Buying a stock is a moment of great hope. Owning it is a daily reality check.
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. 75: WANT TO give to charity or family? We’ll boost happiness and possibly save on taxes by giving now. But if we’re struggling to fund retirement, we should bequeath the money instead.
NO. 47: STRIVING to preserve principal often destroys it. As you aim to maintain your portfolio’s nominal value, you’ll likely buy bonds and cash investments—and could find yourself losing ground to inflation. Worse still, you may chase yield, buying supposedly safe investments that promise big payouts, but which may instead suffer sharp price drops.
MONEY ILLUSION. We have the illusion we’re doing better if we earn 5% on our savings rather than 1%, even if these yields simply match the inflation rate—and hence in both cases we aren’t making any financial progress. In fact, earning 5% when inflation is 5% leaves us worse off, because we’ll lose more to taxes than in the lower-yielding scenario.
PREPARE FOR a long life. For a quick gauge of your life expectancy, try the Social Security and Society of Actuaries' Longevity Illustrator calculators. What will you learn? First, the longer you live, the longer you can expect to live. Second, lifespans vary widely. Educated, health-conscious Americans might live three or four years longer than average.
NO. 75: WANT TO give to charity or family? We’ll boost happiness and possibly save on taxes by giving now. But if we’re struggling to fund retirement, we should bequeath the money instead.
AS A PHYSICAL therapist, I’ve spent a large slice of each work day teaching and encouraging patients as they exercise their way to better health. Along with other elements of treatment, each patient pays for a custom exercise program tailored for their specific problem.
These are folks looking for a way past the debilitating effects of injury or disease. Even so, many of them find it hard to follow my plea to “do your exercises”.
Physical strength is essential to making our way in this world. While we may not have to rally our muscles to subdue wild beasts or unruly neighbors, we do need them to accomplish our daily objectives. At a minimum, we have to muster the energy to get from bed to bathroom to breakfast table. Even if we make money with our minds, rather than our bodies, chances are we’ll need the stamina to sit up and manipulate a keyboard.
For us Medicare types, it’s that Part D time of year again. In mid-September I received an email from our Part D insurer, Aetna Silverscript, saying I could see the Annual Notice of Change online. I did so and got a shock. My wife’s and my monthly premiums were going from $9.80 each to $44.80 each beginning in January 2025.
I did a little reading online, and contacted our broker, and learned that due to some recent legislation Part D plans were in for some big changes in 2025.
Not that this is a great surprise but a sad state affairs for those who are enticed by the “low” premiums with added benefits but feel eventually trapped by MA when they need it the most. For the folks in NY (in this article) who are lucky enough to be able to switch from MA to Original Medicare. I can’t imagine for those in states where they can’t switch and are truly trapped.
https://www.msn.com/en-us/money/insurance/the-sickest-patients-are-fleeing-private-medicare-plans-costing-taxpayers-billions/ar-AA1tUtML?ocid=nl_article_link
One of the most well known advocates for elder care, who worked for a prominent national health center, was talking with me about a year ago. When I asked him what his plan was for he and his wife, as they aged, he replied “ I have four daughters”.
This was pretty shocking to me, given that he worked in this industry, and specialized in helping adult children and their parents to talk about future health care planning.
How long will we live? Based on an article I just read, I’m guessing that it is probably longer than we think. Here’s why.
The authors pointed out that statistics (and I suspect my intuition) are based on death rates, which only take into account the people who have…wait for it…already died. Those still alive are living longer than they used to, based on the trend of longer, healthier life that has persisted up until now.
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Tax Efficiency
ArticleBogdan Sheremeta | Apr 4, 2026
TAX EFFICIENT FUND placement is an often underrated topic. The goal of the tax efficient fund placement is to minimize taxes within your investments, and select the right account for those investments.
But how much does that actually matter?
Vanguard’s research finds that a thoughtful asset location strategy can add significantly more value than an equal location strategy. The value added typically ranges from 5 to 30 basis points of after-tax return, depending on circumstances (e.g., income, portfolio size).
Investors generally have access to different account types, including:
If you are an employee that may not have access to a retirement plan, you could perhaps consider a Solo 401(k) if you have "side hustle" business income.
Generally, if your investments are all in tax-deferred or tax-free accounts, fund placement will not make a huge difference for you. That is because these accounts already come with tax efficiency.
If that's your case, two things become important though:
1. Consideration between pre-tax, like Traditional 401(k) or after-tax account, like Roth 401(k). Put simply, this decision generally comes down to your marginal tax rate now versus marginal tax rate in the future (which isn't something easy to predict due to the ever-changing tax landscape).
2. Account allocation. It becomes equally important where exactly you are investing. Roth accounts grow tax-free and qualified withdrawals are tax-free. You likely don't want to hinder that growth by choosing conservative assets (like fixed income, Money Market Funds, and so on).
Tax-efficient fund placement becomes extremely important when you also have a taxable brokerage account, along with tax-advantaged accounts. Many funds pay dividends and distribute capital gains if placed in your taxable brokerage account. At the end of the year, you receive a 1099 with that income and must pay taxes on the dividends and certain distributions.
One thing to call out from history is that you generally shouldn't hold Target Date Retirement mutual funds (or any "proprietary" funds) in your brokerage account. This is because unexpected redemptions could cause a huge tax bill.
You may remember a Vanguard 2021 fiasco where Vanguard opened an institutional TDF to more investors (lowered the minimum investment from $100M to $5M), which caused smaller retirement plans to sell out of individual funds and move into the institutional fund. This triggered massive unexpected capital gains for anyone invested in the individual funds if held in a brokerage account.
All of those unnecessary taxes could've been avoided by:
Let me give you a simple example:
Let’s say you are in a 22% federal tax bracket and a 5% state tax bracket, and you have some money invested in a dividend fund like Schwab US Dividend Equity ETF (SCHD). SCHD dividends are generally qualified, which means that the dividends get preferential treatment at a 15% federal tax rate for this investor.
The dividend yield is 3.43%. Considering the tax rates, the tax drag is (15% + 5%) * 3.43% = 0.686%.
To put this in perspective, a $10,000 investment will yield ~$343 in annual dividends. The tax impact on that investment will be $60.86.
Of course, if that money was in a Roth IRA, you would pay $0 in taxes on dividend distributions. Alternatively, this is something you may need to decide whether a dividend-focused investing strategy is the right one for you. For example, a Total US Stock Market ETF could have almost 3x less tax drag, and potentially more growth.
As someone in their 20s (who is subject to the Net Investment Income Tax) my focus is 100% on a growth investment strategy, rather than income generation. For someone in their 60s, that strategy could be different (even though selling shares for capital gains is better from a tax timing point of view).
A few more important points:
REIT stocks/ETFs are the least tax-efficient asset class to hold in a brokerage account because their distributions aren’t qualified, so you pay more tax (even though it may qualify for a 199A deduction).
Stocks that don’t pay dividends are the most tax-efficient to hold within your taxable account (Adobe, Amazon, Netflix, and others). However, holding individual stocks may not be the best strategy from an investment and diversification standpoint.
A big benefit of a taxable account is that the money is always easily accessible (liquidity), and you can control your withdrawal timing. While there are strategies that allow you to withdraw from retirement accounts before age 59 (like Rule of 55, 72(t) SoSEPP, Roth conversions), a brokerage account is more flexible. Therefore, analyzing the contributions and investments that go into this account is crucial.
How do you maximize tax efficiency? Let us know in the comments!
Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.