% assets-under-management fee can become enormously expensive over time
The one question to ask every prospective advisor: “What would you do with $100,000 of my money?”
Why real market experience—and humility—matters when things get ugly
How to confirm your advisor is a fiduciary 100% of the time
Why your investments should always be held with an independent third-party custodian
How guarantees, deadlines, and high-pressure sales tactics reveal misaligned incentives
What to watch for once you’re a client, including churning and unnecessary cash drag
How to leave an advisor without creating an avoidable tax bill

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.

The Greatest Financial Advisor You Never Knew You Had Sep 14, 2026

Show notes

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.
DeleteMe⁠→ joindeleteme.com/tyler20⁠ Use code Tyler20 for up to 20% off!
Thrive Market⁠ → Use link thrivemarket.com/tyler to get $30 off your first two orders. You cannot get this deal on the website — it's only through my link. And that right there covers your membership fee, so sign up now before this exclusive offer ends
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, you might want to check this one out today.

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.

How to Build the Perfect Portfolio - Part 2 of 2 Sep 07, 2026

Show notes

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.

How to Build the Perfect Portfolio - Part 1 of 2 Aug 31, 2026

Show notes

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.

The 4 Greatest Money (And Life) Lessons I Have Ever Learned Aug 24, 2026

Show notes

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.

The $4.2 Million Man Who Couldn't Spend His Own Money Aug 17, 2026

Show notes

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.

The Subtle Art of Doing Nothing (And Making More Money While Doing It) Aug 10, 2026

Show notes

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.

The $250,000 Mistake Most Retirees Never Know They Made Aug 03, 2026

Show notes

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/tyler⁠for $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.

The Withdrawal Order Nobody Taught You (And How to Save 10% on Taxes Annually in Retirement) Jul 27, 2026

Show notes

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. This has been a game-changer for me.

⁠⁠⁠⁠Copilot Money: → ⁠⁠www.copilot.money/tyler⁠⁠ — use code TYLER2 for two free months, and learn why this is the only budgeting app that makes it into our group texts.

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.