To someone outside his profession, I told him, this seems like a preposterous—even enabling—nonsolution. Why couldn’t her father have given her $75,000 for the year and accomplished the same thing?
“Because if her father were to pick an arbitrary number,” he answered, “what would typically happen is, she’d have blown through the money, and she wouldn’t have learned anything. The first step, at least, was about taking ownership over the money she’s already spending.”
And that may be the best you can do in a situation like this: forestall the regression toward shirtsleeves for yet another generation. But that’s not a very high hope to pin on your children, is it? To pray that they don’t undo all you’ve done?
Let’s say you’re a normal person with a normal income and struggles,” says Tommy Gallagher of Tiger 21. He’s the Crown Heights–born son of a toll collector and school crossing guard and, as such, still looks at his money a bit as an outsider would. “You have a child,” he continues, “and that child decides to do something. You’re going to try to help them in a way you can help them. But I can really help my child if he wants to do something. I can pay his rent. I can buy a house for him. I can enable him forever. And that’s really tempting.”
“The funny thing is,” he adds, reflecting on it, “if you’re sitting around with the members at Tiger, four or five of them will always say, ‘The most important thing I ever learned in my life is, when I fell down, I could get up.’ And that’s one of the things you’re taking away from these kids. We don’t let them fall down.”
Talking to Gallagher, one realizes that wealth, to some degree, simply exaggerates the instincts and urges that all parents experience. All parents, for instance, have to restrain themselves from spoiling their children at some point or another. And as Gallagher points out, almost all parents, from the moment their children are born, fantasize about being able to protect and help them in a sustained and continuous way. Yet it may not be the best thing for them. I ask if there’s any one particular way his peers won’t allow their kids to fall down. “Yeah, college,” he says. He mentions his days in the brokerage industry, when he’d watch his colleagues stream through the chairman’s office like supplicants, hoping he’d be able to get their kids into the Ivy League school where he served on the board. “The acknowledged understanding,” says Gallagher, “was that you’d eventually need to give a million dollars in some way, shape, or form if your kid were accepted.”
The uglier face of this protective instinct, of course, is wanting to control every aspect of your child’s life—limiting their pursuits, trying to mold them into Mini-Mes. Again, it’s an urge that most parents have, whether they’re rich or poor—seeing their own children as extensions of themselves, fighting their own vanity in order to allow their kids to become who they’re supposed to become. But wealth tests this instinct to the breaking point.
“When I was active,” says Jay Hughes, a retired estate planner who wrote Family Wealth and Family: The Compact Among Generations, “one of the things that happened almost every time I was working with a new family is that they’d all start out by saying work was critical. But every single time, they’d also say, ‘Well, we can’t have anyone in this family become a surfer.’ And I’d say, ‘Well, what if they had a life-goal to win the medal at Waikiki?’ Because if you found the journey of your family on the premise of your child dreaming your dream, you’re founding it on a fallacy.”
“We often talk about this at meetings,” Gallagher says. “That what we have to do as parents is not prevent our kids from doing their passion. So if one kid wants to go off and be involved in horse racing, or try professional golf or start a rock band … what are you going to do? It’s not the end of the world. In two years, they might have had enough of the racetrack and go back to school. At 18, you’re entitled to make some mistakes.”
And what about private jets? “I think the better question, which my wife and I argued over, is whether or not our kids should fly first class or coach,” he says. “Because even most rich people can’t afford their own planes. We couldn’t. But for many years, we rode in coach with our children though we could afford first class. But at some point, we surrendered. These kids went on all these fabulous vacations to all these fancy resorts. What am I trying to prove by making myself uncomfortable?” So he bought his entire family first-class tickets. He’s aware it’s not a choice all parents would make. “But at some point in time,” he says, “you make an evaluation of your kid, and how they treat money, and how respectful they are of other people, and how generous they are. Me, I’m lucky. I have plenty of issues with my kids, but them taking advantage of me? Or wanting more than they should? No. One’s in the military and has been for ten years. And the other one’s a communist, a self-hating rich kid.” He thinks. “Of course, he’s a self-hating rich kid who’s been to Cuba, India, and China—twice. Who the hell paid for all this stuff?” Then he stops himself, realizing that perhaps this boy deserves more credit than he’s giving him. “I want to walk down Madison Avenue and have people think I’m a super in one of their buildings,” says Gallagher. “But my son, he always says, ‘Dad, they’re going to look at your watch and they’re going to know you’re rich.’”