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:

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:

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

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:

The core idea is simple:

Your timeline is your allocation.

Stop asking how a 60-year-old should invest.

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.

A special thanks to this week's sponsors:

Bilt: if you are looking to level up your rewards game, time to check out how to get something back for your biggest annual expense: your rent or mortgage. Check out joinbilt.com/tyler today.

Copilot Money: it's rare that I recommend apps to my friends, but when I do, it's because they're actually useful and dialed on what we need in finance. Check out try.copilot.money/tyler to see if Copilot Money is right for you.

Gelt: I've said it before, and I'll say it always: if you haven't prioritized finding the right tax partner as a high net worth individual or business owner, you're prioritizing the wrong things. Check out joingelt.com/tyler today.

A simple retirement plan is easy to explain.

Living with it is harder.

In this episode, Tyler revisits his 90% stocks / 10% money market retirement strategy — not to defend it, but to answer the practical questions that matter:

When do you cut spending?

This is the execution episode.

In this conversation, Tyler covers:

The strategy remains intentionally simple: spend from cash during downturns, rebalance annually, and let math — not headlines — drive decisions.

This episode isn’t about market timing.

It’s about having rules in place so you don’t panic when volatility shows up.

If the original 90/10 allocation made sense to you, this episode shows you how to actually stick with it.

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.

A massive "thanks," as always, to this weeks's sponsors:

Anthropic: I use Claude every hour of every day to optimize my life. If you haven't explored what Claude can do for you and your business, it's time. Check out Claude today at claude.ai/tyler

LMNT: I drink LMNT before and after each workout, and I have never felt better. Mango Chili and Watermelon Salt are my go-tos, and take advantage of the sampler pack, so you can find yours today. Check out LMNT before your next workout at drinklmnt.com/tyler

Facet: I continue to partner with Facet in 2026 because I have yet to find a financial planning resource more fitting and cost effective for my audience. Check them out today to see where you've been leaving money on the table. Go to facet.com/tyler to learn more.

And now on to the show notes!

At some point, the financial industry starts telling you that once you cross a certain number — $5 million, $10 million — you need something more sophisticated.

In this episode, Tyler explains why that’s mostly nonsense.

After his “How to Invest $2 Million” episode, the big follow-up question was whether wealth changes the strategy. The answer: it doesn’t.

The fundamentals stay the same — time horizon, asset allocation, tax efficiency, fees, and real diversification.

In this episode, Tyler breaks down five portfolio options:

None require hedge funds.

Tyler also explains why “accredited investor” status often just means you’re being sold something expensive — and why many ultra-wealthy investors still stick with index funds.

This episode isn’t about leveling up your portfolio.

It’s about keeping it simple — no matter how much money you have.

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.

If you're interested in learning more about this week's partners:

Copilot Money: I rarely recommend financial apps to my friends, but after suggesting that a few of my friends (all of whom work in finance) check out Copilot Money, not only did they all sign up, but they all think it's the best money app they've seen to date. So if you want to get your financial life in order, check out Copilot Money today at try.copilot.money/tyler.

Gelt: My biggest business mistake to date? Waiting too long to establish a relationship with a reliable and proactive tax strategist. I left tens of thousands on the table. If your business is consistently netting over $200k, and you're lost as to next steps, you need to check out Gelt today at joingelt.com/tyler.

And on to the show notes!

Most retirement advice sounds confident and means almost nothing.

“Save a million.”
“Ten times your salary.”
“Seventy percent of your income."

None of that tells you what you actually need.

In this episode, Tyler walks through how to calculate your real retirement number — one based on your spending, your timeline, and the kind of life you actually want. The goal isn’t motivation. It’s clarity.

Instead of vague targets, Tyler breaks retirement planning into three practical numbers:

Along the way, he explains why investing matters more than saving alone, why time beats contribution size, and why conservative assumptions create flexibility instead of fear.

This episode isn’t about chasing a magic number.

It’s about knowing what you’re building toward — so you can stop guessing and start making decisions with confidence.

If you’ve ever wondered whether you’re on track, this episode gives you a framework you can actually use.

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

Hope this gives you something to think about this week.

