June’s pre-order incentive for my book Real Wealth is now live. Pre-order this month, tell me you did at tylergardner.com/book, and I’ll send you a three-part exclusive podcast series—the unfiltered version of my own financial story that didn’t make it into the book. The mistakes, the pivots, the moments that actually shaped how I think about money. Delivered digitally in early July. Pre-order now and you’re also locked in for every monthly incentive through the December 1st release.

Pre-Order Real Wealth

Here are the 5 Reasons Why I Will Never Retire. And Why the Premise Itself Might Be Wrong.

1. Retirement used to make actuarial sense. It no longer does. The retirement system was designed in 1935 when the average American life expectancy was around 62 and the retirement age was 65. The system was designed, quite deliberately, around the assumption that most people would not survive long enough to enjoy it. This was either very practical or very dark depending on your disposition, but either way it has absolutely nothing to do with your life in 2026.

We are now routinely looking at twenty to thirty years of post-career life. Twenty to thirty years. I like pickleball. I enjoy a good walk. I have bloodhounds who require significant daily exercise and have strong opinions about which route we take to optimize their sniffari experience. But the idea of structuring the back third of my life around the absence of meaningful work genuinely terrifies me in a way that no market downturn ever has.

2. The people who never got the memo. Here is just a partial list of people with more money than any reasonable person could spend in multiple lifetimes who are nonetheless completely, almost frantically engaged in continuing to build things:

Warren Buffett tap-dances to work at 95. Burton Malkiel writes more per day at 93 than most graduate students manage in a semester. Alex Cooper built Call Her Daddy from a microphone in an apartment into a media company worth hundreds of millions and has shown no interest whatsoever in stopping. Whitney Wolfe Herd founded Bumble at 25 after being pushed out of Tinder, took it public, and keeps building. Sara Blakely built Spanx from $5,000 in savings into a billion dollar company and immediately started her next thing. Charlie Munger was reading, writing, and arguing about ideas until the week he died at 99.

Note: I don’t highlight any of the above names because they have money; I highlight them because none of them seem to care about the money.

The pattern across all of them is not workaholism. It is not pathology. It is what Csikszentmihalyi spent his career trying to describe: flow. Being so absorbed in something genuinely meaningful and engaging that the question of whether to continue simply never arises.

3. The one question worth sitting with. Here’s your dose of philosophical reflection for the week: If there were no concept of retirement waiting for you at the end—no finish line, no date circled on the calendar, no penalty-free permission slip from your 401k—what would you change about how you’re living right now?

And the harder version: if you had to do exactly what you’re doing today for the rest of your life, what would you change?

Because if the answer to either question is “everything” or “a lot,” that is not a retirement problem. That is a today problem. And the retirement system has been very conveniently designed to let you defer that problem for decades, which is an extraordinary service to provide to an industry that profits from your continued participation in a system you’re not sure you believe in.

4. And in case that wasn’t enough, retirement asks you to wish away your life. This is the part that bothers me most and that I talk about online probably more than is socially acceptable.

The traditional retirement model is, at its core, a transaction. You trade the years when you are most capable, most energetic, most mentally sharp, and most physically able for a number in an account. And then you wait. You wait until you are older, possibly less healthy, certainly less flexible, and then you cash in the chips and figure out what you actually wanted in the first place.

David Foster Wallace said he hoped everyone could experience success early enough to realize it doesn’t solve the problems. Jim Carrey said the same thing with considerably better delivery. The real problems in our lives—the existential ones, the ones that keep you up at 3am—are not solved by a number. They are not solved by a date. They are solved by autonomy. By doing good work. By being around people you actually care about. And mostly (and I speak from pure lived experience here) by waking up each and every day to something worth doing well.

And the best part: none of that requires you to be 65. Or retired. None of that requires you to have $1 million in the bank. And none of it—not a single part of it—is improved by having spent forty years in a job you were counting down from rather than building toward.

5. I challenge you to find the work from which you don’t want to retire. I did not start this newsletter thinking about the day I’d get to stop writing it. I didn’t start making short form videos dreading the process of figuring out how to talk about money in sixty seconds. And I certainly didn’t start writing the book counting down the days until I could hand it in and never think about it again. That is not how this works. Take this newsletter as exhibit A: I write to you every week because the thinking it requires is the kind of thinking I want to be doing, and the dialogue it sparks among those of you reading it is the kind of dialogue worth having in this life.

But, and this is the key take-away, the day it stops feeling that way is the day I’ll change something, not the day I turn 65.

Here’s the only question that actually matters: if 65 weren’t coming to save you, what would you change about today? Answer that truthfully, and you’ll have more answers than most.

And if you want the full version, this week’s episode of Your Money Guide on the Side explores why the wealthiest people I know, literally and figuratively, have zero plans to retire. If you find the show useful, a review helps more than you’d think—it’s how new listeners find the show, and how I know the topics I find fascinating aren’t just fascinating to me and the hounds.

Listen on Apple | Listen on Spotify

Two Things I’m Currently Thinking About

1. One Year of Experience, Fifteen Times in a Row. Years ago, I was attending a coaching clinic put on by the Harvard squash coaches when someone in the room mentioned they had fifteen years of coaching experience, to which the Harvard coach responded—without missing a beat—“Do you have fifteen years of experience? Or one year of experience fifteen times in a row?”

It is the wisest thing I have ever heard someone say while wearing a Harvard fleece.

And I have been holding on to that line ever since.

Because most of us assume that simply by showing up—by accumulating years, by being present for the passage of time—we are somehow growing. That experience is something that accrues automatically, like interest. But the coach’s point is that many of us become so automated in our habits, so settled in what we already know, that we stopped actually learning somewhere around year three and have simply been repeating ourselves with increasing confidence ever since.

It changes how I think about hiring, about promoting, about the word “experience” on a resume. The question worth asking isn’t how long someone has been doing something. It’s what they actually absorbed from the doing of it in the first place.

2. The Remains of the Day and the Art of Actually Absorbing Experience.

Which brings me, as these things tend to do, to an English butler.

I can’t get enough of Kazuo Ishiguro’s writing. In The Remains of the Day, Stevens—our narrator, a butler whose lifelong goal is to achieve professionalism of the highest order—reflects on what separates the merely competent [butlers] from the truly great. The great butlers, he concludes, are those who have “acquired [greatness] over many years of self-training and the careful absorbing of experience.” Note: not the accumulating of experience. The absorbing of it.

That’s the word that I read that brought me back to the squash courts.

The Harvard squash coach and Ishiguro’s butler are making the same argument from opposite ends of the century. You can have thirty years in a room or thirty years of growth from a room. And only one of those is worth putting on a resume. Only one of those produces a legend.

What are you doing with your minutes? Are you absorbing them, or are you just letting them pass by and calling it experience?

And Before You Go…

This week’s newsletter is brought to you by LMNT.

Heading into summer, LMNT just dropped what is essentially their version of an Arnold Palmer—Lemonade Iced Tea—and I currently have a full pitcher of it in my fridge. A little caffeine alongside the salt and electrolytes is exactly what I want after a long walk with the hounds, or in the late afternoon when I’d otherwise be reaching for a second cup of coffee that I don’t actually need.

Now, here’s what makes it different: Most energy drinks use synthetic, isolated caffeine. LMNT uses full-spectrum organic black tea extract from Kericho, Kenya— 7,000 feet of elevation—so the caffeine comes with its naturally occurring L-theanine and polyphenols. The result is steadier energy, less spike, less crash, and only 50mg of caffeine per serving. Enough to matter. Not enough to regret.

I will also say this: my old cycling crew, people I hadn’t heard from in years, have all suddenly resumed contact with me with remarkable enthusiasm. And my sister—an elite marathoner who is extremely particular about what goes in her body—calls more than she used to. The pattern is consistent: every call starts with “hey, great to hear your voice” and ends with “so when can you send me more LMNT?” I have become, without intending to, a distributor, and I cannot decide if that’s a product endorsement or a personal confession.

So if you want to know what we’re all hyped up about, head to drinklmnt.com/tyler, become an LMNT Insider, and get four boxes for the price of three. That’s drinklmnt.com/tyler. And even though I am obsessed with the new flavor, this does nothing to diminish my feelings about mango chili and watermelon salt.

As always, hope this gives you something to think about throughout the week ahead.

—Tyler

June’s pre-order incentive for my book Real Wealth is now live. Pre-order this month, tell me you did at tylergardner.com/book, and I’ll send you a three-part exclusive podcast series—the unfiltered version of my own financial story that didn’t make it into the book. The mistakes, the pivots, the moments that actually shaped how I think about money. Delivered digitally in early July. Pre-order now and you’re also locked in for every monthly incentive through the December 1st release.

Pre-Order Real Wealth

Why Wealthy People Don’t Save for a Rainy Day.

Let’s start with the number nobody leads with because it feels, well, slightly morbid.

A 2018 study by United Income found that retirees typically die with roughly 80% of their pre-retirement wealth intact. People who spent forty years deferring trips, driving the sensible car, and adhering to some arbitrary 2.3% rule—dying with most of it unspent. To me, this borders on tragedy.

Here are reasons I don’t want you saving money for a rainy day:

1. Your bank is making money off your money. When you deposit cash into a traditional savings account, your bank does not put it in a drawer with your name on it. They lend it out as mortgages at six percent, invest it in bonds, and pool it into assets you could buy yourself. Then they hand you back 0.47% and call it a savings rate. The spread between what they earn and what they pay you goes directly to the bank. You are providing them with extraordinarily cheap capital and receiving table scraps in return. If that doesn’t bother you, to have banks making money off of your money, I don’t know what will.

2. The math your bank hopes you never do. That savings account earning 0.47% against 3% inflation isn’t even maintaining your basic purchasing power. It’s losing ground. Every year you hold cash in a traditional account you are earning a negative real return, meaning your money is worth less at the end of the year than the beginning. $10,000 in a savings account for 30 years = $11,616. The same $10,000 in a diversified index fund at 7% = $76,122. Your bank has understood this math since before you were born. It’s why they name buildings after themselves and you do not.

At the every least, do yourself a wealth-building favor and research the following: money markets, HYSAs, T-bills, I-bonds, and TIPS.

3. Now forget about the emergency savings account all together. Set aside 1-2% of your disposable income/year into a separate emergency “spending” account, and spend that money on experience, not stuff. My wife and I just used our emergency spending account on a trip to Rockport, Maine, where on our nightly walk with the hounds, we stumbled across a sign reading “No Trespassing. We Don’t Call 911.” With a picture of an automatic weapon beneath it. I cannot think of a better argument for the emergency spending account than experiencing that sign, together, and knowing we’ll hang on to that memory and those laughs forever. (And yes, we turned around.)

4. Stop spending money on your personal highlight reel. Cambridge research shows spending aligned with your actual personality produces more lasting happiness than spending designed to signal something to other people. I once spent four days in the Adirondacks with the hounds, a cooler of questionable cheese, and zero cell service. No content. No documentation. The hounds required three baths upon return, but the week cost almost nothing and produced everything.

5. And please, do the post-tax, post-inflation math on your HYSA before you convince yourself it’s a long term investing strategy. 4% APR minus 3% inflation = 1%. Minus your tax bracket on the interest = somewhere between zero and a number without a name.

Calculate what your cash position actually cost you in real terms last year, and let it bother you briefly. Because mild financial irritation is the beginning of every good decision I’ve ever watched someone make.

And if you want the full version, this week’s episode of Your Money Guide on the Side explores why wealthy people don’t spend their time saving for a rainy day. If you find the show useful, a review helps more than you’d think—it’s how new listeners find the show, and how I know the topics I find fascinating aren’t just fascinating to me and the hounds.

Listen on Apple | Listen on Spotify

Two Things I’m Currently Thinking About

1. The Unwelcome Guest. Over a hundred years ago, Fitzgerald gave us one of the great accidental prophecies in American literature. Early in The Great Gatsby, Nick Carraway describes a phone call interrupting a dinner party as “the fifth guest’s shrill metallic urgency.” He was writing about an affair. But he was also, without knowing it, writing about every dinner you’ve had in the last decade where someone’s iPhone lit up and nobody said anything because we’ve all agreed, without ever agreeing, that this is fine now.

It’s not fine.

The vibration in your pocket manufactures urgency where none exists, both for you and for those having to hear the vibrating hum that you have somehow convinced yourself is silent.

And for the record: I am deflated consistently enough by this additional guest’s shrill metallic urgency that I offer the following breath of fresh air: by this time next year, I’ll be back on a flip-phone, and I double dog dare you to try to add me to your group text.

2. Have the Courage to Have Your Own Thoughts. In Marilynne Robinson’s Gilead, Reverend John Ames offers his son some simple and timeless advice: “I’m saying you must be sure that the doubts and questions are your own, not, so to speak, the mustache and walking stick that happen to be the fashion of any particular moment.”

We are living through a golden age of borrowed opinions worn as personal identity. Will Hunting called it out in a Boston bar in 1997. We laughed because we recognized the type immediately: the guy who regurgitates something simply because it sounds wicked smaht. But Robinson and Hunting both have me left wondering where our opinions come from, how they solidify or soften over time, and why so few of us have the courage (or capacity?) to hold opinions of our own that don’t just follow the (insert your party line du jour here).

Have your opinions. Have strong ones. Just spend a minute every now and again making sure they’re actually yours.

And Before You Go…

This week’s newsletter is brought to you by Facet.

Two questions land in my inbox almost every week:

The first: “Tyler, I’m retiring in two years with about a million saved. What should I be investing in?”

The second: “Should I take Social Security at 62, 67, or 70? I genuinely don’t know.”

I want to help. It’s why I do this. But neither of those questions has a universal answer—only your answer. And your answer depends on your health, your spouse, your other income, your tax situation, your timeline, and roughly forty-three other variables I cannot responsibly weigh in on for a general audience of five million people.

Those questions deserve a real answer from a real professional. Not a guy on the internet speaking generally. A CFP® who sits down with your actual numbers—Social Security timing, Medicare, Roth conversions, RMDs, long-term care—and builds a plan that’s specifically yours.

That’s what Facet does. Real CFP® professionals. A flat annual membership fee—not a percentage of your assets, not a commission, none of the fee structures I’ve spent years telling you to avoid.

If retirement is close enough that the stakes feel real, this is the conversation worth having now.

Check out Facet today by clicking here, and see how their team can help you answer the questions you’re actually asking.

I’m not a member of Facet. I have an incentive to endorse Facet as I have an ongoing fee-based contract for cash compensation, as well as a percentage of equity in Facet based on this endorsement. Facet is an SEC registered investment advisor. All opinions are my own and not a guarantee of a similar outcome.

As always, hope this gives you something to think about throughout the week ahead.

—Tyler

A reminder that May’s pre-order incentive for my book Real Wealth is live! When you pre-order this month, and tell me you did at tylergardner.com/book, I’ll be sending you two chapters that didn’t make the final cut—chapters I genuinely love and wish I could’ve kept—delivered digitally in early June. Pre-ordering also locks you in for every monthly incentive between now and the December 1st release.

Pre-Order Real Wealth

And now for some Monday morning car talk…

The average American spends $12,000 per year on vehicle ownership. For most people, that’s more than they put into their 401(k). Sit with that for a second.

So in an effort to advocate for your 401(k), here are the five worst cars you could buy from a purely financial perspective, and the five best. By the end of this, you will either feel smug about what’s in your driveway or mildly devastated by it. Or both.

The 5 Worst

5. Any luxury German car over five years old. BMW. Audi. Mercedes. The warranty expired. The maintenance issues didn’t. Ten-year maintenance cost: up to $20,000. Toyota’s ten-year maintenance cost: $4,500. A $10,000 repair bill is not a question of if. It’s a question of when you were planning to have other plans.

4. The Jeep Wrangler. Everyone wants one. Who knows, maybe it’s for that Instagram pic. But 18 MPG = $1,150 more per year in gas than a standard sedan. Over five years that’s nearly $6,000 in fuel premium alone for a truck bed you’ll use twice and doors you’ll remove once and then immediately put back on because it’s cold. Yes, you get to wave to other people with Wranglers…and yes, that’s about as far it goes.

3. The Range Rover. Any model. Any year. Depreciates 61.7% over five years, losing nearly $70,000 in value on a $90,000 purchase. The electrical system has been described by owners with the specific haunted expression of someone describing an event they’re still processing. A magnificent vehicle. Also a wealth transfer mechanism disguised as an SUV.

2. Any brand-new truck—unless you actually need it (Or you’re like me, and you just can’t help yourself). Somewhere between 60-70% of full-size truck owners rarely or never use the truck bed for anything beyond a Costco run. A $60,000 F-150 loses roughly $25,000 in value in five years. So unless you’re hauling things for a living, you bought a lifestyle vehicle at tool prices. Nothing wrong with that. Just call it what it is.

1. A financed Tesla. Finance $48,000 at 7% over 60 months and you’re paying $62,000+ total. On a car whose value has dropped significantly since you signed. With insurance premiums that reflect proprietary repair costs. With a repair network that has exactly as much pricing competition as you’d expect from a network with no competition. The car is impressive; the rest of the equation is simply not.

The 5 Best

5. Used Honda Civic, 3-5 years old. 36 MPG. $368 average annual maintenance. Someone else absorbed the depreciation. $15,000-$20,000 gets you ten-plus years of reliable transportation with roughly the emotional range of a kitchen appliance, which in personal finance terms is a compliment.

4. Used Toyota Camry, 3-5 years old. Toyota’s average annual repair cost is $441 versus the industry average of $652. The Camry holds its value with a stubbornness that borders on philosophical. It’s also boring enough that insurance companies charge you less for it, because the actuarial data on Camry drivers is legendarily uneventful.

