A smart, sardonic Boston real estate developer said to me some time ago, “In Boston, I’m a rich old man. In Palm Beach, I’m a poor young one.”

There are at least five truly insecure places in America: Beverly Hills, the East Side of New York, East Hampton, Palm Beach, Fla., and, probably coming in at number one, Washington, DC. But the last suffers from a different kind of insecurity. “What’s my power base?” is Washington’s obsession. “How rich am I?” is the killer in the other four. In Palm Beach especially, the number one topic on everyone’s lips is money. It drives people crazy that the people at the next table have millions more than they have. The only asterisk on this subject may be the remnants of really old money, patricians who look better than anyone else ever could in Henry Poole blazers and no socks, who came to Palm Beach from Manhattan and Greenwich and Winnetka and Lake Forest and Oyster Bay. They’re mostly oblivious to what’s going on around them. And when they notice, they disapprove.

But if you are curious about the various tribes in America, Palm Beach is also loaded with characters, mavericks who enjoy irony, see the excesses and absurdities in society and are comfy in their own skin. These people are passionate about ideas and share them with me. They don’t take Palm Beach seriously. They live there to be amused and, after years of hard work, to soak up some sunshine and let their opinions flow.

One of them is Billy, an old friend who divides his time between Palm Beach and Milan, where he teaches entrepreneurship to students. My energy expert for years, he was the first person back in the mid-1990s to preach to me about the huge energy demand that would eventually come from India and China. That’s when oil was $30 a barrel.

“At least there are no Russian oligarchs here,” Billy said. “They’re everywhere else that’s glitzy. But they’d have to pay U.S. taxes, and the oligarchs don’t pay taxes. In Milan, they travel with bodyguards with guns. And they’ll pay to shut down a store like Bulgari or Chanel for hours at a time, send their blond Natashas in to shop with the window blinds down. Palm Beach has enough American oligarchs to keep the stores busy in-season.” Then Billy paused and ordered a Mozart vodka, neat but ice cold. “And don’t mention Los Angeles to me,” he added. “In LA, people rent everything; it’s leveraged money. In Palm Beach, everyone can pay cash.”

When he dropped me off after dinner, he affirmed his belief in mining companies for the future. “The meek may inherit the Earth someday,” he said, “but not the mineral rights.” He is in Palm Beach, but he itches for action that retirement can never provide.

My next character did college in three years, business school in one, and could really make numbers work in magical ways from an early age. “I’ve spent my life being the grit in the oyster, and I don’t care what the world thinks,” he said. “I have the sun on my bod and no state taxes. And I can tell the world to take a hike.” He does that, but serves on nonprofit boards where he’s valuable because he’s not afraid to speak his mind, and he’s generous to those who pay attention. Every loner has a soft spot, and they all secretly want to be loved. And envied, too.

Driving me to play golf, his Bluetooth buzzed. It was a young partner of his, calling about a flight to San Francisco that night to cement a deal. “By the way,” he said, “what’s the name of this company? And the name again of their biggest product?”

The young partner wasn’t sure of the answer to either question. I thought outrage would ensue since they were flying out for a pitch the next day. “Oh well,” he said on the phone, “we can hash this out on the plane.”

“You’re not nervous?” I said. “You didn’t even know the name of the company?”

He cranked up his Bose sound system, playing Pachelbel, and calmly said, “In New York for years, ulcers, three heart operations, a marriage or two. I’ve done hundreds of deals and, after all this time, they’re all like one another. Find the weakness, what makes them quiver on the other side, and zero in. If you act as if you don’t need the deal, everyone loves and wants you.”

We hit the golf club, one of the many high-end treats in Palm Beach, a town packed with tony stores and restaurants—but its people watching is free and can be the biggest treat of all. Coming out of Maus & Hoffman, a store on Worth Avenue with the best men’s shoes I’ve ever seen outside of London, I saw a man walking a pig on a leash. You need to have a strong sense of yourself and a pile of money to have a pet pig. Or no money at all and a low sense of self. But on Worth Avenue, I figure it’s the former.

One night, I came back late to my hotel and crashed a black-tie event thrown by a major bank for the leading mortgage producers. It was a flashback to the glory days before the meltdown in ’08: costumes, flappers, gangsters, gun molls, slicked-back-haired masters of the universe. So much more real than the latest DiCaprio version of Gatsby. I watched an entertainer, a tap dancer, strut his stuff to boozy jazz. No one else paid any attention; they gabbed all through the act. I talked with him, sad about the rudeness. “I’m used to this down here,” he said, “but the show goes on. They don’t care.”

I visited another hotel and went to their beach and pool one afternoon. An attendant had grown up in the North End, on Hanover Street. I asked him about the mood in Palm Beach. “Well,” he said, “see those cabanas? They rent for about $1,600 a day. After the Bernie Madoff scandal, business dropped dead down here. Then people who never showed up before, locals, came in to rent them. They wanted to show the world that they weren’t affected by Madoff, even if they were. The appearances are everything.”

Fun to visit, but you miss the grit and sardonic honesty of Boston.