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Luck, Stupidity, Automation and Inertia

"Mark, I really enjoyed this. We often give ourselves too much credit for the good decisions and not enough credit to the people and chance encounters that quietly changed our lives. That salesman probably had no idea the impact he would have, just as you had no idea that an arbitrary number picked at age 20 would shape your future. It’s a wonderful reminder that while discipline matters, sometimes luck opens the door and inertia wisely keeps us from closing it."
- Andrew Clements
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Automatic Income stream? How important to you?

"Agreeing it can be a wise choice, I’ll add this. One of the reasons we haven’t pulled the trigger on an immediate annuity is reluctance to create excess income. On top of our small steady income stream we realize additional income as desired, generally by selling assets or doing Roth conversions. If we also had an annuity coming in every month, it would remove the space we have to do this. So while I understand the value of a steady income stream, for now I prefer the flexibility of taking what income we want when we want it. "
- Michael1
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Why can’t more people plan for their retirement future?

"That’s the key for sure. Just curious, what do you mean 50 additional contributions? Lump sums beyond payroll deductions?"
- R Quinn
Read more »

Four Walls

"Thank you Dan. I believe it's a philosophy that reminds us of what we have in common rather than what divides us."
- Andrew Clements
Read more »

How do you prepare for the long term care cost as retiree?

"The LTC deductions must also exceed the standard tax deduction make a difference on your taxes. To claim this medical expense deduction you must itemize on schedule A to utilize tax-deferred IRA or 401K dollars to pay for long term care (LTC) expenses on your taxes that exceeds 7.5% of your Adjusted Gross Income (AGI)."
- dhack11
Read more »

Investment Wisdom

THE INVESTMENT WORLD is full of storytellers. And while these folks might be entertaining, they generally aren’t very helpful. There’s one category of stories, however, that I do think is useful: They’re what I might call investment fables. They’re apocryphal stories that likely aren’t real. But they’re helpful nonetheless because each carries a useful lesson. Here are some of the more popular ones. Consumer choice. In 1999, Richard Mille and a partner launched a company to make wristwatches. By 2001, the company was ready to begin taking orders for its first model, the RM 001. They knew they wanted to target a high-end market, so they chose the Financial Times for their first advertisement. According to legend, however, a graphic designer at the newspaper made a mistake. Instead of including the watch’s intended price of $13,500, an extra zero was added, making the price $135,000. At first, the company was furious at the newspaper for the mistake. But then the phone started to ring. The sky-high price turned out to be attractive to a certain class of buyers, and the initial run of the 001 quickly sold out. Today, Richard Mille sells several models priced in the hundreds of thousands, and some limited editions carry price tags north of $1 million. For its part, the company denies this story, maintaining that $135,000 was always the price it intended. But whether this story is true or not, it illustrates a concept in personal finance known as the Veblen effect. This occurs when the traditional shape of a demand curve gets turned upside down. Instead of consumers buying less of something as its price rises, when it comes to Veblen goods, consumers want to buy more as the price increases. Hermes handbags and Ferrari sportscars are other examples. What should we make of the Veblen effect? To answer this question, it’s worth examining its origins. Thorstein Veblen was a sociologist and economist. Perhaps owing to his background as the sixth of 12 children growing up in modest, rural surroundings, Veblen became broadly critical of capitalism. In his 1899 book, The Theory of the Leisure Class, he coined