3. Mazda CX-5, used. The one SUV on this list that earns its place. 28 MPG highway. Lower insurance than a CR-V. An interior that feels more expensive than it is, which is the exact opposite of what luxury brands deliver. Around $25,000 used for a 2020-2021 model. Highly recommended for people who genuinely need an SUV and are honest with themselves about what “genuinely need” means.

2. Toyota Prius, any year. 50+ MPG. $10,000-$12,000 in fuel savings over ten years versus a 25 MPG vehicle. Hybrid batteries routinely last 150,000-200,000 miles. The battery concern that killed Prius sales in 2004 is approximately as valid today as worrying your microwave will explode. The Prius heard the question “what if I just wanted a car that cost as little as possible to operate” and took it seriously.

1. Any Toyota Corolla made after 2015. Annual repair cost: $362. Probability of any given repair being major: 7%, versus 12% for the average vehicle. Runs 200,000+ miles. Cheap insurance. Strong resale. The reliability rating is 4.5 out of 5, ranking first out of 36 compact cars. It will not make your neighbors look up from their phones when you pull in, but it will start every morning for twenty years and cost you less than almost anything else on the road. That, in personal finance terms, calls for a standing ovation.

The ten-year total cost gap between the Range Rover near the top of the worst list and the Corolla at the top of the best list is somewhere between $80,000 and $100,000. Not counting what happens if you invested the difference.

Buy boring. Drive it into the ground. And love what’s possible with the money you didn’t spend. (Or, buy whatever the heck you want, and drive it like you only have one life to live because you do.)

And if you want the extended podcast version of the above, check out this week’s episode of Your Money Guide on the Side where I do my best to explore this topic in all of its necessary nuance. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

You voted. I listened.

A few weeks ago I asked whether you wanted a second weekly newsletter. Two thousand of you answered. A thousand wrote actual notes. I read every one.

82% said yes to more. But what you wrote said something more discerning: you want more from me, but not necessarily more email for you. You’re protective of this format. And more than a few of you told me not to burn myself out producing content for the sake of content.

And as one of you quoted Bob Proctor: “If I had more time, I’d write less.”

So: we’ll stick with one newsletter, Mondays, exactly as it is. What I will do is use the questions you sent—and there were a lot, especially around retirement drawdown, Roth conversions, and the leap from saver to spender—to drive future content here and on the podcast. You told me exactly what gap to fill. Consider it filled.

Thank you for caring enough to write back. It is always and forever appreciated.

Two Things I’m Currently Thinking About

1. Every dollar you spend is a door you’ve locked forever. I’m reading Simone Stolzoff’s How To Not Know and paused on this line: “Decision making is hard because before we make a choice, every option is available to us. Making a choice requires forgoing other opportunities, which can feel like a loss.”

For me, it was my first house. For about three months after closing, I was convinced I’d made a catastrophic mistake—not because I didn’t love the house, but because I had just watched $100,000 of other possibilities walk out the door. Yes, this is textbook opportunity cost. But I think it goes deeper than Economics 101.

Because it’s not just the cost of no longer having other things. It’s the existential weight of knowing you’ve taken one road, which means every other road is now officially a road not taken. That’s why I’ve always preferred having money to spending it. Having money means endless possibility: I could do that if I wanted. I could buy that if I wanted. Spending money means something is over. That dollar can never be used for anything else, ever again. It’s gone. It has become: house.

Stolzoff writes a great page-turner, by the way. Thought-provoking and genuinely fun. Hard to find that balance these days.

And speaking of balance.

2. Julian Barnes found the dark version of it. I just finished The Sense of an Ending, in which Tony Webster—a man who has spent his entire life carefully avoiding inconvenience—reflects: “I had abandoned the ambitions I had entertained. I had wanted life not to bother me too much, and succeeded—and how pitiful that was.”

So here’s where these two books collide in my brain at 6am.

Stolzoff’s insight is that spending money means closing doors. Barnes’ insight is that too much door-closing is how you end up with a very comfortable, very small, and self-contained life. Post-COVID, those of us with enough money to afford the premium got very good at buying our way out of inconvenience: at-home food, at-home workouts, at-home happy hours, curated subscription boxes delivered to our door. Thoreau, I believe in Walden, called the house nothing more than an early casket if you never leave it. Mildly disturbing image, Henry. But not wrong.

Alex Honnold said it differently in Free Solo: “The thing is, anybody can be happy and cozy. But nobody achieves anything great by being happy and cozy.”

Webster’s desire for life not to bother him isn’t pitiful—it’s basically everyone’s relationship with money, if we’re being honest. But it’s a good reminder that the goal isn’t to use money to eliminate all friction. It’s to use it strategically, keeping the annoying inconveniences out, while deliberately putting ourselves in the way of the meaningful ones. The hike that wrecks your knees. The trip where nothing goes according to plan. The moments that are inconvenient enough to remind you that you’re actually alive.

Having money should mean infinite possibility, not infinite bubble wrap.

And before you go…

This week’s newsletter is brought to you by Gelt.

Tax day has come and gone, and the question worth asking is clear: how did your CPA treat you this season? Did they reach out proactively, walk you through your options, and make you feel like a priority? Or did you hear from them in mid-March, feel rushed, and wonder afterward if you left money on the table?

That second experience is not normal. You just haven’t experienced what a great CPA can do for you or your business. Yet. A great CPA is a year-round partner, not a once-a-year fire drill. And Q2 is the best time to switch: your new CPA has bandwidth, your numbers are fresh, and there’s a full year ahead to make moves that actually matter.

Gelt is offering two opportunities for new clients who sign up before June 30th: First, if you filed an extension, a focused 30-minute session with a CPA to find everything that can still impact your 2025 taxes before the October deadline. Second, for any new Q2 clients, Gelt will go back through recent returns and find deductions you may have missed, and in many cases recover them. Both are paid add-ons that often cost you nothing net by the time they’re done.

So if you’re a business owner or a high net worth individual, and your CPA made you feel like an afterthought this season, head to joingelt.com/tyler and see what the “new” normal should look like for your tax planning in 2026 and beyond.

As always, hope this gives you something to think about throughout the week ahead,

—Tyler

A reminder that May’s pre-order incentive for my book Real Wealth is live! When you pre-order this month, and tell me you did at tylergardner.com/book, I’ll be sending you two chapters that didn’t make the final cut—chapters I genuinely love and wish I could’ve kept—delivered digitally in early June. Pre-ordering also locks you in for every monthly incentive between now and the December 1st release.

Pre-Order Real Wealth

How to Divorce-Proof Your Finances

I have never been divorced. I hope I never am. But I have spent enough time in personal finance to know that the financial damage from a divorce has almost nothing to do with who was right and who was wrong in the marriage. It has almost everything to do with who was prepared and who wasn’t.

These ten lessons are for everyone. Not just people in the middle of a divorce. Anyone building a financial life with another human being needs to know what’s below.

Act One: Prevention

1. Never let one person control the finances. In roughly 80% of American households, one person handles the money. The other person says five of the most financially dangerous words in the English language: “It’s fine. They handle that.” The average age of widowhood for American women is 59. Death and divorce do not send save-the-dates. Both people need to know everything.

2. Access and passwords. A shared, secure document. Updated annually. Every account, every institution, every username, every password. It’s not romantic. But neither is spending six months trying to log in to your own retirement account during the hardest week of your life because the only person who knew the password is no longer answering their phone.

3. Know your team before you need them. Your CPA, your financial advisor, your estate attorney. Both spouses need to have direct relationships—not “I’ve heard him mention her once.” And while we’re here: do you have a will? A healthcare directive? A durable power of attorney? Dying without a will can cost $10,000 to $50,000 in legal fees and take one to three years to untangle. A basic will costs about $1,500.

4. Your own account. Openly. Transparently. In your name. With a few months of personal expenses in it. Note: this is not a secret account (see numbers 1 and 2). This is the opposite of a secret account. An account that ensures your ability to feed yourself never depends on someone else being in a cooperative mood.

Act Two: Protection

5. Why winning the house battle might mean losing the financial war. A $400,000 house with a $250,000 mortgage is not a $400,000 asset. It is a $150,000 asset attached to a mortgage, a roof, a water heater that is about to fail, and a property tax bill that does not care how your year is going. The spouse who walked away with the liquid investments that continue to compound with minimal maintenance fees? While the house winner is on YouTube trying to figure out what a thermocouple is? Well, I’ll let you all attach the appropriate weight to your memories.

6. The QDRO. Pronounced “quadro,” which is itself a small linguistic indignity. It stands for Qualified Domestic Relations Order, and it is the federal document that governs how retirement accounts get divided in divorce. Without one, every dollar that moves between retirement accounts can trigger income taxes plus a 10% penalty, regardless of what your divorce decree says. Get a specialist who does this for a living. This is not where you should be trying to save money on fees.

7. Beneficiary designations. Retirement accounts and life insurance policies do not pass through your will. They pass through the beneficiary form you filled out in forty-five seconds on your first day at a job fifteen years ago, and have not looked at since. The Supreme Court has affirmed multiple times that this form supersedes everything—including your divorce decree, including your will, including what you would have absolutely wanted. Forms beat feelings. Always.

8. Your credit score is yours alone. Open a credit card in your own name. Use it for small things. Pay it off in full every month. Within twelve to eighteen months, you’ll have an independent credit history. Start before you need it.

Act Three: Recovery

9. The financial freeze. Six to twelve months. No exceptions. I talked about this on last week’s podcast in the context of inheriting a large sum of money, and the rule is identical here. If you’ve just received a settlement, put it in a high-yield savings account or money market fund and do not make a single significant decision with it. Your nervous system, in the immediate aftermath of a divorce, is not in optimal condition to be making thirty-year decisions. This is neuroscience, not a character flaw. The portfolio can wait. You genuinely should not be allowed near it for a while.

10. The predatory advisor. A specific kind of advisor has identified recently divorced individuals as a primary target market—and I am so far from kidding it isn’t funny. They are warm. Reassuring. Exceptionally good at making you feel seen at a moment when you have not been. A 1% AUM fee on a $500,000 settlement compounds to roughly $200,000 in lost growth over twenty years. Take your six-to-twelve month pause. Interview at least three advisors. The one who creates the most urgency is almost always the one trying to capitalize on your vulnerability. The right advisor is patient. The wrong one has a discounted retainer expiring on Friday.

And if you want the extended podcast version of the above, check out this week’s episode of Your Money Guide on the Side where I do my best to explore this topic in all of its necessary nuance. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two Things I’m Currently Thinking About:

1. Bel Canto and the Vanity of Titles. The May mornings are still cold here in Vermont, and I’ve been starting them slowly: coffee, Ann Patchett's Bel Canto, the bloodhound at my feet, the day not yet asking anything of me. The premise: a roomful of very important people—diplomats, executives, a Japanese industrialist worth more than several small countries—are taken hostage at a birthday party in an unnamed South American capital. The siege lasts months. And in those months, the job titles stop mattering. The bank accounts stop mattering. What rises to the surface, in the absence of all of it, is the thing that was apparently underneath the whole time: a desire for connection, for beauty, for love. People fall in love. They learn to cook. They learn to share language. They listen, every morning, to an opera singer who is also being held captive, and discover that the music is more than enough.

My take-away: strip away the vain titles and our endless pursuit to appear busy and important, and what most of us are actually looking for is a sustained and patient form of connection. Which, last I checked, is free.

2. You Owe Your Employer Nothing. And speaking of titles and connection…

Years ago I was debating leaving a teaching job, hesitating because I had just signed on to be the English department chair—understood to be a four-year commitment. I mentioned this to a colleague, who paused for a beat and said: “Has the school just committed to you for four years?”

I have thought about that sentence almost every week since.

Here is what the question exposed. We trade our minutes for money. That is the entire arrangement. In the best cases, we also get some meaning. But the trade is transactional, regardless of how it feels in the moment, regardless of how many group chats you’re in.

Which means the only real question, on any given Monday morning, is whether the minutes you are giving up are worth what you are getting back. And the moment the answer is no, the rest collapses. We don’t owe two weeks. We don’t owe a “smooth transition.” We owe nothing of the kind. The loyalty we feel toward institutions that have never structurally felt the same way back is one of the most expensive habits of modern working life. And I fear we pay for it in minutes. Minutes that we never get back.

In Bel Canto, the men in the embassy spent the first weeks of the siege assuming the world outside could not function without them. The story they had told themselves about their own irreplaceability was, in many cases, the central organizing belief of their adult lives. And then the siege went on for over four months. The markets remained opened. The deals continued to close. The world, it turned out, was alarmingly capable of getting along without them.

We are, every one of us, expendable. Which sounds bleak until you realize what it actually means: if you are expendable, you are also free. So if you want to leave, leave.

And before you go…

This week’s newsletter is brought to you by Copilot Money.

One of the most skeptical people I know about consumer finance apps spent twenty years as a financial advisor, tracks more spreadsheets than most accounting firms, and considers any “personal finance” software fundamentally beneath him. He started using Copilot Money five months ago. The last time we spoke, he told me—these are his exact words—“I do not understand why everyone isn’t using this.”

This is a man who, for years, told me consumer fintech was “designed for people who don’t understand money.”

Here’s why people who actually know money land here: Copilot Money tracks spending, net worth, investments, savings goals, and budgets in one dashboard—and it’s genuinely beautiful to look at, which shouldn’t matter but does when you’re trying to build a habit. It auto-categorizes transactions. It tracks subscriptions, so you’ll finally find the streaming service you forgot and the gym membership you’ve been emotionally lying to yourself about since February (IYKYK). It works across iPhone, iPad, Mac, web. And, my favorite part, they don’t sell your data.

It’s the only personal finance app to win an Apple Editor’s Choice Award, was an Apple Design Awards finalist, and holds 4.8 stars across more than 28,000 reviews.

Check out Copilot Money today, by clicking here, and use code TYLER2 for two free months.

As always, hope this gives you something to think about throughout the week ahead,

— Tyler

A reminder that May’s pre-order incentive for my book Real Wealth is live! When you pre-order this month, and tell me you did at tylergardner.com/book, I’ll be sending you two chapters that didn’t make the final cut—chapters I genuinely love and wish I could’ve kept—delivered digitally in early June. Pre-ordering also locks you in for every monthly incentive between now and the December 1st release.

Pre-Order Real Wealth

Now…How to Invest $1,000,000: 3 Moves, 3 Mistakes, 3 Red Flags

My 3 first moves, in order of priority:

1. Move it to a money market or HYSA before anything else. Not a checking account. Not a traditional savings account. A high-yield savings account via Marcus, Ally, SoFi, or a money market fund like Vanguard’s VMFXX or Fidelity’s SPAXX. Why does this matter? 3% on a million dollars is $30,000 per year. In a checking account earning 0.01%, that same million earns $100. The difference between those two numbers is someone’s salary. Might want to collect it while you think about what to do next.

2. Pay off any debt above 7%, then invest by timeline not age. The long-term real return of the stock market is roughly 7%. Any debt above that rate is a guaranteed return to pay it off. Credit cards at 22%? Gone. Then, once debt is clear, invest what remains according to when you need it. This is my 3-bucket money management system—Zero to two years: HYSA or money market, full stop. Two to ten years: years until you need it multiplied by ten equals your equity percentage, remainder in risk-free assets. Keep the equity component in something broad and cheap: VOO, FXAIX, or VTI. Ten-plus years: 100% equities, untouched, compounding. This goes in a taxable brokerage account—keep it tax efficient, which means index funds, not REITs.

3. Consider putting some of it into your primary residence. Everything above is stocks, bonds, and cash. Your house is real estate—a different asset class, different tax treatment, zero management fee. The top capital improvements by return at sale: minor kitchen remodel (keyword: minor), bathroom remodel, adding usable square footage (especially outdoor areas), replacing aging major systems, and turns out, highest ROI = replacing garage door and front door. Yes, potential buyers do in fact judge your house by the cover. Beyond the return, every dollar of qualified capital improvement raises your cost basis. Higher cost basis means a smaller taxable gain when/if you sell—and with the $250,000 single or $500,000 married filing jointly exclusion, you may owe nothing at all. You diversified. You improved your tax position. You got a nice backsplash. Only do this if your buckets are funded and you don’t need the liquidity—but if that’s true, hard to beat as a next step.

The 3 Things I Would Definitely NOT Do…

1. Let someone manage it immediately. The moment you have a million dollars you are all of a sudden “on the list”. The calls will come. The people on the other end will mention tax inefficiencies they’ve identified. They have not identified anything—they have identified your name and that you all of a sudden have $1,000,000. A 1% AUM fee on a million dollars is $10,000 per year, every year, compounded over twenty years into somewhere between $200,000 and $300,000 in foregone returns. The money is safe in the money market. You are not losing anything by taking sixty days to think. Let the calls go to voicemail, or even better, block them entirely.

2. Dollar-cost average or try to time the market. The market rises in roughly 75% of all calendar years. Lump sum investing outperforms twelve-month dollar-cost averaging in roughly two-thirds of all historical periods, by an average of 2.3% according to Vanguard’s own research. On a million dollars that’s $23,000 in expected foregone returns for the psychological comfort of spreading the risk. The bucket framework exists specifically so you can invest your long-term money immediately without needing to sell it during a downturn—because your short-term needs are already covered in bucket one. Invest according to your timeline.

