LAST CALL for August’s Pre-Order Incentive for my new book, Real Wealth!

Pre-order today at tylergardner.com/book, let me know you did, and receive a bonus chapter from the second book that I am already working on (hint: it explores the five things you need to do to retire tomorrow). Not even my editor at Norton has seen this one yet, and I’m excited to share it with you first and get some early feedback. It will be delivered to you digitally in early September.

And remember, once you pre-order, you are eligible for every monthly incentive between now and the book’s release on December 1st. As always, appreciate your support, and hope the book proves useful.

Pre-Order Real Wealth

How to Build the Perfect Portfolio

For the past two decades, I have been quasi-obsessed with a single question, and I suspect, if you’ve subscribed to this newsletter, you have been too: is there such a thing as a perfect portfolio?

Well, as is true of most things in life, it doesn’t just depend on you, it also depends on who you ask.

So over the next two weeks, I’m going to let ten of the greatest minds who have ever thought and written about investing answer the question for you. All research comes from In Pursuit of the Perfect Portfolio by Professors Andrew Lo of MIT and Stephen Foerster of Western University. The book is outstanding, but it’s not what I’d call a 1.0 read, so if you’re comfortable with terms like beta, Sharpe ratio, and sector rotation, then it’s worth your time. If not, see below. I’ve got you covered.

What is the perfect portfolio to you?

This week: Markowitz, Sharpe, Fama, Bogle, and Scholes.

Harry Markowitz: if you don’t know Markowitz, you should. He gave us Modern Portfolio Theory (MPT) in 1952 and changed finance forever. His punchline: what matters isn’t how risky each individual stock is; it’s how they move relative to one another. So if two assets move in the identical direction in response to market conditions, you’re not diversified. You’ve just purchased the same risk twice. But if you own things that don’t move together, you reduce risk without necessarily sacrificing return.

So check your portfolio for concentration. And no, buying 30 U.S. tech stocks does not solve the problem.

Bill Sharpe: decided to build on Markowitz with a rather brilliantly simple directive for all of us: use the market portfolio for your “risk on,” and use a riskless asset for your “risk off.” (I hope this sounds familiar, as it’s certainly the gospel I’ve inherited and now do my best to pass down the line.) For risk-on, just use low-cost index funds, and for risk off, use TIPS (treasury inflation protected securities). Sharpe also couldn’t have been more clear about the basic math behind using low cost index funds: if all investors = the market, the average active investor must match the market’s performance BEFORE fees. So take the logical next step: the average active investor must (again, on average) underperform the market net fees.

So look up the expense ratio on every fund you own, and if you’re paying above .2%, that fund manager better be mowing your lawn, plowing your driveway, and bringing you DoorDash daily with zero expectation of an additional tip.

Gene Fama: gave us the gift of the Efficient Market Hypothesis: markets prices all available information immediately making it almost impossible to consistently outperform any given index. He also found that small cap and value stocks had historically higher returns but only because you’d be taking on additional risk. His most important practical guidance for building the perfect portfolio: don’t base your dang decisions on past performance (I might have added the dang). Just because a fund has outperformed for five years doesn’t mean anything about the next five.

So if you hold active funds, look up at least their ten-year performance net of fees vs. the index that those funds track. Then decide if you still like the story you’ve been telling yourself about why you’re paying more for an annual round of dart throwing.

Jack Bogle: founded Vanguard and created the first index fund. Bogle changed the investing lives of tens of millions of people, including you. His Cost Matters Hypothesis is one of the greatest simple concepts in finance history: every dollar you pay in fees is a dollar that doesn’t compound for you. And over thirty years, the difference between a one percent expense ratio and a .03% ratio is the difference between a comfortable retirement and an active manager’s comfortable retirement.

So calculate how much you’re paying in dollar terms each year to hold what you hold, and do the math on how that impacts a 30 year investing return.

Myron Scholes: our one dissenting voice among the first five. Where the others are saying, essentially, own the market and go for a walk, Scholes begs us to consider one simple question: but what happens if I’m holding the market and we have another 2008? His focus was on what we call tail-risk: the rare but dramatic downturns that can destroy a portfolio. His response to this concern puts him back in line with the others: only take on the amount of market risk you can bear, as it’s not a matter of if but when.

So if you’re 90% risk on and 10% risk off, but you know that you can’t stomach (or afford to stomach) a 30% drop tomorrow, you need to adjust and be slightly more “active” in your own DIY management.

So what’s shared? Diversification matters. Costs matter. And your portfolio should always reflect your own circumstances and risk tolerance. I know…you’d think the world’s leading financial experts might have something else up their sleeves…nope. They don’t.

What’s that? You’re interested in learning more about the perfect portfolio but you’d rather have me read this to you than read it yourself? Check out this week’s episode of the podcast Your Money Guide on the Side, and if it proves useful, please consider leaving a review, as it helps new listeners find the show and helps me know that this endeavor in free financial literacy for all remains relevant.

Listen to Your Money Guide on the Side

Two Things I’m Currently Thinking About:

1. How to Die (or Live) Happy. And now that we’ve spent the first part of this letter talking about building the perfect portfolio, let’s swerve (slightly) and talk about how to build the perfect moment. In Othello, a storm hits Cyprus and scatters the Turkish fleet. Othello, thinking he’s lost his wife to the sea, comes ashore to find her waiting. In what is perhaps one of the most beautiful lines in all of literature, he reflects: If it were now to die, ‘twere now to be most happy. Far from being morbid, he’s noticing that he’s arrived at the top of his life and regardless of what happens going forward, it won’t ever be better than this.

   I’ve been fortunate enough to have several of these moments throughout my life (most involving a sandwich from Jersey Mike’s or a walk in the woods). And I want to clarify that I’m not talking about perfect days: I’m talking about the specific moment in which if the lights were to go out here, I’d have no complaints and no regrets. The unfortunate part is that we can’t exactly manufacture these moments; we can’t schedule them for later this week. What we can do is notice when they’re happening and maybe choose to feel it rather than try to capture it on Instagram.

2. Never Quit in the Rain. Years back, a friend who had just completed the Appalachian Trail told me that he only followed one rule the entire time: never quit the trail when it’s raining. He would allow himself to quit—you know, because the entire endeavor is 100% voluntary, takes about five months of your life, and involves at least four existential crises—but he would only allow himself to do so on a good day: when the sun was out, his feet were dry, and he had had a decent breakfast.

   His point, that has stuck with me throughout all of my endeavors, is that the rain is the thing that makes us want to quit, not necessarily the endeavor itself. And there’s a crucial distinction between, “I don’t want to do this anymore,” and, “I don’t want to do this in the rain.” I’ve since applied this directly to creating daily social content for over four years, working out at 5am each morning, and navigating the assembly of at least one chest of drawers from a Swedish company that shall remain nameless…and it has held up every single time. If you’re happy and rested and you want out, awesome, and you’ve just gathered real information. But if you quit just because it’s raining, that’s the weather making a decision that ought to be yours to make.

And Before You Go…

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

I have started applying a simple test to everything I download on my phone: I don’t ask whether it’s “good,” but whether it’s still there in six months.

And, surprise, almost nothing passes. My phone has become a kind of graveyard of apps from years gone by: the meditation one, the habit tracking one, and the language one whose owl (I’m pretty sure) is still disappointed in my inability to convert present tense verbs.

Copilot Money is one of maybe four things that I’ve kept, and it’s the only finance app among them.

Here’s why it passed: it tracks your spending, net worth, investments, savings goals, and budgets all in one place. It categorizes your transactions, which means you can stop pretending you’re going to sort through your statements “soon.” It tracks subscriptions, which is how you finally come to appreciate that you’ve been paying for that gym membership you have been emotionally lying to yourself about since the second week of January. And it works across iPhone, iPad, Mac, and their web app. Best part: they don’t sell your data.

I’ll also add one thing that might not seem consequential but matters to me when someone’s trying to build a habit: it’s a stunning design. I’ve spent too much time throughout my career staring at brokerage sites and finance apps that were designed circa 2006, so I’ve come to appreciate what it looks like when someone finally cares. An app that you enjoy opening is an app that stays on your phone.

It’s also the only personal finance app to win an Apple Editor’s Choice Award; it was a finalist for the Apple Design Awards; and it currently holds a 4.8-star rating from more than 30,000 reviews. That’s 30,000 people who, like me, downloaded it and chose to keep it around for a while.

Try Copilot Money today and use code TYLER2 for two free months.

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

-Tyler

August’s Pre-Order Incentive for my new book, Real Wealth is in full swing!

Pre-order today at tylergardner.com/book, let me know you did, and receive a bonus chapter from the second book that I am already working on (hint: it’s focused 100% on the art of retirement). Not even my editor at Norton has seen this one yet, and I’m excited to share it with you first and get some early feedback. It will be delivered to you digitally in early September.

And remember, once you pre-order, you are eligible for every monthly incentive between now and the book’s release on December 1st. As always, appreciate your support, and hope the book proves useful.

Pre-Order Real Wealth

Here Are the 4 Things I Wish I Knew in My 20s but Appreciate Knowing in my 40s:

1. Time is Not Your Greatest Asset. Knowing What to do With it is. The dominant message in modern personal finance is that time is the ultimate asset and our goal should be to free up as much of it as possible. But “free” time (whatever the heck that means, as we all choose what to do with our minutes as they pass), in and of itself, is a completely neutral (if not somewhat terrifying) concept: we can either fill the minutes with activities that fulfill us and leave us satisfied, or we can fill the minutes with activities that leave us empty and more depressed than we were when we woke up. A quick confession: Saturday is my least favorite day of the week. Not in a tragic way, but in a “what am I supposed to do with this” way. The absence of structure leaves me feeling a low-grade anxiety that I haven’t figured out what time is supposed to be for. When I left teaching, my father told me the thing I would miss most is the rhythm and structure to the academic year (I probably nodded politely and as is true of most things fathers say to sons, didn’t really hear it until about ten years later). The time itself is the raw material, the blank canvas. Enormously valuable in the abstract and almost entirely worthless in practice unless you have figured out what to do with it. So before you organize your financial goals around “buy back my time,” just make sure you know what you’re going to do with that time once it’s truly yours.

2. Work is not the enemy. Working on the wrong projects with the wrong people is the enemy. Yep, I’ll die on this metaphorical hill: humans are not designed to be idle, nor are we designed to resist challenging projects. I don’t buy it. We just don’t like being told what to do, when to do it, and who to do it with (surprise). The problem, as I’ve noted in previous letters, is that we continue to conflate the word “work” with the worst version of the 9-5 grind imaginable: no escape, no choice, endless (useless) meetings, endless (meaningless) careers. Again, I don’t buy it. You have a choice. You might not like the risk that comes along with that choice, and that’s a fair pushback, but at least call it what it is. The happiest retirees I know, without fail, are the ones who never “retired” because they found projects to work on that were interesting to them and useful to others.

3. There will never be a heroic week. There will only be a thousand unheroic mornings. When I first started creating content, I made four videos a day for six months. They were terrible. I’m not being modest; they’re still all up on my profiles if you want the hard proof. My wife would, on occasion, walk by me in the kitchen and smile with the patient love of someone who has decided to support her partner’s mid-career experiment regardless of how it winds up. And after six months, my first video went viral. What I learned is the opposite of what most folks assume. By the time that first video went viral, I had spent six months learning, usually without even noticing, what worked and what didn’t work. That viral moment wasn’t an innate understanding of how to reach a mass audience on social channels; it was the visible peak of an iceberg or unheroic weekday work that nobody had seen. It took Samuel Johnson over nine years to write the first English dictionary. That’s 3,285 mornings in which he woke up and mumbled to himself some version of, “So what comes after aardvark?” And after what must have seemed like endless unheroic weekday mornings, he reached zootomy.

