Everyone will tell you to move to Florida or Texas to retire tax-free. But the truth? Taxes are more complicated than a “No State Income Tax” billboard. In this first part of a two-part series, we unpack The Great Tax Mirage and reveal why some so-called high-tax states like New Jersey, Pennsylvania, and Iowa may leave retirees with more money in their pocket than the sunny paradises they’re fleeing.

We dive into Fidelity’s latest study modeling retirees withdrawing $100,000 a year from an IRA and show how effective tax rates—what you actually pay after exemptions and deductions—can dramatically flip conventional wisdom on its head. For example, a couple retiring in Oregon might pay close to 13% in effective taxes, while a move to Iowa could drop that number to 7.5%, potentially growing tens of thousands of dollars over a decade.

We also explore the underrated power of marriage in retirement planning. Married couples filing jointly can save around six percentage points on combined federal and state taxes versus singles—enough to add tens of thousands of dollars to a nest egg over ten years.

Key takeaways from this episode include:

• No state income tax doesn’t automatically mean you keep more money.
  
  
• Certain high-tax states offer exemptions and deductions that outperform so-called tax havens.
  
  
• Marriage can be one of the most powerful retirement tax strategies.
  
  
• Your effective tax rate—not the headline rate—determines what you actually keep.
  
  
• Planning where to retire is about life satisfaction as much as taxes.
  
  

Whether you’re dreaming of beaches, cornfields, or just a comfortable, worry-free retirement, this episode will change the way you think about where your money—and your life—goes next.

Part Two drops next week, where we’ll rank the best and worst states for retirees, explore the real impact of marital magic, and dig into other often-overlooked factors that matter more than taxes when choosing where to spend your golden years.

If you enjoy the show, please leave a review on Apple Podcasts or Spotify and share it with a friend who’s plotting their retirement escape. It helps more than you know—and makes sure that no one accidentally retires somewhere that quietly nibbles their nest egg.

This is part two of our financial order of operations series.

In part one, we covered the non-negotiables—the oxygen mask, debt payoff, insurance, and the foundation of every real financial plan. This week, we get into the gray areas. The places where conventional wisdom isn’t just outdated—it’s expensive.

Here’s what we cover:

7️⃣ The Emergency Fund Myth
You’ve heard it before: “Keep six months of expenses in cash.” The problem? That advice was built for a world where savings accounts paid double-digit interest. Today, it’s fear-based and mathematically backward. Most people will go years without a true financial emergency, and keeping $20,000 in cash for a maybe costs far more than it saves. Learn how to balance liquidity with growth without putting your future on pause.

8️⃣ The Taxable Brokerage Account Advantage
Once you’ve maxed your Roth IRA, captured your 401(k) match, and funded your HSA, it’s time to open a taxable brokerage account. This is your flexibility play—your bridge between today and retirement. Access your money anytime, invest in low-cost index funds, and take advantage of long-term capital gains rates that beat most income taxes.

9️⃣ The Right Way to Think About Debt
Debt isn’t moral—it’s mathematical. If your rate is above 5%, pay it off first. If it’s below 5%, investing probably wins over time. But if it’s keeping you up at night, pay it off anyway. Personal finance is personal—and peace of mind compounds, too.

🎯 Bonus: The 20-Minute “Tiered Pricing” Hack
Call your phone, internet, and streaming companies once a year. Tell them you’re considering canceling. Decline their first “special offer,” and watch the discounts appear. It’s the modern coupon—no scissors required—and it can save you $1,000+ a year to redirect into your investments.

At the end of the day, this two-part series gives you a complete, math-first roadmap for building wealth that lasts. It works whether you’re starting out or managing seven figures.

And if you're interested in learning more about this week's show sponsor, Facet, check out facet.com/tyler today to learn more!

🎧 Listen now wherever you get your podcasts.

💌 Join the newsletter for weekly financial clarity (and the occasional heretical take): https://socialcapconnect.substack.com/subscribe

This week we’re tearing apart one of personal finance’s most overused frameworks: the “financial order of operations.”

You’ve heard a version of it before—pay this, save that, sacrifice now, maybe retire someday. The problem? Most of those systems were built by people who either (a) never had real financial stress, or (b) have spent too long in the Dave Ramsey cinematic universe.

So, I rebuilt the order from scratch. And it actually works in the real world, whether you make $40,000 or $400,000.

Here’s what we cover:

1️⃣ Put your own oxygen mask on first.
Take care of yourself before your kids. Financial stability isn’t selfish—it’s responsible.

2️⃣ Obliterate credit card debt.
The “snowball method” is financial astrology. Attack the highest-interest balance first.

3️⃣ Get insurance.
If someone depends on your income, you need term life and long-term disability. No gimmicks.

4️⃣ Max out your Roth IRA.
It’s flexible, tax-free, and doubles as a stealth emergency fund.

5️⃣ Grab your 401(k) match.
A 50% employer match is the only free lunch on Wall Street.

6️⃣ Max out your HSA (if you can).
The triple tax advantage—deductible going in, tax-free growth, tax-free withdrawals—is unbeatable.

We’ll go deeper into emergency funds, taxable brokerage accounts, and smart debt strategies in Part 2 next week.

And a MASSIVE thank you to this episode's sponsor, Facet. If you are tired of paying more to an advisor simply because you make more, check out facet.com/tyler today to learn more.

👉 PLUS: stick around until the end of the episode for a modern trick that helps you find the money to do all of this in under 20 minutes—without canceling Netflix or giving up your morning coffee.

If this episode helps you—or if you simply enjoy hearing someone roast bad financial advice with love—please consider leaving a review on Apple or Spotify or share this with a friend who still believes paying off a $200 credit card before a $20,000 one is “confidence building.”

🎧 Listen now wherever you get your podcasts.