3. Buy depreciating assets with the principal. A million dollars at 7% returns $70,000 in year one. Spend $60,000 on a car on day one and you now have $940,000 working for you—$65,800 per year. The car cost you $4,200 annually, forever, plus its own depreciation. But if you leave the principal alone for two years at 7% compounding, you have roughly $1,145,000. The interest alone in year three is $80,150. Buy the car with the interest. The principal is untouched. So my one self-imposed rule: one million is the base, I do not touch it. Everything I want to buy, I buy from what it earns. Once you have a base of a million and genuinely leave it alone, you’d be amazed how many things become effectively free.

And 3 Behaviors I Would Watch For…

1. Mistaking volatility for loss. When the market drops and your balance is down $80,000, you have not lost $80,000. You own the same shares of the same companies. The price changed. The asset did not. When your Zillow estimate drops, you still own the same house. You only lose money when you sell. The average intra-year S&P 500 decline is roughly 14%—and in three quarters of those years, it still finishes positive. The investor who sells during the decline locks in the loss. The investor who holds owns the recovery.

2. Mistaking complexity for competence. When you have a million dollars, people suggest you need more sophisticated investments (remember those phone calls you’re all of a sudden getting?). Private credit. Structured notes. Alternatives. Thirty-two slides later, and surprise, there is not a single peer-reviewed study showing the average investor improves after-fee returns by adding complexity. Burton Malkiel is 93 years old, has sat on the Vanguard board, has seen every investment product invented since 1973, and his answer is still the same: low-cost index funds, minimal fees, ignore the rest. Risk on: VOO or VTI. Risk off: money market or HYSA. Real estate diversification: renovate the bathroom. That is the entire portfolio. Complexity is the trap.

3. Feeling like you’re supposed to act like a millionaire. My grandfather came into money and drove the oldest reliable car he could find. My father drives a Subaru because it handles Vermont snow and he is not trying to prove anything to anybody. I will officially call this the Bill Belichick approach to wealth: a subtle “who could care less” competition to see who could, indeed, care less about external status while winning more than almost everyone. When you have a million dollars, you feel the pressure to make it visible—the car, the house, the wardrobe. Most of that pressure comes from a story about what a millionaire is supposed to look like, not from anything you actually want. Ask yourself what freedom means to you specifically. For me it’s not having a boss. It’s running my own days. It’s never having to pick up a phone call from someone telling me how to spend my minutes. That’s what the money bought. Not anything you could see from the outside. Figure out your version of that answer. Spend toward it. Ignore everything else.

And if you want the extended podcast version of the above, check out this week’s episode of Your Money Guide on the Side where I do my best to create a clear and pragmatic roadmap for that $1,000,000 that you’re inheriting tomorrow. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

A quick ask before this week’s “Two Things”…

I’m considering splitting this newsletter in two starting in early July: Monday becomes “The Practice” (the practical money tactics, the concrete frameworks, the allocation strategies), and a new Thursday edition called “The Theory” (the books, the philosophy, the section you’re about to read). Both sections would be developed more fully.

But before I commit to publishing twice a week and trying to talk myself out of it on Thursday morning, I want to know if any of you actually want it.

So please consider taking two minutes to answer four questions to help me continue to help you receive as much free value as possible:

Take Newsletter Reader Survey

Genuinely appreciate it.

Two Things I’m Currently Thinking About:

1. The Bell at Noon, the Bell at Midnight. When I left the W-2 world, I dreamed about the same thing every disgruntled employee dreams about: control of my time. No alarm. No commute. No bell. I would wake when I wanted, work when I wanted, and live like someone who had finally beaten the system and escaped the matrix.

I now control my time completely. And, I still get up at 5 a.m. every day. The discipline did not loosen when the cage opened. If anything, it tightened, because now I’m the only one watching.

This is somewhat Amor Towles’ fault. In A Gentleman in Moscow, Count Rostov organizes his life around two bells. The chime at noon is a daily reckoning: has the morning been used well, has the work been done. If so, he can sit down to a wonderful lunch with a clear conscience. The bell at midnight is the one he dreads, because if he’s still out and about when it rings, he knows he’ll pay for it tomorrow. Towles suggests that a meaningful day requires both bells. The one that asks if you’ve earned your morning. The one that warns you not to squander your night. I have, for better or worse, inherited the Count’s guilt, except nobody is actually ringing the bells, so I have, helpfully, started ringing them myself. I guess the cage was never the schedule; the cage was always me.

2. The Watch You Should Sometimes Forget. Sorry (read: not sorry) for back-to-back Faulkner weeks. What can I say…the man knows how to philosophize.

The opening of Quentin’s section in The Sound and the Fury has been rattling around in my head for years, and I keep coming back to it. Quentin’s father—quoting his own father, the Compson grandfather—hands Quentin a watch and says, more or less: “I give it to you not that you may remember time, but that you might forget it now and then for a moment and not spend all your breath trying to conquer it.”

The exact line, for the Faulkner faithful: “I give it to you not that you may remember time, but that you might forget it now and then for a moment and not spend all your breath trying to conquer it. Because no battle is ever won, he said. They are not even fought. The field only reveals to man his own folly and despair, and victory is an illusion of philosophers and fools.”

I know, it’s Monday morning. Too much, Tyler. Too much.

Faulkner is doing several things in that passage, but the line I keep returning to is the gift. I give it to you not so you may remember time, but so you might forget it now and again. The watch—the very instrument designed to enforce time—is being offered as a tool for escaping it.

We have a modern word for this: flow. The psychologist Mihaly Csikszentmihalyi coined the term in the 1970s to describe the state in which a person becomes so absorbed in what they’re doing that the clock disappears entirely. The work, the activity, the experience itself becomes the whole world, and time stops being a thing you track and starts being a thing you forget. Anyone who has ever been deep in a piece of writing, a long run, a great conversation, a meal that ran an hour past schedule with people you love—you know what I mean. You look up and three hours are gone and you have no idea where they went. More importantly, you don’t care.

This is the argument I want to keep making about money, and it sits underneath everything else I write: when I say money can buy happiness, what I actually mean is that money, used well, can buy you more moments where you forget the watch. More flow. More hours that disappear because you weren’t watching them. You weren’t counting down. The trick is figuring out what produces those moments for you and spending accordingly. For me it’s driving, cooking, writing, a long walk in the woods with the bloodhound. Yours will be different. But the question is the same one Quentin’s grandfather was asking: are you using the watch to be all too conscious of time? Or are you using it to remind yourself, from time to time, to forget about it.

Even if just for a moment today, forget the watch. Because that’s where real wealth actually lives.

And before you go…

This week’s newsletter is brought to you by Gelt.

Tax day has come and gone, and the question worth asking is: how did your CPA treat you this season? Did they reach out proactively, walk you through your options, and make you feel like a priority? Or did you hear from them in mid-March, feel rushed, and wonder afterward if you left money on the table?

That second experience is not normal. You just haven’t experienced what a great CPA can do yet. A great CPA is a year-round partner, not a once-a-year fire drill. And Q2 is the best time to switch: your new CPA has bandwidth, your numbers are fresh, and there’s a full year ahead to make moves that actually matter.

Gelt is offering two things for new clients who sign up before June 30th: First, if you filed an extension, a focused 30-minute session with a CPA to find everything that can still impact your 2025 taxes before the October deadline. Second, for any new Q2 clients, Gelt will go back through recent returns and find deductions you may have missed, and in many cases recover them. Both are paid add-ons that often cost you nothing net by the time they’re done.

So if you’re a business owner or a high net worth individual, and your CPA made you feel like an afterthought this season, head to joingelt.com/tyler and see what the “new” normal should look like for your tax planning in 2026 and beyond.

As always, hope this gives you something to think about throughout the week ahead,

— Tyler

See below for a quick video update…and the most expensive technical mistake of my career.

Yep, May’s pre-order incentive for my book Real Wealth is live! When you pre-order this month, and tell me you did at tylergardner.com/book, I’ll be sending you two chapters that didn’t make the final cut—chapters I genuinely love and wish I could’ve kept—delivered digitally in early June. Pre-ordering also locks you in for every monthly incentive between now and the December 1st release. tylergardner.com/book. Click the button that says “I PRE-ORDERED”. Takes two minutes.

**Note: for all who pre-ordered in April: your webinar link was sent to you Sunday, May 3rd, at 11am EDT. Please check promotions or other folders if you do not see it.

And Now for The Greatest Interview I’ve Ever Had…That You’ll Never Hear…

Last week I had an hour on Zoom with Burton Malkiel—the man who in 1973 wrote the book that told ordinary people they didn’t need Wall Street to build wealth, and who has been right about that ever since. He’s also ninety-three, which is why I spent the two weeks preceding the interview worrying his tech would be the problem. His tech was flawless. The forty-three-year-old who makes his living on the internet exited the meeting before hitting stop recording. The hour is gone. And the world has a funny way of slapping you in the face for being ageist. I deserved it. What follows is everything I refused to let disappear with that recording.

1. The most dangerous idea in the history of finance was (and continues to be) “buy everything and do nothing.”

Before index funds existed, Wall Street had a simple and extraordinarily profitable arrangement: you couldn’t invest without them. The information gap was real, the transaction costs were steep, and the pitch was emotionally compelling—you want someone smart and connected fighting for you. Active managers charged one to two percent annually (if only this were actually just a thing of the past…alas…), plus transaction fees on every trade, in exchange for an implicit (and often explicit) promise to beat the market. The problem a handful of very contrarian people started noticing in the 1950s was that these “experts” weren’t beating it. Not before fees. Certainly not after. Harry Markowitz proved mathematically in 1952 that diversification reduces risk without reducing return—and that the logical endpoint of more diversification is simply owning everything. Paul Samuelson said in 1974: show me the evidence that active managers beat the market consistently. He couldn’t find it. He compared the whole enterprise to alchemy. The only problem? There was no alternative. Yet.

2. Jack Bogle built the fund that put the theory into practice—and people called him “Un-American”.

Bogle had just been fired from the company he largely built after a disastrous merger. As part of the separation, he retained control of the funds’ board. Rather than go quietly, he used it to start Vanguard—named after Admiral Nelson’s flagship at the Battle of the Nile—and launch the first S&P 500 index fund for ordinary investors in August 1976. The plan was to raise $150 million. They raised $11.3 million. Fidelity ran ads asking “Who wants to be average?” A senior executive called it un-American. The financial press called it Bogle’s Folly. By 1980 the fund had less than $100 million in assets. It took twelve years to reach a billion dollars. Twelve years for the most obviously correct investment idea of the twentieth century to gain traction. Oh yeah, and that industry that called it un-American now manages over thirty trillion dollars in index funds. Whoops.

3. The market always recovers. The investors who sell do not.

Black Monday, 1987: the Dow fell twenty-two percent in a single day. Active managers did not get out. The market was back to pre-crash levels within two years and setting new highs by 1989. The investors who panicked locked in their losses. The ones who did nothing came out whole. Then came 1996, when Alan Greenspan used the phrase “irrational exuberance” to describe stock valuations. He was right—eventually. The Nasdaq did fall eighty percent from its peak in 2000.

But Malkiel told me something about that speech that I will never forget: if you had sold your equities the day Greenspan said those words, you would have missed three more years of an enormous bull market before the correction came. Being right about the direction tells you nothing about the timing. And in markets, the cost of being early is indistinguishable from the cost of being wrong. 2008 told the same story. The S&P fell fifty-seven percent. The market recovered. The investors who held through March 2009 watched it double, triple, quadruple. The ones who sold locked in the bottom.

4. Even Burton Malkiel is worried about concentration. His advice is the same anyway.

Malkiel wrote a piece last year warning about dangerous concentration in tech stocks—the ten largest S&P 500 companies now represent roughly a third of the entire index. I pushed him on the tension: if you believe markets are efficient, that concentration is rational. If something worries you enough to write an op-ed, isn’t that market timing? His answer was historically grounded and characteristically consistent. The market has always been concentrated, he said—railroads, steel, computers, internet, AI. The investors who tilted away from dominant sectors have historically paid for that bet in underperformance. And concentration being real tells you nothing about when it corrects (again, that pesky timing thing). So what does the committed index investor do when even Burton Malkiel is nervous? Buy an index fund. Hold it. Because, say it with me, you won’t outguess the market. There is something almost maddening about the consistency of that answer. There is also something deeply reassuring about it.

5. The number in your account is not the thing that gets you out of bed.

I closed by asking Malkiel what retirement actually means to him at ninety-three. His practical answer for people wondering how to invest in retirement: TIPs and municipal bonds at four to five percent real return for the fixed income portion, heavy equities throughout—the lion’s share of the portfolio, not the whole thing, because the data still supports equities as the best long-term inflation hedge. One hundred percent stocks when you’re young. Don’t flee to bonds just because it feels safer. The math doesn’t support it.

But the thing I’ll carry longest from that conversation had nothing to do with asset allocation. Malkiel’s retirement advice beyond the allocation strategy: Stay engaged. Not for retirement—for life. He is ninety-three years old and recommending books and writers. He cited Jason Zweig as a writer we should all be reading (I agree). The money matters. Getting the financial piece right gives you options nothing else can. But it is not the thing that gets you out of bed. Stay engaged. Keep reading. Keep showing up for the ideas that make you feel alive. That’s what Burton Malkiel is doing at ninety-three, and that’s what I hope to be doing for as long as possible.

And if you want to hear more about the Malkiel interview that you will never hear, check out this week’s episode of Your Money Guide on the Side where I do my best to recreate the interview and its broader implications in its entirety. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two Things I’m Currently Thinking About:

1. That Final Smile. I’ve been on a Cruise and Paltrow tear lately—caught Marty Supreme last week and rewatched Top Gun: Maverick for what is, not remotely embarrassingly, somewhere around the tenth time. And what got me wasn’t the action or the performances, both of which are exceptional. It was the meta-text underneath both films. Two actors at this particular point in their careers—neither remotely irrelevant, but both unmistakably aware that the runway is finite—choosing to make something that openly grapples with fading relevance and the question of whether you’ve got one more beautiful piece left in you.

The moment that stayed with me, though, was Paltrow’s smile during her opening night performance when the crowd welcomed her to the stage—that involuntary, full-body smile when the applause finally lands. For those of us who perform in any capacity, myself very much included, that smile is why we do what we do. The applause is great. The smile is honest.

William Faulkner—I think it’s in Go Down, Moses, and if it isn’t, it’s somewhere close—describes this moment perfectly: the last act on a set stage. The beginning of the end of something. Whether you’re Tom Cruise or a guy with a podcast and a bloodhound, the stage is the same stage. The applause is the applause. And the smile, when you’re lucky enough to get the smile, is a thing to notice, and to hang on to, while we’re being signaled to exit stage left.

2. The Snow Leopard. As I mentioned above, I had an hour with Burton Malkiel a few weeks ago. Most of you who follow this newsletter know what that would mean to me. The man wrote A Random Walk Down Wall Street, which is one of the books that genuinely shaped how I think about investing, how I talk about it and write about it, and how I made the decision, years ago, to stop trying to beat the market.

And as you also know, I am devastated that I am unable to share it with you. His responses were pure gold.

But then I reflected on why I was upset by the loss of the audio…what was underneath that disappointment?

There is a scene in The Secret Life of Walter Mitty where Mitty finally tracks down the elusive photographer Sean O’Connell, played by Sean Penn, in the mountains of the Himalayas. O’Connell is sitting with a camera trained on a snow leopard—the “ghost cat,” the impossible shot, the photograph he has spent his career chasing. He sees the leopard. He doesn’t take the picture. Mitty asks why. O’Connell says, more or less, that sometimes when something is beautiful, he doesn’t want the distraction of the camera. He just wants to be in it.

I think about this scene often, and I thought about it the day I sat down with Malkiel. In our era—and especially in mine, since I make my living posting things for public consumption—the bravest financial act (or artistic act) I can think of is having an experience for the experience itself (art for art’s sake, my friends). Not for the post. Not for the engagement. Not to keep up with your neighbors. And not as evidence that the thing actually happened. Though I’m sorry I didn’t get to share that hour with you, I’m also glad I didn’t, because, honestly, the impulse to share it would have been less about you and more about me, and I am old enough now to know the difference and try, very imperfectly, to act on it.

And Before You Go…

This week’s newsletter is brought to you by Facet.

Two questions land in my inbox almost every week.

The first: “Tyler, I’m retiring in two years with about a million saved. What should I be investing in?”

The second: “Should I take Social Security at 62, 67, or 70? I genuinely don’t know.”

I want to help. It’s why I do this. But neither of those questions has a universal answer—only your answer. And your answer depends on your health, your spouse, your other income, your tax situation, your timeline, and roughly forty-three other variables I cannot responsibly weigh in on for a general audience of five million people.

Those questions deserve a real answer from a real professional. Not a guy on the internet speaking generally. A CFP® who sits down with your actual numbers—Social Security timing, Medicare, Roth conversions, RMDs, long-term care—and builds a plan that’s specifically yours.

That’s what Facet does. Real CFP® professionals. A flat annual membership fee—not a percentage of your assets, not a commission, none of the fee structures I’ve spent years telling you to avoid.

If retirement is close enough that the stakes feel real, this is the conversation worth having now. Check out Facet today, and see how their team can help you answer the questions you’re actually asking.

I’m not a member of Facet. I have an incentive to endorse Facet as I have an ongoing fee-based contract for cash compensation, as well as a percentage of equity in Facet based on this endorsement. Facet is an SEC registered investment advisor. All opinions are my own and not a guarantee of a similar outcome.

As always, hope this gives you something to think about throughout the week ahead.

-Tyler

Last call for the April pre-order incentive for my book, Real Wealth, as it expires on April 30th.