A massive thank you to those who make this show possible!

Facet: Every January we obsess over physical health. But what about your financial health? If you're ready to actually get a plan instead of just hoping for the best, Facet pairs you with CFP® professionals who build personalized strategies for a flat fee. Head to facet.com/tyler to get $250 into your brokerage account when you invest $5,000 in your first 90 days, plus waived enrollment fees for new annual members.

Fabric: If anyone relies on your paycheck, term life insurance isn't optional—it's the safety net that catches them if you're not there. Fabric by Gerber Life lets you apply online in ten minutes with no health exam, and a million dollars in coverage often costs less than a dollar a day. Head to meetfabric.com/tyler to get covered before you finish your coffee—policies issued by Western-Southern Life Assurance Company, not available in certain states, prices subject to underwriting.

And now on to the show notes!

Saving money for retirement gets all the attention. Spending that money intelligently is the hard part.

In this episode, Tyler tackles the part of retirement no one really teaches: how to draw down your money without running out, losing sleep, or overpaying in taxes. Accumulation is mostly math and discipline. Decumulation is judgment, flexibility, and understanding tradeoffs.

This is a practical walkthrough of dynamic retirement income strategies — not rigid rules — and why the approach your parents used probably doesn’t work anymore.

In this episode, Tyler breaks down:

Along the way, Tyler explains why flexibility beats optimization, why peace of mind matters as much as returns, and why most retirees end up using a blend of all three strategies, not just one.

This episode isn’t about squeezing every last dollar out of your portfolio.

It’s about making your money last long enough to enjoy it — and knowing how to adapt as markets, taxes, and life change.

If you’re approaching retirement, thinking about early retirement, or just want to understand how the endgame actually works, this episode gives you a solid framework to start from.

And if the show has been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps.

As always, hope this gives you something worth thinking about this week.

This week's episode is brought to you by:

Facet. They provide you with access to a team of fiduciary CFP® professionals who gets paid to help you—not to sell you whole life insurance to fund their boat payment. New year, new financial plan that actually makes sense. Learn more at joinfacet.com/tyler.

Copilot Money. The only finance app I've ever recommended to friends unprompted. Three finance professionals signed up, all three stuck around—which tells you everything. If you want to actually organize your money without turning it into a part-time job, check it out at try.copilot.money/tyler.

Gelt. I spent six months doing everything right in my business—automated savings, proper accounting, the works—except I forgot to get a tax strategist. Rookie move. Should've been the first call, not an afterthought. If you're running a small business or a high earner, don't make my mistake. Check out joingelt.com/tyler.

And on to the show notes!

Most of what the insurance industry sells falls somewhere between unnecessary and borderline predatory.

That’s not hyperbole. That’s the point of this episode.

Here, Tyler breaks down what insurance is actually for, what you truly need, and why so many popular policies are aggressively oversold, misunderstood, or designed to benefit everyone except the person buying them.

This is a blunt, behind-the-scenes look at how insurance really works — informed by Tyler’s time inside the finance industry — and why mixing insurance with investing is almost always a mistake.

In this episode, Tyler covers:

Along the way, Tyler explains how commissions shape “financial advice,” why bad products stick around, and how to spot sales tactics dressed up as planning.

This episode isn’t anti-insurance.

It’s about using insurance for what it’s good at — transferring risk — and avoiding products that pretend to be investments.

And if the show has helped you avoid a mistake — or ask better questions — leaving a quick review on Apple Podcasts or Spotify genuinely helps.

Hope this gives you something useful to think about this week.

This week's endeavor in free financial literacy for all, brought to you by:

LMNT: You can have all the money in the world, but if you don't feel good physically, none of it matters. For years, I'd finish my morning workout and be foggy-headed with a headache by 1 PM—turns out I was chronically under-hydrated and needed actual electrolytes, not just water. LMNT has 1,000mg sodium, 200mg potassium, 60mg magnesium, and zero sugar that keeps me sharp all day. My routine: one during my workout, then a Sparkling LMNT around 4 PM (Mango Chili is the move). Right now they're offering a free sample pack with any purchase at drinklmnt.com/tyler.

