Your Money Guide on the Side

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:


What rebalancing actually means, and why age-based formulas are mostly nonsense


Why goals matter more than age when deciding your allocation


When rebalancing barely changes outcomes — and when it actually matters


How target date funds handle rebalancing for you, and when they work well


How to rebalance yourself without overthinking it, especially inside retirement accounts


Why rebalancing in taxable accounts is trickier, and when paying taxes is actually the right move


How to rebalance using new contributions instead of selling — and why taxes shouldn’t paralyze you

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.

Here are some truly helpful resources from this week's sponsors:

First, the ONLY way I am able to make this much content, day in day out, is by feeling my best. Always. And that starts with my working out each morning and needing something that doesn't leave me feeling like I just ate four pounds of candy. Enter LMNT. It is literally the product designed for people like me: need the fuel, don't need the crash, game on. Check out LMNT today here.

And if you're looking to start 2026 with a bang, like, a "get my act together financially once and for all" type bang, check out Facet. They continue to practice what I preach, and they provide real advice from real experts for real people. Check them out today here.

And now on to this week's the show notes!

Most people say they believe in long-term investing.
Far fewer people actually behave like it — especially when markets are at all-time highs.

In this episode, Tyler tackles one of the most common (and expensive) investing mistakes there is: sitting in cash while waiting for the “right time” to invest. The twist? That “right time” almost never shows up, and the data is brutally clear about what it costs.

Despite how uncomfortable it feels, buying stocks at all-time highs has historically been a perfectly reasonable — and often superior — strategy compared to waiting on the sidelines.

In this episode, Tyler walks through five reasons why staying in cash is costing you a fortune:


All-time highs are normal — markets hit them far more often than most people realize


Even terrible timing beats no timing — buying at the worst possible moments still outperforms sitting in cash


“This time is different” almost never is, no matter how convincing the headlines sound


Missing the best days destroys long-term returns, and those days often arrive during chaos


Doing nothing is still a decision — and it carries real risk

Along the way, Tyler breaks down decades of market history, real return data, and behavioral traps that convince smart people they’re being cautious when they’re actually sabotaging themselves.

This episode isn’t about ignoring risk or investing recklessly.
It’s about recognizing that waiting for certainty is just another way to lose money.

Markets go up. Markets go down.
But sitting in cash while hoping to outsmart two centuries of economic progress has never been a winning strategy.

If you’ve ever told yourself you’re “just waiting for a pullback,” this episode is for you.

And if this helped you rethink your approach — or finally get out of your own way — leaving a quick review on Apple Podcasts or Spotify genuinely helps. It helps other people find the show and keeps this whole thing moving.

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

For those of you looking for more helpful resources, check out the amazing companies that make this endeavor in free financial literacy possible:

1) If you are running small business and DON'T want to make your taxes yet ANOTHER small business, check out Gelt today. They can help small business owners and high net worth individuals who are looking for strategy beyond filing.

2) And if you are tired (as I was for WAY too many years) of paying rent and feeling as if you were getting nothing in return, check out Bilt, and consider joining their renters' loyalty program. It is an amazing way to -finally- get something back after years of feeling like you're throwing money towards someone else's equity.

Most people spend a lot of time obsessing over what to invest in.

Very few people think seriously about where those investments should live — and that mistake can cost you tens of thousands of dollars over a lifetime.

In this episode, Tyler breaks down account placement strategy — the unglamorous, aggressively unsexy topic that quietly determines how much of your money you actually get to keep. Because just like real estate, with investing it’s all about location, location, location.

This isn’t about finding the perfect fund.
It’s about putting the right investments in the right accounts.

In this episode, Tyler covers:


The three main types of investment accounts — tax-deferred, tax-free, and taxable — and what each one is actually for


Why taxes matter more than most people realize, and how bad account placement creates avoidable tax bills


Which investments belong in retirement accounts (and which absolutely don’t)


How access and liquidity should shape where your money lives, especially if you want flexibility before retirement


Why volatility feels different depending on the account, and how to use that to your psychological advantage


Real-world examples showing how small placement changes can save real money over time

Along the way, Tyler explains why “max everything and figure it out later” isn’t always smart, how over-locking money can quietly limit your life choices, and why the goal isn’t tax perfection — it’s alignment.

Alignment between your accounts, your investments, your time horizon, and the life you actually want to live.

This episode isn’t about optimizing every dollar with spreadsheets and IRS tables.
It’s about not making preventable mistakes.

Put tax-inefficient investments where they’re protected.
Put volatile investments where you’re less likely to panic.
Put short-term money where you can actually reach it.

And stop throwing money into random accounts and hoping it works out.

If this episode helped something click — or made you realize you might want to move a few things around — leaving a quick review on Apple Podcasts or Spotify genuinely helps. It helps other people find the show and keeps this whole project going.

As always, the goal isn’t perfection.
It’s getting one step closer to alignment.

Hope this gives you something to think about this week.

This week's helpful resources: Fabric (term life) and Gelt (small business taxes).

Term life insurance sits at step three in my financial order of operations—before your emergency fund—because if something happens to you, it becomes the emergency fund for everyone you leave behind. Get covered in ten minutes at meetfabric.com/tyler.

If you're a small business owner or high net worth individual, finding the right tax partner isn't optional—it's the first domino that determines whether you keep your money or hand it to the IRS. Start with a free consultation at joingelt.com/tyler.

And now back to the show(notes!) :)

Most investing mistakes don’t feel like mistakes while you’re making them. They feel reasonable. Sometimes they even feel responsible.

In Part 2 of this behavioral economics series, Tyler moves past the “greatest hits” and into the deeper, quieter biases that don’t get talked about as much — but are still quietly wrecking portfolios day after day.

Think album tracks, not radio singles. If Part 1 was Madison Square Garden, this episode is the smaller venue where the real damage happens.

In this episode, Tyler breaks down five lesser-known behavioral biases:


The Disposition Effect — why we sell winners too early and cling to losers too long


The Ostrich Effect — how avoiding uncomfortable information can sabotage your plan


Mental Accounting — why treating dollars differently based on where they came from is costing you real returns


The Gambler’s Fallacy — how seeing patterns in randomness leads to terrible timing


The Action Bias — why doing something often feels better than doing the right thing (which is usually nothing)

Along the way, Tyler explains why these behaviors feel correct in the moment, why willpower doesn’t fix them, and why most investors don’t need better predictions — they need better systems.

Automation. Rules. Fewer decisions. Less fiddling.

This episode isn’t about becoming more active or more sophisticated. It’s about accepting a hard truth: successful investing is supposed to be boring. If it’s exciting, you’re probably paying for that excitement with your returns.

If this episode helped you recognize one habit you need to break — or one urge you need to stop indulging — leaving a quick review on Apple Podcasts or Spotify genuinely helps. It helps other people find the show and keeps this whole experiment going.

Until next time, remember: the best investors aren’t the smartest. They’re the ones who do the least amount of dumb stuff.