Your Money Guide on the Side

As always, a MASSIVE thank you to this week's sponsors!


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Anthropic: → ⁠claude.ai/tyler if you're looking for the best business and thought partner I have EVER had.

And on to the show notes!

Most financial advice focuses on optimization.

This episode is about something else entirely: alignment.

In this more personal episode, Tyler shares five lessons from spending two months “snowbirding” in Sedona — and what the experience revealed about money, time, and the life we think we want.

Because sometimes the biggest financial insights don’t come from spreadsheets.
They come from living differently long enough to notice what actually matters.

In this episode, Tyler reflects on:

Why buying back time only works if you know what to do with it

The idea of a “path dividend” — testing lifestyles before committing to them

How lifestyle upgrades quickly become your new normal (and lose their impact)

Why major life changes require understanding what you’re leaving, not just gaining

The illusion that a new place will create a new version of you

Along the way, Tyler connects everyday moments — cooking dinner, staying in Airbnbs, almost buying a house — to deeper financial decisions around spending, relocation, and retirement.

The core idea:

Wherever you go, there you are.

Money can change your environment.
It doesn’t automatically change you.

This episode isn’t about maximizing efficiency.

It’s about building a life that actually fits — before you build the plan to fund 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 First Book, Real Wealth, ⁠⁠here⁠⁠ & be immediately eligible for exclusive bonuses between now and December 1st!

April Bonus: Free two-hour digital live event on Wednesday, May 6th from 7-9pm EDT, where Tyler will answer the most commonly asked questions and walk through what you can expect from the book!

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

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→ try.copilot.money/tyler — use code TYLER2 for two free months.

And on to the show notes!

Most people think investing is about finding the next big thing.

The reality is much less exciting — and far more effective.

In this episode, Tyler sits down with Chris Hill, longtime host of Motley Fool Money, to talk about what actually drives long-term success in investing — and why so many people get distracted along the way.

From launching a podcast during the 2008 financial crisis to interviewing some of the biggest names in business and finance, Chris shares lessons from decades inside one of the most influential investing platforms.

In this conversation, Tyler and Chris discuss:

How Motley Fool Money started during a crisis — and why simplicity won

Why investors obsess over “hot stocks” and excitement (and why that hurts returns)

The importance of time in the market — and not interrupting compounding

Why the best companies are often the ones everyone already knows

The balance between simple index investing vs. active stock picking

Chris also reflects on what makes a great investor over time — and it’s not intelligence or access.

It’s patience.

Discipline.

And the ability to ignore noise when it matters most.

The core idea:

Investing isn’t about being clever. It’s about staying consistent long enough for compounding to do its job.

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 First Book, Real Wealth, ⁠here⁠ & be immediately eligible for exclusive bonuses between now and December 1st!

April Bonus: Free two-hour digital live event on Wednesday, May 6th from 7-9pm EST, where Tyler will answer the most commonly asked questions and walk through what you can expect from the book!

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

Thrive Market: Get $20 off your first three orders plus a FREE

$60 gift if you order at thrivemarket.com/tyler today.

Facet: find out why I have been endorsing Facet for over 18 months now by checking out ⁠facet.com/tyler⁠. They are a one-stop shop for financial planning, investment management, tax strategy, and retirement planning. And best part: it's all for one flat annual membership fee.

And on to the show notes!

No one wants to think about long-term care.

Which is exactly why most people don’t plan for it.

In this episode, Tyler tackles one of the most uncomfortable — and most overlooked — parts of financial planning: what happens if you live long enough to need care.

Because longevity is a gift.
And financially, it’s also a risk.

In this episode, Tyler covers:

The reality that ~70% of people over 65 will need some form of long-term care

What long-term care actually means (it’s not just nursing homes)

The real costs — from home care to assisted living to memory care

Why long-term care is separate from normal retirement planning

The four ways to pay for it: self-insuring, Medicaid, traditional insurance, and hybrid policies

Why Medicare doesn’t cover what most people think it does

How to estimate your true long-term care exposure (and why it can reach seven figures)

The biggest mistakes people make — including relying on kids or “figuring it out later”

Tyler also lays out a clear, practical framework:

Understand your numbers.
Decide who pays.
And make the decision before you need it.