4. Money can buy happiness. You just need to know what makes you happy. You have surely heard the standard formulation that money can’t buy happiness, and I’ll suggest that’s not only incomplete but also dangerous. The research from Killingsworth (where he updated Kahneman’s finding) suggests that happiness continues to rise with income for many people well past the levels we had originally thought. The problem has never been that money can’t buy happiness; the problem is that most of us have spent our lives buying the wrong things. We spend the first half of our lives buying what others have told us to buy; and we spend the second half of our lives wondering why money never bought us happiness. I would encourage us to shift this latter half of our lives towards an experimental mindset (what I call the Path Dividend) in which we’re always keeping track of how we use money and how we feel about those purchases. My list, as I’ve shared before, involves writing, teaching, nature, dogs (big, big dogs who slobber frequently) and the occasional fast car or big truck. Your list will be entirely different, and it’s your job to figure out what’s on it.

What’s that? You’re interested in exploring these topics further but you’d rather have me read this to you than read it yourself? Check out this week’s episode of the podcast Your Money Guide on the Side, and if it proves useful, please consider leaving a review, as it helps new listeners find the show and helps me know that this endeavor in free financial literacy for all remains relevant.

Listen to Your Money Guide on the Side

Two Things I’m Currently Thinking About:

1. The Art of Creating Memories. I spent this past weekend in upstate New York with a cohort of friends from my college days. We reunited last year for the first time in twenty years and decided that, fortunately, we still enjoy one another’s company even if a few of us now have artificial joints. After partying too hard on Friday night and pretending that we could somehow still keep up with the 21-year-old versions of ourselves, we spent the morning on Saturday playing Disc Golf (we’re UVM alums, did you expect anything different?). The sun was hot, the bugs were real, and the poison ivy was far more prevalent than I would have appreciated. And as should come as no surprise, when you are trying to figure out what eight grown men want to do on any given day, there will be competing interests, temperaments, and comfort levels. Needless to say, after a few holes, a few of us would have preferred being by a pool with something that rhymes with meenya molada.

   But here’s what all of us seemed to understand at 43 that we might not have understood at 21: the discomfort, the heckling, the jeering, the mild temper tantrums…those were all going to part of the ultimate story that we would share with one another when we do the same dang uncomfortable thing next summer. As Robert California (James Spader) observes in one of the final episodes of The Office when he’s reflecting on how the best stories seem to be made when we’re wondering why we’re not happier in the moment:

   Bear witness…while I’ve been mourning the nights that never were, one of them has been unfolding here before me. This is no get-together. This is a party.

   And remembering California’s words in that moment helped me appreciate that life is always what we experience in the moment while we’re busy planning for the future.

2. Our Search for Order in a World of Chaos. I don’t want to end this week’s letter on a sad or deflating note, but I will share that for the first time in about a decade, I cried while reading the ending of a book: Wallace Stegner’s Crossing to Safety. A great English professor once told me that you should read books three times in your life: once when you’re young just to see what the book is about, once when you’re middle-aged, so you can appreciate the details you missed, and once when you’re older, so you can read and reflect on things you have now experienced yourself. This was my second reading of Stegner’s final novel, and I guess once you’ve lost someone or some thing, irrevocably, seeing death or reading death becomes that much more shared. And in the closing lines, Stegner’s narrator, Larry Morgan, a writer and university English instructor, reflects not only on the loss of a friend, but on how difficult it is to accept that any of us won’t ultimately become the version of ourselves we trusted we would one day become:

   The vision of her floundering in the wake of the concentrated helpers and their feeble charge turned my distress into outrage. Not at any of the helpers…No, at it, at fate, at the miserable failure of the law of nature to conform to the dream of man: at what living had done to the woman my life was fused with, what her life had been and was. What she had missed, how much had been kept from her, how little her potential had been realized…

   To end with hope, and to tie this week’s letter together: the unheroic weekday mornings, those micro-moments, are what ultimately reflect our life’s work. What Morgan missed in the above is that the character in question, Charity, had more than lived into her potential as she clearly had a deep impact on our narrator, enough of an impact to be crystalized in prose for others to see and feel. And that, to me, is more than enough.

And Before You Go…

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

If you’re reading this newsletter, odds are, you have a CPA. And I have no doubt, you are consistently thinking about how to optimize your tax game.

But it’s not just about having an accountant; it’s about what type of relationship you have with them and whether or not they’re acting like a once-a-year-filer or an actual thought partner and strategist.

In my first year running my own business, I left a lot of money on the table (read: gave it to the IRS) because I simply didn’t know what I didn’t know, and my accountant’s only contact that year was an email in late April: “Your taxes have been filed.”

I’ve come to appreciate that the moves worth making are the ones that happen in the off-season, like right now. So if you’ve been confused by PTE elections, S-corp timing, K-1 cleanup, or what contributions you could still make for the prior tax year, check out Gelt today to see what you’ve been missing.

Gelt is the dedicated tax partner who gets in touch with you, not the other way around. Gelt is for solopreneurs, real estate investors, business owners, and high net worth individuals who are looking for a year-round strategist.

Gelt is taking on new clients this quarter, so visit joingelt.com/tyler to get started.

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

-Tyler

I am thrilled to announce August’s Pre-Order Incentive for my new book, Real Wealth:

Pre-order today at tylergardner.com/book, let me know you did, and receive a bonus chapter from the second book that I am already working on. Not even my editor at Norton has seen this one yet, and I’m excited to share it with you first and get some early feedback. It will be delivered to you digitally in early September.

And remember, once you pre-order, you are eligible for every monthly incentive between now and the book’s release on December 1st. As always, appreciate your support, and hope the book proves useful.

Pre-Order Real Wealth

The $4.2 Million Man Who Couldn’t Spend His Own Money

We’ll start this week with a man I’ll call Edward. A retired engineer, around $4.2 million in relatively liquid assets, no mortgage, no debt, monthly Social Security checks as icing on the retirement cake, and one confession that he hesitated to tell me for the first thirty minutes of our call:

“Tyler, things are great. I love retirement, and I’ve been very relaxed. The only problem is my wife and I haven’t taken a vacation in eleven years.”

…

“We’re just worried about the state of the markets, and we don’t want to spend a chunk of our principal right before something bad happens.”

…

We sat on the call for another thirty minutes and ran every projection you could imagine. As should come as no surprise, not a single one of these projections ended with Edward or his spouse dying penniless. Far, far from it. Each one ended with them dying with millions of additional capital, regardless of how many vacations they chose to take.

Six months later, when we followed up, Edward still hadn’t taken a vacation.

(Now, before I risk sounding too much like a self-righteous ding-dong handing down wisdom from on high: I bought an absurdly expensive white t-shirt last year after watching too many episodes of The Bear and wore it exactly once before deciding to hang it up in my closet and never wear it again because I didn’t want to risk its getting dirty.)

This is our last edition and episode in the decumulation series: the 6 Moves to Make Before You Retire, the Withdrawal Order Nobody Taught You, the $250,000 Mistake Most Retirees Never Know They Made, the Subtle Art of Doing Absolutely Nothing, and now, alas, how to spend the money you just worked so hard to accumulate. So put on a pair of headphones and stare at your screen diligently, so your colleagues think you’re on a vitally important conference call and won’t interrupt you for the next four minutes.

Here Are the 3 Things I Want You to Think About This Week:

1. You Can’t Just Flip a Switch and Start Spending. If you’ve spent the past 40 years accumulating, you can’t just become a spender. This is all tied up in your identity as a saver and wealth-builder. So, you need to start practicing deliberate, repeated acts of spending that violate your old identity (That sounds so much more aggressive than I mean it to).

2. The True Cost of Over-Saving. In the past two weeks, I have had two separate conversations with friends over 70 years old, both of whom are projecting out their retirement plans, neither of whom is front-loading their “high decay” experiences as much as I believe they should be. During those go-go years, you have a mental and physical capacity that simply won’t stand the test of time. High impact sport plans? Do them now. Long travel plans? Do them now. Cribbage circuit? That one can wait.

3. What Was the Money For? For what it’s worth, I still can’t answer this one myself. I know I like the idea of accumulating assets, and I know I like the idea of true financial security. What I don’t know is once the assets are accumulated and the finances are secure, what does that then buy that I can’t experience today? Those answers need to direct the portfolio, not vice versa.

What’s that? You’re interested in exploring these topics further but you’d rather have me read this to you than read it yourself? Check out this week’s episode of the podcast Your Money Guide on the Side, and if it proves useful, please consider leaving a review, as it helps new listeners find the show and helps me know that this endeavor in free financial literacy for all remains relevant.

Listen to Your Money Guide on the Side

Two Things I’m Currently Thinking About:

1. The Kaizen Method: Born in America, but Made in Japan. During WWII, the US military needed to produce massive amounts of tanks, planes, and ammunition but didn’t have the time to build new factories or other necessary infrastructure. So instead, the government launched a training program called Training Within Industry (or TWI). The slogan? Find a way to do it better with what you already have. It was only after the war, when American experts brought the TWI program to Japan and the Japanese named it Kaizen (Kai for Change and Zen for Good), that the Japanese fully embraced the “art of the tiny tweak.”

   Cut to the 1950s, Eiji Toyoda and his engineer Taiichi Ohno, just back from a visit to a Ford factory in America and realizing they couldn’t possibly afford a factory of that size and stature, adopted (and adapted) the Kaizen method to become the Toyota Production System. They gave every worker in the factory the right to pull a single cord that would stop the entire assembly line if anyone noticed a way that someone could do something even just 1% better. And it wasn’t until 1986 when organizational theorist Masaaki Imai published Kaizen: The Key to Japan’s Competitive Success that the world became obsessed with consistent and incremental improvements in every facet of our lives.

2. So Why is Tyler Talking About Toyota in a Finance Newsletter? Because I have a set of Stoic Reminders next to my desk, and each morning, I read a new one. This morning’s: It is not that we have a short time to live, but that we waste a lot of it.

   This immediately reminded me of a piece of advice I heard from Mark Cuban years back: learn to think in minutes, not in hours. If it’s 9:14am, and we have a call at 10am, instead of thinking that we have 46 useless minutes ahead of us, you might choose to think about those minutes like Sid does in Wallace Stegner’s Crossing to Safety:

   Accustomed to making every hour count, he reads a hundred pages of Middlemarch while he waits.

   Now, back to avoiding sounding like the man in the ivory tower: last week, I had thirteen minutes before a call, and rather than opening Eliot, I used those minutes to watch YouTube videos of the Great Molasses Flood of 1919, which took the lives of twenty-one people in Boston and is precisely as bad as it sounds. I have thought about it since and have yet to be in a position to use the information. Until now, I guess.

And Before You Go…

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

Even up here in Vermont, this summer has been a scorcher. Beyond my daily dose of Watermelon Salt in the morning after my swim, I have also loved mixing it up with LMNT’s version of the Arnold Palmer: Lemonade Iced Tea. I currently have a pitcher of it in my fridge, and it’s my new go-to for a quick afternoon pick-me-up instead of making another cup of coffee that I simply don’t need.

Now, here’s what makes this drink different: countless energy drinks use synthetic, isolated caffeine (not to mention some hybrid of eleven thousand other ingredients of which you’ve never heard). LMNT, however, uses full-spectrum organic black tea extract from Kericho, Kenya—at 7,000 feet of elevation—so the caffeine comes with naturally occurring L-theanine and polyphenols. The result? A much steadier energy throughout the day instead of the spike and the inevitable crash.

I will also add, I have become an unofficial distributor, if you will, for LMNT, as anyone who I’ve ever known throughout my life has all of a sudden gotten back in touch with me and just conveniently at conversation’s end asks if I have any additional LMNT lying around the house that I don’t need. Yes, my friends, I am more than happy to spread the salty word.

If you want to know why my friends are psyched, and I’m psyched, and why I haven’t had a dehydration headache all summer despite the heat, head to drinklmnt.com/tyler, become an LMNT Insider, and get four boxes for the price of three. And if you like things both salty and spicy, check out the Mango Chili, my favorite flavor to date.

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

—Tyler

I am thrilled to announce August’s Pre-Order Incentive for my new book, Real Wealth:

Pre-order today at tylergardner.com/book, let me know you did, and receive a bonus chapter from the second book that I am already working on. Not even my editor at Norton has seen this one yet, and I’m excited to share it with you first and get some early feedback.

And remember, once you pre-order, you are eligible for every monthly incentive between now and the book’s release on December 1st. As always, appreciate your support, and hope the book proves useful.