the term “conspicuous consumption.” And while Veblen didn’t explicitly see himself as a socialist, he leaned in that direction. He would have been bitterly critical of something like a Richard Mille watch. In making spending decisions, though, I wouldn’t worry too much about value judgments like this. The reality is that each of us is different, and we each value different things. That’s why I prefer to stick to the numbers. The most important thing, in my view, is simply to have a framework for your household finances, to ensure that your overall spending level is in line with your long-term plan. Other people’s subjective judgments, in my opinion, shouldn’t factor in. Investment gains. When it comes to investing, what’s the best strategy? According to lore, Fidelity Investments once looked into this question by examining the performance of all of the accounts on its platform. What did they find? The accounts that had done the best were those that had been abandoned due to the death of the owner, with the result that the investments hadn’t changed for years. There’s no evidence that this story is true, but it’s repeated frequently because it aligns with real data. In studies going back more than 25 years, research has shown that frequent trading is generally associated with worse investment results. This is true for both individual and professional investors. To be sure, some active managers have delivered impressive results. In the past, this has included the likes of Warren Buffett and James Simons. More recently, a 24-year-old named Leopold Aschenbrenner has delivered returns of more than 1,000% in the two years since he founded a hedge fund to bet on AI stocks. But cases like this are the exceptions that prove the rule. For most investors, most of the time, the data tell us that it’s better to trade less rather than more. Market tops. On a related note, there’s a tale about Joseph Kennedy—President Kennedy’s father. He was an active investor in the 1920s, but he said he realized it was time to sell when the fellow giving him a shoeshine one day started offering stock tips. What’s interesting about this story is that Kennedy did actually sell his stocks and even took a short position early in 1929, earning him a fortune when the market dropped. The shoeshine aspect of this story likely isn’t true. But it’s a favorite because it carries a useful message. Veteran investor Jeremy Grantham has often talked about the market signals he pays attention to. In addition to P/E ratios and other quantitative measures, he’s noted that he looks for “signs of craziness”—things like the GameStop mania in 2021. When the stock market begins to look more like a casino—and when we see YouTube influencers making stock calls from their gaming chairs—Grantham gets nervous. Intuitively, this does make sense, but it may not be very useful. Consider how the market has performed in recent years. After Grantham urged caution in 2021, the market did drop in 2022. But then it rose in 2023, 2024, 2025 and in the first half of 2026. So an investor who sold in 2021 would have missed out on significant gains. The bottom line: Just as the number of world-class stock-pickers is limited, so too is the number of tactical traders who have profited in the way Joe Kennedy did by getting out at just the right moment. Market forecasts. What’s a better way to think about the stock market? According to another Wall Street tale, J.P. Morgan was once asked what he thought the market would do over the coming year. His reply: “It will fluctuate.” There’s no evidence that Morgan ever actually said this, but in this case too, the story is popular because it sounds right. And in my view, this is exactly the right way to think about the stock market. At the end of the day, the only thing we can know for sure about the stock market is that it will either go up, go down or stay about the same. If we can structure our portfolios so we won’t be too negatively affected whichever way it goes, that, in my opinion, is the road to success.   Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.
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Lessons Learned Along the Way