Bilt: I spent my late 20s throwing thousands at rent in Vermont while maxing out retirement accounts, feeling like I was getting nothing back. ⁠Bilt⁠ fixes that by turning rent and mortgage payments into actual rewards—flights, hotels, fitness classes, or Amazon purchases. Join at ⁠joinbilt.com/Tyler⁠ and make money you're already spending work harder.

Facet: Every January we prioritize physical health like it's the New Year's resolution Olympics, but why don't we give our financial health that same energy? I get hundreds of messages weekly asking for personalized advice, and while I want to help, I can't responsibly address your specific situation in a podcast. That's why I partner with ⁠Facet⁠: you get dedicated CFP® professionals who build actual financial plans tailored to your life, charging a flat fee instead of a percentage of assets. Connect with Facet at ⁠facet.com/tyler⁠ and start 2026 with both your health and your wealth dialed in.

And on to the Show Notes!

Somewhere between "retire at 30" and "work until 70," there's a middle path. Tyler talks with Andy Hill, host of Marriage, Kids and Money and author of Own Your Time, about how he and his wife reshaped their financial life to work 20–25 hours a week while staying financially secure—without winning the lottery or selling a tech company.

This isn't a FIRE hype episode. It's a grounded conversation about tradeoffs, mistakes, marriage tension, and building a life that doesn't feel like a trap.

Tyler and Andy discuss why extreme FIRE often breaks down in family life, how "Coast FIRE" creates a realistic middle ground, why income growth matters as much as cost-cutting, how money conversations can go wrong in marriage, and what it actually took to leave corporate work without blowing up financial security.

Andy shares three concrete starting steps for anyone who feels stuck or burned out and wants to reclaim control over their time. This episode isn't about escaping work—it's about finding work you don't need to escape from.

If the show has been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps more people find it.

A massive thank you, as always, to this week's sponsors:

⁠Copilot Money⁠: Want to actually see where your money goes without judgment or manual spreadsheets? ⁠Copilot Money⁠ connects all your accounts in one place, tracks subscriptions automatically (no more surprise renewals), and uses AI to categorize spending so you're not tagging transactions like a digital archaeologist. It's privacy-first (they don't sell your data), and they're an Apple Design Awards finalist. Use code TYLER at ⁠copilot.money⁠ for two free months, plus 26% off your first year for new users. If you're starting 2026 wanting clarity around your finances, this is worth trying—especially for free.

Gelt: If you're like me, a solopreneur or a high net worth individual, and you do NOT want to make managing your taxes a SECOND full time job, visit Gelt today and see what they can do to turn your tax strategy around in 2026 and let YOU get back to doing literally anything else. Visit joingelt.com/tyler to see if they're the right fit for you and your business.

⁠Fabric⁠: And if you have ANYONE who depends on your income, term life insurance is essential. That's why it's Step 3 in my financial order of operations, long before an emergency savings account or funding a Roth IRA. This is what will actually help the family if something happens to you. And you can get covered in ten minutes from your couch while watching Survivor. Go to ⁠meetfabric.com/tyler⁠ today and get the coverage you need.

And on to the show notes!

Rebalancing gets treated like financial gospel.

Something you must do on a strict schedule, or else you’re somehow being irresponsible with your money.

In this episode, Tyler pulls that idea apart.

Yes, rebalancing matters — but it’s far less urgent, far less precise, and far less sacred than the financial industry wants you to believe.

This is a practical, anxiety-reducing look at what rebalancing actually is, when it’s worth doing, and when you can probably stop worrying and go live your life.

In this episode, Tyler breaks down:

Along the way, Tyler explains why rebalancing isn’t about hitting a perfect allocation, why most people exaggerate its importance, and why alignment beats optimization every time.

This episode isn’t about micromanaging your portfolio.

It’s about making sure your money still reflects your goals — and knowing when you can safely stop tinkering.

If you’ve ever wondered whether you should rebalance, whether it’s worth triggering taxes, or whether you’re overthinking the whole thing — this one’s for you.

And if the show has been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps. It helps other people find the show and keeps it going.

As always, hope this gives you something useful to think about this week.