Pre-order the book, head to tylergardner.com/book, and tell me you did it. That’s it. You’re in for the live Q&A on May 6th from 7 to 9pm Eastern, where we’re covering basic portfolio allocation with one to five funds, a three-bucket money management system built to last a lifetime, and whatever else you want to bring. Two hours, live, just us.

And remember, as soon as you pre-order, and tell me you did, you’re eligible for every monthly incentive between now and the book’s launch on December 1st.

Go to tylergardner.com/book.

And now, let’s talk about taxes in retirement! (Please, try to contain your enthusiasm.)

What Nobody Tells You About Taxes in Retirement

After the 90/10 portfolio episode of the podcast (the most downloaded episode of 2025 by a long shot), a third of your responses were some version of: “Great, but what about taxes?” Fair. I left a giant door open. Today I’m walking back through it.

Same $2 million portfolio. Same retiree. And here are the five things the IRS will help themselves to if you’re not paying attention:

1. The pre-tax time bomb. Every dollar you pull from a traditional IRA or 401(k) is ordinary income, not capital gains, not some special retirement rate. It stacks with Social Security, RMDs, and can trigger Medicare surcharges you never planned for. The goal is to choose when and how the IRS gets paid, rather than letting them choose for you. And yes, this is possible and crucial.

2. Roth conversions: the best tax move most people do too late. The years between retirement and age 73 are often the lowest-income years of your adult life. In 2026, the 12% federal bracket for married couples runs to roughly $100,800. If your income is below that ceiling, you can convert traditional IRA money to Roth, pay 12% on most of it now, and never pay taxes on that money again. Compare that to being forced into a 22% bracket by RMDs in your late 70s. The window is limited. Start using it.

Additionally: for those who aren’t retired yet, remember that what I’ll lovingly refer to as a “gap” year in your career, earnings, life, etc., is also a GREAT time to consider a conversion. I should have done this in my first year running SocialCap Media, when my gross income fell somewhere between “a few free LMNT packets” and “honey, are we okay?”—but I didn’t. And now it’s too late.

3. The 0% capital gains bracket exists and almost nobody uses it. In 2026, married couples with taxable income below $98,900 pay zero federal capital gains tax on long-term gains. You can sell appreciated investments, pocket the profit, and owe the federal government nothing. This is legal, IRS-sanctioned, and widely ignored. And often far less frequently discussed, if your household income (for MFJ) sits between $98,901 and $613,700 (because, the IRS loves making up arbitrary numbers that look official), you still have access to the 15% long-term gains tax rate. So, see below!

4. The taxable brokerage account is not a consolation prize. No RMDs, no withdrawal rules, long-term capital gains rates, and a step-up in basis at death. If you have money to invest beyond your tax-advantaged maximum, a taxable brokerage is (to me) the greatest account for early retirees. Pro tip: after you get the company match on a 401(k), or you max out an IRA, focus your efforts on the brokerage account and treat it like a retirement account. There is no better way to retire early and have access to your own assets without penalty than by funding and investing in a brokerage account starting…today.

5. Withdrawal order determines everything else. The conventional wisdom (taxable first, pre-tax second, Roth last) is a reasonable starting point, one which I’ve explored with you all before, but it’s not a permanent answer, nor is it a one-size-fits-all. In some years, spending Roth while converting pre-tax funds is the better play. The account you pull from first, in any given year, is a tax decision as much as it’s a spending decision. See this week’s podcast episode for the full breakdown.

***Your key take-away: Investment returns get almost all the attention. Tax efficiency gets almost none. But over a twenty-year retirement, the after-tax dollar is the only dollar that actually matters.

And if the above seemed either obvious or over-simplified, check out this week’s episode of Your Money Guide on the Side for a much deeper dive with numerous practical take-aways and action items. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Please work with a CPA or tax-aware planner before making specific moves based on some Vermonter’s newsletter.

Two Things I’m Currently Thinking About:

1. The Deferral. I’ve been sitting with Kazuo Ishiguro’s Never Let Me Go for two weeks and I can’t put it down in the way you can’t put something down even after you’ve finished it (if you’ve read it, you know exactly what I mean; if you haven’t, stop reading this and go read that). Near the end, Tommy and Kathy, two clones raised to donate their organs and die young, approach their former headmistress Miss Emily with a rumor they’ve been holding onto for years: that if two clones can prove they’re genuinely in love, they can receive a “deferral.” A few more years. A stay of execution. Hope.

   Miss Emily tells them it isn’t true. It was never true. And then she says the thing that prompted this note: she knew about the rumor and let it persist. Because it gave all of the donors something to dream about.

   She gave them a fiction to desire because the alternative, a life with nothing to want, was somehow worse.

2. “Give Me Something to Desire.” Samuel Johnson wrote that line in 1759, in Rasselas, and it has not aged a single day. Just ask Ishiguro. Johnson’s protagonist isn’t asking for a specific thing. He is asking for the state of wanting itself. The desire is the point. The object is almost incidental.

   I think about this constantly in the context of consumerism. We don’t buy things because we need them. We buy them because the wanting feels like aliveness. The new car, the new phone, the new whatever…they are less about the thing than about the brief, electric feeling of having something ahead of you. And the moment you have it, the wanting migrates to the next thing. Seamlessly.

   Hemingway ends The Sun Also Rises with Lady Brett asking Jake whether things might have been different between them. “Isn’t it pretty to think so?” Jake says. Yes, Ernest. It is. And we tend to think this way daily. Every time we open a browser tab at eleven o’clock at night looking for something we can’t quite name. It’s just pretty to think that there’s something out there that we could purchase that might just solve that thing we cannot name.

   My point (and please forgive the seemingly endless literary exploration to get here #sorrynotsorry): The most radical financial act I know is learning to want what you already have. Not as a deprivation strategy. As a genuine reorientation toward what’s actually in the room. Most of us never try it. The economy, I suspect, is quite grateful for that.

And Before You Go…

This week’s newsletter is brought to you by Thrive Market.

I want to tell you something about my relationship with grocery shopping. It is not what I’d call “good.” I have spent considerable energy optimizing every corner of my financial life–expense ratios, tax brackets, withdrawal sequencing–and then completely fall apart in a produce aisle because someone rearranged the almond butter and now nothing makes sense and there are people behind me. Don’t pretend you don’t feel the same. We all had a system. We were each, briefly and beautifully, the star of our own episode of Supermarket Sweep—and then some well-meaning stock associate moved the nut butters to aisle seven and took it all away from us.

Thrive Market is, genuinely, the solution to a problem I didn’t know I could solve. High-quality, pre-vetted healthy food delivered to your door. They’ve restricted over a thousand ingredients before anything reaches the site, which means the label-reading anxiety is already handled before you open the app. Ninety dietary filters. Member pricing up to 30% off. Free delivery on qualifying orders. No per-order fees. No tip math. Five dollars a month, which most people recoup in their first two orders.

And my favorite detail: every paid membership sponsors a free one for a family in need, a teacher, a first responder, or a veteran. Five dollars doing more than one thing will always be my favorite kind of five dollars.

My last order: Yellowbird Habanero Hot Sauce, because life is short and breakfast burritos deserve better. Aloha Plant Based Protein Shakes in Chocolate Sea Salt, obviously. And Bocce’s Bakery Beef Liver Freeze Dried Dog Treats because the bloodhounds monitor every package that arrives at this house with the focused intensity of someone who has been slighted before, and I was not going to hear the end of it.

Head to Thrive Market today by clicking here for $20 off your first three orders plus a free $60 gift. And with a thirty-day risk-free guarantee on the annual membership, there is truly no reason not to.

As always, hope this gives you something to think about throughout the week ahead.

—Tyler

Over 3,000 people have already pre-ordered my first book, Real Wealth, and if you’re not one of them yet, here’s what you’re missing:

On May 6th I’m hosting a live two-hour Q&A exclusively for pre-order readers. We’ll cover simple portfolio allocation using one to five funds, the three-bucket system for managing your money across your lifetime, and then open the floor to your real questions. Live, 7–9 PM Eastern. (And I promise, no sales pitch, as if you’re there, you’ve already bought the book.)

Pre-order at tylergardner.com/book and you’re automatically in. The link comes to you the night before.

You also get seven more months of incentives through December: bonus chapters, a raffle to hike Vermont with a raging introvert, a get together in NYC, and more.

And if none of that moves you: the bloodhounds have heard me talk about this book for two years and have never once looked impressed. Help me prove them wrong.

tylergardner.com/book

Now, let’s get into this week’s topic!

The 5 Things Nobody Tells You Before You Become a Snowbird

I am forty-three years old. I have a financial podcast, a book coming out, and two bloodhounds who have opinions about everything. And this past winter, for the first time in my life, I became a snowbird.

We packed up the car, loaded the pups, and drove from Vermont to Sedona for two months. I arrived with a romantic set of assumptions about who I was going to become out there. I returned to Vermont having learned five things.

1. Saving time is only valuable if you know what you’re saving it for. One of our great Sedona fantasies was proximity to food options—we were a five-minute walk from Whole Foods and surrounded by every type of takeout imaginable. No more figuring out dinner. No more standing in the kitchen at 6pm debating whether we had the motivation to cook the thing we had planned to cook. We were going to reclaim that time. And we did. What we didn’t anticipate was the question that followed: okay, now what? Mostly our phones. It turned out that cooking was never the problem—it was just the noise covering up the actual question of what we wanted to do with our time. Some of the best things in life are not time-efficient. That is not an argument against them. That is the whole point.

2. Every Airbnb is a free financial experiment. Six stops on the way home, six seminars in our own preferences. Asheville told us about porches. Santa Fe told us about sufficiency. Charlottesville told us that photography lies and aesthetics are not the same as livability. In the book I call this a Path Dividend: before you upgrade your life, rent someone else’s version of it first. Gather the data as you go. The preview is always cheaper than the purchase.

3. Keep it special—or it won’t be. By week five, the immaculate weather was just weather. The spa appointment that felt indulgent the first time was just an appointment by the third. This is the hedonic treadmill, and it is ruthless. The only protection is contrast. Keeping things special is not a mindset—it’s a structural decision.

4. You always think about what you’re gaining. Almost nobody thinks about what they’re leaving. It takes three to seven years to build the depth of social connection in a new place that most people leave behind when they move. Before any major relocation, make two lists. What you’re gaining. And what you’re leaving. Write the second one with the same care you gave the first.

5. Wherever you go, there you are. I had a vision of Sedona-Tyler. He was going to meditate at sunrise and become an extroverted community-builder. Regular Tyler showed up, because he was in the car the whole time. I meditated twice and mostly thought about lunch. Seneca said it two thousand years ago: you take yourself with you.

The real work—financial and otherwise—is knowing who you actually are before you build the plan. A plan aimed at the right life is one of the most efficient financial tools there is. A plan aimed at the wrong one is just an expensive way to find out.

And for those of you interested in hearing more about what we learned from this experiement, check out this week’s episode of Your Money Guide on the Side. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two Things I’m Currently Thinking About:

1. The Thing Nobody Wants to Hear About Getting Better at Something.

   When I was an English teacher in my 20s, I heard a common refrain from my students: “But Mr. Gardner, I’m just not a good writer.” My response, always: “Well, how often do you write?” The answer was always some version of an hour a week, under duress. Well. There you go.

   I’ve been reading Epictetus lately (because how else could I call myself a middle-aged podcaster if I didn’t claim to be one with the Stoics), and I came across an even better response: If you wish to be a writer, write. Two thousand years old. Still the whole answer. It is also the single greatest differentiator between the people I know who are building something real and the people still discussing building something real. The doing is not the path to the identity. The doing is the identity. If you wish to be something…then go do something.

2. The Masters and the radical luxury of nowhere else to be.

   A few years ago my father and I attended a practice round at Augusta National. No phones on the grounds—that’s the rule—and (surprise) something genuinely strange happens when you walk in: everyone is just there. Present. Looking up. My father and I watched golf for eight hours and talked about nothing important and everything that mattered, with no way to pretend we were somewhere else.

   I’ve thought about that day more than almost any other in recent memory. Not because of the golf. Because of what it felt like to actually be somewhere. I keep asking myself why it takes a rule to get us there and why more places don’t have the institutional confidence to try. Truly, a tradition like no other.

And Before You Go…

This week’s newsletter is brought to you by Copilot Money.

I want to tell you about a text I sent to a group chat that includes some of the most financially sophisticated people I know. CFOs. People who get paid specifically to understand where money goes and why. I told them I’d found a finance app worth downloading. They pushed back…because these are people who are paid to push back…and they have seen every financial app ever built and have opinions about every single one of them. They downloaded it anyway. Three weeks later, unprompted, one of them texted back: still using it daily. Haven’t said that about an app in years.

That’s the thing about Copilot Money that I cannot explain entirely with features and star ratings, although the features are excellent and the rating is 4.8 from over 28,000 reviews and it is the only personal finance app to win an Apple Editor’s Choice Award. What I can tell you is that it is the rare app that makes your financial life feel genuinely under control rather than just monitored. There is a difference. Most apps give you data with a mild dose of guilt. Copilot Money gives you clarity with a much stronger dose of confidence.

Your spending. Your net worth. Your investments. Your subscriptions (including the ones you forgot about, which for most people represents a genuinely surprising monthly number). All of it. One place. Beautiful to look at. Actually useful to live with. Just ask the CFOs in the room.

Head to try.copilot.money/tyler. Use code TYLER2 for two free months.

As always, hope this gives you something to think about throughout the week ahead.

—Tyler

Before we get into it…

My first book, Real Wealth, is two weeks in, and the May 6th live Q&A is filling up fast. If you haven’t pre-ordered yet: do it this month at tylergardner.com/book and you’re automatically in. (Link will be sent to all when we get closer to event.)

One non-incentive reason to pre-order: my 10th grade English teacher passed me on the condition I never took another English class. I then wrote 70,000 words and convinced Norton to publish them. My former teacher is aware. Pre-orders help my case.

Pre-order after April? You still get every remaining monthly incentive through December. tylergardner.com/book — takes two minutes.

Now enough about the book—let’s learn from someone who’s been doing financial podcasting longer than I’ve been doing, well, just about anything.

Five Things I Learned from the Man Who Helped Invent Financial Podcasting

Chris Hill hosted Motley Fool Money for over a decade, interviewed Malcolm Gladwell, Michael Lewis, and Mark Cuban, and, this is my favorite part, narrated Morgan Housel’s Psychology of Money audiobook having never narrated anything before in his life, purely because he told Morgan he would. All that to say, when he speaks, I listen. And here’s what stuck with me from this week’s interview on my podcast, Your Money Guide on the Side:

1. The boring stocks are the good stocks. Chris spent years watching investors chase the hot tip, the meme stock, the company nobody’s heard of yet. His conclusion after thousands of hours of financial conversation: the best-performing stocks of the last thirty years are almost entirely businesses everyone (including you!) already knows. Familiar, unsexy, and hiding in plain sight behind their perfectly reasonable P/E ratios. The excitement, it turns out, is the trap. The boring thing is usually the right thing. I have built an entire “finfluencer” career on this premise and I still have to remind myself of it quarterly.

2. If you’re losing sleep, you’re doing it wrong. He calls it the sleep factor. If your portfolio is keeping you up at night, that’s not the market talking—that’s your nervous system telling you your risk tolerance and your actual portfolio have never formally met. Introduce them. Adjust accordingly. The math might say one thing, but your 3am brain gets a vote too, and it votes loudly.

3. Time in the market is the answer nobody wants to hear. When listeners wrote in during the 2008 crisis asking what to do, Chris kept returning to Charlie Munger’s famous line: the first rule of compounding is never interrupt it unnecessarily. Twenty years of hosting a financial show and his answer to “what do I do now” was essentially “the same thing you were doing before, just with more discomfort.” Not a popular answer. Correct anyway.

4. Pay for the good seats. Chris went to watch Michael Jordan’s final season in Washington and sat so far from the court he spent most of the game watching the jumbotron. He vowed never again. His rule since: if you’re going to a live event, pay up for seats worth having. This is not frivolous. This is the Path Dividend in action—spending intentionally on experiences that you know will actually deliver, rather than technically showing up and calling it done. The worst financial decisions aren’t always about stocks. Sometimes they’re about nosebleed sections and binoculars.

5. The best business book nobody thinks of as a business book. Chris has used Phil Knight’s Shoe Dog as a teaching tool with college students and young entrepreneurs for years, and his reason is simple: it’s the most honest account of what building something actually looks like. Not the highlight reel—the near-collapses, the impossible odds, the fighting with the very people who are supposed to be supporting you. Nike, before it was Nike, was a fragile and frequently terrifying thing. His point—and I think he’s right—is that Shoe Dog does for entrepreneurship what a good bear market does for investors: it shows you what’s actually required before you’ve committed to finding out the hard way. I’ve said it before, and I’ll say it forever: this book is required reading whether you’re starting a business or just wondering why your sneakers cost $200.

And for the full interview with Chris Hill (one of my absolute favorite yet), check out this week’s episode of Your Money Guide on the Side. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two Things I’m Currently Thinking About:

1. I recently finished John Williams’ Stoner last week and have been both unsettled and inspired by it ever since—which is, I suspect, exactly what Williams intended. It arrived as part of a ten-book order I placed immediately after hip surgery, operating on the theory that recovery would leave me choosing between screen and page, and that I would choose page until I didn’t. So far, so good.

