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 The places where conventional wisdom isn’t just outdated—it’s expensive.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.

Guest: Chris Hutchins, host of All the Hacks

Episode theme: Building wealth with meaning—how to design a career (and life) you actually want, while optimizing the money side.

What we cover:

• Meaning > money-first: Chris didn’t start out chasing wealth; he chased options. Early jobs in consulting/banking felt misaligned (little meritocracy, lots of “performance”). That tension pushed him toward work that creates—startups, product, and eventually a podcast.
  
  
• From layoff to leverage: A 2008 layoff forced reinvention. He broke into tech by doing unglamorous, high-initiative work, learning in public, and obsessively networking. Key tactic: create value before you’re hired (he built a full market brief to win a BD role).
  
  
• Career as a cash-flow asset: Once he found work he loved, savings were easier because the job itself provided energy, purpose, and upside. That shift—liking the work—reduced the need to “buy happiness” elsewhere.
  
  
• Optimization without overwhelm: All the Hacks exists to find the 80/20 in money, travel, health, and life. You don’t need to become a points guru or biohacker; borrow Chris’s research and apply the simple levers.
  
  
• Counterintuitive insurance take: When he priced plans, the “best” (premium) plan cost ≈$24k/yr more than the “worst,” while the “worst” plan’s out-of-pocket max was less than that difference. With a real emergency fund and a strong stomach, a high-deductible plan can be rational. (Psychology is the hard part.)
  
  
• Prepay for joy: Pre-buying (subscriptions, passes, prepaid trips) can remove friction and guilt, increasing actual use and happiness.
  
  
• Know your enough: People who don’t know what money is for default to “more.” Define the life you want, price it, then fund that—not a moving target.
  
  
• Audience resonance: “Mini-retirements,” negotiation tactics, and insurance optimization were huge hits; even niche episodes can be life-changing for the right listener.
  
  

Actionable takeaways

1. Design a role you’ll keep doing. Treat your job like part of your portfolio’s fixed-income sleeve: dependable cash flow, lower stress, and compounding skills.
   
   
2. Front-load value. Pitch with a one-pager or mini-audit tailored to the company—proof you’ll do the work.
   
   
3. Run the insurance math (with your EF). Price premiums vs. out-of-pocket max; let your emergency fund shoulder higher deductibles if the numbers favor it.
   
   
4. Prepay strategically. Use prepayment to align behavior with values (fitness classes, transit, annual memberships).
   
   
5. Write money rules. E.g., “Invest 20% before lifestyle,” “Use points for intl. biz class only,” “If it saves 10+ hours/yr, buy it.”
   
   

Lightning-round fun

• Best <$100: Ultrasonic cleaner (for retainers/aligners)—tiny daily upgrade.
  
  
• Most overrated advice: Social-media tax “hacks” that cross legal lines.
  
  
• Apps he likes: A clean net-worth tracker + Copilot for spending (iOS).
  
  
• Guilty pleasure spend: Big annual fees on premium cards—only if the benefits net out.

Find Chris: All the Hacks (weekly deep dives). A great starting point: his “Top 50 Lessons” episode.

Please take a moment to complete this brief survey so I can learn more about YOU and what it is YOU want from this show! I promise, it will take no longer than 97 seconds, and it will help me continue to make the show better for you. 

There’s a strange YouTube genre called “What’s in My Bag?” where people pull out chapstick like it’s a state secret. This episode is basically that…except the bag is my financial life. And instead of chapstick, it’s index funds and money markets. Not sexy. Not even the flavored kind. Just the plain, unscented stick you find in your coat pocket three years later — still somehow usable.

So, what’s in my financial bag? Today I’m walking you through my actual accounts: Roth IRA, taxable brokerage, SEP IRA, and yes, the glorified piggy bank that is my money market fund. I’ll explain what’s in each, why it’s there, and how I think about these buckets so you can use the same framework as a mirror for your own setup.

Along the way, I’ll share how I went from aspiring Peter Lynch to preferring mental bandwidth. Why I sometimes hoard cash like a squirrel on Adderall. And why even the smug “just buy the S&P 500 and chill” crowd (myself included) still falls into the trap of trying to outsmart the market — usually by tilting toward “the next big thing” in the most boring way imaginable.

Here’s what we cover:

• Roth IRA: My tax-free sandbox. 100% growth funds. If there’s ever a place to take swings, it’s here.
  
  
• Taxable brokerage: My liquid nest. Efficient, simple, with a healthy pile of cash-like funds as a psychological shock collar reminding me to actually live life.
  
  
• SEP IRA: My tax-bracket tamer. Boring, tax-deferred, locked away for “future Tyler.” (Poor guy.)
  
  
• The irony of tilts: How even with all this simplicity, I still fall into the trap of trying to beat the market with the market.
  
  

The goal isn’t just to get rich. The goal is to make your portfolio so boring you forget it exists — because you’re too busy living the life it was supposed to buy you in the first place.

Hope you all enjoy the show and it offers you something to think about this week!

Before you hit play: I’ve put a quick listener survey together for listeners. It takes less time than finding your password for your old 401(k), and it helps me shape future episodes around what you actually care about.

Please take a moment to fill out this 3 minute listener survey here.

This week I’m wading into a swamp I usually avoid like lukewarm gas-station sushi: money and politics. Talking about 401(k) policy across administrations feels like trying to explain cricket at Thanksgiving — half the room politely nods, the other half throws turkey legs.

But here’s the thing: retirement policy matters, no matter who you love or hate in Washington. Whether you get to retire at 65 or keep working until 87 shouldn’t depend on which political team you root for.

In this episode, I walk through how the Obama administration approached retirement savings (think: auto-IRAs, myRA accounts, the Fiduciary Rule) and how Trump’s team countered with their own changes (think: loosening MEPs, alternative assets in 401(k)s, and rolling back fiduciary standards).

We’ll break it down into five big ideas you should care about regardless of politics:

1. Access — Millions of Americans still don’t have a workplace retirement plan. Obama pushed for broader access through auto-IRAs, while Trump’s changes were more incremental. Access matters because participation skyrockets when saving is automatic.
2. Simplicity vs. Shiny Objects — Obama tried to make retirement foolproof with boring products like myRA. Trump went the opposite way, pushing for private equity and alternatives inside 401(k)s. Both miss the middle.
3. Fiduciary Rules — Obama’s Fiduciary Rule aimed to make advisors legally put your interests first. Trump’s team scrapped it. What’s left is a murky marketplace where some advisors are fiduciaries and some aren’t — and most Americans can’t tell the difference.
4. Risk & Alternatives — Alternatives like private equity and real estate can add value — if you know what you’re doing. But without education and guardrails, they’re a chainsaw handed to someone who’s only ever used safety scissors.
5. Education — At the end of the day, policies don’t fix behavior. Education does. Whether you’re handed training wheels (myRA) or a Ducati (alternatives), what matters is whether you know how to use them safely.

My goal here isn’t to stump for anyone. I’m not campaigning (I don’t even like campaigning for Girl Scout cookies). This is about helping you understand how policy shifts could impact your money and your future.

📚 At the end of the episode, I also share a book recommendation that completely changed how I think about investing: Richard Ferri’s All About Asset Allocation. If you’ve ever wanted to understand how to slice up your portfolio without losing your sanity, this is the one.

👉 Listen in to learn how retirement policy really affects your wallet — and how to separate political noise from financial signal.