Pre-Order Real Wealth

The Subtle Art of Doing Nothing (And Making More Money While Doing It)

It was October of 2008. A 68-year-old retiree, let’s call him Clifford, watched his $1.6 million portfolio drop to about $980,000. He then did what every rational person does, regardless of financial acumen, in response to a true financial crisis: he started reading every article he could find on the internet, and those articles led him to one conclusion: this time really was different, and if he didn’t reposition the portfolio, he’d be one year away from spending his retirement selling used Kris Kross CDs under the bridge for soup money.

So, he moved his remaining assets to cash. Market continued to drop. Recovered by 2010. New all-time highs by 2013. Clifford didn’t start to DCA his way back into the market until 2014, but by that point, he had missed much of the early run.

This week: How to Avoid Being Clifford.

We’re now four weeks into the decumulation series: the 6 Moves to Make Before You Retire, the Withdrawal Order Nobody Taught You, the $250,000 Mistake Most Retirees Never Know They Made, and now (finally) we’re through the dense stuff and get to focus on the #1 driver of returns for retail investors: our behavior. So put on some Lofi Beats, take ten deep breaths and center yourself, and let’s dig in.

Here Are the 5 Things I Want You to Think About This Week:

1. Climate vs. Weather. The weather is what some ding-dong is screaming at you about every day on Mad Money; the climate is the 30-year return of a 75/25 portfolio. A bad month in the market is a weather problem; your retirement is a climate question. You don’t cancel your trip to Florida because there’s a chance of rain on Thursday; you just don’t plan on living in Florida in August. Know the difference between the two.

2. The First 5 Years. We went over this one last week briefly: your biggest risk window in retirement is the first five years. To mitigate the risk of an early down market impacting years of returns, you could choose to keep working part-time, position your portfolio (before the day you stop working) to reflect a balanced approach to mitigate downside risk, and/or make sure you have that 1-2 year cash buffer. I plan on having at least a two year buffer sitting in TIPS or money market so the market’s noise is just noise, and ultimately, I plan to keep working as long as I can.

3. The Reverse Glide Path. Every target date fund in the world goes from stock-heavy to bond-heavy, and in my mind, that’s entirely wrong. Time and again, the biggest risk to a 20-30 year retirement window is not the market crash but inflation eating away at a 3-4% fixed return while you continue to draw down the portfolio’s principal. So be as conservative as you’d like for that first five year window, and then gradually increase equity exposure (usually best done with new money) as the sequence of returns risk window closes.

4. The Guardrails You Need to Install. Guyton-Klinger. Let’s say your starting draw is 5%. If that draw as a percentage of your current principal drops below, say, 4%, give yourself a 10% raise the following year. In turn, if your draw climbs above 6%, take a breather and cut the salary by 10% the following year. Pick one date, and check on that date.

5. Now Write the Letter. I know this sounds insultingly woo-woo, blame Sedona-Tyler, but take a moment this week to write a letter to your future worried self. Outline what steps you’ll take when the markets are tumbling and the sky is (yet again) falling. Reflect on what happened the last time and what your long term plan is.

Want to learn more about investor behavior and the art of doing nothing? Check out this week’s episode of the podcast Your Money Guide on the Side, and if it proves useful, please consider leaving a review, as it helps new listeners find the show and helps me know that this endeavor in free financial literacy for all remains relevant.

Listen to Your Money Guide on the Side

Two Things I’m Currently Thinking About:

1. The 3 Ingredients to a Happy Life: Psychologists Edward Deci and Richard Ryan have spent the better part of their careers on a (seemingly) simple question: what motivates us to get out of bed in the morning? They propose we need three psychological ingredients:

   1. Autonomy - the sense that we have agency over our actions

   2. Competence - the sense that we’re good at something or getting better

   3. Relatedness - the sense that we matter to other people.

   Now, whether we choose to admit it openly or not, our traditional work structure, though usually terrible at providing us with autonomy, was an oddly exceptional provider of both competence and relatedness. You most likely got good at something (whether you meant to or not), and you were handed forty people to connect with every day (whether you wanted to or not).

   My only point (for now): do be careful what you wish for because I think work, regardless of how much we do or don’t like having someone to tell us what to do with our time, has been providing us with two of the three key nutrients, and we’ve just been too busy complaining about our boss (and perhaps our colleagues) to acknowledge as much. And I’ll confess, my own relatedness pipeline currently consists of eight people I have seen every morning at the gym for six years, two of whom I have actually spoken to.

2. The Warning Sign for the Bucket List. I semi-promise that this is the last time (this summer) that I’ll mention Ishiguro, but I’m almost finished with The Unconsoled, a novel about a famous pianist who has trouble getting anywhere on time or saying no to anybody (so it’s obviously incredibly infuriating to read), and there’s a moment when one of our central characters, Sophie, is talking to her son, Boris, about his grandfather who has just experienced a potentially life-threatening moment:

   This is a warning. Your Grandfather, he’s getting older.

   And shortly after, the line that really got me:

   Other people, they just carry on like there’s all the time in the world. I’ve never been able to do that.

   It’s worth noting that Sophie says this as (potentially) the only sane character in the book. Because of her (relative) clarity, her warning is read as a gift: to Boris, and to us, the readers. Your parents are aging, you are aging, and those troubling test results or that momentary lack of balance (mentally or physically), might just be the nudge you need to remember that we don’t have an endless window of time here. We build our beautiful castles in the sky whose central assumption is this will come to fruition later. Once we reach a certain number, once we reach a certain age, or once the dang market finally decides to cooperate. The only problem? We spend so much of our lives crafting a bucket list with no expiration date…so…it’s just a list.

   Let Sophie’s warning be your warning: I’m not going to tell you to go spend your money, as I’ve said it before, and it’s mostly useless. But I am going to ask you to look at whatever list you might be keeping and to identify the one thing on that list that has a clear expiration date attached to your own body or somebody else’s calendar. Those are the items worth crossing off before the year’s out.

And Before You Go…

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

If you’re reading this newsletter, odds are, you have a CPA. And I have no doubt, you are consistently thinking about how to optimize your tax game.

But it’s not just about having an accountant; it’s about what type of relationship you have with them and whether or not they’re acting like a once-a-year-filer or an actual thought partner and strategist.

In my first year running my own business, I left a lot of money on the table (read: gave it to the IRS) because I simply didn’t know what I didn’t know, and my accountant’s only contact that year was an email in late April: “Your taxes have been filed.”

I’ve come to appreciate that the moves worth making are the ones that happen in the off-season, like right now. So if you’ve been confused by PTE elections, S-corp timing, K-1 cleanup, or what contributions you could still make for the prior tax year, check out Gelt today to see what you’ve been missing.

Gelt is the dedicated tax partner who gets in touch with you, not the other way around. Gelt is for solopreneurs, real estate investors, business owners, and high net worth individuals who are looking for a year-round strategist.

Gelt is taking on new clients this quarter, so visit joingelt.com/tyler to get started.

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

-Tyler

P.S. And as a potential reward for those who stay focused and complete newsletters, Norton’s giving away 15 copies of Real Wealth on Goodreads. Entering takes about nine seconds and shelves the book, which is how it reaches readers who have never heard of me.

Enter the Giveaway Today!

I am thrilled to announce August’s Pre-Order Incentive for my new book, Real Wealth:

Pre-order today at tylergardner.com/book, let me know you did, and receive a brand new bonus chapter from the second book that I am already working on. Not even my editor at Norton has seen this one yet, and I’m excited to share it with you first and get some early feedback.

And remember, once you pre-order, you are eligible for every monthly incentive between now and the book’s release on December 1st. As always, appreciate your support, and hope the book proves useful.

Pre-Order Real Wealth

The $250,000 Mistake Most Retirees Never Know They Made

Years ago, I had a video call with a couple from New York. Mid-sixties, $3.2 million saved, and an abundance of confidence from spending the past four decades doing everything “right.” I asked them if they had considered Roth conversions yet, as they were currently earning nothing and had yet to take Social Security. They told me they hadn’t. Not because it didn’t interest them, but because nobody had ever told them it could save them tens of thousands of dollars over the course of their retirement. We did some quick back-of-the-’ol-metaphorical-envelope-math (as I don’t actually own any physical envelopes), and we calculated that if they did not do conversions, based on how they were planning to spend from their mostly pre-tax accounts, that single choice could cost them anywhere between $180,000 and $250,000 in taxes that they never needed to pay in the first place.

This week, I want to make sure that you, at the very least, aren’t leaving this option on the table because nobody ever told you it was an option and when it might be a good option.

We’re now three weeks into the decumulation series, the 6 Moves to Make Before You Retire, the Withdrawal Order Nobody Taught You, and now, for better and worse, the truly dense one: Roth Conversions, IRMAA Cliffs, and Penalties for Widows. So sit back, grab another cup of coffee, and let’s dig in.

Here Are the 5 Things I Want You to Think About This Week:

1. Take advantage of the “cheaper” years to do Roth conversions. Here’s what I know you’ve heard before: take advantage of the window from retirement (around 65) to when RMDs kick in (73, soon to be 75), to execute Roth conversions. Because for many of us, that’s the lowest tax bracket we’ll be in for the rest of our lives, as earned income might be zero, and we might not be collecting Social Security yet. And here’s what I want you to hear today: there are also intermittent windows throughout our lives where the exact same logic applies: maybe we’ll take a lower-paying job in our 40s, 50s, or 60s for quality of life; maybe we’ll take a gap year (or three); or maybe we’ll leave a stable six-figure job with benefits to pursue “finfluencer” status according to at least one random post on Reddit. The tax code doesn’t care when we have a lower relative income; it just provides us with opportunities throughout our lives to convert to a Roth that most people miss completely because they’re waiting for that textbook retirement window.

2. How Do We Actually Execute a Roth Conversion?1

   1. Log into your custodian. Search for “Roth Conversion,” then click the button.

   2. Ideally, we’d have both accounts at the same custodian, as cross-institution conversions can take much longer. (This is one of the many reasons why I love having most of my assets under one roof.)

   3. Do NOT have taxes withheld, as any dollar withheld will go directly to IRS today. And, surprise, we’d rather pay them later. Say it with me: interest free loans are a good thing.

   4. Look for the tax bill in April. The custodian will issue form 1099-R. Larger conversions may require quarterly payments. Your CPA should flag it. If they don’t, time to get a new CPA.

   5. And remember the 5-year-rule. In an attempt not to lose 250,000 readers in one paragraph, to learn more, check out Fidelity’s break-down, as it’s the most comprehensive page I’ve found on the subject yet.

3. Remember that IRMAA is a cliff, not a gradual climb. If your MAGI (fancy acronym for your adjusted gross income plus any tax-exempt interest, but note: this is before the standard deduction which constantly trips folks up) is $274,000 (as of 2026), your Medicare surcharge is about $80/month per person. But go just ONE DOLLAR OVER, yep, to $274,001, and the surcharge can jump to $205/month per person. That one additional dollar can cost you about $3,000 between spouses. In more argument-enhancing terms: the marginal rate on that dollar is about 300,000%. Yes, for realsies. So before any potential conversion, run your projected MAGI through an IRMAA calculator.

4. Teach Yourself About SSA-44. This is your gift from this week’s letter: If you had a big income in 2024 (like a business sale or large Roth conversion), Medicare would use that number for 2026 premiums (because why would they want to make any of this simple?). They use a two-year “look back” period. But if you complete and submit Form SSA-44, you can ask Social Security to let you recalculate based on a “significant life event,” and retirement does indeed count. This form alone can save recently retired couples between $5-$10k a year.

5. The Widow’s Penalty. No, this is not an announcement for the new Lisa Jewell novel. This is far, far less entertaining: When one spouse dies, the survivor is now, unfortunately, a single filer. Single filer brackets and IRMAA thresholds are roughly half of married ones. So those conversions that you didn’t take advantage of at 12% now would come out at 22% or 24% just because of the single filing status. This can wind up costing the surviving spouse between $30,000 and $50,000 a year…for life.

Want to learn more about IRMAA cliffs and Roth Conversion Windows? Check out this week’s episode of the podcast Your Money Guide on the Side, and if it proves useful, please consider leaving a review, as it helps new listeners find the show and helps me know that this endeavor in free financial literacy for all remains relevant.