   It’s a novel about a man who spends his entire life doing the thing he loves in obscurity, largely unrecognized, and dies having never quite escaped the smallness of his circumstances. Tragic by any conventional measure. And yet I couldn’t stop thinking about his classroom. The way Williams describes Stoner’s relationship with literature—the physical pleasure of a sentence that does exactly what it should—sent me back to a version of myself I had almost forgotten. Before the platform, before the sponsorships, before I had any idea that talking about money would become a career: I was a high school English teacher whose entire day (read: life) was spent reading great books and then convincing sixteen-year-olds they should care about them. Some days it worked. Those days were extraordinary. I make money now so I can buy time. But for a long time, time was all I had, and I spent it in the best possible way without knowing it. Stoner reminded me that the life that looks like failure from the outside sometimes looks like everything from the inside. The philosophical punchline: I’m not sure money improved on what I already had. But I am certain it gave me the freedom to find my way back to it.

2. And speaking of existential thoughts that occur while lying on a couch post-surgery, watching your own leg like it belongs to someone who made worse decisions than you: The most dangerous day in any good habit isn’t the hard day. It’s the day after the missed day—when the voice in your head reclassifies you from “someone who does this” to “someone who used to do this.” I know this voice well. It is not motivational. What I’ve learned, after years of watching myself and others fall off habits with the graceful arc of a poorly thrown frisbee, is that the only rule worth keeping is this: do your best to never record a zero (or split infinitives). Not a full workout—just not a zero. After my surgery, the physical movement I wanted was not available to me. But what was available to me was two light weights and a Peloton ride that my surgeon would describe as “acceptable” and I would describe as “humbling.” Did it feel like enough? No. Was it infinitely better than nothing? Mathematically, yes. The streak that matters isn’t how many consecutive perfect days you have. It’s how many times you refused to let one bad day become a month-long permission slip.

And Before You Go…

This week’s newsletter is brought to you by Thrive Market.

As most of you know, I am a raging introvert who lives in the Vermont woods and considers the grocery store a mild form of psychological warfare. Fluorescent lighting. Too many decisions. Fourteen-syllable ingredients I have to Google while blocking the aisle like a confused tourist.

Thrive Market solved this for me in one sentence: high-quality, pre-vetted healthy food, delivered to your door. That was the pitch. I didn’t need the rest of it—but the rest of it is good too. They’ve restricted over a thousand ingredients before anything hits the site, so the label-reading anxiety is already handled. Ninety dietary filters mean you only see what actually fits how you eat. And the membership is five dollars a month, which most people recoup in their first two orders through member pricing alone—up to 30% off, free delivery on qualifying orders, no per-order fees, no tip math.

Also, my favorite part, every paid membership sponsors a free one for a family in need, a teacher, a first responder, or a veteran. So the five dollars is doing more than one thing, which is my favorite kind of five dollars.

My last order consisted of a few of my favorites that I simply can’t find in rural Vermont: Yellowbird, Habanero Hot Sauce (if that’s not in your breakfast burritos, you’re missing out); Aloha, Plant Based Protein Shakes (Chocolate Sea Salt, obviously…), and Bocce’s Bakery, Beef Liver Freeze Dried Dog Treats (because the hounds would have been livid if it was all for me…).

Go to thrivemarket.com/tyler for $20 off your first three orders plus a free $60 gift. Oh, and with a thirty-day risk-free guarantee on the annual membership, there is absolutely no reason not to try it.

As always, hope this gives you something to think about throughout the week ahead.

—Tyler

Quick thing before we get into this week’s content.

My first book, Real Wealth, hit #1 in Business & Finance on Amazon in its first week. I’m going to pretend I saw that coming. I did not. To the roughly 1,000 of you who pre-ordered in the first 48 hours—genuinely, thank you. The kid who passed 10th grade English on the condition he never took another English class did not expect to be writing those words.

If you haven’t pre-ordered yet: do it in April, register at tylergardner.com/book, and you’re automatically in for a free two-hour live Q&A on Wednesday, May 6th from 7–9pm EST. No algorithm. No clickbait nonsense. Just your most commonly asked questions, finally getting the time they deserve.

Pre-order after April? You still get every remaining monthly incentive through December. So the only downside to waiting is…waiting.

Two minutes. Everything I’ve ever thought about money & investing in one place. Pre-order today at tylergardner.com/book.

And now for the $172,000 retirement expense nobody warned you about! :)

70%.

That’s the probability a 65-year-old will need some form of long-term care before they die. Not a tail risk. The base case. And approximately 7% of Americans over 50 have a plan for it. The other 93% have opted for the time-honored financial strategy of simply not thinking about it, which works right up until it doesn’t.

Five things worth knowing.

1. This is the wildcard the Social Security math ignores.

Last episode: longevity determines when Social Security pays off. Same variable here, different consequence. The longer you live, the more care risk accumulates. Your retirement plan isn’t complete until it answers both questions.

2. The numbers inflate faster than you think.

Median assisted living today: $64,000 a year. Memory care: $72,000. Nursing home private room: $116,000. Healthcare costs inflate at roughly 5% annually—meaning these numbers double every 14 years. If you’re 50 now, mentally multiply everything by two. Go to genworth.com/aging-and-you/finances/cost-of-care and get your actual number for your actual city. Ten minutes. Do it this week.

3. You have four options and one isn’t really an option.

Self-insure—viable at $2.5M+ in liquid assets, risky below $1.5M. Medicaid—a safety net, not a strategy; requires spending down to nearly nothing first. Traditional LTC insurance—buy it in your mid-to-late 50s while you’re still insurable; Mutual of Omaha and Nationwide are the strongest remaining carriers that I know of. Hybrid life/LTC policies—money goes in, pays for care if you need it, pays a death benefit if you don’t; Lincoln MoneyGuard and Pacific Life PremierCare are worth a look. Use an independent broker, not a captive agent. (Note: I have no financial incentive to name any companies above; they’re just genuinely some of the better ones I’ve come across. As always, do what works for you!)

4. The mistake that destroys otherwise solid plans.

Assuming Medicare covers long-term care. It does not. You’re thinking of Medicaid. They are different programs. This single misconception is responsible for more retirement plan failures than almost any market event I can name.

5. The three things to actually do.

Get the Genworth cost estimate this week. Get a quote from at least two LTC carriers—it’s free and replaces all your current guesses with real numbers. And get your legal documents in order: durable power of attorney, healthcare proxy, advance directive. An estate attorney executes all three for $500 to $1,500. If you don’t have them, your plan has a hole that your portfolio can’t fill.

Planning for this is an act of love. Uncomfortable, completely unavoidable, and worth every minute of the kitchen table conversation you’ve been putting off.

And for the full breakdown, check out this week’s episode of Your Money Guide on the Side for a much deeper strategic and more practical dive. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two Things I’m Currently Thinking About:

1. I have been ambushed recently by smell. Not in a concerning medical way—in the Proustian way, where you catch a whiff of something ordinary and suddenly you are nine years old and the whole weight of passing time lands on you at once. Elizabeth Bishop wrote a poem called “One Art” about losing things, and the devastating joke at its center is that she spends the whole poem insisting loss is masterable—right up until she encounters the loss that proves it isn’t. What strikes me, coming from someone whose entire career is built on the premise that money is a useful tool, is how completely useless it is here. The financial planning industry has products for nearly every contingency and not one of them covers this. The things money can’t touch, it turns out, are the things most worth paying attention to.

2. My morning workouts have undergone a humbling evolution. What began as an enthusiastic effort to build muscle and aerobic capacity in my 20s has gradually, without my full consent, become a daily negotiation with my own skeleton. Less bench press, more “can my left hip rotate in the direction hips are theoretically supposed to rotate.” I have become a person who does mobility work, which I previously associated with physical therapists and cats. The results, though, have been transformative. The days are slightly more intentional, and subtly focused on things that matter more than how much I can (or cannot) bench. My only regret is not starting twenty years ago…which is the same regret I have about index funds, sunscreen, and not learning to cook. The boring foundational thing always turns out to have been the thing.

And Before You Go…

This week’s newsletter is brought to you by Facet.

I use AI every single day. So I want you to understand that what follows is not a Luddite manifesto. It’s just three things I’ve noticed.

One. When you ask AI to help plan your finances, you’re feeding a learning model your proprietary data—salary, debt, retirement accounts, your entire financial biography—and somewhere in that terms-of-service document longer than your mortgage is language granting fairly broad rights to that conversation.

Two. AI hallucinates. The industry’s delightful word for “confidently presents invented information as fact.” As a test, I recently asked a popular AI tool for the 2026 SEP IRA contribution limit. Wrong. I pushed back. New number. Also wrong. Charming quirk in a poem. Meaningful liability in tax planning.

Three. Garbage in, garbage out. AI is only as good as the questions you bring to it, and most of us don’t yet know the right questions to ask about our own financial lives.

And because we don’t always know the right questions to ask, here’s what I want you to do:

I want you to use AI to get curious. I want you to use AI to learn the language. But when you’re making choices that dictate the rest of your life, you need a human in your corner. That’s why I want you to check out Facet today and connect with a team of real CFP® professionals who combine technology with actual human insight, all for one flat annual membership fee. AI can give you a definition, but Facet will help you live the life you worked so hard to build.

Connect with Facet today here to see if they’re the right fit for you.

I’m not a member of Facet. I have an incentive to endorse Facet as I have an ongoing fee-based contract for cash compensation, as well as a percentage of equity in Facet based on this endorsement. Facet is an SEC registered investment advisor. All opinions are my own and not a guarantee of a similar outcome.

As always, hope this gives you something to think about throughout the week ahead.

—Tyler

Before we get into it this week, a VERY SPECIAL (and newsletter exclusive) video announcement that I am THRILLED to make:

Yep. I wrote a book. :)

Real Wealth. Out December 1st, 2026.

Pre-order at tylergardner.com/book and you’re in for eight months of exclusive bonuses — live events, Q&As, bonus chapters, and at least one raffle where the prize is a day hiking with me in Vermont discussing your asset allocation. Some people would pay for that. Others would need to be compensated. Either way, it’s free.

Enough with the book-talk, Tyler…just tell us when to take Social Security…

The internet will tell you to wait until 70 to take Social Security. The internet is not wrong, exactly. It’s just answering a simpler question than the one you should actually be asking. This week’s podcast episode and newsletter make the full case: math, philosophy, and the two things almost nobody mentions. Here’s the preview.

1. The break-even math is simpler than you think.

Take at 62 and you get roughly 75% of your full benefit—permanently. Wait until 70 and you get 124%. The break-even point between those two strategies is around age 80-81. Before that age, early wins. After it, waiting wins. The average 62-year-old woman lives to 85. The average man, 82. Do with that what you will, but at least now you’re working with the actual number instead of the advice from “that guy” on the interweb.

2. A dollar at 63 and a dollar at 83 are not the same dollar.

Bill Perkins wrote an entire book about this called Die with Zero and I recommend it approximately every third episode. The short version: your capacity to enjoy your life peaks and then declines. The go-go years—early retirement, healthy, mobile, capable of doing the thing—are finite. A benefit that starts at 62 funds those years. A benefit that starts at 70 funds years that might look different. That difference doesn’t show up when you calculate your aggregate benefits…it should.

3. The healthcare gap will ambush you if you let it.

Medicare starts at 65. Not 62. Which means retiring at 62 and taking Social Security early creates a three-year window where you are entirely responsible for your own health insurance. COBRA can run $1,500–$2,000 a month for a family. ACA marketplace plans vary wildly based on your income. This number can completely change whether early retirement is financially viable, and most people discover it after they’ve already retired. Go price it out at healthcare.gov before you make any decisions.

4. If you’re still working, early claiming is mostly pointless.

The Social Security earnings test: if you’re under full retirement age and earning above roughly $24,480 a year, the SSA withholds $1 of your benefit for every $2 you earn over that limit. Work a full-time salary and take Social Security at 62 and most of your benefit disappears anyway, at least temporarily. The good news: those withheld benefits come back as a higher monthly check at full retirement age. The practical takeaway: the real claiming decision happens the day you actually stop earning substantially, not the day you turn 62.

5. The six questions that matter more than the math.

How’s your health, honestly? How are you covering healthcare from 62 to 65? Are you still working and does the earnings test bite you? Do you actually need this income now or do you have other resources? Are you the higher earner, and have you thought about your spouse’s survivor benefit? And finally: what specifically do the go-go years fund, and if you’re 92 and collecting a reduced benefit, is your financial foundation solid enough to hold?

Answer those six questions honestly and you’ll know what to do. The actual math is just a starting point.

If any of the above resonates, or you’re interested in learning more about some of the nuance here, check out this week’s episode of Your Money Guide on the Side for a much deeper strategic and more practical dive. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two Things I’m Currently Thinking About:

1. At various points in my life, in what I can only describe as a series of increasingly self-righteous experiments, I have given up coffee, alcohol, and dessert—not all at once, I’m not a monk, but in rotating shifts—in an attempt to find some kind of nutritional or mental baseline. To meet, as it were, the unassisted version of myself. The findings were not entirely flattering. It turns out that a meaningful portion of what I had been calling “my personality” was just caffeine. But the bigger discovery was something I didn’t expect: what I missed most wasn’t the substance itself. It was the ritual. The morning coffee isn’t really about the coffee. It’s about the thing that says the day has begun. The evening drink isn’t really about the drink. It’s about the thing that says you made it. My wife and I have done this together, which sounds noble and is mostly just mutually inconvenient, and what we keep bumping into is the same question: without the carrot at either end of the day, what’s the carrot? We haven’t fully solved this yet. I’m genuinely in the market for a daily ritual—free or otherwise—that doesn’t come in a glass or a mug but still manages to feel like a small reward for rolling the rock up the hill one more time. If you have one, I’d like to hear about it.

2. I’m currently reading That Will Never Work, Marc Randolph’s account of founding Netflix. He makes the point—and he makes it with the natural confidence of someone who has earned the right—that virtually nothing useful has ever been decided in a boardroom. That the entire exercise of sitting around a table and discussing whether something will work is, at best, an elaborate way to feel productive without being productive. The only data point that actually matters is what happens when you put the thing into the world. Launch the product. Offer the course. Build the app. Post the video. The market will tell you things in twenty-four hours that a conference room full of smart people could not tell you in a calendar year. I know this intellectually, and I know this practically. And yet I still catch myself occasionally talking about doing a thing instead of doing the thing, which is apparently a bug in human cognition that survives even direct exposure to the counterevidence. Randolph launched Netflix by mailing a single CD to himself to see if it would arrive unbroken. It did. The rest is a documentary on the very service he founded. There is a lesson in there somewhere and I think it is this: your first test can be embarrassingly small, as long as it is actually a test.

And Before You Go…

This week’s newsletter is brought to you by Copilot Money.

I have spent the better part of my career telling people to keep their financial lives simple. Fewer accounts. Fewer apps. Fewer subscription services draining your bank account an additional .99 cents at a time. So when I tell you I downloaded a finance app and then talked about it unprompted for three consecutive weeks, I want you to understand the weight of that admission.

Here is what separates Copilot Money from every other app currently decomposing in your phone’s graveyard folder: it actually respects your intelligence. It tracks your spending, net worth, investments, savings goals, and budgets in one place, and does it without making you feel like a golden retriever being praised for sitting. It’s the only personal finance app to win an Apple Editor’s Choice award, was a finalist for the Apple Design Awards, and carries a 4.8-star rating from over 28,000 reviews. People download it and they stay. In this category, that is essentially a miracle.

It automatically categorizes your transactions, which means your weekend no longer needs to involve sorting receipts like an accountant who lost a bar bet. It tracks your subscriptions, so you will finally, after all this time, discover that you have been paying $12.99 a month for a meditation app you opened once in 2023 and have felt nothing but low-grade resentment about ever since. You can set savings goals with progress tracking that motivates without guilt-tripping you, and it runs across iPhone, iPad, Mac, and a web app. They also don’t sell your data, which in 2026 is about as common as a financial advisor who will look you in the eye and say index funds are enough.

If you want your financial life organized without building a spreadsheet that requires its own spreadsheet to interpret, check out Copilot Money today using this link, and use code TYLER2 to get two free months added to your subscription.

As always, hope this gives you all something to think about throughout the week ahead.

—Tyler

This week’s podcast and newsletter focus on AI’s continued rise in the financial space. Specifically: what it can actually do, what it cannot, and the exact prompts that make it useful. Because “use AI for your finances” without specifics is advice in the same way that “eat better” is a meal plan.

Here is a number that should bother you (and yes, I’ve shared it before): according to DALBAR, the average equity investor has underperformed the S&P 500 by 1.5 to 4 percentage points annually for thirty straight years. The culprit isn’t bad stock picks. It’s behavior. Panic-selling. Excitement-buying. Treating a long-term portfolio like a mood ring.

AI can help with this. Not all of it. But more than you’d expect. And this week, we get specific.

Here’s what you need to before using AI as a financial planner:

1. Give it your whole situation before asking anything.

AI doesn’t know you. Start every financial conversation with this:

“Act as a knowledgeable financial guide — not a licensed advisor. Here’s my situation: age, income, monthly take-home, expenses, emergency fund, every debt with balance and rate, retirement account balances, time horizon, and my biggest financial fear right now. Ask me follow-up questions until you have what you need. Then tell me the three most important things I should do first.”

The follow-up loop is where generic becomes specific. Don’t skip it.

2. Use it as a guardrail before doing something irreversible.

The market drops. CNBC has a countdown clock. Your neighbor sold everything and is being smug about it. You are composing a text to your spouse that begins “I’ve been thinking.” This is precisely when you should not be trusted with your own brokerage login.