"It was quite an adventure. I can't have any regrets because I have ended up in a very good place. I am grateful for that."
- Dan Smith
Read more »

Does Vanguard Know Something?

"Well, quick solutions are either an equal weight fund (not quite 493, but minimizes the concentration issue) or an S+P fund plus 7 put options. The risk is real; are you willing to pull the trigger on a change, though?"
- Mike inLA
Read more »

Misleading Indicator

LISTEN TO THE financial news, and you’ll often hear reference to “the VIX.” But what exactly is the VIX, and how important is it? The VIX index is intended to be a measure of investor sentiment. For that reason, it’s often referred to as the market’s “fear gauge.” How can investor sentiment be measured? While the math is complex, it’s based on a straightforward principle: When investors get nervous, they look for ways to protect their portfolios and are sometimes even willing to pay for that protection. This was the insight that led to the initial development of the VIX back in 1989. Two finance professors, Menachem Brenner and Dan Galai, observed that stock options—and specifically, the prices of those options—provided a sort of X-Ray into investors’ feelings. That’s because certain options, known as “put” options, are designed to protect portfolios from losses. They’re like insurance. So when demand for put options increases, and as a result, pushes up the prices of those options, that’s an indication that investors are feeling more nervous. On the other hand, during periods when investors are feeling optimistic, put options will fall in price. Instead, “call” options, which allow investors to magnify their gains in rising markets, will go up in price. The relative prices of these two types of options can tell us a lot about investors’ mindset, and that’s the basis of the VIX. In very simple terms, when put option prices are rising, the VIX rises. And when put option prices are falling, the VIX falls. A higher VIX reading thus means investors are becoming more fearful. Because of its function as a sentiment gauge, market commentators like to talk about the VIX, especially when it’s rising. But I’m not sure we should put too much stock in it. That’s for two reasons. First, and most importantly, the VIX is limited because it’s only able to measure current investor sentiment. It doesn’t know anything about what will happen in the future. Consider how the VIX behaved during some significant market events over the past 20 years.  In August 2008, the VIX was at a relatively low level, right around 20. It seemed to be indicating calm seas. But just a month later, Lehman Brothers went into bankruptcy, and the stock market began to fall. The VIX did eventually spike up in response to this crisis, ultimately rising all the way to 80—a very high reading—but by that point, it was too late. It was effectively reporting yesterday’s news. At other points, the VIX has been misleadingly high. In the spring of 2020, when the market dropped more than 30%, fear levels were running high, and the VIX spiked up to 82. But with the benefit of hindsight, we can see that the VIX wasn’t communicating anything useful. That’s because the spring of 2020 would have been an ideal time to buy. Between March 16, when the VIX hit its peak, and the end of that year, the S&P 500 rose 57%. The VIX provided no hint that this rally was coming. Nearly the same sequence of events occurred in 2025. In April, when investor worries were running high over the White House’s new tariff policies, the VIX spiked up, topping 50 on April 8. But that also would have been an ideal time to buy. A short time later, the White House changed course on tariffs, and the market rebounded, gaining 37% through the end of the year. Why is the VIX such a poor predictor? In his book Finance for Normal People, Meir Statman describes how investors are susceptible to recency bias. He cites a Gallup survey that asked investors, “Do you think that now is a good time to invest in financial markets?” Almost invariably, investors answered “yes” when markets had been rising. In February 2000, for example, 78% of those surveyed responded positively—just a month before the market fell into a multi-year bear market. The problem is that our minds’ are prone to extrapolating from current conditions. And since the VIX simply mimics investors’ thinking, it too just extrapolates. The VIX has no idea when the market is about to reverse course, as it did in 2000, 2008 or 2025. Despite this flaw, however, you might wonder if the VIX would nonetheless be useful as a portfolio hedge. In other words, even if the effect is delayed, the VIX seems like it might be helpful if it goes up when the market goes down, and vice versa.  In The Four Pillars of Investing, William Bernstein looks at this question. He examines a popular ETF (ticker: VXX) that tracks the VIX index. On the surface, this looks like an effective way to protect a portfolio. In the first three months of 2020, for example, when Covid arrived, and the stock market began to drop, this ETF rose more than 200%. But that was one narrow time period. Other periods were punishing for VXX. Bernstein points to 2010-2011, when the S&P 500 rose about 8.5% per year, on average. What did VXX do? You might expect that it would have fallen proportionately. But it cratered, losing 74% of its value. Bernstein asks wryly, “You didn’t expect that someone would sell you bear market insurance for free, did you?” That, unfortunately, is the issue. Because of the way it’s constructed, the VIX doesn’t work as a perfect offset to the stock market. That’s why, in my view, investors are best served by a much simpler portfolio structure, consisting of stocks and primarily short-term Treasury bonds. While this combination isn’t flawless, it’s delivered far less volatile results over time than any strategy built around the VIX. Like many things in finance, the VIX is interesting, but ultimately not very useful.   Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.
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Billy’s Certificate – 1937

"U, ”If you are generating anything close to a market return (less fees) for your particular asset allocation, you’re doing great.” We have an 8.7% annual return in the past 10 years, and just this year crossed the mark where in our total investing time have made more in returns than the amount invested."
- DavidHLancaster
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When to Leave Your Portfolio Alone

"I don’t have any better insite into the future than you do but I do know what my past performance has been. When I pick a stock to invest in, I have an expectation as to what return I will get. If that return has been suboptimal for too long, I decide to sell it. On the other hand stocks that have done well for me in the past, I will reevaluate as well, but just because they have become a larger percentage of my portfolio due to their exceptional growth, I’m not ready to sell. One example would be Berkshire Hathaway, I invested in 1982 and it became a very significant part of my portfolio. I liquidated most of it last year. I don’t think it’s a bad investment, but I don’t think it’s going to have the spectacular returns going forward so it is now a much smaller part of my portfolio."
- Bob Zwick
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Luck, Stupidity, Automation and Inertia

"Mark, I really enjoyed this. We often give ourselves too much credit for the good decisions and not enough credit to the people and chance encounters that quietly changed our lives. That salesman probably had no idea the impact he would have, just as you had no idea that an arbitrary number picked at age 20 would shape your future. It’s a wonderful reminder that while discipline matters, sometimes luck opens the door and inertia wisely keeps us from closing it."
- Andrew Clements
Read more »

Automatic Income stream? How important to you?