Listen to Your Money Guide on the Side

Two Things I’m Currently Thinking About:

1. 3 Minutes and 5 Seconds: the amount of time you’re able to focus on one task without being distracted by another. According to her research in informatics at UC Irvine, Dr. Gloria Mark found that office workers switch tasks or are interrupted roughly every 3 minutes and 5 seconds. But before you run to HR and present your closing arguments for why you should be allowed to work from home in 2027, know that Dr. Mark’s findings have often been misinterpreted by popular articles and new sources. What the data actually showed is that the distractions weren’t just from external sources (the boss’ “urgent” email; the colleague’s baby pictures), but also (and sometimes far moreso) from internal sources (we need to book that flight; we want to find that recipe for dinner; we want to get a quick dopamine hit from some arbitrary notification on some random platform).

   Oh, and in her more recent 2023 book Attention Span, Dr. Mark suggests things have (surprise) gotten even worse and that our average attention on any single screen is down to 47 seconds. So if you’ve made it this far in the newsletter, I salute you.

2. 23 Minutes and 15 Seconds: the amount of time it takes you to refocus once you’ve become distracted. And no, it’s not because your brain needs almost a half hour to shift “cognitive gears” and refocus; it’s because once you give yourself permission to take that initial “break,” you choose to handle, on average, 2.3 other tasks before cycling back to the original point of focus.

   I just rewatched The End of the Tour last night, a biographical drama starring Jason Segel as David Foster Wallace. That, in turn, led me to watch some actual interviews with Wallace late into the night. And I was reminded (ironically enough while watching his clips on YouTube) that DFW chose not to own a television because he feared wasting his life in front of a screen providing endless hours of passive entertainment. And for those of you who have snapped back into reality after a few hours of Netflix and Chilling, with that existential sense of dread that comes along with knowing that you were just gonna’ watch one episode that magically turned into half a season of Yellowstone…well, you know exactly why Wallace was terrified, and let’s just say, I’m far more worried about our inability to focus on deep work than I am about where the S&P is heading in 2027.

And Before You Go…

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

If you know who Frank the Tank is and your idea of a “nice little Saturday” involves heading to Home Depot…this is for you. Because I see you, Gen X, and I want to make sure you’re ready for retirement.

If you’re currently looking for a financial planner, there are three things a percentage-based advisor is hoping you just don’t think about:

1. It is not necessarily harder to manage more money, yet these advisors will often charge you more just because you happen to have more. Same asset allocation plan. Same phone calls asking how the kids are. And yet the fee continues to grow.

2. And the line they feed you? The “we do better when you do better,” sounds great until you appreciate that the fastest way for them to do better might just be to put you in riskier assets than you wanted or needed. Your risk tolerance and their incentive structure need to be properly aligned. Period.

3. Finally, notice how they may never tell you the actual fee in dollars? Only the percentage. That’s because when it’s not dollars anymore, it doesn’t feel like dollars anymore. And that’s the point.

Facet works differently. One flat annual membership fee based on the services you need. No percentage of your assets. No commissions. Just a dedicated team of CFP® professionals who will help you figure out what you want your money to say about your life.

Book your intro call today, and you’ll still have plenty of time to make it to Bed, Bath & Beyond.

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

P.S. Norton’s giving away 15 copies of Real Wealth on Goodreads. I’ve intentionally waited until the postscript to reward those of you who can focus for more than 47 seconds. Entering takes about nine seconds and shelves the book, which is how it reaches readers who have never heard of me.

Enter the Giveaway Today!

This is your last opportunity to take advantage of July’s pre-order incentive for my book, Real Wealth. Pre-order today at tylergardner.com/book, let me know you did, and receive a one-hour video (give or take depending on how many cups of coffee I have before filming) delivered to your inbox digitally in early August, that is specifically meant for our 2.0 DIY investors: those of you who have already internalized the “invest in an index fund and don’t touch the dang thing,” and are interested in going further down the rabbit hole. The video will cover portfolio “tilting,” asset location, sector rotation, and sequence of returns risk mitigation in early retirement.

And once you pre-order, you are eligible for every monthly incentive between now and the book’s release on December 1st. As always, appreciate your support immensely.

Pre-Order Real Wealth

The Withdrawal Order Nobody Taught You: Part 2/5 of our Art of Decumulation Series

For those who missed last week’s newsletter, as a refresher, we are spending the next few weeks covering decumulation (asset drawdown) strategies in retirement. Last week, we covered the 6 Moves to Make Before You Retire, and this week, we’ll cover how to think about our first 1-5 years of retirement: bracket loading, asset location, the asymmetry of sequence of returns risk, when to sell assets, and the appropriate order in which to draw down from different types of accounts.

Here Are the 5 Things I Want You to Think About This Week:

1. Bracket Loading. Way less glamorous than it sounds (though we may have just coined a new phrase for NCAA tournament manipulation). The difference between your 12% tax bracket and your 22% tax bracket is, wait for it: 10%. I know that part’s obvious, but the implications usually aren’t: if you’re married filing jointly and spending only $75k/year from your pre-tax 401(k), just think about what you’re leaving on the table for future years. By filling the remainder of the 12% bracket in that year, you are guaranteeing yourself a 12% marginal tax vs. an unknown tax in the future on that 100,801st dollar. Take the deal now while you can, and put the money in your taxable or a Roth if you don’t yet need it.

2. Asset location. Just like in real estate, investing is all about location, location, location. I know, asset allocation gets all the attention, but asset location matters way more. The basic concept: anything that provides you with annual dividends, coupon payments, interest, put in tax-deffered; anything that is designed for growth, put in your Roth, as it’s a tax-free haven for life (and your kids’ lives); and anything that is vanilla, boring, non-turnover, non-churning, like passive index funds and ETFs, that’s for the taxable brokerage. The key: don’t ever let a dollar be taxed that doesn’t need to be taxed unless you a) need the money or b) are bracket loading (the non-NCAA kind).

3. The Asymmetry of Sequence of Returns Risk. Many of you have heard the horror stories: retire in 2000 at the height of the dot com bubble, and your first three years of retirement were an absolute landslide. The good news: especially if you’ve already internalized the tips from last week’s letter about having that cash buffer ready to go, sequence of returns risk is a highly solvable problem: in early retirement, we can do two things: 1) We remember to have a 1-2 year cash buffer, so odds are we don’t have to sell assets at a massive loss; 2) We can be more conservative (heavier allocation to bonds/money markets/TIPS), as those first few years ultimately have a much greater mathematical impact on your long-term financial outlook than when you’re in your 70s/80s. This strategy is called the “reverse-glide-path,” I absolutely love it and plan on using it myself, and for the full academic paper by Pfau/Kitces, continue your reading here.

4. When do I Sell My Assets? Monthly? Annually? The answer you all love to hate: it depends. If you’re a purely rational actor and want to roll through retirement based on math and history alone: you DCA (dollar-cost-average) your way out of markets, as markets tend to be higher 75% of the time at year’s end than at the beginning. But if you’re like me (and most other irrational ding-dongs out there), odds are you don’t necessarily want to incur 11 more monthly headaches this year for the chance on selling some of your assets at a slightly higher value. Realistically, sell assets when it makes sense for you and your family. If you’re ok doing it monthly, that’s the odds-on-favorite.

5. And in What Order Should I Withdraw? 99% of you will not go wrong by withdrawing from taxable, then pre-tax, then Roth. The logic is neat and tidy: keep deferring those taxes (so you don’t interrupt the compounding), and let the Roth sit as long as possible as it’s always 100% tax free. BUT, again, we’re dynamic humans, and our scenarios change annually. So maybe there’s a year when you know you’re going to spend less and want to bracket load from that 401(k). Great. Do it. The order that’s right for you will ultimately be far more art than science just with slightly less Elmer’s glue and construction paper.

And if this decumulation series interests you, and you’re looking to explore the above in greater depth, check out this week’s episode of the podcast Your Money Guide on the Side, and if it proves useful, please consider leaving a review, as it helps new listeners find the show and helps me know that this endeavor in free financial literacy for all remains relevant.

Listen to Your Money Guide on the Side

Two Things I’m Currently Thinking About

1. The Concept of Expertise. No surprises here, I’m still finding myself spending my free hours with something written by Kazuo Ishiguro. I’m half way through The Unconsoled, have absolutely no idea what’s happening (which is on point, as the greatest rule of story-telling is simply (or not so simply) to make them want, then make them wait), and just paused on the following passage spoken by one of our more intellectual characters, Christoff:

   By that point in my life I’d come to accept I was no genius. Or anything approaching one…a number of things had happened which had forced me to see my limitations…I did understand something [though]…I looked around me and thought, well, yes, I could make a contribution here.”

   In Malcolm Gladwell’s Outliers, Gladwell defines an expert/master as someone who has practiced something for 10,000 hours.1 And though I agree with this arbitrary rule whole-heartedly, I’ll suggest it’s not exactly satisfying for us as a (mostly) skeptical society.

   Because we have no way of knowing who has and who has not put in the 10,000 hours unless we are comfortable judging expertise and mastery solely by output. And based on what I see in comment sections daily, we’re not. We seek credentials; we seek external validation; we seek some random series of arbitrary letters after someone’s name to show us that it’s safe for us to believe them.

   My point: if we learned anything from Will Hunting (other than the fact that it’s not your fault), it’s that there is someone out there with zero credentials who’s a genius; and there’s also someone out there with a world of credentials who’s a complete quack. The content is the credentials. Period.

2. The Art of Making Good Time. About once a year, I revisit Pirsig’s Zen and the Art of Motorcycle Maintenance. It puts me in a good place. My favorite annual reminder is when our unnamed narrator is reflecting on making “good time,” with the emphasis on good rather than on time. Rather than focusing on getting from Point A to Point B, let’s focus on what happens between A and B.

   This line crept back up on me this week when I was out with the hounds. Hound A began to sniff Branch A within about twenty feet of our front door. Hound B then began to sniff Branch B which was within about five millimeters of branch A. Hound A then changed placed with Hound B, and so began the smooth choreography (other than the tangled leashes) of the Hounds rotating sniffs between Branches A and B.

   Thirteen minutes passed, and we were no closer to moving our actual feet and paws towards Point B. And being the Type A that I am, I was becoming quickly frustrated, not at Hound A, per se, for starting this whole thing, but at our lack of forward movement. And that’s exactly when Pirsig reminded me to place the emphasis elsewhere: What was Point B, after all? For all I know, it could have been Branch B. And that, my friends, is making good time. Just ask the hounds.

And Before You Go…

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

If you’re reading this newsletter, odds are, you have a CPA. And I have no doubt, you are consistently thinking about how to optimize your tax game.

But (speaking of expertise), it’s not just about having an accountant; it’s about what type of relationship you have with them and whether or not they’re acting like a once-a-year-filer or an actual thought partner and strategist.

In my first year running my own business, I left a lot of money on the table (read: gave it to the IRS) because I simply didn’t know what I didn’t know, and my accountant’s only contact that year was an email in late April: “Your taxes have been filed.”

I’ve come to appreciate that the moves worth making are the ones that happen in the off-season, like right now. So if you’ve been confused by PTE elections, S-corp timing, K-1 cleanup, or what contributions you could still make for the prior tax year, check out Gelt today to see what you’ve been missing.

Gelt is the dedicated tax partner who gets in touch with you, not the other way around. Gelt is for solopreneurs, real estate investors, business owners, and high net worth individuals who are looking for a year-round strategist.

Gelt is taking on new clients this quarter, so visit joingelt.com/tyler to get started.

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

-Tyler

July’s pre-order incentive for my book, Real Wealth, is now live, and this one is for the investors who have already mastered the basics and are ready to go deeper. Pre-order this month, tell me you did at tylergardner.com/book, and I’ll send you Beyond the Basics: Investing and Money Management 2.0, a full one-hour digital video presentation delivered straight to your inbox in early August, yours to keep.

We’ll cover portfolio “tilting,” the details of asset location, sector rotation for those of you who just can’t help yourselves, and how to mitigate sequence of returns risk early in retirement. Pre-order now and you’re also locked in for every monthly incentive through the December 1st release date.

Pre-Order Real Wealth

You Asked for It.

