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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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Rule of 55: Early Retirement

Bogdan Sheremeta  |  Nov 1, 2025

MOST PEOPLE THINK their retirement accounts are completely locked until age 59½ due to the 10% early withdrawal penalty, but that’s not really true. There are many ways to access your money earlier without the penalty, and knowing them can give you flexibility. Of course, you shouldn’t be touching your retirement accounts unless you’re ready to retire.
Here are some distributions that are not subject to the 10% penalty, per the IRS list:

Birth or adoption (up to $5,000 per child)
Series of substantially equal payments (72t)
First-time homebuyer (up to $10,000,

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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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Roth Hidden Benefits

Bogdan Sheremeta  |  Oct 25, 2025

WHEN MOST PEOPLE think of Roth IRAs or Roth 401(k)s, they just think “tax-free withdrawals.” But that’s only part of the story.
Roth accounts can protect you from financial traps that catch many retirees off guard. Here are five key advantages to keep in mind:
 
1. Tax Rate Protection
One thing we can’t control is future tax rates.
Did you know that in the 1980s, the highest federal tax rate was 50%?

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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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Backdoor Roth Explained

Bogdan Sheremeta  |  Oct 18, 2025

ROTH IRA IS A powerful account. It grows tax-free and withdrawals are tax-free during retirement. Roth IRA also has income limits.
For 2025, if you are filing your taxes as single and make less than $150,000 ($236,000 if married filing jointly) of modified adjusted gross income, you can contribute a maximum amount of $7,000.
But if you make $165,000 (single) or $246,000 (married jointly), you are ineligible to contribute to a Roth IRA directly.

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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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LLC Tax Benefits

Bogdan Sheremeta  |  Oct 11, 2025

I WAS RANDOMLY scrolling on social media and saw this post:

“Can you just open an LLC and write things off?”
That’s a real question someone asked, and I’ve seen this question asked many times.
There are a lot of misconceptions around LLCs, their purpose, and how LLC changes your tax structure. With TikTok, there are “tax experts” sharing terrible advice, so let me clarify how it could be useful.
 
First, what is an LLC?

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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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Cash Balance Plan Explained

Bogdan Sheremeta  |  Oct 4, 2025

IMAGINE YOU ARE already doing all things possible to minimize your taxes:

You are maxing out your pre-tax 401k
You do tax loss harvesting
You did tax efficient placement
You are maximizing Roth IRA through Backdoor Roth

But what other strategies can you use to minimize taxes? You also might not want to start a business or buy real estate.
Another option that many people aren’t aware of is the cash balance plan (CBP).

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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 of Jonathan’s HumbleDollar Posts

Bogdan Sheremeta  |  Sep 27, 2025

WE LOST A brilliant mind and generous writer, Jonathan Clements, whose words guided thousands on life, finance, and happiness. Even as he faced the unimaginable, he continued sharing wisdom with clarity, humor, and humanity.
I wanted to take some time and dig into Jonathan’s earliest posts on HumbleDollar. Posts that even the most loyal readers may not have read. With that, I also summarized some main takeaways and learnings that can help us all better navigate our own complex lives.

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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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New 2025 Tax Deductions

Bogdan Sheremeta  |  Sep 20, 2025

THE IRS JUST released a new form called Schedule 1-A, which includes all the new tax bill deductions.
I wanted to quickly go through some of it, so that you are more aware of the new potential savings opportunities.
I’ve previously discussed some portions of the bill, but this is the first time we have a peek of the new lines.
All of these deductions are in addition to the standard deduction or itemized deduction.

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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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