"Agreeing it can be a wise choice, I’ll add this. One of the reasons we haven’t pulled the trigger on an immediate annuity is reluctance to create excess income. On top of our small steady income stream we realize additional income as desired, generally by selling assets or doing Roth conversions. If we also had an annuity coming in every month, it would remove the space we have to do this. So while I understand the value of a steady income stream, for now I prefer the flexibility of taking what income we want when we want it. "
- Michael1
Read more »

Why can’t more people plan for their retirement future?

"That’s the key for sure. Just curious, what do you mean 50 additional contributions? Lump sums beyond payroll deductions?"
- R Quinn
Read more »

Four Walls

"Thank you Dan. I believe it's a philosophy that reminds us of what we have in common rather than what divides us."
- Andrew Clements
Read more »

How do you prepare for the long term care cost as retiree?

"The LTC deductions must also exceed the standard tax deduction make a difference on your taxes. To claim this medical expense deduction you must itemize on schedule A to utilize tax-deferred IRA or 401K dollars to pay for long term care (LTC) expenses on your taxes that exceeds 7.5% of your Adjusted Gross Income (AGI)."
- dhack11
Read more »

Investment Wisdom

THE INVESTMENT WORLD is full of storytellers. And while these folks might be entertaining, they generally aren’t very helpful. There’s one category of stories, however, that I do think is useful: They’re what I might call investment fables. They’re apocryphal stories that likely aren’t real. But they’re helpful nonetheless because each carries a useful lesson. Here are some of the more popular ones. Consumer choice. In 1999, Richard Mille and a partner launched a company to make wristwatches. By 2001, the company was ready to begin taking orders for its first model, the RM 001. They knew they wanted to target a high-end market, so they chose the Financial Times for their first advertisement. According to legend, however, a graphic designer at the newspaper made a mistake. Instead of including the watch’s intended price of $13,500, an extra zero was added, making the price $135,000. At first, the company was furious at the newspaper for the mistake. But then the phone started to ring. The sky-high price turned out to be attractive to a certain class of buyers, and the initial run of the 001 quickly sold out. Today, Richard Mille sells several models priced in the hundreds of thousands, and some limited editions carry price tags north of $1 million. For its part, the company denies this story, maintaining that $135,000 was always the price it intended. But whether this story is true or not, it illustrates a concept in personal finance known as the Veblen effect. This occurs when the traditional shape of a demand curve gets turned upside down. Instead of consumers buying less of something as its price rises, when it comes to Veblen goods, consumers want to buy more as the price increases. Hermes handbags and Ferrari sportscars are other examples. What should we make of the Veblen effect? To answer this question, it’s worth examining its origins. Thorstein Veblen was a sociologist and economist. Perhaps owing to his background as the sixth of 12 children growing up in modest, rural surroundings, Veblen became broadly critical of capitalism. In his 1899 book, The Theory of the Leisure Class, he coined the term “conspicuous consumption.” And while Veblen didn’t explicitly see himself as a socialist, he leaned in that direction. He would have been bitterly critical of something like a Richard Mille watch. In making spending decisions, though, I wouldn’t worry too much about value judgments like this. The reality is that each of us is different, and we each value different things. That’s why I prefer to stick to the numbers. The most important thing, in my view, is simply to have a framework for your household finances, to ensure that your overall spending level is in line with your long-term plan. Other people’s subjective judgments, in my opinion, shouldn’t factor in. Investment gains. When it comes to investing, what’s the best strategy? According to lore, Fidelity Investments once looked into this question by examining the performance of all of the accounts on its platform. What did they find? The accounts that had done the best were those that had been abandoned due to the death of the owner, with the result that the investments hadn’t changed for years. There’s no evidence that this story is true, but it’s repeated frequently because it aligns with real data. In studies going back more than 25 years, research has shown that frequent trading is generally associated with worse investment results. This is true for both individual and professional investors. To be sure, some active managers have delivered impressive results. In the past, this has included the likes of Warren Buffett and James Simons. More recently, a 24-year-old named Leopold Aschenbrenner has delivered returns of more than 1,000% in the two years since he founded a hedge fund to bet on AI stocks. But cases like this are the exceptions that prove the rule. For most investors, most of the time, the data tell us that it’s better to trade less rather than more. Market tops. On a related note, there’s a tale about Joseph Kennedy—President Kennedy’s father. He was an active investor in the 1920s, but he said he realized it was time to sell when the fellow giving him a shoeshine one day started offering stock tips. What’s interesting about this story is that Kennedy did actually sell his stocks and even took a short position early in 1929, earning him a fortune when the market dropped. The shoeshine aspect of this story likely isn’t true. But it’s a favorite because it carries a useful message. Veteran investor Jeremy Grantham has often talked about the market signals he pays attention to. In addition to P/E ratios and other quantitative measures, he’s noted that he looks for “signs of craziness”—things like the GameStop mania in 2021. When the stock market begins to look more like a casino—and when we see YouTube influencers making stock calls from their gaming chairs—Grantham gets nervous. Intuitively, this does make sense, but it may not be very useful. Consider how the market has performed in recent years. After Grantham urged caution in 2021, the market did drop in 2022. But then it rose in 2023, 2024, 2025 and in the first half of 2026. So an investor who sold in 2021 would have missed out on significant gains. The bottom line: Just as the number of world-class stock-pickers is limited, so too is the number of tactical traders who have profited in the way Joe Kennedy did by getting out at just the right moment. Market forecasts. What’s a better way to think about the stock market? According to another Wall Street tale, J.P. Morgan was once asked what he thought the market would do over the coming year. His reply: “It will fluctuate.” There’s no evidence that Morgan ever actually said this, but in this case too, the story is popular because it sounds right. And in my view, this is exactly the right way to think about the stock market. At the end of the day, the only thing we can know for sure about the stock market is that it will either go up, go down or stay about the same. If we can structure our portfolios so we won’t be too negatively affected whichever way it goes, that, in my opinion, is the road to success.   Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.
Read more »