A few weeks ago I asked what you wanted me to write about. Over 3,000 of you took the survey, which I believe makes it the largest group of people ever assembled to politely ask a man to stop talking about index funds. Message received. What you want is the part almost nobody writes about: how to actually spend the money you spent forty years saving.

So for the next five weeks, the newsletter and podcast are devoted to what I’m lovingly calling The Art of Decumulation Series, because the technical term for drawing down your savings is decumulation, a word with all the charm of a parking garage in Cleveland, so I figured adding “The Art” to it was cheaper than rebranding the entire financial industry.

Here’s Part 1.

The 6 Money Moves to Make Before You Stop Working

1. Build the cash buffer twelve to twenty-four months out. Twelve to twenty-four months of projected spending in a high-yield savings account or money market fund (Marcus, Ally, SoFi, SPAXX, VMFXX) the day you retire. Fund it from new savings, your final-year bonus, severance, and zero-bracket capital gains harvesting: for 2026, married couples filing jointly pay 0% on long-term gains up to $98,900 of taxable income, and because that’s measured after the $32,200 standard deduction, a couple can gross over $130,000 and still harvest at zero. The buffer exists because the first downturn is coming. I don’t know when. Neither does anyone on television, though they are, admittedly, better dressed than I am. The buffer is the infrastructure that neutralizes loss aversion when willpower won’t.

2. Roll the 401(k) to an IRA unless you’re taking advantage of the Rule of 55. Move every employer 401(k) you’ve accumulated to a single traditional IRA at Fidelity, Vanguard, or Schwab. You get better funds (FZROX at zero expense ratio, VTSAX at 0.04%), consolidated beneficiaries, one RMD calculation, and dramatically less cognitive overhead, which matters, because you did not save for forty years in order to spend your retirement remembering seven passwords. The one exception: if you’re leaving your job in the year you turn 55 or later and might need that money before 59½, leave it at the plan administrator. Rolling it into an IRA kills your Rule of 55 access forever, and “forever” is a word the IRS uses with unsettling comfort.

3. Make the Social Security decision based on actual longevity, not industry default. The break-even age for delaying from 62 to 70 is roughly 79 to 81, which means the “right” answer requires knowing your own expiration date, a piece of information the actuarial tables have and you, mercifully, don’t. The conventional advice says delay. The conventional advice is overconfident. Claim at 62 if you’re retired and don’t need the income, and let the portfolio compound untouched. Claim at 67 for the middle path. Delay to 70 if you have strong longevity, excellent health, and other income to bridge the gap. Part art, part science, entirely up to you.

4. Plan the healthcare bridge to 65, because the rules just changed on you. Medicare doesn’t start until 65, and as of January 2026, the enhanced ACA subsidies are gone and the old subsidy cliff is back. Here’s what that means: cross roughly 400% of the federal poverty level, mid-$80,000s of MAGI for a couple, by even one dollar, and your entire premium subsidy vanishes. Not shrinks. Vanishes. Under the cliff, an older couple pays around 10% of income for the benchmark plan, roughly $700 a month at an $80,000 income. Over it, the same coverage can run $20,000 or more a year, out of pocket. Because subsidies are based on your modified adjusted gross income, not your assets, this is a game you can actually play (and win): draw from cash, taxable accounts with low gains, and Roth contributions while delaying traditional IRA withdrawals, and keep MAGI safely under the line. One overly-aggressive Roth conversion in the wrong year can now cost you five figures. MAGI management before 65 is no longer an optimization; it’s a cliff walk, and the withdrawal order is the only railing to which you have access. (And conveniently, that’s Part 2.)

5. Audit beneficiaries and have the spousal conversation. Multiple times. Beneficiary designations supersede your will. We’ve been over this before. Every IRA, every 401(k) from every previous employer, every life insurance policy, every annuity: log in, confirm your current spouse is primary, “current” being the key word there, and add your kids as contingent. Then sit down with your spouse and walk through everything: account locations, logins, allocations, advisors, the password manager. Create a single document. Update it annually. The version of your spouse who will eventually need this is not the version sitting next to you tonight. You are leaving a letter, in advance, for that future version of them.

6. Re-allocate the portfolio before you retire, not after. Most people sell equities post-retirement to build the cash and bond positions they should have already had, potentially realizing gains, potentially in a down market. Start twelve to eighteen months before your last day, while you’re still earning, so the buffer and bond position are funded from new savings rather than from selling. For the nautically minded: turn the ship slowly, before the harbor, ideally without a documentary crew. The “100 minus your age” formula is from an era when retirement lasted twelve years. Modern retirements last thirty. You can be smarter than your target-date fund. It’s a fund. The bar is achievable.

Tyler’s Take-Away: If you do this work in the twelve months before you retire, the day itself is anticlimactic (in a good way). You wake up on Monday. The portfolio is structured. The cash is sitting there. The beneficiaries are right. Your spouse knows where everything is. Your healthcare is covered. And then, you realize the calendar in front of you is genuinely, completely yours. The way an entire ocean belongs to no one in particular. Just keep swimming, my friends.

Where we’re headed from here:

Part 2: The Withdrawal Order: which accounts to tap first, and why the sequence matters more than almost anything else you’ll do.

Part 3: Roth Conversions, RMDs, and IRMAA (yep, the dense one). Bring a pen and, ideally, a beverage.

Part 4: Market Downturns in Retirement: what counts as danger versus noise.

Part 5: From Saver to Spender: your permission, finally, to enjoy the thing you built.

And if you want to listen to The Art of Decumulation Series - Part 1, check out this week’s episode of Your Money Guide on the Side. If you find the show useful, a review helps more than you’d think, as it’s how new listeners find the show, and how I know I’m not just another random guy walking through the woods of Vermont talking about money to squirrels.

Listen to This Week's Full Episode

Two Things I’m Currently Thinking About

1. Your Lamb House. I’ve been reading Colm Tóibín’s The Master, which is a novel about Henry James, which I realize is a sentence that just cost me half my readership, but I already gave you the practical money take-aways, so this is where I, in turn, get to ramble about literature & life.

One moment that particularly struck me: Henry finds a house. Lamb House, in Rye, and he wants it the way most of us have wanted maybe three things in our entire lives. This is a man who wants almost nothing, and here he is, wanting. Then his older brother William weighs in. Too expensive. Poorly negotiated. Should have haggled. And Tóibín gives us the impact of the older brother’s gut-punch:

Henry pointed out that he had never lacked faith in his brother’s purchases nor sent him advice not sought for. He added that his joy at the prospect of getting the house had shriveled under his brother’s warnings…[I]t was such a rare joy for him to want anything as he wanted Lamb House.

His joy “shriveled.” One comment from one sibling about what Henry should have done with his money, and the rarest feeling of his life got smaller.

Here’s my confession of the week: I make a lot of content about consumer spending and how to find the best deals. Hidden fees, negotiation tactics, daily discounts, and industry red flags. And the most common comment I get, on nearly everything, is some version of Henry’s response: But Tyler, we LOVE going to Disney and buying the Memory Maker Photo Pass -regardless- of price. We are a nation of younger brothers looking for those things that money can buy that bring us pure joy, and the last thing we want is some ding dong older brother telling us that we should have simply taken the photos ourselves on our $1400 iCameras.

So let me be clear about the actual thesis of everything I write and create: the entire point of getting the money stuff right is so you can spend freely, joyfully, and without apology on your version of Lamb House. The Photo Pass. The daily latte. The seventh bloodhound. Whatever it is that you rarely allow yourself to want.

Negotiate hard on everything else precisely so that when the rare want arrives, you don’t have to negotiate with yourself or your older brother or some random guy in the woods of Vermont.

Oh, and when a friend shows you their Lamb House? You say it’s wonderful. Because it is. Full stop.

2. The Beautiful Game, Plural. The World Cup ended this weekend, and I’m already grieving. Not the soccer, exactly. What I’ll miss most is the Tartan Army singing in places that have never heard that much bagpipe-adjacent joy. The Norwegians doing the row. The Dutch turning entire city blocks into one enormous orange dance floor, bouncing left, then right, in a display of coordinated happiness that should honestly be studied by scientists.

But here’s the lazy take-away that I’ve already seen touted on social media: see, people are fine, it’s just the politicians who ruin everything. I get the appeal. It’s a tidy story. It’s also a single story, and single stories are exactly the problem.

Chimamanda Ngozi Adichie gave a TED talk about this called “The Danger of a Single Story.” It’s nineteen minutes long and worth every second of our attention. She says it far better than I do, but her main point is clear: nobody is one thing. No person, no nation. The danger isn’t that single stories are false. It’s that they’re incomplete, and we cling to them because complete is complicated and we are tired.

What the World Cup did for a month is hand us extra stories, slightly less mediated than usual. Strangers hugging strangers in three languages at once. A defender consoling the man whose heart he just broke. You watch enough of that and the single stories you’ve been carrying about entire countries start to wobble, which is the most useful thing a television can do.

Because that’s the actual beauty of the beautiful game. Not that it proves we’d all get along if we just had a ball. We wouldn’t. It’s that for one month, everybody gets to be more than one story. So maybe next World Cup, the broadcasts show the Japanese fans doing literally anything other than cleaning up Section K, Row 4, because even the flattering single stories are still single.

And Before You Go…

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

This summer has been an absolute scorcher, but good news, 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. 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

July’s pre-order incentive for my book, Real Wealth, is now live, and this one is for the investors who have already mastered the basics and are ready to go deeper. Pre-order this month, tell me you did at tylergardner.com/book, and I’ll send you Beyond the Basics: Investing and Money Management 2.0, a full one-hour digital video presentation delivered straight to your inbox in early August, yours to keep.

We’ll cover portfolio “tilting,” the details of asset location, sector rotation for those of you who just can’t help yourselves, and how to mitigate sequence of returns risk early in retirement. Pre-order now and you’re also locked in for every monthly incentive through the December 1st release date.

Pre-Order Real Wealth

And Now for That 93.6% Decision Most Investors Skip…

Many of you continue to ask about specific allocation breakdowns, and you’ll get exactly that in this week’s podcast episode, where I build the actual portfolios fund by fund, ticker by boring ticker. But in this week’s newsletter, I want to give you something (hopefully) far more useful: the three most practical things I’ve learned from managing portfolios, things I wish someone had told me before I spent years learning them the expensive way. None of this is revolutionary, and that will always be the point.

Tip #1: Spend your energy on the split, not the funds. One of the most famous (and most misquoted) findings in all of finance: the landmark Brinson study found that 93.6% of a portfolio’s variability comes from its allocation across asset classes. Note the word variability. Not returns. This study gets butchered daily by people claiming “90% of your returns come from allocation,” which it never said, and which follow-up research (Ibbotson and Kaplan, 2000) showed simply isn’t true. It’s the financial equivalent of a game of telephone, except everyone playing manages money professionally and the sentence never gets funnier. I know, bummer.

But what the study actually found is far more useful for the DIY investor: your stock/bond/real estate/alts percentages determine almost everything about how your portfolio behaves over time.

So here’s the practical tip: the one decision worth your time is that initial split itself: 90/10? 70/20/10? Everything downstream is a rounding error with a ticker symbol. Picking the perfect fund inside those percentages is choosing the throw pillows before you’ve picked the neighborhood. And if you’re doing this yourself, that’s genuinely liberating news: the part that matters most is the part you’re most qualified to decide, because it’s about your life, your timeline, and your stomach, you know, the three subjects on which you are the world’s leading expert.

Tip #2: Before you buy international, check what you already own. Here’s where I depart from the standard three-fund orthodoxy, and I want to be clear that thousands of reasonably smart people disagree with me. Loudly. Often in my comment sections, sometimes with charts or reminders of how many letters they have after their names. So take this one as my personal approach, not gospel.

The classic argument for a big international slice goes something like this: nobody knows whether the U.S. or the rest of the world will outperform going forward. And that’s 100% correct. Nobody does. I certainly don’t, and I say this as a man who once confidently predicted the Subaru Outback would never catch on in Vermont, where it is now functionally the state bird. But that argument (the international one, not the Outback one) assumes that buying a U.S. index fund means betting only on the U.S. economy, and that assumption stopped being true decades ago.

