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Same But Different: The AI Bubble That Isn’t (Quite)

Mark Crothers  |  Oct 12, 2025

Have you been getting that familiar tingling sensation lately? The one that says “you’ve seen this all before.” Watching AI stocks soar, then keep on going, I can’t help but think back to the year 2000. I genuinely knew a guy back then who quit his job to day-trade dot-com stocks from his house. He now works in insurance. There’s a lesson in there somewhere I guess.
Comparisons to the dot-com bust are rife. I may be a slightly thick Irish guy,

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That Dumb Stock Market

Ken Cutler  |  Oct 11, 2025

The proposition of an article I recently read was “this is the dumbest stock market in history.” Why is it dumb? In part because of an increasingly popular approach to investing—one that most in the HumbleDollar community, including myself, subscribe to.  According to the article, passive index investing is “the very definition of dumb money, because indexers buy stocks without any regard to valuation.” Here are some other points that caught my attention in the article,

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Wade Pfau has put me in a funk. Are you dealing with the stages of retirement?

R Quinn  |  Oct 11, 2025

Wade Pfau has an interesting article on RetirementResearch.com about the non-financial aspects of retirement and the various stages. 
In it he states, “Mid-retirement often reveals the cracks beneath the surface. Six months to a year in, many retirees face the “most dangerous day,” when the novelty wears off and the emptiness of unscheduled time sets in. Without purpose or structure, days can feel repetitive. This is when boredom or unease can set in, sometimes leading to unhealthy patterns.”
Since this never happened to me,

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ROTH Conversions and Fixed Indexed Annuities

Charles Ellison  |  Oct 11, 2025

I am 65. I plan to execute ROTH conversions over the next 10 years before I hit  RMDs. Obviously, handling the taxes at the conversion is front and center, pay with cash on hand or take out from the conversion. I understand there is an option to ROTH convert into Fixed Indexed Annuities, where the bonus (15-18%) may cover the entire tax burden. The one I have looked at is a 5-year contract, then you can take the money and put it back into the market.

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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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Selling our Business – The Aftermath

greg_j_tomamichel  |  Oct 10, 2025

On the 8th August we worked the morning, then put on a barbeque lunch for our staff and customers. And by 5pm it was all over. The sale was complete, our bank balance was a bit higher, and a group of people all entered a new phase of their lives.
The sale and handover of our automotive workshop went very, very well. The new owners spent about a month working along side us, and we tried to impart every morsel of knowledge that we possibly could.

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The Wine Chronicles

DAN SMITH  |  Oct 10, 2025

I became a connoisseur of fine wine 55 years ago, when I was 18 years old. If you’re wondering if a kid that age could legally buy wine, the answer would be heck no. However, by virtue of my job in the beverage department at the local supermarket, I had juice to get my juice. The wine salesman was happy to bring me a case of their finest, and I would pay the wholesale price in cash.

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A Short History of Money

Mark Crothers  |  Oct 10, 2025

I’ve been feeling pretty ropey these last few days, with a dose of COVID keeping me from my normal activities. Reading my beloved history books has been keeping me occupied. My current read is “The History of Money by Jack Weatherford”, highly recommended if that’s your thing. Because I’ve nothing better to do, I thought you might find a little article on the subject of interest.
Let’s face it, the concept of a “store of value”

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2026 IRS Inflation Adjustments

Bogdan Sheremeta  |  Oct 9, 2025

The IRS just published their 2026 inflation adjusted numbers.
Some notes:
1. Standard Deduction
In 2025, the standard deduction for a single taxpayer is $15,750 ($31,500 for married filing jointly). In 2026, the standard deduction is increasing by $350: $16,100 (single), $32,200 (mfj)
2. Brackets
2025 brackets:
10% for income $11,925 or less ($23,850 MFJ)
12% for income over $11,925 ($23,850)
22% for income over $48,475 ($96,950)
24% for income over $103,350 ($206,700)
32% for income over $197,300 ($394,600)
In 2026,

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Retirement Income Goals: Bottom Up Beats Top-Down

David Powell  |  Oct 9, 2025

When I was younger, I pictured retirement as a life much like our working years, minus child-raising and commuting costs, but with more travel and higher medical bills. That vision was easy. The harder part was translating it into a retirement income goal.
This is where confusion sets in, and why discussions about “income replacement ratios” often go in circles. People’s situations differ too widely for one-size-fits-all advice. Some work jobs with steady income, others have income which varies a lot each year.

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Why Delaying Your Social Security Benefits May Not Make Sense

Mark Bergman  |  Oct 9, 2025

https://www.wsj.com/personal-finance/retirement/delay-social-security-retirement-cc6e1bbc?st=MZWHJR
Gift link to an article by Derek Tharp in the WSJ from a few days ago. He was (? still is) one of the contributors to Kitces et al.
It’s refreshing to see an article written  that suggests the opposite of the “dogma” of delaying  SS, which I personally have never agreed with.
 
 

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Hit With Dynamic Pricing! Has this happened to you?

Sonja Haggert  |  Oct 9, 2025

My husband and I are big fans of Broadway Theatre. We went to see a show recently and decided to buy tickets for a future performance while we were in town. The last time we did this, the box office saved us the fees typically charged online.
Imagine our surprise when, thanks to dynamic pricing, we actually paid more at the box office.
We were in the city with close friends on Thursday, September 4th, and decided to buy tickets for &Juliet on October 19th.

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Are You Invested in International Markets?

David Lancaster  |  Oct 9, 2025

The information below seems to show that those who are invested in international markets will benefit from the devaluation of the dollar as they have this year. The reason is as the value of international currencies increase relative to the US dollar investments in international holdings increase in value even without future earnings from their sales.
https://www.morningstar.com/markets/will-dollar-keep-falling?utm_source=eloqua&utm_medium=email&utm_campaign=MorningDigest&utm_content=None_68062&utm_id=35352
In the first half of 2025, the US dollar saw its steepest decline in over five decades. The DXY index—which tracks the dollar against major trading partners—fell about 11% from January to June.

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Are You a Dividend Investor? If so Read This!

David Lancaster  |  Oct 9, 2025

https://www.morningstar.com/stocks/stock-buybacks-are-booming-2025-thats-bad-news-dividend-investors?utm_source=eloqua&utm_medium=email&utm_campaign=MorningDigest&utm_content=None_68062&utm_id=35352
The link above from Morningstar discusses dividends vs stock buybacks and how they affect investors.

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