“I’m about to make a financial move and I want you to pressure-test it. Here’s my situation: [snapshot from Prompt #1]. Here’s what I’m thinking of doing: [action]. Here’s why: [honest answer…fear, a tip, a feeling, my brother-in-law]. Give me: (1) what the historical data says about this kind of move at this kind of moment, (2) the steelman case FOR doing it, (3) your honest take. Then ask me: what would have to be true for this to be a good decision?”

That last question is crucial. Usually the answer is “I would have to be frightened,” which is not a portfolio strategy.

3. My concerns. And, yes, they are real.

Three things, quickly: First, you’re typing your income, debt, and financial fears into a language model. Read the privacy policy of whatever tool you’re using. Use round numbers. Leave out your Social Security number and account numbers. If the information would make you nervous on a billboard, reconsider what level of detail you actually need to provide.

Second, AI hallucinates, and in finance, hallucinations are expensive. Contribution limits, fund expense ratios, tax rules: verify everything at primary sources (irs.gov, the actual fund page) before acting. The framework AI gives you is usually solid. The specific numbers you must check.

Third: it’s a tool. It is only as good as you are at using it. A violin in the hands of someone who’s never practiced is just an expensive source of unpleasant noise.

If any of the above resonates, or you’re interested in learning more about how you can use AI as a financial guide, check out this week’s episode of Your Money Guide on the Side for a much deeper strategic and more practical dive. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two things I’m currently thinking about:

1. I have officially, permanently, and without apology opted out of hotels. Not because I have anything against a mint on a pillow…I have plenty against a mint on a pillow, but that’s not the point. The point is that an Airbnb is a chance to sample someone else’s life for 24 hours, which turns out to be one of the more clarifying things you can do financially. Bear with me. We’ve done this recently on our cross-country drive back to Vermont in Santa Fe, Oklahoma City, Memphis, Asheville, Charlottesville, and Easton—actual homes, actual neighborhoods, actual coffee makers that require a new manual each time—and what I keep noticing is the same thing every time: you spend the first night figuring out what you love about their life, and the second night figuring out what you love about your own. That’s not nothing. The king bed with the city view tells you very little about yourself. The 1940s craftsman in midtown Memphis with someone else’s books on the shelf and their cast iron skillet in the drawer tells you considerably more. It’s a Path Dividend in the most literal sense: you’re paying a modest nightly rate to run a quick life experiment. I find that very good value.

2. While at said Airbnbs, I watched Netflix’s Members Only: Palm Beach—the one about the Palm Beach social scene, the rules, the committees, the hats you can and can’t wear—fully prepared to enjoy a comfortable hour or two of mockery. And then about twenty minutes in I had to put the mockery down, because I realized something mildly inconvenient: every tribe has its rules. Every single one. The Palm Beach set has their gala etiquette and their membership protocols and their very specific feelings about how loud you’re allowed to talk while in a restroom. My tribe has its index funds and its 5% rule and its very specific feelings about whole life insurance salespeople. Your tribe has something. The rules only look absurd from outside. From inside, they’re the whole point—they’re how you know who’s in, they’re how you signal what you value, they’re the grammar of belonging. I’m not in the Palm Beach tribe and I have no intention of joining it (nor would I be accepted). But I’ve stopped laughing at it. If it’s your tribe, it’s sacred. If it’s not, go find yours and stop auditing theirs.

And One Thing that Might Actually Help, Brought to You by LMNT.

My wife and I had friends visit us in Sedona last week. High desert, 4,500 feet of altitude that sneaks up on you in the specific way that makes you feel both humbled and mildly deceived. I had a solid stash of LMNT samples in the kitchen. They were gone by afternoon—claimed by the morning crowd, the “I didn’t realize Sedona was at 4,500 feet” crowd, and the people returning from hikes who needed to feel like humans again rather than very tired cacti. I watched people who had never heard of LMNT become LMNT people in real time. I have created salt monsters. And I regret nothing.

LMNT is an electrolyte drink with 1,000 mg of sodium, 200 mg of potassium, 60 mg of magnesium, and zero sugar. No crash, no liquid candy, no ingredient list that requires a chemistry degree. Just what your body actually needs—whether you’re hiking, traveling, working out, or simply trying to feel less like a houseplant that forgot to water itself.

My flavor of choice is Mango Chili. My friends are now converts. The samples are gone. And it’s time to go back to Vermont to get more from my endless supply of this stuff. Yes, it is that good.

LMNT is offering a free sample pack with any purchase, so check out drinklmnt.com/tyler today. And trust me on the mango chili.

As always, hope this gives you all something to think about throughout the week ahead.

—Tyler

Nobody warns you about the specific parenting anxiety that hits in the delivery room: you’re holding a brand new human being, completely overwhelmed with love, and your first coherent thought is this is going to be extraordinarily expensive.

You’re right. It is. But the single most powerful financial thing you can do for your child costs $250 a month, takes ten minutes to set up, and has nothing to do with a college savings account.

Here’s what you need to know:

1. The Most Expensive Thing You Can Do For Your Kid Is Wait

Investing $3,000 a year from birth to age 18—$42,000 total—is projected to grow to $7.3 million by the time your kid turns 65 (at 10% real rate of return in a growth fund). The secret ingredient isn’t a hot stock tip. It’s just time.

Wait until your kid is 20 to start? You’re looking at $1.5 million instead. Same money. Same math. That $5.8 million gap is the actual cost of procrastination. Every year you wait, you’re not saving money. You’re spending it.

2. Three Accounts. Pick Your Fighter.

UGMA—No earned income required. Open it at birth, invest in a growth fund, ignore it. $42,000 becomes $7.3 million by 65. Kid gets full control at 18, which is either fine or terrifying depending on the kid you raised.

Custodial Roth IRA—Requires earned income, but every dollar of that $3.6 million comes out tax-free in retirement. The IRS never touches it. Best deal in the tax code and almost nobody uses it for their kids.

Your Own Brokerage—You invest in your own name, keep full control, and when you die your kid inherits it with a “step-up in basis”—meaning all the capital gains that accumulated over your lifetime simply disappear. Legally. It’s right there in the tax code…AND you keep control.

3. The 529 Is Fine. It’s Also Overrated (In My Occasionally Humble Opinion)

A 529 over 18 years gets you to roughly $103,000 (based on glidepath towards conservative investments). A UGMA in a growth fund over the same period gets you to $133,000 after taxes—more money, more flexibility, no penalty if your kid skips college entirely. (Note: there is a VERY good reason the 529s invest more conservatively as your child needs the money, so please take this as nothing more than an interesting thought exercise.)

The 529 makes sense if your state offers a generous tax deduction, or if you need the penalty to stop yourself from raiding the account for a kitchen renovation. No judgment. The penalty works.

But don’t open one just because that’s what you’re supposed to do. Do the back-of-the-envelope math on the trade-offs and limited investment options.

4. Start Now. Even Small.

$3,000 a year is $250 a month. One fewer dinner out per week. The streaming tier you forgot to cancel. Almost certainly less than you’ll spend on your kid some other way that won’t compound into $7 million.

Can’t do $3,000? Do $500. Compound interest doesn’t care how impressed you were by the big number. It only cares that you started.

And for the full breakdown, where I explore which funds I actually used in all calculations above, check out this week’s episode of Your Money Guide on the Side for a much deeper strategic and more practical dive. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two things I’m currently thinking about:

1. I’ve been thinking about David Foster Wallace’s Infinite Jest lately—specifically his theory of advertising, which he described as an industry built around manufacturing an imaginary lack, then swooping in to satisfy it by purchase. You’re not missing anything. Then suddenly you are. Then conveniently, here’s the thing that fixes it. This is essentially what Hanna and I spent an hour unpacking last week on the podcast, and DFW articulated it in one sentence in 1996. The reason it’s so effective is that most of us haven’t done the hard work of defining what “enough” actually looks like for us, which leaves a vacuum, and vacuums get filled. Usually by someone else’s idea of what your life should look like. The defense isn’t willpower. It’s knowing what you actually want. Then, and only then, manufactured lack loses most of its power.

2. On a slightly darker (but related) note: Wallace finished Infinite Jest at 33. By any external measure, he had “made it”—published what many consider the defining novel of his generation, achieved the kind of literary recognition most writers spend careers chasing. And by most accounts, he was deeply unhappy afterward. Because “enough”—the finish line he’d been running toward—turned out to just be the starting line of a new race. He’d satisfied the lack. And then the lack moved. I think about this whenever someone tells me they’ll finally feel okay once they hit a certain number, or pay off the house, or make the list. The goal isn’t bad. The belief that reaching it will quiet something permanent, well, that’s the part worth examining.

And One Thing that Might Actually Help, Brought to You by Gelt.

I rarely give blanket financial advice. I don’t know your situation, your goals, or whether you’re the kind of person who keeps receipts or just shoves them in a drawer and hopes for the best (maybe that’s just me).

But here’s one piece of advice I’ll give freely and with complete confidence: if you’re a small business owner or high net worth individual, prioritize finding the best tax partner you can find. Before anything else.

I spent six months as a solopreneur optimizing everything except my tax planning. Money was coming in. I was investing it. I was checking all the boxes that I tell you to check. But I had no one proactively helping me figure out what to do with it and when to make sure I kept more of it in my own business instead of handing it over to the IRS.

Enter: Gelt.

They’re the exact company I’ve been looking for. Here’s why:

• Proactive, not reactive. You’re not spending time you don’t have chasing them down. They reach out. They plan ahead. They actually care about your business staying ahead of tax deadlines and opportunities.

• Tailored strategies. This isn’t cookie-cutter tax prep. They build strategies specific to your business so you’re not getting a one-size-fits-all approach that ignores what you actually need.

• The platform is shockingly good. I’m talking not just user-friendly but actually fun to use. Taxes and fun. Yeah, I said what I said.

If this sounds like the missing piece of your business, check out joingelt.com/tyler for a free consultation with their team.

As always, hope this gives you all something to think about throughout the week ahead.

—Tyler

I recently sat down with Hanna Horvath—CFP, behavioral money expert, and someone who left traditional finance for basically the same reason I did: the inherited playbook was exhausting everyone and helping almost no one.

Here are your five key take-aways from this week’s podcast conversation (you can listen here):

1. Information Is Not Your Problem

We have more financial information available than at any point in human history. Free. Instant. Infinite. And yet most people still feel like they’re drowning.

Hanna’s take: the traditional finance industry is essentially an information industry. It hands you the facts, you nod along like a very agreeable golden retriever, and then three months later nothing has changed.

You already know you should be investing. Knowledge isn’t the gap. Behavior is. And behavior is driven by emotions, identity, and whatever weird money baggage you’ve been hauling around since childhood.

2. “Enough” Is Not a Number

Hanna was refreshingly honest here: she hit her net worth target, exhaled…and immediately started stress-checking her bank account six times a day.

The truth is that enough is a moving goalpost if you let it be. It’s not a math problem, and it never will be. It’s a mindset problem. What Hanna landed on, and what I think is genuinely profound: enough is a state of being, not a balance sheet line item.

You decide what kind of life you want, then back into the number. Most of us do it backwards and hope the good life shows up eventually like a delayed flight.

3. If You Don’t Decide What You Want, Someone Else Will

My favorite line of the whole conversation. If you haven’t figured out what you want your money to do for you, someone else will happily make that decision for you—probably a 26-year-old writing Instagram ad copy designed to make you feel one purchase away from your best life.

Marketing doesn’t sell you a product. It sells you a version of yourself you haven’t become yet, and keeps you perpetually in a state of lack. The antidote, unsexy as it sounds, is getting annoyingly clear about what you actually value. Not what your college roommate values. You.

4. Convenience Is Costing You More Than You Think

We live in the most convenient era in human history, and somehow a lot of us are miserable and lonely. Turns out, when you outsource everything, you don’t just save time, you accidentally outsource the friction that used to create community.

And loneliness is genuinely expensive, because isolated, scrolling-on-the-couch you is a marketer’s dream consumer.

Hanna’s advice: add friction back. Go to the coffee shop. Host the dinner party. Show up consistently even when it’s awkward. Community is built in unglamorous repetition, not one perfect social event.

5. Stop Telling Yourself You’re Bad With Money

Hanna hears it constantly: “I’m so bad with money.” She pushes back every time—not to be polite, but because it’s a self-fulfilling prophecy. The moment you internalize that identity, you make it structurally very hard to change it.

You’re not bad with money. You’re undertrained. One is identity. One is just a practice problem.

Hanna writes on Substack, “Your Brain on Money” and works with clients on the behavioral side of financial planning. Worth a follow.

If any of the above resonates, check out this week’s episode of Your Money Guide on the Side for a much deeper strategic and more practical dive. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two things I’m currently thinking about:

1. Last week I posted a social media video on “5 Things I Refuse to Do With My Money in 2026,” and it became the most-watched thing I’ve made in months. Which tells you something. Maybe people are just tired of being told what to do and found it refreshing to hear someone talk about what they’re not doing. Either way, here’s what I keep coming back to: your financial “nos” are more powerful than your “yesses.” The people I’ve watched build real wealth—not “rich on paper while miserable in practice” wealth, but actual I-sleep-well-and-own-my-time wealth—they all had a clear list of things they simply didn’t spend money on. Not because they couldn’t afford them. Because the decision was already made, long before the sale email arrived or the neighbor got a new boat. A standing “no” to that thing was a standing “yes” to something they actually cared about. Make your nos clear enough, and you’ll always have enough for your yesses.

2. I’ve been spending time back in The Brothers Karamazov—not because I’m someone who rereads Dostoevsky recreationally and wants you to know that, but because I had four hours on a plane and forgot to download anything else. Alyosha is the youngest brother, the “good” one, the one who ended up in a monastery while his siblings were busy committing various 19th century disasters. What I can’t stop noticing: he never tries to fix anyone. People confess the worst things to him and he doesn’t flinch, doesn’t lecture. He just stays. And somehow that presence does more than any advice could. I keep thinking about what it would mean to apply that to money conversations: to spend less time fixing people’s financial behavior and more time sitting with the anxiety underneath it. Sometimes the most useful thing isn’t a framework; it’s someone who simply listens and doesn’t leave.

And One Thing that Might Actually Help, Brought to You by Facet.

Here’s something nobody tells you: the three years before you retire might matter more than the thirty years you spent saving for it. There are decisions sitting in that window that can either save you tens of thousands of dollars—or cost you that much if you get them wrong.

Medicare and IRMAA. Your premiums aren’t based on what you make when you retire—they’re based on what you made two years prior. Big income year, sold a business, took a large bonus? Medicare finds out. We’re talking your Part B premium jumping from around $200 a month to nearly $700. That’s $6,000 extra per year because of a lookback window most people don’t know exists.

Roth conversions. Your early 60s are often the lowest-tax period of your entire adult life—the perfect window to move IRA dollars into a Roth at a discount. But convert too aggressively and you spike your income, trigger IRMAA, and get pushed into a higher bracket. Convert too little and you miss the window entirely, then get walloped by required minimum distributions at 73.

Social Security timing. Take it at 62 for a guaranteed income floor, or delay to 70 for 8% annual increases and a larger survivor benefit. Get this one wrong and you’re living with the consequences for the rest of your life. Literally.

Most people don’t realize they need a plan until they’re already in it. Facet gives you a dedicated team of CFPs® who build the roadmap through all of this—Roth conversions, Social Security timing, Medicare planning—for one flat annual membership fee, not a percentage of your assets. Learn more today, and find out if Facet is right for you.

As always, hope this gives you all something to think about throughout the week ahead.

—Tyler

You’ve been lied to about how to invest.

(Not maliciously…and it’s not your fault…)

But the “subtract your age from 110” rule that’s been drilled into your head since the Reagan administration? It’s lazy thinking dressed up as wisdom.

Here’s why it’s broken and exactly what to do instead:

1. Age tells you nothing. Timeline tells you everything.

   Two 60-year-olds with $2 million saved. One has a pension and won’t touch the money for 15 years (legacy fund for grandkids). The other retires in two years and needs to live off it.

   Age-based advice says they should both be at 50% stocks, 50% bonds.

   Timeline-based advice says the first person should be 100% stocks (they have 15 years). The second should be moving heavily into bonds and cash right now (they have 2 years).

   Same age. Completely different allocations. Your timeline dictates your risk, not your birthday.

2. The Three-Bucket System I Use: 0-2 years, 2-10 years, 10+ years

   Every dollar you save goes into one of three buckets based on when you’ll spend it:

   1. Bucket 1 (0-2 years): Cash only. High-yield savings, money market funds. Zero stock exposure. If you need this money soon, you can’t afford a 30% drop.

   2. Bucket 2 (2-10 years): Glide path. Here’s the formula: Years until you need it x 10 = % in stocks.

      • 10 years out = 100% stocks

      • 5 years out = 50% stocks / 50% bonds

      • 3 years out = 30% stocks / 70% bonds

   3. Bucket 3 (10+ years): 100% stocks. Let it compound. This is where real wealth gets built.

3. When a 70-year-old can be more aggressive than a 30-year-old

   Example: A 30-year-old saving $40,000 for a house down payment in 18 months should be 100% in cash or bonds.

   A 70-year-old with $40,000 earmarked for a New Zealand trip in 10 years should be 100% in stocks.

   Who’s more aggressive? The 70-year-old. Because they have a decade. The 30-year-old has 18 months.

   This is timeline-based investing.

4. The specific funds you need (and nothing else)

   You don’t need 63 funds. You need two, maybe three:

   1. Total Market Stock Funds: VTI (Vanguard), FSKAX (Fidelity), SWTSX (Schwab)

   2. Bond Funds: BND (Vanguard), FXNAX (Fidelity), SWAGX (Schwab)

   3. Cash: High-yield savings (Ally, Marcus, Wealthfront) or money market funds (VMMXX, SPAXX, SWVXX)

   Match your allocation to your timeline. Rebalance once a year. Done.

