Your Money Guide on the Side

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.

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!

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. Check out facet.com/tyler and see if they're the right fit for you!

And on to the show notes!

Many parents want to help their kids financially — but often focus on the wrong things.

Saving for a wedding, helping with a down payment, or paying for grad school can help in the moment. But the biggest advantage you can give a child financially is time.

In this episode, Tyler breaks down how investing small amounts early in a child’s life can turn into millions thanks to compound growth — and walks through the most practical ways parents can do it.

In this episode, Tyler covers:

How investing $3,000 per year for a decade could grow into millions over a lifetime

The power of giving a child 20–30 extra years of compounding

How UGMA/UTMA accounts work and their tax implications

Why a custodial Roth IRA can create completely tax-free retirement wealth

A lesser-known strategy: investing in your own brokerage account and passing assets down with a step-up in basis

Why 529 plans are useful — but often overhyped and less flexible

The key takeaway: when it comes to investing for your kids, starting early matters far more than the amount you invest.

Even small, consistent contributions can grow into life-changing sums over decades.

If this episode helped clarify your approach to investing for your family, consider leaving a quick review on Apple Podcasts or Spotify — it helps others find the show.

As always, a massive thanks to this week's sponsors:

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.

Bilt: If you're not earning rewards from your biggest annual expense (rent and mortgage!), you might just be missing out. Learn more about their three new credit cards and how you can start earning rewards for your biggest expenses at joinbilt.com/tyler.

Gelt: And I'll go to my grave with this one: the single biggest mistake I have made in business thus far is not prioritizing finding a tax strategist and partner before anything else. Go to joingelt.com/tyler to see if they can help your business find what it's been missing.

And on to the show notes!

Most financial advice assumes money decisions are rational.

Spend less. Save more. Invest consistently.

But in reality, our financial decisions are often driven by psychology, identity, and social pressure far more than spreadsheets.

In this episode, Tyler sits down with Hannah Horvath, CFP and writer of Your Brain on Money, to explore why traditional financial advice misses the behavioral side of money — and why understanding your values matters just as much as understanding the math.

In this conversation, Tyler and Hannah discuss:

Why information alone rarely changes financial behavior

How social comparison shapes spending and lifestyle choices

Why defining “enough” is more psychological than financial

How marketing profits from creating a sense of lack

The hidden cost of hyper-convenience and digital isolation

Why community and real-world connection matter more than we think

The core idea: money is a tool, but if you don’t define what you actually value, it’s easy to spend your life chasing someone else’s version of success.

If you’d like to explore more of Hannah’s work, you can find her newsletter Your Brain on Money, where she writes about the psychology and culture behind our financial decisions.

And 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 partners:

Fabric: if anybody relies on your income, you need to consider term life insurance asap. Check out meetfabric.com/tyler to find out the right coverage for you and your loved ones.

Facet: and even though I WANT to offer you all direct advice, I can't, as I don't know you. But Facet can, and they continue to practice exactly what I preach. Check out joinfacet.com/tyler today.

And on to the show notes!

“How should a 60-year-old invest?”

It sounds like a reasonable question.

It’s also the wrong one.

In this episode, Tyler dismantles the idea that your age should determine your portfolio — and replaces it with a framework that actually works: invest based on when you need the money, not how many birthdays you’ve had.

Because two people the same age can — and often should — invest completely differently.

Instead of age-based formulas like “110 minus your age,” Tyler introduces a simpler system:

The Three Bucket Framework


Bucket 1 (0–2 years): Cash, money markets, short-term treasuries. Zero stock exposure.


Bucket 2 (2–10 years): A glide path. Years until goal = % in stocks.


Bucket 3 (10+ years): 100% stocks in low-cost index funds.

That’s it.

This episode walks through real examples — retirees, early retirees, 30-year-olds saving for houses, 70-year-olds investing for grandkids — to show why timeline beats age every time.

Tyler also explains:

Why sequence-of-returns risk matters more than age

How to structure withdrawals using the bucket system

Why most “conservative by default” advice is lazy

The 10 investing terms you actually need to understand

How to match allocation to goals without overcomplicating it

The core idea is simple:

Your timeline is your allocation.

Stop asking how a 60-year-old should invest.
Start asking when the money will be spent.

If this framework changes how you think about your portfolio, leaving a quick review on Apple or Spotify genuinely helps.

Hope this gives you something to think about this week.