📩 Join my newsletter for weekly financial philosophy that treats you like an adult: https://socialcapconnect.substack.com/subscribe

What if you could skip the index fund and build your own? In theory, you can. In practice…well, it’s a bit like building your own refrigerator. You’ll learn a lot, and maybe even get a working model, but you’ll also discover why the factory-made version is so efficient in the first place.

In this episode, we dive into the peculiar urge to “DIY” the market, and why the exercise can be incredibly educational—even if you never actually follow through. Along the way, you’ll learn:

• The 11 Sectors of the Market: From flashy Tech to steady Utilities, every portfolio starts with understanding the cast of characters.
• How Benchmarks Really Work: Why the S&P 500 is more active (and more tax-efficient) than most people realize.
• The Temptation of Tilts: When to add seasoning like value or small-cap, and when ego is just disguising speculation.
• Building Your Own Fund: How to use sector ETFs to replicate the market—and why rebalancing can become a full-time job.
• Keeping Costs and Ego Down: The S&P’s hidden advantages in cost and tax efficiency, and why humility may be the cheapest asset in your portfolio.

The takeaway? You can build your own index fund. You might even enjoy the process. But the real lesson is what it reveals: index funds are masterpieces of design, combining diversification, tax efficiency, and ruthless discipline—all while letting you spend your time on things that matter more than spreadsheets.

And if you are interested in learning more about those who support this content and make the show possible, visit facet.com/tyler today! And see why they're the only partner I've brought to you thus far as a resource.

👉 If you found this episode useful (or at least more entertaining than quarterly earnings reports), please leave a review on Apple Podcasts or share it with a friend. It’s the best way to help the show grow—and keeps me from muttering about sector weights to myself in the Vermont woods.

Your 50s are a tax-planning sweet spot—a decade when smart strategies can save you tens or even hundreds of thousands over the course of retirement. In this episode, Part Two of our two-part series, we explore four advanced but practical moves to keep more of your money compounding where it belongs.

Here’s what we cover in this episode:

• The HSA Triple Play: Why this account is the most underrated retirement tool, and how to turn it into a stealth IRA with triple tax benefits.
• Social Security Timing & Taxes: How your claiming age affects not just your benefit but how much the IRS quietly takes back.
• Charitable Giving with Donor-Advised Funds: A Costco-sized deduction now, with the ability to give on your terms for years. Plus, how Qualified Charitable Distributions can kill two birds with one IRA.
• Bracket Shifting by Gifting to Kids: Move money to lower tax brackets within your family—legally—while supporting education, housing, or even a responsible jet ski purchase.

Together with Part One (Roth conversions, withdrawal sequencing, and tax-efficient investing), this gives you a full seven-strategy toolkit for your 50s. No gimmicks, no offshore shell games—just thoughtful planning that keeps more money in your pocket and less in Uncle Sam’s.

👉 If this series has been helpful, please leave a review or share it with a friend. It’s the best way to help the show grow—and it keeps me from muttering about Roth conversions to my dogs in the Vermont woods without witnesses.

Taxes in your 50s may not be cocktail party conversation, but they can make or break your retirement plan. In this episode, I kick off a two-part series on the smartest tax moves to make once the kids are (hopefully) off your payroll and you’re staring down retirement.

In Part One, we cover four essential strategies:

• Roth Conversions: Why your 50s and early 60s may be the perfect window to pay taxes on your terms, not Uncle Sam’s.
• Withdrawal Sequencing: The order in which you raid your taxable, pretax, and Roth accounts can extend your portfolio by years.
• Tax-Efficient Investing: How to avoid paying tax on “phantom income” by using ETFs, low-turnover funds, and muni bonds.
• Tax Loss Harvesting: Turning portfolio lemons into lemonade by using losses to offset gains and shrink your tax bill.

Think of this episode as a tax tune-up: no jargon—just practical strategies that can save you tens or even hundreds of thousands over your lifetime.

And this is only Part One. Next week, we’ll cover the HSA triple play, Social Security timing, and two bonus strategies for the charitably inclined and family-minded.

👉 Subscribe so you don’t miss Part Two, and if you’re finding these episodes helpful, consider leaving a quick review. It helps more people discover the show — and keeps me from muttering about Roth IRAs to my dogs in the Vermont woods entirely in vain.

Most portfolios don’t implode in one dramatic crash; they leak slowly. A percent here, a hidden fee there, and before you know it, your retirement fund has been funding someone else’s yacht. (Cough, cough...your advisor's...)

In this episode, I shine a light on ten common wealth leaks that quietly drain portfolios, plus practical fixes for each one.

We’ll cover:

• How a “tiny” 1% fee can cost you a third of your returns.
• Why overtrading turns your portfolio into Swiss cheese.
• The real silent killers: taxes, spreads, and cash drag.
• Why your own emotions can be more expensive than any advisor.

You’ll walk away with a checklist to plug the holes, lower your costs, and keep more of your money compounding where it belongs — in your account, not Wall Street’s.

👉 Think of this episode as financial plumbing: we’re finding the leaks before they flood your future.

Your portfolio’s performance isn’t about finding the next hot stock; it’s about how you slice the pie. In this episode, I break down the real math behind compounding, why losses hurt more than wins help, and three simple allocation models you can actually follow without losing sleep.

We’ll cover:

• Why “average returns” are misleading and compounding is what matters.
• How diversification really works (hint: it’s not about guessing winners).
• Three practical allocation strategies for different levels of risk tolerance.
• The surprising case for the “reverse glide path” in retirement.

Whether you’re cautious, balanced, or adventurous, you’ll leave with a framework to match your investments to both your spreadsheet and your stomach.

And if you’ve ever wondered whether you should own more stocks, more bonds, or just more Advil to deal with it all once you retire — this episode’s for you.