The core idea:

A retirement plan isn’t complete until it answers one question — what happens if care is required?

Because this isn’t just a financial decision.

It’s a decision that affects your spouse, your kids, and how the last chapter of your life actually plays out.

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 First Book, Real Wealth, here & be immediately eligible for exclusive bonuses between now and December 1st!

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

LMNT⁠: regardless of who much money you have, if you're not feeling your best physically and mentally, it means very little. That's why I drink ⁠LMNT⁠ daily (well, multiple times a day) to continue to be as productive as I can be after my workouts. Try ⁠drinklmnt.com/tyler⁠ today and let me know what your favorite flavor is!

Copilot Money⁠: if you are looking for one of the most well-designed money apps out there, check out ⁠Copilot Money⁠ today. My friends and family continue to rave about it, and they now have all of their money needs in one place. Check out ⁠try.copilot.money/tyler ⁠today and use code TYLER2 for two free months, so you can see if it works for you!

Anthropic⁠: I use Claude AI every single day as a thought partner and business strategist. To become more efficient and solve problems more quickly and effectively, check out ⁠claude.ai/tyler⁠ today. There is no single business move I have made in the past year that has been more worthwhile and productive.

And on to the show notes!

When should you take Social Security?

It’s one of the most debated — and most personal — financial decisions you’ll ever make.

In this episode, Tyler makes a serious, data-backed case for taking benefits at 62 — not as a blanket recommendation, but as a counterpoint to the conventional advice to always wait.

Because this decision isn’t just math.
It’s math layered on top of real life.

In this episode, Tyler covers:


The break-even math between taking benefits at 62, 67, and 70


Why waiting only “wins” if you live past your late 70s or early 80s


The idea that a dollar at 62 isn’t equal to a dollar at 82


How the “go-go, slow-go, no-go” phases of retirement change how money is experienced


The often-overlooked healthcare gap between 62 and 65 — and what it can cost


How the earnings test reduces (but doesn’t eliminate) benefits if you keep working


Why Social Security decisions should factor in your spouse’s survivor benefit

Tyler also introduces a practical framework — six key questions — to help you make the decision based on your own life, not a generic rule:

Health.
Healthcare.
Work status.
Income needs.
Spousal impact.
And how you actually want to spend your time.

The core idea:

This isn’t about maximizing dollars. It’s about maximizing life.

For some people, waiting is the right call.
For others, taking it early — and using that money when it matters most — may be the better decision.

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.

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

Gelt: I will forever regret not prioritizing a tax strategist early in my solopreneur journey. Don't make the same mistake I did and leave money on the table. If you are a business owner or a high net worth individual, check out Gelt today at joingelt.com/tyler.

Fabric: there is a reason that term life insurance is number 4 in my financial order of operations, before an Emergency Fund, and before funding the Roth IRA. If anyone else depends on your income, cross this off your list today in ten minutes at meetfabric.com/tyler.

And on to the show notes!

AI isn’t replacing financial advisors.

But it is getting surprisingly good at doing one of the most valuable parts of the job: stopping you from making bad decisions.

In this episode, Tyler breaks down how to actually use AI as a financial tool — not for stock picks or shortcuts, but for clarity, structure, and behavioral coaching.

Because the biggest gap in investing isn’t information.
It’s execution.

In this episode, Tyler covers:

Why most investors underperform the market — and how behavior drives that gap

How to build a complete financial snapshot for better decision-making

How to use AI to uncover your real risk tolerance (not the one you think you have)

How to create a simple, diversified investment strategy using structured prompts

Why asset location (where you hold investments) matters more than most people realize

How to stress test your plan using worst-case scenarios and Monte Carlo thinking

How to use AI as a behavioral guardrail during market volatility

The real risks: privacy concerns, bad prompts, and AI hallucinations

The core idea: AI is a tool, not a replacement for judgment.

Used well, it can help you think more clearly, avoid emotional decisions, and build a plan you actually understand.

Used poorly, it can give you confident-sounding answers to the wrong questions.

If you take one thing from this episode, it’s this:

Better inputs lead to better decisions.

And if AI helps you slow down, ask better questions, and avoid one major mistake, it’s already paid for itself.

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.