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Adam Grossman

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    • I once asked Jonathan the origin of the HumbleDollar name, and this is how he explained it: "I racked my brain for months trying to come up with a name for the site. It had to be something to do with money, and I wanted a word that would express my financial philosophy. Somewhere in the middle of the night, the words 'humble' and 'dollar' met in my brain. I got out of bed, it was 2:00 a.m., and I went to GoDaddy and banged in humbledollar.com, and it was available. And that’s how HumbleDollar was born."

      Post: Why HumbleDollar?

      Link to comment from September 22, 2026

    • Thank you. That 1996 article is terrific. No surprise that Jonathan was 30 years ahead of me in articulating these points!

      Post: 2026 Financial Plan

      Link to comment from January 4, 2026

    • Edmund, this is such an important topic. Often, finances are where signs of cognitive decline first appear -- e.g., missed bills. Sadly, some number of people inadvertently let their life insurance policies lapse each year after years, or even decades, of making payments. There's also a lot of elder financial abuse. It's great when older folks allow their adult children to be involved, if only as another set of eyes.

      Post: Decision Frameworks

      Link to comment from November 30, 2025

    • Thanks, David. I'll second that recommendation on "Thinking in Bets."

      Post: Decision Frameworks

      Link to comment from November 30, 2025

    • Thanks, Martin. I'm 100% with you on simplicity. It's a virtue in my general, I think, but especially when it comes to investments. It's an uphill battle, though, because Wall Street loves financial engineering and is very good at marketing their latest concoctions.

      Post: Decision Frameworks

      Link to comment from November 30, 2025

    • Very true. Organizing your thoughts is at least half the battle. When I was in school, I remember being most impressed by the kids who asked questions that I hadn't even thought of.

      Post: Decision Frameworks

      Link to comment from November 30, 2025

    • Thanks for sharing your story. I've seen this up close too. I think a key challenge is that you can spend all day analyzing an investment (as I once did myself), but since no one can see the future, it's still hard to get it right. In other words, a lot of people in wealth management are well-intentioned, but in many cases, they're trying to do something which is nearly impossible.

      Post: Decision Frameworks

      Link to comment from November 30, 2025

    • Thank you. The most well known proponent of frameworks was probably Charlie Munger. It's a great way to approach questions.

      Post: Decision Frameworks

      Link to comment from November 30, 2025

    • Agreed. I thought it was so meaningful that in Jonathan's last year, he continued to work on HumbleDollar because that was what made him happy. In other words, when he received his diagnosis, the fact that he didn't decide to do anything different was confirmation that he was already spending his time exactly as he wanted.

      Post: Money, Happiness, and Choice

      Link to comment from November 23, 2025

    • That's another area where the research is clear: Social media definitely contributes to unhappiness. Even people who don't observe the religious Sabbath have started to observe a digital sabbath when they put away their phones, and that seems like a nice idea.

      Post: Money, Happiness, and Choice

      Link to comment from November 23, 2025

    Articles

    Why Bonds Matter

    Adam M. Grossman   |  Oct 3, 2026

    RECENTLY, A READER—let’s call him Tom—posed this question: If stocks historically have delivered far better returns than bonds, then why should an investor own any bonds at all? Even with the stock market’s unpredictable ups and downs, wouldn’t you end up way ahead by betting only on stocks over the long term?
    It’s a fair question. Over the past 100 years, stocks have delivered returns of roughly 10% per year, while bonds have returned just 5%.

    Financial Lessons

    Adam M. Grossman   |  Sep 26, 2026

    WHAT’S THE MOST important idea in personal finance? It’s hard to single out just one, but over the years, I’ve found the following dozen ideas to be among the most useful.

    Whether it’s on TV or online, there’s never any shortage of market prognosticators. Especially during a bull market, everyone seems to have an opinion on where things are headed. The reality, though, is that people can only guess about how the economy, the market or any individual investment will perform.

