FROM AN EARLY AGE, my son showed an interest in business and investing. As a toddler, he’d watch CNBC with me. When my wife and I discussed legal and accounting issues, he’d have his “listening ears” on. (Yes, our dinner table conversations are pretty exciting.)
By the time he was eight years old, he was giving me investing input. He thought Microsoft overpaid when it bought Minecraft maker Mojang for $2.5 billion in 2018.

WHEN I WAS GROWING up, one family in the neighborhood lived differently from all the others. In their garage was a Rolls-Royce. When each of the sons turned 16, a new BMW showed up in the driveway. Because it was so out of the ordinary, it caught my attention. It caught everyone’s attention.
Looking back, this is what I find interesting: This kind of privileged upbringing looked like a guaranteed recipe for demotivating their children.

I RECENTLY HIT THE “pay now” button on what I believe will be the last of 20 years of college tuition bills. That’s right, we have five kids. All went to college. None took out student loans.
Was it worth it—not just paying the tuition bills, but the decision to have children in the first place? It’s a pressing question. A birth dearth is hitting the U.S. and other countries around the world, as many adults opt to go childless.

AS A PARENT, IT’S my responsibility to teach my children good financial habits. Core among these are deferring gratification, saving diligently, giving generously and making sensible spending choices. I feel it’s also important to make my children aware of financial pitfalls. Succeeding financially—and in life generally—seems to be as much about avoiding self-destructive habits as it is about cultivating good ones.
My wife and I have been homeschooling our children for the last couple of years.

DURING THE BULL RUN of the 1990s, when the S&P 500 soared 417%, I had a brilliant idea: Why not start an investment club? I invited my father and sister to participate. My mother declined. It turned out she was the smart one in the family. We met periodically, usually on a Sunday, to decide which companies to invest in.
I was serious about this endeavor and determined to make it successful. I even gave our new investment club a name: DSD.

I AM THE FIRST TO admit that I’m no star when it comes to math. I was so enthralled with calculus in college that I took it twice. To make matters worse, math keeps changing. Just ask a 10-year-old to show you how to multiply.
I am not alone. At the high school from which I graduated in 1961, the current math proficiency rate is 2% The national average is 46%. The lowest ranked state is at 22%.

WHEN I WAS A KID, I never liked the game Monopoly. I found it slow and uninteresting. But now, as a parent, I see its value. I’ve tried a lot of things to teach my children about money, but nothing comes close to Monopoly in its ability to convey important personal finance lessons.
Sure, it helps kids practice basics like addition and subtraction—but there’s a lot more to it. If you’ll be spending time with children over the holidays,

THIS YEAR’S PANDEMIC has unleashed financial turmoil for many American families, so data from last year might seem irrelevant. Still, there’s one set of 2019 data that deserves our attention—the Federal Reserve’s latest Survey of Consumer Finances, which was released last month.
Conducted every three years, the survey is perhaps the most in-depth look we get at the state of America’s personal finances. For the 2019 survey, 5,783 families (who may be individuals living alone) were interviewed at length about their income,