Roughly 40% of S&P 500 revenue is generated overseas. When you buy the U.S. market, you’re buying Apple’s sales in China, Microsoft’s cloud contracts in Europe, and Coca-Cola’s remarkable ability to appear in every corner store on the planet, including ones that don’t appear to have electricity. Bogle himself made exactly this case, to the mild horror of the three-fund faithful: American multinationals already hand you the world’s profit centers, wrapped in American accounting standards and shareholder protections. So your fun fact of the day, deployable at your next dinner party: the famous “3-fund Bogle portfolio”—U.S. stocks, international stocks, and U.S. bonds—wasn’t actually endorsed (or created) by Bogle. It came from Taylor Larimore, the great Boglehead evangelist who popularized it in Bogle’s honor. So now you know something that most people charging 1% to manage your money do not.

The practical tip inside the opinion: before adding any fund because you feel underexposed to something, look at what your current funds actually hold. The largest U.S. companies are multinationals by revenue, not just by branding: their earnings already carry significant exposure to foreign demand, currency movements, and global economic cycles. You may be more internationally diversified than you were taught.

Tip #3: Let the headline pass before you touch anything. After last week’s discussion of inflation plays, the most common question I got was some version of “so when should I shift my portfolio into those inflation-proof allocations?” And I want to answer it clearly, because this might be the most practical tip of the three: you shouldn’t. Not because the headlines are wrong, but because acting on them is, by definition, active management. Every reallocation triggered by news is two market-timing decisions: when to get out of what you own, and when to get back in. Decades of data say professionals fail at that pair of decisions with impressive consistency, and they have Bloomberg terminals, research departments, and lunch meetings about it. You have a phone and a hunch.

But here’s the part that should let you exhale: a basic index fund already is an inflation hedge. Period. Companies raise their prices during inflation. That’s what inflation is. It’s not some mysterious vapor. Those higher prices flow through to revenues and earnings, which is why stocks have outrun inflation by roughly four to five percentage points a year over the last century.

So the tip, in one sentence: when a headline makes you want to change your allocation, wait until it stops being a headline. The news will change next quarter. Your allocation shouldn’t. That was true last week, it’s true today, and it’ll be true the next time the news invents a reason to tinker (which, if history is any guide, is scheduled for approximately seventeen minutes from when you finish reading this line).

And if you want the full breakdowns of a few sample portfolios and how the initial allocation percentages work in practice, check out this week’s episode of Your Money Guide on the Side. If you find the show useful, a review helps more than you’d think, as it’s how new listeners find the show, and how I know I’m not just another random guy walking through the woods of Vermont talking about money to squirrels.

Listen to This Week's Full Episode

Two Things I’m Currently Thinking About

1. Every story ends in a wedding or a funeral, and that’s why we either loved or hated the ending to The Sopranos. Shakespeare, bless him, left us exactly two ways to end a story: everybody gets married (comedy) or everybody dies (tragedy). Four hundred years later, we have streaming platforms, prestige television, and CGI budgets exceeding the GDP of Iceland, and we are still working (mostly) with the same two exits. Wedding or casket. Pick one, then plan emotional response accordingly.

Fair warning: the next paragraph spoils the endings of La La Land and The Sopranos. Yes, they’re 10 and 19 years old respectively. Yes, you’ve had time. But if you’re still saving them for a special occasion, I honor that, and you may skip ahead to #2.

Which is why the endings that refuse to pick remain the ones we can’t stop arguing about. La La Land had the audacity to let two people love each other and not end up together, and audiences walked out of theaters looking like they’d been personally divorced. And then there’s The Sopranos, which solved the wedding-or-death problem by simply cutting to black mid onion ring—arguably the most original ending in television history, or an act of consumer fraud, depending on which uncle you ask at Thanksgiving. There is no middle position. Nobody has ever said “the Sopranos finale was fine.”

So here’s what I’ve unilaterally decided that says about us: we don’t actually want complex stories; we want closure. An ambiguous ending is an unpaid invoice, and it will sit in the inbox of your brain forever. David Chase understood this and did it anyway, which makes him either an artist or a menace.

And seeing as I’ve been thinking about that ending for nineteen years, I’ll say artist.

2. There’s Someone Better Out There (A Message From Hollywood): Here’s a game I want you to play right now. Name a romantic comedy. Almost any one will do. Now check the opening act: is our hero already in a relationship? They are, aren’t they. And is that partner (through absolutely no fault of their own beyond being mildly boring at dinner parties) someone the movie desperately wants you to despise? Ninety-nine times out of a hundred, the answer is yes. Hollywood’s most reliable romantic formula isn’t boy-meets-girl. It’s boy meets girl-who-already-has-other-boy, but don’t worry, he’s the worst, and we’ll all hate him by minute seven.

The message, delivered in surround sound since roughly the Eisenhower administration: your current relationship is not that good, and there is always someone else out there. Someone better. Someone waiting in a bookshop or a rain storm.

And here’s where it connects to Thing One, because the wedding ending isn’t just convenient for closure, it’s also a cover-up. These movies end at the altar (or the first kiss) precisely so we never see the following Monday (or even the second kiss). We never have to accept that the thrilling new person will quickly become the regular old person who loads the dishwasher like a raccoon and has a few thoughts about thermostats. We get the honeymoon, permanently freeze-framed, and we’re left to assume it lasted forever. Shakespeare would be proud. Your current partner, not so much.

And Before You Go…

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

Most people reading this already have a CPA. The problem isn’t whether you have one. It’s what they’re not doing.

They react to your tax bill instead of building a strategy around it. They treat the relationship as a transaction. They never call in July to ask if you’ve thought about something. You always have to go to them. And the cost of that passivity is real money, your money, left on the table every single year.

The moves that actually reduce your tax bill don’t happen in March. They happen now. PTE elections. S-corp timing. K-1 cleanup. Prior-year retirement contributions. Real tax strategy takes months to implement and summer is exactly when the smart decisions get made. By January the year is already over.

Gelt is the dedicated tax partner who reaches out to you, not the other way around. Built for solopreneurs, real estate investors decoding a stack of K-1s, and business owners who deserve a year-round strategist instead of an annual transaction.

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Gelt is taking on new clients this quarter, so if you’re a business owner or a high-net-worth individual, visit joingelt.com/tyler to get started.

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

—Tyler

July’s pre-order incentive for Real Wealth is now live, and this one is for the investors who have already mastered the basics and are ready to go deeper. Pre-order this month, tell me you did at tylergardner.com/book, and I’ll send you Beyond the Basics: Investing and Money Management 2.0, a full one-hour digital video presentation delivered straight to your inbox in early August, yours to keep.

What we’ll cover:

1. The Art of Portfolio “Tilting”

2. The Importance of Asset Location

3. The #1 Way to Keep More Money (And It Has Nothing to do with Market Returns)

4. Sector Rotation and the GICS Framework

5. Glide Path and Sequence of Returns Risk Mitigation Strategies

This is the session for the person who already owns the index fund and wants to know what comes next. Pre-order now and you’re also locked in for every monthly incentive through the December 1st release date.

Pre-Order Real Wealth

5 Money Milestones and the Lie Each of Them Tells

Fair warning: this week leans philosophical, and it might be worth reading this poem first, a century-old Greek poem about a journey home that has more to say about personal finance than anything currently trending on CNBC.

I’ve been building this business for a few years now, and I still haven’t identified the moment it’s somehow supposed to feel “finished.” There was a follower number I had in my head that I thought would feel like something. It didn’t. Then another one. Also nothing. Then a revenue number. Nothing. I’m not telling you this to complain (as by any reasonable measure things are going well), I’m telling you this because I think it’s the most honest version of the question I want to ask today: when exactly does the building end? And what happens when you get there and the answer is that it doesn’t?

Why does getting what we wanted so rarely feel like what we thought it would? Psychologists call it hedonic adaptation: within roughly six months of any positive life event, humans return to their baseline happiness level almost completely. And I think this explains more about financial behavior than most financial content will ever acknowledge.

1. The First Six Figures. Many of us grew into our professional careers believing that once we “hit six figures,” we’d feel something. But then we get there. And we are still the same person, with the same anxieties, looking at a paycheck that after federal tax, state tax, FICA, healthcare, retirement contributions, rent, and life lands somewhere considerably less impressive than the gross suggested. The number was supposed to fix something. It didn’t.

2. Coast FIRE. The milestone where the math says you can stop contributing to retirement and still hit your “number.” On paper, this looks like freedom. In practice, it feels more like what Samuel Johnson called in 1759 “the conclusion in which nothing is concluded.” You still wakeup tomorrow, and now instead of worrying about building the base, you’re worried about making sure it doesn’t disappear in the next market downturn.

3. Retirement. Many of us are taught to defer life now for the country at the end of the road. But the country, when we arrive, looks a lot like the country we left. Ishiguro’s Never Let Me Go—a novel about clones who believe in a deferral that was never real to begin with—is the most honest thing ever written about the retirement myth. I recommend it with the caveat that you will need a long walk afterward.

4. The Capstone. Maybe you’re writing a book. Maybe you’re building a company. Let’s just call it the Capital “I” Ithaka that we’re all traveling towards…that place or achievement you’ve been telling yourself will retroactively justify everything. Like when David Foster Wallace finished Infinite Jest in 1996 and did not find the redemption he had been imagining. Cavafy knew this would happen: Ithaka has nothing left to give you now. If you find her poor, she has not failed you.

Tyler’s Take-Away (because I can’t resist alliteration): note the plural in Cavafy’s poem. There is no singular Ithaka, nor should there be. The wisdom is in appreciating that we need these destinations to structure our days while knowing that reaching the destination itself won’t solve anything lasting. It will just give us the chance to set out for the next adventure.

If you have a moment to yourself today, write down your next three Ithakas. Not the one you’re currently chasing, but the three after that to make sure that your naviation system is immediately recalibrated once you reach your current destination.

Because that transition period between organizing principles is where most people fall apart.

And if you want a deeper dive on all of the above, check out this week’s episode of Your Money Guide on the Side. 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 I’m not just speaking into the endless void of personal finance podcasts.

Listen to This Week's Full Episode

Two Things I’m Currently Thinking About

1. Ex Machina. If you haven’t seen Alex Garland’s 2014 film, stop reading this and go watch it. I’ll be here when you get back.

For those who have: the film is structured around the Turing Test, Alan Turing’s 1950 proposition that a machine could be considered intelligent if a human evaluator couldn’t reliably distinguish it from another human. What Garland understood, and what makes the film genuinely unsettling, is that Ava (the machine being examined) doesn’t just pass the Turing Test. She administers it. The entire film is her evaluating Caleb (the purported examiner), figuring out whether he is useful, whether he is manipulable, whether he is the kind of human she needs him to be. The examiner becomes the examined.

But now we have another problem on our hands…

2. The Reverse Turing Test. The original Turing Test asked if a machine could fool a human into thinking it’s human. We have largely answered that. The answer is yes, and we arrived there (fortunately and/or disturbingly) faster than almost anyone predicted.

The question we are now trying to answer is the reverse. Can a human convince another human that they are not a machine? I have been called AI (several times a day and with increasing frequency) on my own social media pages. I laughed it off initially. I’m less amused now and slightly more intrigued by generating content that somehow passes a type of Reverse Turing Test that we have yet to create.

Because there’s a new social (media) anxiety—a background hum of suspicion that didn’t exist five years ago and now colors almost every digital interaction we have. The LinkedIn post from your former colleague that felt slightly off and may have used one too many em-dashes. The video on IG that seems just slightly too polished (and monotonous). The customer service conversation that resolved your issue unusually efficiently. And if you haven’t noticed any of these things, it’s time to start paying closer attention.

Because we are already flagging real humans as AI, dismissing genuine writing as generated, treating authentic emotion as performed. The Reverse Turing Test, as currently practiced, is producing false positives at a rate that should concern us.

And as is true of most things worth grappling with in life, there may not be a clean technical solution. The definition of “human-created” is already complicated. If I use AI to generate a first draft and rewrite every sentence, is it mine? If my editor cuts two jokes that weren’t funny, do I still own the tone? The line between tool and author has never been clean, as writers have always used editors, researchers, and ghostwriters (ask James Patterson how he publishes a book an hour). AI just accelerates the blurring that was already happening.