5. Your homework: Audit every dollar you have (not as tedious as it sounds…)

   Open every account. 401(k), IRA, brokerage, savings.

   And then ask one question: When will I need this money?

   Then allocate it to the right bucket:

   1. 0-2 years = cash or bonds

   2. 2-10 years = glide path (years x 10 = % stocks)

   3. 10+ years = 100% stocks

   Simple, boring, mathematically sound.

   And when someone asks you, “How should a 60-year-old invest?” you can smile and say: “You’re asking the wrong question.” Boom, baby.

If any of the above is confusing, check out this week’s episode of my podcast Your Money Guide on the Side for a much deeper strategic and more practical dive. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two things I’m currently thinking about:

1. One last James Wedmore thought from Sedona and then I’ll stop (maybe). He asked the room: What is the one thing you’d need to do to 10x your business this year? Not improve it. Ten times what it is now. The interesting part wasn’t the answers, as most people knew immediately. Launch the course. Write the book. Build the membership. The interesting part was the follow-up: So why haven’t you done it? And the room went quiet in a way that told you everything. The obstacle is almost never information or resources. It’s you. It’s the version of you that decided what’s realistic, built a ceiling out of those assumptions, and called it common sense. Try it this week. Write down the one concrete thing that you would do to 10x your business. Then notice how fast your brain starts explaining why you can’t. That voice is not wisdom. It’s a habit. Time to break that habit in 2026 and expand what you thought was possible.

2. There’s a moment in Virginia Woolf’s Mrs. Dalloway I think about more than almost anything else I’ve read. Doris Kilman—awkward, proud, painfully earnest—has been tutoring Elizabeth Dalloway, and as they part she says, almost involuntarily: “Don’t quite forget me.” She’s not asking to be loved or praised. She’s asking for the smallest, most fundamental thing any of us want from people we’ve worked alongside or taught or built something with: just don’t forget I was here. Don’t forget we shared this moment. I think about this every time someone emails to say a video helped them open their first brokerage account. It’s nice to be remembered. Go read Mrs. Dalloway. It’s short and it will rearrange something inside you that you didn’t know was out of place.

And One Thing that Might Actually Help, Brought to You by Gelt.

I almost never give universal financial advice. I don’t know your situation, your goals, or whether you file your receipts in a labeled folder or stuff them into a kitchen drawer and let fate sort it out. (I have done both, sometimes in the same week.)

But here’s one thing I’ll say with complete confidence: if you’re a small business owner or high net worth individual, the single most important hire you can make is a great tax partner. Before the financial advisor. Before the bookkeeper. Before the guy on Fiverr who’s going to redesign your logo for the fourth time.

I spent my first six months as a solopreneur optimizing everything except my taxes. Revenue was growing. I was investing. I was checking every box I tell you to check. Meanwhile, I was leaving money on the table. A lot of money. Because no one was proactively telling me what to do, when to do it, or how to keep more of what I’d built instead of gifting it to the IRS, who, I assure you, did not send a thank-you note.

That’s when I found Gelt, and they’re exactly the type of tax partner I didn’t know I was missing.

• Proactive, not reactive. You’re not burning hours you don’t have chasing people down for answers. They reach out to you. They plan ahead. They treat your deadlines like their deadlines, which is a shockingly low bar that almost no one clears.

• Tailored strategies. This isn’t assembly-line tax prep where they run your numbers through the same template they used for a dentist in Omaha. They build strategies specific to your business, your structure, and your goals.

• The platform is genuinely great. I’m not going to say doing your taxes is fun. But I will say Gelt makes it the least painful financial task on your list.

So if you’re a business owner or high earner who’s been white-knuckling tax season every year, go to joingelt.com/tyler for a free consultation with their team.

As always, hope this gives you all something to think about throughout the week ahead.

—Tyler

A few months ago, I broke down how I’d allocate a $2 million portfolio: 90% stocks, 10% money market. That episode got more responses than anything else in my first year of creating—so today, I’m answering your best follow-up questions about actually managing this strategy day-to-day.

Quick Recap: The 90/10 (or 70/20/10) Strategy

90% in VOO or VTI, 10% in SPAXX. That’s it. For the more conservative crowd: 70% VOO/VTI, 20% BND or VIG, 10% SPAXX. Both work for 99% of us.

Why so simple? Because stocks historically return roughly 10% nominally (7% after inflation), while bonds return about half that. The 10% money market fund gives you two years of spending during crashes—so you’re never forced to sell stocks at a loss. From a $2 million portfolio, you withdraw $120,000 annually (6%), and increase to $180,000-$200,000 as the portfolio grows.

How to Manage the Portfolio:

1. Use Guardrails

   Dynamic Guardrails tell you when to adjust spending. You can set upper and lower boundaries around your withdrawal rate:

   1. Lower guardrail: 7% withdrawal rate

   2. Upper guardrail: 5% withdrawal rate

   If your portfolio drops to $1.5 million, your $120,000 withdrawal becomes 8%—you’ve crossed the lower guardrail. Cut spending by 10% to $108,000. Still comfortable, but fare more sustainable.

   In turn, if your portfolio grows to $2.5 million, your $120,000 withdrawal becomes 4.8%—you’ve crossed the upper guardrail. Increase spending by 10% to $132,000. You’ve earned it.

2. When to Reduce Withdrawals (And When to Increase Them)

   Adjust annually, not monthly. If you cross a guardrail, make the change and stick with it for at least one full year before reassessing.

   Example: Retire in 2020 with $2 million, withdrawing $120,000 (6%). By 2021, your portfolio hits $2.6 million—cross the upper guardrail, increase to $132,000. Then 2022 crashes everything back to $2 million. Your $132,000 withdrawal is now 6.6%—still within guardrails, so don’t adjust. By 2023, you’re back to $2.4 million at 5.5%—still good.

   Pick your reassessment day (ideally January 1st/2nd) and stick to it. The more organized this is, the less tempted you’ll be to make emotional changes.

3. How and When to Rebalance

   Rebalance once per year, and only if your ideal allocation drifts by more than 5 percentage points. If you’re at 95% stocks / 5% cash, rebalance back to 90/10. If you’re at 91/9, leave it alone.

   How? If stocks have grown, sell enough to restore 90/10. If stocks have crashed and you’ve been spending from cash (now at 85/15), just wait—let the portfolio naturally rebalance as stocks recover.

   Pro tip: Use your withdrawals to rebalance. If stocks are at 95%, take your $120,000 withdrawal entirely from stocks. If at 85%, take it entirely from the money market fund. You’re rebalancing without triggering unnecessary trades.

   Critical rule: Don’t rebalance during a crash. Stick to your annual schedule. The market will recover.

4. Replenishing Your Money Market Fund After a Crash

   Most-asked question: “If I spend from my money market fund during a crash, how do I rebuild it without missing the recovery?”

   Answer: Replenish slowly, and only after the market has clearly recovered.

   Example: 2022 crashes 25%. Your $1.8 million in stocks becomes $1.35 million. You spend $120,000 from your $200,000 money market fund, bringing it to $80,000. You’re now 87% stocks / 13% cash.

   2023 recovers 20%. Your stocks hit $1.62 million. Your money market is still $80,000—now 95% stocks / 5% cash. This is when you rebalance. Sell enough stocks to bring your money market to $170,000 (10% of your $1.7 million total). You’re not trying to get back to $200,000 immediately—just restoring 90/10 based on current value.

   Key principle: Never sell stocks to replenish cash during a downturn. Only rebuild during recovery.

A Few Other Practical Strategies

• Automate everything. Set up automatic monthly withdrawals ($10,000/month if withdrawing $120,000/year). Remove emotional decision-making.

• Stop checking constantly. Once per quarter is plenty. Daily checking will drive you insane.

• Keep a “sleep well” spreadsheet (optional, for data lovers). Track portfolio value, withdrawal rate, and guardrails quarterly. Five minutes, zero drama.

• Remember volatility is normal. The S&P 500 drops an average of 14% intra-year before recovering. A 10-15% drop isn’t a crisis—it’s just another Thursday.

• Write a “what if” plan now. What would you do if your portfolio dropped 30% tomorrow? Write it down while you’re calm. Don’t make panic decisions later.

• Remember you probably have other income. This allocation assumes zero other sources. Social Security alone is massive fixed income for many—why hold bonds if that already covers your bills?

Final Thought

Managing a 90/10 portfolio isn’t complicated—that’s the whole point. But it does require discipline. Guardrails prevent overspending or underspending. Annual rebalancing keeps allocation on track. Spending from cash during downturns avoids selling at losses. And replenishing during recoveries keeps you ready for the next dip.

If any of the above is confusing, check out this week’s episode of Your Money Guide on the Side for a much deeper strategic and more practical dive. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two things I’m currently thinking about:

1. As I mentioned in last week’s letter, I recently spent three days at James Wedmore’s mastermind in Sedona, and the line I can’t shake was his closing thought: the only time he’s ever truly screwed up in business is when he built the next step around something he didn’t actually want to spend his time doing. Not when he priced wrong. Not when he launched too early. When he optimized for revenue instead of enjoyment and fulfillment. I grew up in Vermont, where Ben & Jerry’s stamped “If it’s not fun, why do it?” on every pint. I spent most of my life treating that as a cute slogan, not an operational philosophy. But every time I’ve chased a project because the math was good and the work felt like a chore, it either failed or succeeded in a way that made me miserable, which is just failure with slightly better accounting. Every time I’ve built toward something I genuinely wanted to wake up and do (you know, like create financial literacy content for all of you), the energy showed up and the audience could tell the difference immediately. Your clients can smell obligation. They can also smell joy. So if it’s not fun, why do it?

2. If you haven’t read Marilynne Robinson’s Housekeeping, stop reading this, and go read that. Its central character, Sylvie, does something I can’t stop thinking about: she enjoys doing things precisely because they take a long time. Not in spite of the time. Because of it. We’ve built an entire culture around the assumption that the goal is to get through things as efficiently as possible. Save time. Batch tasks. Eliminate friction. Get to the end so you can…what, exactly? Start the next task faster? Some things should take a long time. A slow walk with no destination. A book that doesn’t need to be summarized into five bullet points. A conversation with no next step. Efficiency is a tool, not a theology. So go read Housekeeping. Take your time with it. Robinson wrote it that way on purpose.

And One Thing that Might Actually Help, Brought to You by Copilot Money.

I’ve built my entire financial life around one idea: your plan should be simple enough that you can explain it to a 10-year-old in one minute without losing them. So when I tell you I downloaded a budgeting app voluntarily, and then talked about it unprompted for the better part of a month, you should take that seriously.

Copilot Money tracks your spending, net worth, investments, savings goals, and budgets in one place. It’s the only personal finance app to win an Apple Editor’s Choice award, was a finalist for the Apple Design Awards, and carries a 4.8-star rating from over 25,000 reviews. But the thing that actually matters is this: people download it and keep using it. In a category where most apps get banished to a back folder within two weeks, that tells you more than any award does.

It auto-categorizes your transactions, which means you’re no longer spending Saturday mornings sorting through charges like a forensic accountant piecing together a crime scene you committed against yourself. It tracks your subscriptions, so you’ll finally catch that meditation app you signed up for in 2023, used exactly once, and have been paying $12.99 a month for ever since. (Ironic, given how not calm that discovery will make you.) You can set flexible savings goals that actually track your progress without making you feel like a disappointment. It works across iPhone, iPad, Mac, and their new web app. And they don’t sell your data, which in 2026 is about as uncommon as a financial advisor who’ll look you in the eye and say an index fund is probably fine.

So if you want to finally get your money organized without building a spreadsheet so complex it needs its own spreadsheet to decode it, go to try.copilot.money/tyler and use code TYLER for two free months.

As always, hope this gives you all something to think about throughout the week ahead.

—Tyler

No. There isn’t.

I know that’s disappointing. I know you wanted me to tell you that once you cross $5 million, you get access to some exclusive club where hedge fund managers whisper the names of private equity deals over single-malt scotch while wearing boat shoes without socks. But the truth is way more boring: whether you have $50,000 or $50 million, the fundamentals of good investing don’t change.

Time horizon. Risk tolerance. Tax efficiency. Diversification that actually makes sense. That’s it.

So this week, we’re breaking down four portfolio options—from the simplest possible approach to a more sophisticated (but still shockingly simple) allocation—and I’m going to show you why nobody needs anything more complex than this.

Portfolio One: The One-Fund Wonder (VTI or VOO)
If you’re in your 20s or 30s with decades until retirement, here’s your portfolio: one fund. VTI (Vanguard Total Stock Market) owns over 3,500 US companies. VOO (Vanguard S&P 500) owns the 500 largest. The performance difference? About 0.1% annually. My preference? VOO, because the S&P 500 has a built-in quality filter—companies have to meet profitability and liquidity standards to get in, and if they falter, they get kicked off. It’s a “winners-only” index. VTI owns everything, including 2,500+ smaller companies that might never become winners. But honestly, both are excellent. Pick one and move on.

Portfolio Two: The Two-Fund Balance (VTI + BND)
Not 25 anymore? Or can’t stomach a 40% market crash without panic-selling? Want to sleep better at night? Enter the two-fund portfolio: VTI (stocks) and BND (bonds). Bonds are boring—they don’t grow much, but they don’t crash much either. When stocks tank, bonds usually hold steady. The old rule was “100 minus your age” for stock allocation (so 60% stocks at age 40). But that’s lazy. The real question isn’t “How old am I?” It’s “When do I need this money?” Money needed in 0-2 years? 100% bonds or cash. Money needed in 10+ years? 100% stocks. Think timeline, not age.

Portfolios Three & Four: Target-Date Funds or the Three-Fund Bogle Portfolio
Don’t want to manually rebalance? Target-date funds (like Vanguard Target 2050 or Fidelity Freedom 2055) do it for you. Pick a fund based on your retirement year, and it automatically shifts from 90% stocks when you’re young to 40% stocks at retirement. Set it and forget it forever. Perfect for people who don’t want to think about investing (although I really do hate the idea that just because you get older, you get more conservative). Alternatively, if you want more control: the classic three-fund Bogle portfolio. US Stocks (VTI/VOO, 60-70%), International Stocks (VXUS, 20-30%), US Bonds (BND, 10-30%). You get global diversification, bond stability, and full control over allocation. Rebalance once a year—takes ten minutes. Both options work beautifully for 99% of people.

Portfolio Five: The 2.0 Allocation (For Optimization Nerds)
This is for people who want to optimize for non-correlation and enjoy thinking about this stuff. Five funds: US Stocks (50-60%), International Stocks (15-20%), US Bonds (10-20%), Real Estate/VNQ (5-10%), and Gold or Crypto (0-5%). Why add these? Because they don’t always move with stocks. Real estate (VNQ) gives you REIT exposure and steady dividends. Gold (GLD) is your “I don’t trust anything” hedge—it holds value when currencies collapse or inflation spikes. Crypto (BTC) had low correlation with stocks and bonds (not so much anymore), and over the last decade it massively outperformed everything (sustainability unknown). Key point: these are small allocations—5-10% combined. Your portfolio is still 70-80% stocks and bonds. You’re not abandoning fundamentals, just adding insurance and potential upside. The five-fund portfolio is for tinkerers. If that’s not you, the three-fund portfolio works just as well.

The Big Lie About Wealth and Complexity
Here’s what the financial industry wants you to believe: more money = more complexity. Hit $1M? Get an advisor. Hit $5M? Add alternative investments. Hit $10M? Private equity, hedge funds, a family office with a guy named Thaddeus who wears cufflinks. But guess what…I know people with $10 million in private equity funds getting charged 2% annually plus 20% of profits who would’ve been FAR better off in VTI. And I know people with $10 million in three index funds who rebalance once a year and outperform them—because they’re not paying ridiculous fees, aren’t locked up for ten years, and aren’t trying to impress anyone at the country club. Complexity isn’t a badge of honor. It’s just expensive.

Your Homework
Pick a portfolio that matches your timeline and temperament. Young and aggressive? One-fund. Older or risk-averse? Two or three-fund. Don’t want to think? Target-date. Want to optimize? Five-fund. Then rebalance once a year and get on with your life.

If any of the above is confusing, check out this week’s episode of Your Money Guide on the Side for a much deeper strategic and more practical dive. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two things I’m currently thinking about:

1. I just spent three days at a performance mastermind in Sedona run by James Wedmore, and I need to be honest—it was the single best event I’ve ever attended. Three days with a room full of entrepreneurs who are building real things, asking hard questions, and actually doing the work instead of just talking about doing the work. If you’re at the stage where you know the next level exists but can’t quite see the staircase, reach out to James immediately. I don’t say that lightly. I say it as someone who is deeply suspicious of anything that sounds like a “mastermind” and who showed up half-expecting to be asked to walk on hot coals. No coals. Just exceptional people and the kind of conversations that make you reorganize your entire life on the flight home.

2. I have officially collected enough data to confirm the following: I don’t like fancy restaurants. This is a massive Path Dividend. After years of dutifully sitting through tasting menus and pretending to be moved by veal medallions drizzled in something a waiter described using four French words, I can now say with statistical confidence that I’d rather have a burger. Every time. This isn’t a flex—it’s a discovery, and discoveries save money. We’re talking roughly $400 a month I can now redirect toward things I actually enjoy, like additional shares of VTI. The whole point of tracking your spending isn’t to spend less—it’s to collect enough personal data to know what you actually value versus what you’ve been performing. Turns out my palate has a Vanguard-level expense ratio: low cost, broadly diversified, and perfectly happy at a place with paper napkins.

