Your Money Guide on the Side

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:


One fund (VTI or VOO) for maximum simplicity


Two funds (stocks + bonds) for risk control


Target date funds for true autopilot investing


The three-fund portfolio for global diversification


The five-fund “2.0” version for small allocations to real estate, gold, or crypto

None require hedge funds.
None require private equity.
None require paying 1% for unnecessary complexity.

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:


Traditional FIRE — the “never work again” number, and why it’s too extreme for most people


Coast FIRE — the Goldilocks option that lets you save hard early and ease off later


The bare minimum — a realistic bridge for people closer to retirement who need options, not perfection

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:


Why retirement drawdown is harder than saving — and why there’s no single “right” rule


The three main income strategies in retirement: selling growth assets, living off dividends, and fixed income


How the 4% rule actually works — and why it shouldn’t be followed blindly


The pros and cons of dividend-focused portfolios, including tax implications


When bonds, ladders, and annuities can make sense as income stabilizers


Why inflation is the silent risk most retirees underestimate

The most tax-efficient order to withdraw from accounts

How Roth conversions, low tax brackets, and timing can save real money

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:


What insurance is meant to do — protect against catastrophic loss, not build wealth

The short list of insurance most people actually need

Why whole life insurance is a bad deal for nearly everyone


How indexed and variable life policies repackage the same problems with more complexity and fees


When annuities can make sense, and when they don’t


Why HSAs are one of the most powerful financial tools available, if you’re eligible

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.