What we may end up with is not a binary but a provenance spectrum. And the question worth sitting with won’t be “did a human make this,” but rather, “does it matter, and if so, why, and to whom.”

My quick modest proposal: bring back the honor code pledge. Not as enforcement, but as psychology. Research on academic honesty consistently shows that simply asking people to sign a statement affirming their integrity before completing a task meaningfully reduces dishonesty, even when the signature is unverifiable. There is something about the act of attestation that activates the part of us that wants to be the person we say we are. “I wrote this. This is mine. This came from a human sitting somewhere, thinking.” It won’t solve the problem, but it might be a good place from which to start.

So, I hereby attest that a human wrote this. Probably.

And Before You Go…

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

If you know who Frank the Tank is, and your idea of a nice little Saturday involves Home Depot, a little wallpaper, maybe some flooring…this one is for you.

There are three things your percentage-based financial advisor is hoping you never think about:

1. It is not twice as hard to manage two million dollars as it is to manage one million dollars. Same asset allocation plan. Same phone calls asking how the kids are doing. Exactly twice the fee. Someone please make that make sense.

2. That line they fed you? You know, the “we do better when you do better,” sounds great until you realize that the fastest way for them to do better is to put you in riskier assets than you wanted or needed. Your risk tolerance and their incentive structure have never been properly introduced. Maybe it’s time.

3. They never tell you the fee in dollars. Only the percentage. Same reason casinos take your cash and give you chips: once it’s not dollars anymore, it doesn’t feel like dollars anymore. Ask your advisor what 1% costs you annually in actual dollars. See how they respond. I’ll be here.

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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

Pre-order my book, Real Wealth, this month, tell me you did at tylergardner.com/book, and I’ll send you a three-part exclusive audio series delivered digitally in early July:

Episode 1: Why it took two bottles of wine, a napkin, and a full actuarial breakdown of my 78-year-old father’s net worth to convince him to buy the car he’d wanted his entire life…and why that still wasn’t enough.

Episode 2: What I learned from buying Peloton at the IPO and selling near the top, including why getting lucky twice is the most dangerous thing that can happen to an investor.

Episode 3: How I became, briefly and without commission, the Jordan Belfort of the cannabis stock craze.

Pre-order now and you’re locked in for every monthly incentive through December 1st.

Pre-Order Real Wealth

Greetings,

U.S. inflation hit 4.2% in May (third consecutive month of acceleration) and I mention this not to ruin a perfectly good Monday morning but because it’s a useful reminder that every now and again, your money can lose its purchasing power.

For our 1.0 readers, there are two numbers that dominate the inflation conversation: the Consumer Price Index (CPI), currently at 4.2%, and the Federal Reserve’s preferred gauge, the Personal Consumption Expenditures index (PCE), at 4.1%. The CPI is the dramatic one, as it’s heavily influenced by energy prices, which means it swings around every time something happens in the Middle East or a refinery sneezes. The PCE is calmer, broader, and adjusts for the fact that when steak gets expensive, people buy chicken.

The Fed watches the PCE. The news watches the CPI. This explains just about all you need to know about both institutions.

The practical implications for your money are straightforward:

• Money you need soon has one job: don’t let inflation eat it. A high-yield savings account, money market fund, or TIPS will do the work. The goal is not to get rich. The goal is to appreciate that your money is keeping up with the headlines.

• Money you don’t need soon has a more ambitious assignment. At 3% average inflation, your purchasing power is cut in half in 24 years: retire at 65, live to 90, and day-one dollar is worth fifty cents at the end. This is why we own equities, why we take risk, and why today’s portfolios are built around the three asset classes with the strongest academic support for outrunning inflation: equities, real assets, and TIPS.

So in an attempt to assuage our long term concerns about monthly inflation data, and to give you something more constructive to do than watch CNBC, where inflation is apparently always either the end of civilization or a buying opportunity, depending on which twelve-minute segment you catch, here are three portfolios that will offset and tend to outpace inflation.

Portfolio One: The Burton Malkiel Special

Allocation: 90% Stocks / 10% TIPS

This isn’t my idea. It’s Burton Malkiel’s. Princeton economist, A Random Walk Down Wall Street, two million copies sold, fifty years of being right before being right was popular. His preferred portfolio is overwhelmingly stocks for risk-on with TIPS as the risk-off component. Not bonds. TIPS. Know thy fixed income.

Stocks (90%): VTI or FSKAX. US total market, already far more global than it sounds, as the companies inside generate roughly 40% of revenues internationally. You’re owning the most competitively dominant multinationals on the planet, who happen to be headquartered here.

TIPS (10%): Treasury Inflation-Protected Securities. These are government bonds whose principal adjusts upward with inflation. Buy a $1,000 TIPS bond, inflation runs 4%, your principal becomes $1,040. You’re not buying these for explosive returns. You’re buying purchasing power preservation backed by the US government. TreasuryDirect.gov for direct ownership, or VTIP/SCHP as ETFs at 0.04-0.05% expense ratios.

This portfolio’s historical real return: 6-7.5% annually after inflation. The financial industry will tell you this is dangerously simple. Their alternative comes with a much larger expense ratio, a risk disclosure that runs forty pages, and a long/short equity strategy that absolutely crushed it from 2019 to 2021 and has been “repositioning” ever since.

Portfolio Two: Add A Slice of Real Estate

Allocation: 75% Stocks / 10% TIPS / 15% Real Estate

Real estate is one of the things inflation is literally measuring. When prices rise, property values and rents rise with them.

REITs (VNQ, SCHH) give you diversified real estate exposure without tenants, toilets, or 2am phone calls. And if you are interested in direct ownership: a $400,000 property with $80,000 down appreciating 4% returns $16,000 on your actual cash, a 20% real return. And your fixed-rate mortgage gets repaid in increasingly cheaper dollars as inflation runs. The bank lent you dollars worth X. You’re repaying in dollars worth 0.85X. Inflation erodes your debt. This is precisely why I don’t pay down my own 3.25% mortgage. And yes, this is the silver lining of inflation: your fixed debt gets cheaper.

Portfolio Three: Add Infrastructure*

Allocation: 65% Stocks / 10% TIPS / 15% Real Estate / 10% Infrastructure

Infrastructure—toll roads, utilities, pipelines, cell towers—has revenues that are frequently contractually linked to inflation. Not “probably keeps up.” Legally required to keep up. That’s a different category of protection entirely.

IFRA, VPU, or IGF for global exposure. But Tyler, why not commodities? Gold doesn’t pay a dividend. Oil doesn’t compound. Infrastructure produces cash flows. Cash flows compound. Compounding is my favorite word in the English language, and that’s saying something when salsa exists.

*Note: this type of portfolio is too “active” of a bet for my taste.

3 Mistakes to Avoid

Too many bonds. Long-duration bonds are an inflation victim, not an inflation hedge. The 2022 bond market dropped 13%, its worst year since the 1970s, while inflation was running hot. Use TIPS for long-term risk-off, money market for short-term buffer.

Too much cash. At 3% inflation, cash loses a quarter of its purchasing power per decade. The right role for cash is operational: 1-2 years of living expenses in a money market as a liquidity buffer.

Over-tinkering. Pick the portfolio that matches your situation. Rebalance once a year. Leave it alone.

And if you want the full breakdown of each portfolio, check out this week’s episode of Your Money Guide on the Side. 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 I’m not just speaking into the endless void of personal finance podcasts.

Listen to This Week's Full Episode

Two Things I’m Currently Thinking About

1. The God You Didn’t Choose. Yep, we’re going deep today. In 2005, David Foster Wallace gave a commencement address at Kenyon College that distills his worldview into twenty-two accessible minutes (which, for context, is roughly the time it takes to read the first footnote of Infinite Jest and decide you’re more of a podcast person).

His central argument: everybody worships something. The question is never whether you have a god. It’s which one you’ve chosen, consciously or, more often, by default. Money. Beauty. Power. Intellect. And the insidious thing about default gods is that you never examine them. You just inherit them, nod along, and call it ambition.

I taught at New England prep schools before I got tired of snowplow parents who wouldn’t let their kids near adversity. The kind of place that mentioned its Ivy League placement rate the way Silicon Valley companies mention their kombucha on tap and bring-your-dog-to-work Thursdays, as though the amenity were the point, and not a very expensive distraction from whether any of it means anything. My students didn’t worship God, exactly. They worshipped the myth of Harvard, or the “Ivy” gods…the idea that if they could just get “there” (preferably in the form of HPY), their anxiety would finally resolve itself into something resembling peace. That Harvard was the finish line and not, as it turns out, just another starting point populated by humans who also can’t sleep at night.

2. The Green God. Rainn Wilson (yes, the Dwight Schrute) has been saying something similar lately about what he calls a crisis of meaning. At the height of his fame on The Office, making more money than he’d ever imagined and playing one of the truly unique and exceptional characters in television history, he was at his most depressed. The green god had delivered exactly what it promised, and it turned out the promise was the problem.

The most unexamined belief system in American life is that net worth and self-worth are the same number. They are not. I know this because I now talk about money for a living and I have met a genuinely alarming number of wealthy people (like, fly a private jet to Japan on a moment’s notice for a quick bite at Sézanne type of wealth) who are completely miserable, and an equally alarming number of people with very little who are not.

The work, and Wallace and Wilson would both agree, is figuring out what you actually believe in before the belief chooses you. That’s harder than getting into Harvard. It’s harder than hitting your number. It’s also, I’d argue, the only thing worth doing.

And Before You Go…

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

Most people reading this already have a CPA. The problem isn’t whether you have one. It’s what they’re not doing.

They react to your tax bill instead of building a strategy around it. They treat the relationship as a transaction. They never call in July to ask if you’ve thought about something. You always have to go to them. And the cost of that passivity is real money, your money, left on the table every single year.

The moves that actually reduce your tax bill don’t happen in March. They happen now. PTE elections. S-corp timing. K-1 cleanup. Prior-year retirement contributions. Real tax strategy takes months to implement and summer is exactly when the smart decisions get made. By January the year is already over.

Gelt is the dedicated tax partner who reaches out to you, not the other way around. Built for solopreneurs, real estate investors decoding a stack of K-1s, and business owners who deserve a year-round strategist instead of an annual transaction.

Done right, your tax strategy could pay for a genuinely excellent summer. Done wrong, someone from the IRS might get that trip to Maui instead.

Gelt is taking on new clients this quarter. Visit joingelt.com/tyler to get started.

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

13 Moves They’re Betting You Won’t Make

Last week I spent fifty-one minutes on the phone with Xfinity.

Not because I wanted to (we live in Vermont, the nearest alternative provider is a guy named Chip who runs fiber out of a barn) but because I knew the script. You call. You tell them you’re changing providers. You get transferred to a human being who has access to a pricing tier that does not exist on any website or in any known universe.

Her name was Melanie. She saved me $43 a month. I now owe Melanie a Christmas card.

There are 13 money hacks (and I’m sure far more) that work the exact same way, and they all exist because the company is betting on one thing: you won’t ask. The hack is asking.

Here are five that you can use starting this week, one from each section of the episode. The other eight are on this week’s episode of the podcast.

1. From the phone hacks → The retention gambit. Call a company. Any company. Say “cancel.” You’ll be transferred to a department whose entire job is keeping you. Their pricing sheet is a different document than the public one. Geico and Progressive might knock 15-20% off. SiriusXM might drop from $17/month to $4 (or free). The move is to never take the first offer, as there are three or four layers of discount underneath it. My father recently had a retention agent ask him, and I am not making this up, how much he was willing to pay. He said four bucks. They took it. Remember: it will always be more expensive for a company to lose you than to simply drop your rate back to intro pricing.

2. From the tax hacks → Front-load your HSA and don’t touch it. If you have a high-deductible health plan, setup the HSA, and then max it every year. Pay medical bills out of pocket instead. Save every receipt. Let the HSA grow, invested, tax-free, for 20-30 years. Then reimburse yourself decades later, 100% tax-free. There’s no statute of limitations. A 2026 dental cleaning can be reimbursed in 2056. Triple tax advantage, which no other retirement account in America has. I wish I’d known this at twenty-five before I used my HSA to buy…Claritin.

