How to outshine competing investors: Save more, pay lower costs, manage risk better—and think longer term.
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.NO. 32: WE SHOULD start with the global market portfolio—the investments we collectively own—and decide what we don’t want in our portfolio. Often, foreign bonds are the biggest subtraction.
NO. 40: NOTHING generates spectacular returns forever. Investment trends can last far longer than expected and, after a few years, further gains can seem inevitable. But that sense of inevitability encourages investors to pay prices far above what the fundamentals justify—and those fundamentals eventually drag the highfliers back to earth.
IMAGINE YOU WERE the executor for your own estate. What would make your job easier? You might consolidate financial accounts, shed illiquid assets like collectibles and investments in private businesses, draw up a letter of last instruction that details all assets and debts, organize key documents, and compile a list of usernames and passwords.
CURRENT VS. FUTURE self. Our daily lives are a constant battle between the whiny demands of our current self and the needs of our future self. We know it would be better for our future self if we exercised, ate healthily and saved diligently—and yet, all too often, we give in to our current self, who wants to sit on the couch, eat junk food and shop online.
NO. 32: WE SHOULD start with the global market portfolio—the investments we collectively own—and decide what we don’t want in our portfolio. Often, foreign bonds are the biggest subtraction.
I GREW UP IN a lower-middle-class family. We lived in a small apartment where I slept on the living room couch. My father sold cars for a living.
Today, my living standard is quite different. On average, 97% of retirees my age have less income and assets than my wife and me. Our friends are in similar economic circumstances. If they weren’t, they couldn’t live where we do.
The minimum needed to live in our condo community is $24,000 a year.
For more years than I remember I have saved my pocket change. Every day I put it in a tray on my dresser. When it overflows, Connie bags it and eventually rolls it for deposit. That happens at around $80.00.
I never pass a penny on the ground. In fact, on occasion I dig one out of the soft tar. Some coins are so mangled it’s hard to tell what they are at first. Sometimes people stare at me,
ONCE UPON A TIME, I thought it was a little unseemly to pay a lot of attention to costs. My father grew up in a farm family with little money. He was the first to attend college and, indeed, went on to law school from there. He did well in his profession and, when I was growing up, we lived a comfortable—though far from luxurious—life.
Maybe because he’d spent his youth worried about money,
IF YOU HAVE A SURPLUS in your household budget, what’s the best use for it? Does it make more sense to pay down debt or to invest those extra funds? With interest rates at such low levels, this is a question I’ve been hearing with increasing frequency.
Suppose your mortgage rate is 3.5%. If you pay down that debt, it’s like earning 3.5%. By contrast, if you invested in the stock market, your annual return would be uncertain.
HERE’S A SOBERING thought: Much—and perhaps most—of the money you’ll accumulate for retirement will reflect the raw dollars you sock away and not the investment returns you earn.
Consider a simple example. Let’s say retirement is 40 years away and your goal is to quit with $1 million. Let’s also assume you can earn an after-inflation “real” annual return of 4%, which is my best guess for the long-run return on a globally diversified,
ACCORDING TO THE World Happiness Report, Finland ranks as the happiest nation in the world, a title it’s held for eight years in a row.
Each time this report is updated, it makes the news for a day or two but then fades. That’s for good reason, I think. As much as Finland might be a nice place, it isn’t necessarily practical to suggest that anyone pick up and move.
The good news, though,
HSA Tips
Bogdan Sheremeta | Feb 28, 2026
- Contributions are tax-deductible
- Earnings grow tax-free
- Withdrawals are tax-free if used for medical expenses
One of the best uses of an HSA is to actually invest the balance. For example, I keep $500 (the minimum required balance) in cash. The rest, I invest in low-cost index funds. This allows me to maximize compounding inside the HSA account. I also receive a $1,000 HSA match. Since I’m young and my medical expenses are low, it’s a great way to minimize taxes and grow the balance. I will also not touch my HSA at all, even if I have medical expenses. I will reimburse myself 20-30 years down the road (more on this in a bit). But if you are paying medical expenses with the HSA, you should have at least a portion of the funds in a Treasury fund or money market fund (MMF) for stability. Generally, this amount should be equal to at least one year of deductible costs. Rules To contribute to an HSA, three things must happen:- You need a high deductible health plan (HDHP). You cannot contribute to an HSA without one. A “high deductible health plan” is defined under §223(c)(2)(A) as a health plan with an annual deductible of more than $1,700 for self-only coverage or $3,400 for family coverage. The maximum out-of-pocket limit is $8,500 or $17,000 (family).
Importantly, before enrolling in a high deductible plan, you need to decide whether it’s worth it in the first place. You will generally receive the biggest benefit from an HDHP if you are in good health (more on this in a bit). 2. You aren’t enrolled in Medicare. 3. You cannot be claimed as a dependent. Importantly, the HSA balance never expires. This account is always yours to keep, even if you leave your employer. Some people confuse an HSA with an FSA (which does expire, aside from a small potential rollover option). The account typically works like a “bank account,” where you make deposits and can withdraw money via online transfers or checks, or invest it like a brokerage account. Contributions The 2026 contribution limit is $4,400 for an individual plan and $8,750 for a family plan, with an additional $1,000 catch-up contribution if you are 55 or older. The contribution limit includes both your contributions and your employer’s contributions. If your employer allows it, contributing to an HSA via payroll deduction is generally better than contributing directly, as it avoids the 7.65% FICA (Social Security and Medicare) taxes. Direct, after-tax contributions only save on income tax when filing, missing the payroll tax savings. Withdrawals Withdrawals for medical expenses are tax-free. IRS Publication 502 has information about which expenses qualify as medical expenses. In addition, as long as you keep proper records, you can reimburse yourself in a later year. I keep track of all my medical expenses in a spreadsheet (e.g., with columns for EOB documents, receipts, bills, etc). I plan to reimburse myself in the future, assuming the law doesn’t change. In 2025, House Bill 6183 was proposed to change the reimbursement limit to expenses no older than two years, but it didn’t gain any traction. If there is a change in legislation, I plan to reimburse myself for all prior medical expenses before enactment. Once you turn 65, you can withdraw money from your HSA for any reason without penalty. However, you will owe income taxes on any non-medical withdrawals, effectively making this similar to a Traditional 401(k) or IRA. Inheriting an HSA Per Publication 969, if your spouse is the designated beneficiary of your HSA, it will be treated as your spouse’s HSA after your death. If your spouse isn’t the designated beneficiary (e.g. your child is the beneficiary), the account stops being an HSA and the fair market value of the HSA becomes taxable to the beneficiary in the year in which you pass away. This is why tax free HSA dollars should ideally be spent before passing down an inheritance due to tax inefficiency. On the other hand, naming a beneficiary in a low-income tax bracket to receive the deceased person’s HSA can also be beneficial for tax purposes. HSA can be powerful, but make sure the math makes sense. If you spend thousands of dollars on medical bills, having a standard plan could outweigh all the tax savings you can get.It’s Never Too Late
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