Lessons Learned Along the Way

"It was quite an adventure. I can't have any regrets because I have ended up in a very good place. I am grateful for that."
- Dan Smith
Read more »

Does Vanguard Know Something?

"Well, quick solutions are either an equal weight fund (not quite 493, but minimizes the concentration issue) or an S+P fund plus 7 put options. The risk is real; are you willing to pull the trigger on a change, though?"
- Mike inLA
Read more »

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Manifesto

NO. 15: WE SHOULD retire our debts before we retire from our job. Paying off debt cuts our living expenses, plus that debt is likely costing us more than we’re earning on our bonds.

humans

NO. 34: WE overestimate our investment results. Got folks boasting about their portfolio’s performance? They may be ignoring the losers they’ve sold, bragging based on a few winners and failing to compare to an appropriate index. They may also suffer from the endowment effect, believing their winners have performed better than they really have.

act

INVEST YOUR TAXABLE account thoughtfully. If you purchase the wrong investments in your taxable account, you may be reluctant to sell because you’ll trigger capital gains taxes. A good choice: low-cost U.S. and international total stock market index funds, which should be tax-efficient—and which shouldn’t ever lag far behind the market averages.

think

ARRIVAL FALLACY. We strive mightily to get that next promotion or amass $1 million, confident we’ll be supremely happy once we achieve our goal. But the resulting happiness quickly slips away. What to do? We should pursue goals where we know we’ll enjoy the journey—and we should make sure we have new goals to replace the ones we achieve.

Forum

Manifesto

NO. 15: WE SHOULD retire our debts before we retire from our job. Paying off debt cuts our living expenses, plus that debt is likely costing us more than we’re earning on our bonds.

Spotlight: Estate Plan

Tempus Fugit, Vol II

Last month, I wrote about a spate of funerals my wife and I attended.  Since then, I recently found out that a close friend and colleague in his early 60s was diagnosed with a “butterfly glioblastoma,” a rare and aggressive form of brain tumor. It’s a recent diagnosis, and his treatment plan is being finalized. A few friends and I drove an hour and a half to take him out to lunch earlier in the week,

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Exit Strategy

IF YOU’RE LIKE ME, you aren’t eager to spend down your investments. What fun is that? Aren’t you curious to see how big your portfolio could grow? Of course, you are.
After my wife and I are gone, my son will have dibs on the money we’ve amassed. We’ve set up a special needs trust to provide him with income when we’re no longer around. My son has no siblings, so we needed the trust to make sure he’s taken care of.

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Preparing for the Unthinkable

My wife and I moved from PA to NJ about 3 years ago. After we moved I looked into whether we should update our estate documents since we changed states. It seemed like a smart thing to do, but it took us 3 years to get around to it.
We recently met with a local estate attorney and reviewed our wills and POAs. There was some specific Pennsylvania language having to do with setting up a trust for contingency heirs – our grandsons – if one of our sons pre-deceased us.