3. From the consumer psychology hacks → The Costco tag code. Costco’s yellow tags are a code. .99 = regular price. .88 or .00 = display model or final sale. .97 = manager-marked clearance, 30-50% off. Little star in the top right corner = discontinued, hoard it like it’s 1999. I was told after posting about Costco earlier this month that I had committed some kind of generational crime by not already being in the Kirkland tribe. Consider this my attempt at reparations.

4. From the power inversion hacks → File the chargeback before you call customer service. When a company screws you, your instinct is to call them first. Don’t. Call your credit card first and file a chargeback. Visa or Mastercard freezes the charge and puts the burden of proof on the merchant. The merchant, realizing they lose automatically if they don’t act, calls you. They suddenly have all the time in the world to fix the problem they didn’t have the time to fix yesterday. The power dynamic inverts entirely. It is the single best consumer move I have ever learned. That said, and I truly mean this, only pull this lever when a company has left you no other option. It costs them real money and real reputation. Don’t weaponize it over a shipping delay.

5. From the hospital hacks → The bill is not the bill. When you receive a hospital bill, you need to do three things. First, request the itemized bill, as errors are routine and the discrepancy between what they charge and what they meant to charge is often startling. Second, ask about prompt pay discounts, as many hospitals will take 20-40% off if you pay in full on the spot (I have personally done this several times and saved thousands). Third, ask about charity care. Most nonprofit hospitals are legally required to offer it, income thresholds are higher than people assume, and almost nobody asks. The system is not designed for you to know any of this. Now you do.

The other eight hacks are all on this week’s episode of Your Money Guide on the Side—including the the four-minute email that earns me 27,000 Amex points annually. 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 I’m not just speaking into the endless void of personal finance podcasts.

Listen on Apple | Listen on Spotify

Two Things I’m Currently Thinking About

1. What My Elementary School Report Cards Got Wrong (Or: A Belated Defense of the B Student). Oscar Wilde once said something that I have spent thirty years wishing someone had said to me in fourth grade. Through Gilbert in The Critic as Artist: “I am afraid that you have been listening to the conversation of some one older than yourself. That is always a dangerous thing to do…”

Every single one of my elementary school report cards contained some variation of the following: Tyler rushes through his tests, finishing in fifteen minutes instead of the forty-five allotted, and consequently misses the small details that would take him from an 85 to a 100. And this was always framed as a problem. I would like to state, for the record, that I did not experience this as a character flaw at the time; I experienced it as a scheduling opportunity.

It turns out there’s an actual economic principle for this, which I did not know in fourth grade and which would have been enormously validating if I had. The Pareto Principle: 80% of results from 20% of effort. I wasn’t being careless. I was, completely by accident, practicing resource allocation. The remaining thirty minutes went toward that evening’s homework, so while my peers were completing their problem sets at home, I may have been glued to the television appreciating the most epic cartoon block of all time: Disney Afternoon.

2. Group Projects and the Mythology of the Real World. The teacher from item one also loved group projects. They all did. And you know exactly what I’m talking about. You’re assigned a project with people you didn’t choose, on a topic you didn’t select, and told (with the practiced confidence of someone delivering a profound life lesson to children who have no choice but to listen and feign inherited wisdom) that this was preparation for the “real world.”

I have some thoughts.

The real world does contain people you didn’t choose. It also contains, and the curriculum reliably omits this, the option to simply not work with them. I want to be clear that I am not good at managing people. I have tried. The people involved have also tried. We have all agreed, privately and eventually out loud, that this is not where I add value. What I do well is work quickly and alone, without the particular entropy that comes from a group project where two people do the work and four have strong opinions about the font on the cover page that ends up mattering to precisely nobody.

I say all of this with genuine affection for teachers. But the group project as universal preparation for adulthood assumes a version of adulthood that is, for a growing number of people, entirely optional. Some of us are going to end up working alone in Vermont, talking into a microphone, with a bloodhound for a coworker. No one assigned us to that group. We chose it.

For a more authoritative challenging of fourth grade curricula, see Arundhati Roy’s The God of Small Things: “…his teachers wrote in his Annual Progress Reports…Does not participate in Group Activities…another recurring complaint. Though what exactly they meant by ‘Group Activities’ they never said.”

And Before You Go…

This week’s newsletter is brought to you by Wispr Flow.

For the better part of three decades, I have operated under the assumption that I am an exceptionally fast typist. Not just fast, but gifted fast. The kind of person who finishes sentences before other people have located the shift key. The kind of person who “won” Mavis Beacon Teaches Typing even though it was never really a competition.

Then I started using Wispr Flow.

And it turns out…I am not fast. I am just slow in a way I had never compared to anything. You can talk roughly three times faster than you can type, regardless of how emotionally attached you are to your eighth grade typing score. My entire self-concept required a slight recalibration.

I now draft podcast scripts, newsletter sections, and social captions by talking. Wispr Flow converts it into clean, ready-to-use text inside Slack, Notion, Claude, ChatGPT—anywhere I’d otherwise be typing. It handles filler words, mid-sentence corrections, names, context. No setup. Works in any app on any device.

It even works on a walk in the woods with the hounds, which is increasingly where my best thinking happens anyway.

Try Wispr Flow Pro free for a month at wisprflow.ai/tyler

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 the S&P 500 is the Best (And Worst) Thing to Ever Happen to Investors

1. The index was never meant to be a scoreboard. So stop treating it like one. When Bogle launched the first index fund in 1975, he wasn’t handing investors a scoreboard. He was handing them a compass. The S&P 500 was built to answer one question: “what is the market doing?”

But humans are, alas, humans. Give us a number and within ten minutes we will find a way to turn it into a competition. We are a nation that has managed to make youth soccer—a sport played by six-year-olds mostly running in the wrong direction—into a full-time parental occupation involving travel teams, a Rolodex of Division I coaches who will never call you back, and at least one family that has flown to Argentina for a tournament involving children who still believe in the tooth fairy. We are constitutionally incapable of encountering a measurable thing without immediately asking who is winning.

It was inevitable we would apply this same competitive spirit to investing. The only problem is most of us are competing against the wrong thing.

2. Stop comparing your diversified portfolio to the S&P 500. It’s like entering your bloodhound in a greyhound race and being shocked when she abandons the track entirely right out of the gates to follow the scent of a child’s nachos twelve rows up. The S&P 500 is 100% equities, 100% large and mega-cap, and 100% domestic. Zero cash. Zero bonds. Zero international exposure. Zero asset class diversification of any kind. It was built to measure one slice of one market in one country. That benchmark was never designed to be your benchmark, so perhaps before calling your financial advisor to demand they beat it, confirm that you are not currently holding 30% in something called a coin and 55% in cash “just in case.”

3. Every number the S&P 500 gives you is incomplete. The only question that matters is: compared to what? When someone tells you the S&P fell 2% today, that sentence is missing its second (and far more important) half. The number is not the story; the timeframe is the story. And the timeframe is almost always chosen to produce the most alarming possible version of events.

This also explains the high water mark problem. Your portfolio hits an all-time high. Then it pulls back 5%. Now you’re not thinking about your actual return. You’re thinking about the gap. That gap becomes the new psychological floor. The number feels catastrophic because you’re measuring it against the peak, not against where you started, not against the year, not against anything that actually matters.

That 2% day everyone panicked and posted about? The S&P was still up 15% for the year. Nobody led with that sentence. They never do.

When in doubt, zoom out.

4. On the dangers of real-time information. In Faulkner’s The Sound and the Fury, Jason Compson pays his broker ten dollars a month for up-to-the-minute cotton futures prices. It is, by some distance, the worst financial decision in the novel. He checks obsessively. He speculates recklessly. He makes catastrophic trades based on noise he has mistaken for signal. He ends up ruined, furious, and alone in a car outside a market he can no longer afford to be in.

Faulkner wrote this in 1928. And surprise, he was somewhat ahead of his time.

We now live in Jason Compson’s world, except the real-time updates are free: they live in your pocket, and you can check them at 2am from a gas station in rural Ohio. Some of you do. But the research is unambiguous: the more frequently investors check their portfolios the worse their returns. Not because checking changes the market. But because checking changes the investor. Every red day becomes a threat. Every green day becomes an expectation your nervous system will punish you for losing.

Jason Compson paid ten dollars a month for the privilege of being driven slowly insane by information he could not act on wisely. You are doing it for free.

The most underrated financial tool available to you right now is closing the app.

5. The market is not a financial instrument. It is a daily referendum on collective human fear and greed. The S&P 500 on any given day is not telling you what American businesses are worth. It is telling you what millions of humans—reacting to headlines, narratives, and each other—are willing to pay for them at that moment. Buffett called it a voting machine in the short run and a weighing machine in the long run.

The voting machine runs twenty-four hours a day and has a Reddit forum and an algorithm designed to show you the most devastating version of whatever just happened. When you obsess over your benchmark you are letting the voting machine run your financial life. You’re letting the collective fear of others run your financial life. But the weighing machine? Yeah, it doesn’t care what the S&P did today.

Neither should you.

And if you want the full version, this week’s episode of Your Money Guide on the Side goes deeper on Bogle, the benchmark trap, and the summer I spent trying to outsmart the market with a subscription service whose name I am still too embarrassed to say in polite company. 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 1st Annual Ty-Athalon. There was a half marathon downtown last weekend—downtown being, for those unfamiliar with Vermont geography, also uptown, midtown, and the outskirts. I did not run it. Instead I completed what I am formally naming the Ty-Athalon: thirty minutes on the Peloton with Olivia Amato, seventy lengths in the pool with flippers on, and a one-hour walk through the woods. (The flippers are non-negotiable, as my fifth grade swim instructor once assessed my aquatic abilities with clinical precision and labeled me, without apparent remorse, a “sinker.” Some truths are permanent.)

At first I was disappointed. The specific grief of someone negotiating between what their body used to be capable of and what it currently is. Two titanium hips by 43 will do that. But then I remembered Murakami. In What I Talk About When I Talk About Running, he describes reaching a point where runners began passing him on the trails and finding, to his own surprise, a kind of peace in it. His goal, distilled to its simplest form: just don’t stop.

I didn’t stop. In flippers, on a Peloton, or walking (quite slowly) through the Vermont woods.

And that was enough. It was a great day.

2. The Dignity of Playing Your Part. After last week’s Ishiguro deep dive I rewatched Downton Abbey, season one and found myself completely undone by Molesley—a footman and valet who takes his role with a seriousness our central character, Matthew Crawley, finds faintly comic. Crawley keeps waving him off—I can do it myself, thank you—and we are, perhaps, meant to laugh along.

But I couldn’t laugh. And ultimately, neither can Crawley. Because Molesley is just trying to play his part. With everything he has.

Shakespeare told us the world is a stage and we are merely players. What he didn’t say, but what Molesley understood instinctively, is that there is no such thing as a small part. There is only whether you play yours with full commitment or phone it in and hope nobody notices.

Don’t phone it in. And don’t laugh at someone else who isn’t.

And Before You Go…

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

Here’s the thing about having a CPA: most people reading this already do. The problem isn’t whether you have a CPA; it’s what the CPA is (or isn’t) doing.

For most of us, it looks something like this: they reacted to your tax bill instead of building a strategy around it. They treated the relationship as a transaction. They never called in July to ask, “Have you thought about this?” You always had to come to them. That’s not your fault. It’s the industry’s. But the cost of waiting until next March to fix it is real money—your money—left on the table every single year.

The moves that actually reduce your tax bill don’t happen in March. They happen now. PTE elections. S-corp timing. K-1 cleanup. Prior-year retirement contributions. September estimates. Real tax strategy takes months to implement and summer is exactly when the smart decisions get made. By January the year is already over.

Gelt is built for exactly this moment. One dedicated tax strategist who reaches out to you—not the other way around—powered by technology handling the grunt work in the background. Gelt is for solopreneurs scaling past the self-directed spreadsheet, real estate investors decoding a stack of K-1s, and business owners who deserve a year-round partner instead of an annual transaction.

Done right, your tax strategy could pay for a genuinely excellent summer. Done wrong, someone from the IRS might get the trip instead.

Gelt is taking on new clients this quarter. Visit joingelt.com/tyler to get started.

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

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.

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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.

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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.

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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