And One Thing that Might Actually Help, Brought to You by Gelt.

I rarely give blanket financial advice. I don’t know your situation, your goals, or whether you’re the kind of person who keeps receipts or just shoves them in a drawer and hopes for the best (maybe that’s just me).

But here’s one piece of advice I’ll give freely and with complete confidence: if you’re a small business owner or high net worth individual, prioritize finding the best tax partner you can find. Before you do anything else.

I spent six months as a solopreneur optimizing everything except my tax planning. Money was coming in. I was investing it. I was checking all the boxes that I tell you to check. But I had no one proactively helping me figure out what to do with it and when to make sure I kept more of it in my own business instead of handing it over to the IRS.

Enter: Gelt.

They’re the exact company I’ve been looking for. Here’s why:

• Proactive, not reactive. You’re not spending time you don’t have chasing them down. They reach out. They plan ahead. They actually care about your business staying ahead of tax deadlines and opportunities.

• Tailored strategies. This isn’t cookie-cutter tax prep. They build strategies specific to your business so you’re not getting a one-size-fits-all approach that ignores what you actually need.

• The platform is shockingly good. I’m talking not just user-friendly but actually fun to use. Taxes and fun. Yeah, I said what I said.

If this sounds like it was the missing piece of your business in 2025, start the new year right by visiting joingelt.com/tyler for a free consultation with their team.

And if you choose to ignore finding a tax partner, well, just don’t say I didn’t put it out there as your priority item.

As always, hope this gives you all something to think about throughout the week ahead.

—Tyler

Let’s be honest: most retirement guidance is about as useful as a screen door on a submarine. “Save a million dollars.” “Aim for ten times your salary.” “You’ll need 70% of your pre-retirement income.” Cool. But what does any of that actually mean for you? With your spending, your timeline, your deep and irrational fear that you’ll end up eating cat food in your 80s?

So this week, we’re calculating three actual numbers. One of them is yours.

Number One: Traditional FIRE (The “Never Work Again” Number)
This is the most aggressive target: the amount you’d need invested to cover all your expenses indefinitely without ever earning another dollar. The formula? Annual spending (net of taxes) × 20. So if you spend $60,000/year, you need $1.2 million. Sounds simple, right? Except getting there requires saving 50-60% of your income for 15-20 years, which is achievable if you’re a tech worker in San Francisco living in a van or a dual-income couple with no kids in rural Nebraska. For everyone else? This number feels impossible because, well, it kind of is. Most people don’t actually want to retire at 35 and never work again—they just want options. Which brings us to...

Number Two: Coast FIRE (The “Just Right” Goldilocks Number)
This is my favorite, and the one I recommend to almost everyone. Coast FIRE asks: “How much do I need invested now so it grows into enough by retirement—without me ever adding another dollar?” You front-load your effort, save & invest aggressively for 5-10 years, hit your number, and then stop. Retirement? Handled. You still work, but you’re no longer saving for the future—you’re just covering current expenses. That extra income you were dumping into your 401(k)? Now it funds travel, hobbies, or telling your boss you’re going part-time because future-you is already taken care of. The formula: Retirement Goal ÷ (1.07)^(Years Until Retirement). Example: Want $1.2 million by age 60? If you’re 35, you need $221,000 invested today. Then you coast. That’s it. You’re done.

Number Three: The Bare Minimum (The “Please Don’t Make Me Work Until I Die” Number)
Maybe you’re 50 with $40,000 saved and thinking, “There’s no universe where I hit those other numbers.” Fair. This one’s about survival, not early retirement. Start by estimating Social Security (go to ssa.gov—it takes five minutes). Let’s say it’s $24,000/year. If you need $55,000 to live, your gap is $31,000. Multiply that by 20: you need $620,000 invested to cover the shortfall. Still a big number? Yes. But way more realistic than $1.5 million. And knowing it gives you a target, even if that means working longer and saving harder than you’d hoped.

Why Social Security Only Shows Up in One Calculation
You noticed, didn’t you? I included Social Security in the bare minimum but not in FIRE or Coast FIRE. That’s intentional. My philosophy: plan for the worst, hope for the best. If you’re 50 with limited savings, you don’t have the luxury of ignoring Social Security—you need every income stream just to make the math work. But if you’re 30 and planning for 35 years out? Social Security might get cut, restructured, or means-tested into oblivion. I have no idea what it’ll look like in 2060, and neither does anyone on cable news (if that’s even still a thing). So build your FIRE and Coast FIRE numbers as if it doesn’t exist. If it shows up later? Fantastic. That’s gravy. But your plan doesn’t need it to work.

One More Thing: These Numbers Assume You Have Nothing Else
No inheritance from Aunt Diane. No pension. No rental income. No side gigs in retirement. For most people, something else will show up—but we’re not counting on it. Why? Because those are maybes, not guarantees. Your parents might need every penny for care. That rental property might sit vacant for six months. You might hate consulting and quit after two weeks. So build your plan assuming you only have what you’ve saved yourself. If extra income appears? Wonderful. That’s margin, not necessity.

Your Homework
Calculate your number this week. Pick one of the three. Do the math. Write it down. Make it real. Use coastfirecalc.com if formulas make your eye twitch. And once you know your number, you can stop spinning and start building a plan that actually works.

If any of the above is confusing, check out this week’s episode of Your Money Guide on the Side for a much deeper strategic and more practical dive. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know if the topics that interest me actually interest you.

Listen on Apple | Listen on Spotify

Two things I’m currently thinking about:

1. Decoy pricing. Restaurants and retailers intentionally add an overpriced option they never expect you to buy just to make the second-most expensive option look reasonable. A $40 burger makes the $28 burger seem sensible, even though you’d never normally spend $28 on a burger. Movie popcorn works the same way—the large is barely more than the medium because they never wanted you buying the medium. Behavioral economists call it “anchoring,” but once you see it, you can’t unsee it. Every menu is designed to make you feel smart for choosing exactly what they wanted you to choose all along. Highest wine markup? The second cheapest bottle, because they know we don’t want to look cheap.

2. And if you haven’t read Richard Russo’s Empire Falls, stop reading this and go read that. It keeps circling back to these small moments of teenage humiliation—the kind that feel nuclear at the time but adults have mostly forgotten or dismissed. The main character’s daughter is navigating high school social dynamics in a dying Maine town, and Russo captures how being a teenager is this weird combination of having zero power over your circumstances while feeling every slight with maximum intensity. It’s making me think about how much of adolescence is just enduring things you can’t control while pretending you’re fine, which honestly (and sadly) might be the best preparation for adult life there is.

And One Thing that Might Actually Help, Brought to You by Facet.

If you are 3 years from retirement…here’s what you need to know now…

There are three critical decisions that will either save you tens of thousands—or cost you that much if you get them wrong.

1. Medicare and the IRMAA Lookback. Medicare premiums are based on your income from two years prior. Planning to retire in 2029? They’re looking at your 2027 income. Had a high-income year from selling a business, taking a bonus, or doing a large Roth conversion? Your Part B premium can jump from $200/month to $680/month—an extra $5,000-$6,000 a year. You need to model your income in the years before Medicare kicks in, not just when you retire.

2. Roth Conversion Strategy. The window between retirement and Social Security—age 62 to 70—is often your lowest-tax period ever. That’s your chance to convert Traditional IRA dollars to Roth at lower rates. But convert too much and you spike your income, trigger IRMAA, and push into a higher bracket. Convert too little and you miss the window—then RMDs kick in at 73 and your tax rate goes up permanently. Finding the sweet spot requires modeling year by year.

3. Social Security Timing. Take it at 62 and you get a fixed income floor protecting you from selling stocks in a crash. Delay to 70 and you get 8% annual increases plus a bigger survivor benefit. The right answer depends on your health, portfolio size, and marital status. This isn’t just break-even math—it’s about sequence of returns risk and tax planning. Get it wrong and it literally costs you for life.

The problem is that most people don’t realize they needed to plan until it’s too late. You can’t undo a conversion that triggered IRMAA. You can’t reclaim missed tax advantages. And once you file for Social Security, it’s permanent.

That’s where Facet comes in. Facet pairs you with a team of CFPs® who can help model your income, map Roth conversions, plan around IRMAA, and strategize your taking Social Security—all for a flat annual membership fee. No commissions. No nonsense.

Check out Facet today to see if they can help you model now so you’re not handing over thousands in unnecessary taxes and Medicare premiums later.

I’m not a member of Facet. I have an incentive to endorse Facet as I have an ongoing fee-based contract for cash compensation, as well as a percentage of equity in Facet based on this endorsement. Facet is an SEC registered investment advisor. All opinions are my own and not a guarantee of a similar outcome.

As always, hope this newsletter gives you something to think about throughout the week ahead,

Tyler

You saved for 30 years. Gold star. Now comes the hard part: spending it without going broke or dying with $2 million you never touched.

5 Things You Need to Know:

1. Your Parents’ Playbook Is Dead

They got a pension and Social Security. Done. You have to create your own paycheck from savings that needs to: generate income, keep growing so inflation doesn’t destroy you, and last until you’re 95. No pressure.

2. The Growth Portfolio: Sell 4-5% Annually

Keep everything in stocks, pull out $40K-$50K per million saved. Your portfolio (hopefully) grows faster than you’re spending. The risk? Retiring right before a crash. The fix? Adjust dynamically—market tanks, tighten your belt. Market soars, buy the fancy olive oil. Be smart about which tax lots you sell to minimize capital gains. Pro tip: if you want to make sure you’re selling the right lots, call the brokerage directly. They’ll help.

3. The Dividend Portfolio: Never Sell Anything

Own stable dividend-payers like Coca-Cola and Johnson & Johnson or funds like SCHD/VIG that pay you 3-4% annually. You get income, shares stay invested, zero selling stress. Tradeoff? Usually lower projected growth than tech stocks, and dividends are taxed annually whether you need the cash or not. Best in retirement when your income is lower and you actually need the income.

4. The Fixed Income Portfolio: Lock In Guarantees

Bonds, CDs, maybe an annuity. A 4% Treasury gives you $4K per $100K, guaranteed. Problem? Taxed as ordinary income and inflation eats your purchasing power. Best use? Cover 5-10 years of expenses so you never sell stocks in a bear market.

5. The Tax-Efficient Withdrawal Order (This Saves You Thousands)

Spend taxable accounts first (favorable capital gains rates). Spend Traditional IRA/401k second (ordinary income tax, but you’ve deferred for decades). Leave Roth alone as long as possible (tax-free forever). Bonus moves: Roth conversions in low-income years, avoid Medicare surcharge thresholds, use Qualified Charitable Distributions after 70½.

The Real Answer? Blend All Three

50-70% growth assets. 20-30% dividend stocks. 10-20% bonds. Optimize withdrawals to minimize taxes.

The goal isn’t to die with the most money. It’s to fund a life worth living.

If any of the above was confusing, check out this week’s episode of Your Money Guide on the Side for a much deeper strategic and more practical dive. And if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know I’m not just talking to myself.

Listen on Apple | Listen on Spotify

Two things I’m currently thinking about:

1. The Law of Attraction. I’ve officially been in Sedona long enough that I now own crystals and have opinions about “energy.” But here’s the non-woo-woo version: if you’re constantly putting out stressed, scarcity-minded energy, guess what shows up in your life? More stressed, scarcity-minded people. Thoughts become things, or at least they become your reality. So audit what you’re inviting into your mental real estate daily, and it will ultimately have an impact on your wealth.

2. And if you haven't read Hernán Díaz's Trust, stop reading this and go read that. It’s a financial mystery wrapped in an unreliable narrator wrapped in three more unreliable narrators. By the end you’re questioning whether you can trust your own memories of what you read 100 pages earlier. Brilliant, unsettling, and it won the Pulitzer—so you can feel intellectually superior while reading it on the beach.

And One Thing that Might Actually Help, Brought to You by Gelt.

Here’s one piece of advice I’ll give freely and with complete confidence: if you’re a small business owner or high net worth individual, prioritize finding the best tax partner you can find. Before you do anything else.

I spent six months as a solopreneur optimizing everything except my tax planning. Money was coming in. I was investing it. I was checking all the boxes that I tell you to check. But I had no one proactively helping me figure out exactly when to keep more of it in my own business instead of handing it over to the IRS.

Enter: Gelt.

They’re the exact company I’ve been looking for. Here’s why:

• Proactive, not reactive. You’re not spending time you don’t have chasing them down. They reach out. They plan ahead. They actually care about your business staying ahead of tax deadlines and opportunities.

• Tailored strategies. This isn’t cookie-cutter tax prep. They build strategies specific to your business so you’re not getting a one-size-fits-all approach that ignores what you actually need.

• The platform is shockingly good. I’m talking not just user-friendly but actually fun to use. Taxes and fun. Yeah, I said what I said.

If this was the missing piece of your business in 2025, start the new year right by visiting joingelt.com/tyler for a free consultation with their team.

As always, hope this newsletter gives you something to think about throughout the week ahead,

Tyler

This week on the podcast, I spent 40 minutes trying to stay polite while discussing the insurance industry. And I would say…I mostly succeeded. If you’ve ever been cornered at a wedding by your college roommate who just became a “financial advisor” and wants to help you “build wealth through whole life insurance,” this episode is required listening.

But for those of you who can’t listen this week, here’s your TL;DR version.

Five Things You Need to Know:

1. Insurance is not an investment—it’s a necessary cost to protect against catastrophic loss. Car insurance for a potential $30,000 accident. Homeowners insurance so you don’t rebuild with a GoFundMe. Insurance transfers risk; it does not build wealth. The insurance company bets they’ll collect more than they’ll pay out. That’s fine for disasters. It’s a problem when they convince you it’s also a “wealth-building tool.”

2. Whole life insurance costs 11x more than term life and grows at half the rate of index funds. If you’re 30 and invest the $400/month difference in the S&P 500, you’d most likely have $900,000 in 30 years. With whole life? Maybe $150,000. About 25% of policies get canceled within three years—at which point the insurance company keeps the difference. The only winners are the company and the agent, who pockets 100% of your first year’s premium as commission.

3. Northwestern Mutual recruits college students to sell overpriced policies to their friends and family. They promise “unlimited earning potential,” then hand you a worksheet asking for 200 contacts with phone numbers and net worth. Students are coached to call 40 people a day pitching whole life. One intern was scolded for selling a policy to his teenage brother that wasn’t expensive enough. About 80% quit within the first month. The ones who stay describe it as “cult-like.”

4. IULs and VULs are just whole life with extra steps and fees. Your returns are usually capped (S&P goes up 15%, you get 8%), fees are insane, and they’re so complex even agents don’t understand them. Several major insurers sent letters telling their own agents to stop marketing these as “wealth-building tools” because regulators caught on. Agents keep selling them anyway because commissions are huge.

5. The HSA is the only account with a triple tax advantage—and it’s actually good. Contributions are tax-deductible, growth is tax-free, withdrawals for medical expenses are tax-free. Max it out ($4,400 individual, $8,750 family in 2026), invest it in index funds, don’t touch it. After 65, it works like a traditional IRA anyway.

Bottom Line: Buy term life if anyone depends on your income. Get disability insurance. Max out your HSA. And run away from anyone selling whole life, IULs, or VULs.

For a complete guide to all things insurance, check out this week’s episode of Your Money Guide on the Side, and if you find it helpful, please consider leaving a review—it’s how the show grows, and honestly, how I know I’m not just talking to myself.

Listen on Apple | Listen on Spotify

Two things I’m currently thinking about:

1. I try not to call out companies by name (ahem, Northwestern Mutual), but I just couldn’t help myself after reading Niamh Rowe’s exceptional piece that exposed some pretty absurd “business” practices from the largest direct provider of insurance in the U.S. You can find her piece here.

2. And instead of spending the next ten years talking about retiring to Arizona, I decided to just get in the car and drive. So if the backdrop on social media shifts from Vermont forests to high desert sunsets, don’t be alarmed—I haven’t joined a crystal healing commune (yet), I just got tired of shoveling.

And Here’s Something that Might Actually Help, Brought to You by Gelt.

I rarely (if ever) give blanket financial advice. But here’s one piece of advice I’ll give freely and with complete confidence: if you’re a small business owner or high net worth individual, prioritize finding the best tax partner you can find. Before you do anything else.

I spent six months as a solopreneur optimizing everything except my tax planning. Money was coming in. I was investing it. I was checking all the boxes that I tell you to check. But I had no one proactively helping me figure out exactly when to keep more of it in my own business instead of handing it over to the IRS.

Enter: Gelt.

They’re the exact company I’ve been looking for. Here’s why:

• Proactive, not reactive. You’re not spending time you don’t have chasing them down. They reach out. They plan ahead. They actually care about your business staying ahead of tax deadlines and opportunities.

• Tailored strategies. This isn’t cookie-cutter tax prep. They build strategies specific to your business so you’re not getting a one-size-fits-all approach that ignores what you actually need.

• The platform is shockingly good. I’m talking not just user-friendly but actually fun to use. Taxes and fun. Yeah, I said what I said.

If this was the missing piece of your business in 2025, start the new year right by visiting joingelt.com/tyler for a free consultation with their team.

And if you sign up by January 31st, they’ll help you calculate your taxes due by April 15th—so you’re not scrambling at the last minute like the rest of us usually do.

As always, hope this newsletter gives you something to think about throughout the week ahead,

Tyler