INSURANCE COMPANIES are disproportionately represented among the world’s oldest companies. John Hancock was founded in the 1860s. Cigna dates to the 1700s. Some insurers are even older. Why is that?

In my opinion, it’s because they employ a strategy called asset-liability matching. In simple terms, insurers organize their finances so cash is always available when they need it.

Let’s say each winter typically results in $100 million of auto claims for a particular insurer.

I HAD THE OPPORTUNITY to view Gustav Klimt’s most famous work of art, The Kiss, while visiting Vienna a few years back. It depicts a couple locked in an intimate embrace. It’s an oil painting with a significant amount of gold leaf—quite distinctive.
A few weeks later, I had an opportunity to buy a Klimt. I was in a gallery in Salzburg and came across a drawing of his which was titled Stehender Rückenakt –

YOU MAY BE FAMILIAR with the term ESG. This is an investment approach that—in addition to traditional financial metrics—also weighs environmental, social and corporate governance considerations when picking investments.
ESG isn’t new, but it’s stirred up a fair amount of controversy recently. As an investor, it’s worth understanding what the debate is about and how you might navigate it.
ESG has been around for years, but its popularity has recently hit an inflection point.

“I’VE GOT SOME REAL estate here in my bag,” croons Paul Simon, as he consoles his lover in the iconic 1968 song America.
The real estate industry’s marketing arm couldn’t have put it better. The industry’s message: If you want to feel secure and be prosperous, get yourself some real estate.
Problem is, many people can’t come up with the down payment for a home or rental property. The good news: There’s an alternative to direct ownership.

EXCHANGE-TRADED funds are popular, but their complex structure makes them difficult to understand. A question I hear frequently: Are exchange-traded funds (ETFs) more tax-efficient than traditional mutual funds?
The evidence suggests they are. One recent study found that ETFs distribute capital gains to shareholders much less frequently than traditional mutual funds and, when they do, those gains are smaller. It’s worth understanding why that’s the case.
Let’s first look at the mechanics of a traditional mutual fund.

I GOT AN ANGUISHED call from an investor last week. Let’s call her Emily. Emily’s accountant was finishing up her tax return and was surprised to see a $113,000 capital gain. The explanation turned out to be just as surprising.
The issue stemmed from a well-intentioned move by Vanguard Group. In late 2020, the firm announced it was broadening access to a set of lower-cost mutual fund share classes.
Mutual fund share classes are like fare classes on an airplane.

I REALIZE THAT MOST HumbleDollar readers share a similar investment philosophy. They believe in market efficiency, keeping expenses low and holding down taxes, all of which leads them to genuflect at the altar of the all-mighty index fund.
Words and phrases such as Robinhood, bitcoin and active management don’t appear often on this site and, when they do, they’re mentioned with disdain. While this may be a good thing in the main,

IN AN EARLIER ARTICLE, I noted that my savings journey began in 1960 with a couple of jars of pennies that I started collecting at age five. I was following family ancestor Ben Franklin’s maxim that “a penny saved is a penny earned.”
One of my uncles also had an interest in coin collecting. He and I began to actively search through countless penny rolls to find pennies with dates that we didn’t have.

IT’S SUMMERTIME in South Florida, where I live. The temperatures are high, the humidity too, and the sandy beaches too hot to walk barefoot on. Then there’s the Atlantic hurricane season. It’s in full swing and runs from June 1 to Nov. 30.
What’s any of that got to do with managing money? Think spaghetti map predictions.
We’ve all seen those spaghetti maps on television and online. They typically appear 10 to 14 days before there’s a possibility of a hurricane or cyclone coming our way.

IF I SAID YOU COULD corral a yield of almost 12% by holding most of the stocks in the Nasdaq 100 index through an exchange-traded fund (ETF), would you think I’ve been smoking something? Well, you’d be wrong.
Global X Nasdaq 100 Covered Call ETF (symbol: QYLD) has pumped out a humongous dividend for more than 100 consecutive months, ever since its 2013 inception. But first a caveat that many will view as a tragic flaw: QYLD is a pure income investment,

I’M A FAN OF SLANG and newly coined words. Think of all the names for money we’ve had over the years, like cheese, clams and cabbage. New words catch on not only because they allow a new generation to put their stamp on the world, but also the words reflect changing attitudes.
That brings me to “stonks,” the name many millennials use for stocks—and one that reflects a different view of investing. No one’s sure where the word originated.

DO YOU INVEST IN options? Think twice before saying that you’d rather go to Vegas. My bold claim: Options investing has a lot in common with investing in stocks and corporate bonds.
Intrigued? Let’s recap a European style call option. It’s a discretionary contract that allows someone to buy an underlying asset at a set strike price at a future date. Let’s say the buyer of the call, Bob, has an option on a stock with a strike price of $100.

DURING THE RECENT bull market, I fell off the wagon and bought some technology companies, once again trying my hand at stock picking. I’m talking about companies like Spotify Technology, MercadoLibre and Roblox. It was a small percentage of my portfolio, but I felt the pain.
I’d tried picking individual stocks when I was younger. I thought I had a better chance now. After all, I was more educated and knew more about researching companies.

I ARGUED LAST WEEK that bitcoin wasn’t a great investment. The reality: Only a minority of investors hold cryptocurrencies, which is a good thing, in my opinion. But there are, alas, many other ways to get off track when building a portfolio.

In fact, if I ever wrote an investment book, it might be in the style of Dr. Seuss and titled Oh, the Investments I’ve Seen. Want to build a sensible portfolio and avoid common pitfalls?

AN OLD WALL STREET adage tells investors to “sell in May and go away.” If you’ve been around long enough to remember that phrase—and you heeded it this year—you’re probably feeling pretty smug, having sidestepped the ugly, unforgiving bear that’s lately been roaming Wall Street.
But such pearls of investment wisdom often make better cocktail chatter than they do an investment strategy, and for good reason: The advice can’t always be counted on. Then again,