“The games you remember most are on the negative side,” Parcells says. “I don’t know why. You’d have to speak to a psychologist about that. But the time you enjoy a win is minimal compared to how long you feel disappointed by losing.” That’s a quote from Parcells: A Football Life by Bill Parcells and Nunyo Demasio. As a lifelong New England Patriots fan, I remember when Bill Parcells became head coach, having won two Super Bowls with the New York Giants and the media attention that surrounded his hiring. As “The Big Tuna,” he was the show, which would be a problem if you, the player, didn’t … [Read more...]

Are you committed? Committed to being a fairly wealthy, highly successful investor? Then this habit is for you. Because I believe you can reach your “promiseland.” I believe you can live your dreams. But can you keep them? Because investing is a lifelong, multi-generational endeavor. Imagine how you’ll feel when you have enough to retire and no longer worry about where your income will come from. I wish I could say it happens the minute you retire. But when the paychecks stop, a new anxiety begins. Having guided hundreds of investors through their retirement lives, my happiest clients … [Read more...]

Your Survival Guy and Gal recently celebrated their 25th wedding anniversary. Before we were married in Key West, surrounded by family and friends in the southernmost state, we were anxiously watching the tail end of hurricane season. Right before the big day, Tropical Storm Mitch hit, rerouting some flights to Miami, making the drive south on Route 1 far from beautiful as causeways were closing left and right just after crossing. Somehow, everyone made it in time for our rehearsal dinner. And the next day was one of those days after the storm, beautiful. That made everyone even happier, … [Read more...]

Dear Fairly Wealthy Investor, You might be better off staying in bed. It's that bad. One morning, you wake up, and there's a full-page spread in the Wall Street Journal on the perils of a balanced portfolio. It reports how owning stocks and bonds in a 60-40 mix is dead. Nonsense. And it's not just them. When you're in the business of selling newspapers, newsletters, or email subscriptions, it's what gets attention that sells. Which is a disservice to you, my valued reader. You and I know investing is hard because we know the work it takes to save 'til it hurts. These guys are about … [Read more...]

When I was a kid, we took a lot of trips to Disney World, and when we were there, we stayed at Fort Wilderness. One day, a day off from the parks, my dad and I rented a canoe. Floating near the shore, we noticed these little animals digging in the dirt with what looked like a shell as hard as armor. “Those are armadillos,” my dad said. “They're harmless.” They didn’t look harmless to me, and I was sure I didn’t need to see them up close, but he thought we should. As we got closer, I said, “Dad, that’s close enough.” “OK,” he said, “I’ll turn us around.” Easier said than done, as … [Read more...]

A lesson in investing: It’s a lot like high school. There’s ups and downs. It can be an emotional roller coaster. But if you own your bonds and stocks outright and hang in there, then there’s a graduation date—your bonds mature, you collect dividends, and you move on to the next step in life. As if it were that easy. It’s not easy. One spring Friday afternoon of my high school freshman year, Your Survival Guy got off the bus looking forward to the weekend only to find my dad at his desk looking over my report card. “What’s going on at school?” he asked. “Not much,” I said. “I … [Read more...]

You don’t need to know a thing about cryptocurrencies to understand the bankruptcy of crypto-exchange FTX, or that the current trial of founder Sam Bankman-Fried is a story less about blockchain and more about human nature. These stories most often are. Because most financial disasters begin with a new technology and fail not because of the new toy but because of the people. That’s why investors need to have guardrails (to borrow a term from WSJ columnist Dan Henninger’s classic piece), in a world where there are fewer of them all the time. My first guardrail is this: I want you to work … [Read more...]

Your Survival Guy knows a lot about highly successful, fairly wealthy people because I talk to them. On the flip side, I know plenty about those who’ve won and lost a fortune. I know about the guy who can’t hold onto his money. He just spends every penny, afraid it might be gone tomorrow. And sure enough, it is. I also know all about the billionaires thanks to the real estate sections, the virtual tours of their homes, the shows on Netflix and HBO, and the books by Walter Isaacson. Plenty of drama to go around. Entertaining. Maybe not the best family life. That’s why when I say I’m … [Read more...]