    Structuring Bonds

    Adam M. Grossman   |  Sep 19, 2026

    IT’S BEEN AN UNUSUAL week in the bond market, and not necessarily in a good way. This has many investors questioning the value of bonds, which is understandable. Bonds are supposed to be the “safe” side of a portfolio, but they’ve struggled in recent years.
    Arguably, the drama we’re seeing in the bond market today began more than 50 years ago. To put today’s situation in perspective, I’ll briefly summarize that long history. Then we can look at what steps you might take to better protect your portfolio from here.

    Financial Choices

    Adam M. Grossman   |  Sep 12, 2026

    FOR MUCH OF THE seventeenth and eighteenth centuries, European monarchs used a financial instrument known as a tontine to help finance their governments. 
    Tontines were first developed in the 1650s by an Italian government worker named Lorenzo Tonti and were similar to annuities: In exchange for a single, lump-sum purchase, tontines offered guaranteed payments for life. But tontines also offered some unique features.
    Unlike an annuity, where payments end with the death of the owner,

    Financial Fraud

    Adam M. Grossman   |  Sep 5, 2026

    RECENTLY, A FELLOW—let’s call him Tom—contacted me with a distressing story of financial fraud. I’ll describe what happened then review steps you might take to prevent this same sort of thing.
    Tom first noticed there might be a problem when he spotted a larger-than-average withdrawal from his checking account. The payee was a 529 college savings plan. But because Tom and his wife—let’s call her Jane—have 529 accounts for their children, the transaction almost went unnoticed.

    Inflation Hedge

    Adam M. Grossman   |  Aug 29, 2026

    THE OPEN KITCHEN restaurant has been a fixture in Charlotte, North Carolina for 75 years. The restaurant has an old-time feel, with memorabilia, including menus from years gone by, lining its walls. Those old menus provided David Enna, a financial journalist, with a laboratory for examining the effects of inflation.
    What did Enna find? The oldest menu on display is from 1963. To state the obvious, today’s prices make those from the 1960s look quaint.

    $40 Trillion of Debt

    Adam M. Grossman   |  Aug 22, 2026

    SOME MILESTONES are auspicious. Others are not.
    This week, the Treasury announced that the federal government’s debt had topped $40 trillion for the first time.
    Government debt is nothing new, but the problem is now of more concern, for two reasons. First, the scale has grown. An apples-to-apples way to look at the government’s debt load is to compare it to GDP—the economy’s total annual output. On this basis, outstanding debt now exceeds 100% of GDP,

    Risk Management

    Adam M. Grossman   |  Aug 15, 2026

    BY NOW, YOU’VE probably heard the story of the 25-year-old wunderkind Leopold Aschenbrenner. After graduating as valedictorian from Columbia University at age 19, he worked for FTX, the crypto trading firm, then found his way to OpenAI, where he worked as a researcher for about a year, until mid-2024.
    In the months after he left OpenAI, Aschenbrenner wrote a 165-page paper titled “Situational Awareness,” in which he detailed his views on the future of artificial intelligence.

    Risk and Taxes

    Adam M. Grossman   |  Aug 8, 2026

    AFTER YEARS OF heady gains in the stock market, many investors are facing the same question: To manage risk, they’d like to cut back on one or more of their holdings. But because of the potentially costly tax bill that might result, they aren’t sure exactly how to do that.
    How can you square this circle?
    One easy option would be to donate appreciated assets to charity. But that would make sense only if it aligns with your charitable goals and,

    Social Security

    Adam M. Grossman   |  Aug 1, 2026

    AT FIRST GLANCE, Social Security appears straightforward. During our working years, we pay into it, and in retirement, it sends us a monthly check, guaranteed for life. Unfortunately, it isn’t always so simple. Below are five aspects of the system that are frequently misunderstood.
    Benefits estimates. Look at a Social Security statement, and an easy-to-read chart provides estimates of the benefits available at various ages. The heading above the chart reads, “Personalized Monthly Retirement Benefit Estimates Depending on the Age You Start.” That seems clear.