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Unsettling Experience

MOM AND DAD WERE products of the Great Depression. I feel like it affected every single day of their lives. Despite their difficult upbringing, they made good financial decisions that allowed them to live comfortably. Part of it was because Dad worked for the same company for almost 42 years. His pension paid him more than I earned in my first job as an engineer.
When Mom died in August 2004, she was almost 84.

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Shrink That Estate

I OUTLINED 10 REASONS everybody should have an estate plan in a 2018 article—and what was true then remains true today, especially for those whose assets could be subject to estate taxes.
Under today’s rules, the federal estate tax applies to individuals with assets over $12.9 million. That might sound like a high number. But in 2026, the limit is set to be cut in half. In addition, many states impose their own estate tax,

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Misplaced Trust

WHEN I WAS A YOUNG adult, my parents sat me down and explained that I might at some point inherit money from my grandfather’s trust, which had also helped put me through college. My grandfather passed away in 1984, and his wife—my father’s stepmother—became the trust’s beneficiary.
My father was an only child. The trust stipulated that, if his stepmother died before him, he would receive two-thirds of the trust, while my two siblings and I would share the other third.

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Spotlight: Mcintosh

Take It to the Limit?

LIKE SOME OF YOU reading this, I get a thrill from seeing my 401(k) contributions start at zero in January and tick up to the annual limit. I’ve been fortunate to maximize my contributions for most of my 24 working years. Last year, my contributions topped out at the 2021 limit of $19,500. In 2022, I’m aiming to make the maximum contribution of $20,500. For those age 50 and older, you can contribute up to $27,000 in 2022. Up to now, I’ve considered it a no-brainer to contribute the 401(k) max. While I’m not making any changes this year, I am starting to think differently as I inch closer to retirement. If you’re in a similar situation, here are three factors you may want to consider when deciding how much to contribute. First, if you’re in a low-tax bracket or live in a low-tax state, the tax benefit of contributing pretax dollars to a 401(k) account could be minimal. If you think your tax rate will be higher in retirement, you could be better off investing through a standard brokerage account and paying tax on your earnings now. You could also opt for a Roth 401(k) if your employer offers that option. Factors that might drive your future tax rate higher include a retirement account that’ll generate significant income or plans to move to a higher-tax state. A second factor to consider is how you’ll invest the funds. If you will be conservative when investing 401(k) contributions, the benefit of deferring tax on investment earnings will be minimal. It may be worth paying the small annual tax bill and having immediate access to your savings. Finally, you should consider how long the funds will be in the 401(k) account. If you have many years—or even decades—before you’ll withdraw the funds,…
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Betting Against

I’M USUALLY BORING when it comes to investing. My portfolio is mostly comprised of stock and bond index funds. I dabble in individual stocks when I come across something I see as interesting, but individual stocks have never made up more than 5% of my portfolio. I currently hold just three individual stocks amounting to less than 2% of my investment holdings. While my interest is occasionally piqued by stocks with upside potential, I’m more often drawn to companies I see as having significant downside. This glass-half-empty orientation likely reflects the professional skepticism that comes with being a CPA. I’ve never acted on my bearish instincts—until now. Recent developments at Peloton Interactive (symbol: PTON) have led me to wager that the stock will continue declining. I’ve followed Peloton closely for years. I love its product. But a series of management missteps have caused me—and many others—to become bearish on the stock. The company’s troubles have included bungling a product recall and unexpectedly bad financial performance. The last straw for me: Peloton recently raised $1 billion through a stock sale—just two weeks after the company’s chief financial officer indicated such an infusion of capital was unnecessary. To act on my bearishness, I decided that buying a put option was the most prudent approach. Unlike shorting a stock—which has an unlimited downside if shares rise—a put option limits my possible loss to the premium I pay for the put. After considering the array of options available, I paid $200 for a put that gives me the right to sell 100 shares of Peloton at a “strike price” of $35 a share in April 2022. There’s a wide range of possible outcomes for this option position, but I’ll give two possibilities. If the stock trades above $35 in April 2022—which is likely, given…
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Value Machine

