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Adam M. Grossman

Adam M. Grossman

Adam is the founder of Mayport, a fixed-fee wealth management firm. He advocates an evidence-based approach to personal finance. Adam has written more than 400 articles for HumbleDollar.

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Decision Frameworks

Adam M. Grossman  |  Nov 29, 2025

IN THE SUMMER of 1966, author John McPhee spent two weeks lying on a picnic table in his backyard. Why?
McPhee was suffering from writer’s block. As he described it, “I had assembled enough material to fill a silo, and now I had no idea what to do with it.”
Investors find themselves in a similar situation today. There’s no shortage of financial information around us. But that doesn’t make it easier to know what to do with it. 

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Money, Happiness, and Choice

Adam M. Grossman  |  Nov 22, 2025

FOR DECADES, RESEARCHERS have been looking at the link between money and happiness. The findings? In short, it’s a mixed bag.
To be sure, there are ways that money can boost happiness, and below are some ideas to consider. But there are also obstacles to contend with. We’ll look first at the obstacles before turning to the recommendations. 
The most significant challenge is the fact that—to a great extent—our happiness level is hard-wired into us.

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Private Equity Traps

Adam M. Grossman  |  Nov 15, 2025

IN APRIL 2005, art dealers Robert Simon and Alex Parish traveled to New Orleans to attend an auction. They were particularly interested in a work titled Salvator Mundi. The painting was in bad shape, having been neglected for years. But Simon and Parish ended up bidding on it and taking it home for $10,000.
After some restoration work, the pair succeeded in having it authenticated as a work of Leonardo da Vinci.

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AI Rally Market Risks

Adam M. Grossman  |  Nov 8, 2025

LAST WEEK, OPENAI founder Sam Altman sat down for an interview with venture capitalist Brad Gerstner and Microsoft CEO Satya Nadella. Both are investors in OpenAI, so it seemed like a friendly audience. But Gerstner posed a question that seemed to make Altman uncomfortable.
Since introducing ChatGPT three years ago, OpenAI has posted impressive growth, but Gerstner wondered whether the company was, nonetheless, getting ahead of itself.
“How can a company with $13 billion in revenues make $1.4 trillion of spend commitments?” Gerstner asked.

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Lessons from First Brands

Adam M. Grossman  |  Nov 1, 2025

SOME NEWS STORIES are unusual in ways that it’s hard to know what to make of them. Such is the case with the recent collapse of a relatively unknown company called First Brands.
On the surface, it might seem like a mundane story. First Brands is an auto parts supplier, making commodity items like brake pads and windshield wipers. The company was founded in 2013 by a fellow named Patrick James, who built it up over the years by acquiring several other,

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The Paradox of Smart Money Decisions

Adam M. Grossman  |  Oct 25, 2025

SOME YEARS AGO, the scientist Edward Fredkin identified a quirk of human behavior.
When it comes to making decisions, Fredkin found, we tend to allocate our time inefficiently. Suppose, for example, you’re at the grocery store, looking for something basic like paper towels. In a big supermarket, there might be a dozen or more choices. The result: Because there are so many options, it can be hard to choose among them. In the absence of big differences,

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Is The Stock Market Overvalued?

Adam M. Grossman  |  Oct 18, 2025

STOCK MARKET INVESTORS are enjoying yet another strong year. The S&P 500 has gained about 14% so far, shrugging off, for the most part, uncertainty over tariffs, interest rates and the latest government shutdown.
Should this worry us?
Since ancient times, soothsayers have been attempting—without luck—to forecast the future. As it relates to investment markets, the frustrating reality is that no one knows what the future will bring. But that doesn’t mean there’s nothing we can do.

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How Not To Invest

Adam M. Grossman  |  Oct 11, 2025

BARRY RITHOLTZ’S NEW BOOK, How Not to Invest, offers investors a cautionary tale—many of them, in fact.
Ritholtz has been in and around the investment industry for more than 30 years—as a trader, a journalist and, most recently, as cofounder of a wealth management firm. 
In short, he is no stranger to Wall Street. His conclusion? It can be a minefield.
Bad actors like Charles Ponzi and Bernie Madoff are well known.

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Managing Concentration Risk

Adam M. Grossman  |  Oct 4, 2025

LARRY ELLISON, THE 81-YEAR-OLD cofounder of Oracle Corporation, recently became the world’s wealthiest person.
Oracle, a software company, isn’t nearly as large as its peers. So how did Ellison’s net worth manage to surpass that of Bill Gates, Jeff Bezos and the founders of other much larger companies?
The answer is simple: In the nearly 50 years since Oracle’s founding, Ellison has almost never sold a share of his company’s stock. According to an analysis by Smart Insider,

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Tributes to Jonathan Clements

Adam M. Grossman  |  Sep 27, 2025

HUMBLEDOLLAR FOUNDER and longtime Wall Street Journal columnist Jonathan Clements passed away earlier this week. He was 62.
I reached out to several of Jonathan’s close friends and colleagues to ask for their remembrances. Taken together, they paint a picture of someone who was as beloved by his peers as he was by his readers.
As Jason Zweig put it, “I have just lost a friend, and so have you.”
Christine Benz,

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Best Bond Funds for Your Portfolio: Treasurys, Corporates, and Municipals Explained

Adam M. Grossman  |  Sep 20, 2025

FOR MANY INVESTORS, talking about bonds is about as interesting as watching paint dry. They aren’t nearly as interesting as stocks. But if you have a portion of your portfolio allocated to bonds, or plan to, it’s a topic worth some discussion.
The bond market is actually much larger and much more diverse than the stock market. For most investors, though, there are just a few types of bonds to consider. We can examine each in turn:
Total Bond Market
Perhaps the most well known type of bond investment is a total-market fund.

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Navigating the Unknowns of Financial Decisions

Adam M. Grossman  |  Sep 13, 2025

WHEN IT COMES to financial decisions, there are, as I’ve argued before, two answers to every question: what the calculator says, and how you feel about it. There’s a fly in the ointment, though: Calculator answers might appear to be based in logic, but they’re still imperfect.
Why?
Ian Wilson, a former executive at General Electric, explained it this way: “No amount of sophistication is going to allay the fact that all knowledge is about the past,

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Inventing Problems

Adam M. Grossman  |  Sep 6, 2025

“INVESTING IS SIMPLE,” observed HumbleDollar’s editor Jonathan Clements. “To be sure, you can make it ludicrously complicated.” And, indeed, Wall Street does just that.
According to a recent analysis by Bloomberg, the fund industry rolled out more than 640 new exchange-traded funds (ETFs) in the first half of this year—an average of more than three a day. There are now more ETFs in the U.S. than there are stocks (4,300 vs. 4,200).

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Risky Business

Adam M. Grossman  |  Aug 30, 2025

NEW RESEARCH CAN help with an age-old question: When constructing a portfolio, how much risk is too much? Especially today, with the market again near all-time highs, this is an important issue.
On the one hand, we could dismiss this concern by noting that all-time highs aren’t as uncommon as they might seem. According to one analysis, the U.S. stock market has been within 5% of an all-time high on 44% of trading days since the 1950s.

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How to Beat the Market

Adam M. Grossman  |  Aug 23, 2025

ANDREW CARNEGIE USED to say that competitors were welcome to tour his factory, to see his production line up close. Why? Because of Carnegie Steel’s massive scale and complex operations, he was confident no one would ever be able to replicate what he’d built.
Hedge fund manager Seth Klarman is a modern-day Carnegie. Klarman founded the Boston-based Baupost Group in 1982, and while performance numbers aren’t publicly available, the firm’s track record is believed to be among the best in the industry.

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