SEPTEMBER WAS A BIG anniversary month for us. In addition to celebrating our 19th wedding anniversary, we celebrated our third Pelo-versary. In the words of my mother-in-law, we are Peloton addicts. Ask us about our favorite instructors at your own risk. The general perception of Peloton—for which the entry price is now $1,495—is that it’s priced too high for most people. While I don’t believe that Peloton is “democratizing fitness,” as its CEO suggests, I do see solid value in Peloton bikes for households that’ll use them consistently. As early adopters of Peloton, we paid $2,200 for our bike, shoes and delivery. We also pay $39 per month to be “connected fitness users,” which allows us to take live and on-demand classes. Our membership covers all four members of our household, though my wife and I are the main users. In addition to bike classes, we have access to strength, yoga, stretching and bootcamp classes. How can a $2,200 bike with a $39 monthly fee be a good value? First, if we spread the $2,200 over the past 36 months and add the monthly fee, the monthly cost is $100. That average compares favorably to what we’d pay for two high-quality gym memberships here in California. Further, if we assume the bike will last two more years, the average monthly cost becomes $76 and the comparison favors Peloton even more. And, of course, the value equation is even better for those buying at today’s lower price point. Another way I look at value is based on cost per workout. Since 2018, between my wife and me, we’ve completed almost 3,000 classes. As we usually complete two or three classes during each workout session, we’ve done about 1,200 workouts—which usually last between 45 and 60 minutes—in the past three years. This…
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College Savings Forum

Over the last 17 years, I have been saving a modest amount each month in a 529 plan. I have been doing the same for my daughter for the past 14 years. Given the market performance and our steady contributions over time, these modest monthly contributions have grown to be a sizable amount. While I am thrilled that we should have most of our college cost covered, I've often wondered if the 529 plan was the best bet in saving for college. I have done much thinking on this topic, and I'm sure many others have as well. I am creating this forum to share some analysis/thinking on this subject and to hear what others have to say.
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Kids These Days

A FEW WEEKS BACK, Jonathan Clements wrote an article reminding readers that they, too, likely made financial missteps in their younger days. His article was in response to comments by HumbleDollar readers about the perceived lack of financial discipline shown by those currently in their late teens and early 20s. Before my recent career change, I would’ve had the same opinion as many readers. With my new job teaching accounting to undergraduates, however, my perspective has changed. While it’s hard to ignore the pricey lattes accompanying many students to class, I’m bullish on the financial future of today’s college students. First, most students are hustlers. Because of the high cost of college, students often work one or more jobs to help pay for college. I have one student who closely monitors his DoorDash app and knows the optimal times of the week to jump in his car to deliver food. This DoorDash driving is on top of his other work and athletic commitments. I also see students taking advantage of internship opportunities. Given the tight labor market, there’s high demand for student workers among local businesses, especially in accounting. I have one student who will have two paid internships during the spring semester. Instead of relaxing because of a lighter-than-usual course load, she’s ramping up the experience—and income—she’ll collect before she graduates. Another trend I’ve seen: Students are much more interested in stock investing than I was as an undergraduate in the 1990s. I’m regularly approached by students who want to learn how to read financial statements and do fundamental stock analysis. I recently had lunch with a freshman who was keen to learn about the meaning of price-earnings ratios and dividend yields. This student now researches stocks and sends investment ideas to me on a regular basis. A final heart-warmer…
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Hotels Over Coffee

WHEN I MATCHED UP our monthly spending with the terms of the Starbucks Rewards Visa card, I calculated that I could potentially get a free drip coffee every day of the year. Given the proliferation of Starbucks in our Los Angeles suburb—including one within 400 yards of my office—it’s tempting to cover my caffeination by swiping my credit card. After some deliberation, however, I’m going to focus instead on amassing travel rewards points. For the past five years, I’ve used the Marriott Rewards credit card, which gives me at least one hotel point for each dollar I spend. The key reason I like this card: With my spending, I’m effectively forcing myself to save for a vacation. While a daily Starbucks coffee would be nice, I can see this reward getting old after a few weeks. I treat myself to Starbucks once or twice per week. A daily dose may be too much. I view it as more prudent to save for a big experience a few times each year rather than focus on getting my daily coffee comped. Another solid feature of the Marriott card: The effective rewards rate compares well to the teaser rates advertised by cash-back cards. Based on our spending level, I place the value for the free nights we earn at about 1.7% of our total spending. While that’s lower than the 2% that Katie Ledecky was advertising during the Olympics, we have a lot more fun with our free hotel nights than we’d get from a periodic credit on our billing statement. An additional benefit I’ve been impressed by—and one not to be taken lightly when evaluating cards—is that it’s been easy to use our hotel points. The rewards points post soon after the dollars are spent, and we’ve never had an issue getting…
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