David and Goliath: Underdogs, Misfits, and the Art of Battling Giants

that different from the world we create for our children. But that’s not true for someone who becomes very wealthy. The psychologist James Grubman uses the wonderful expression “immigrants to wealth” to describe first-generation millionaires—by which he means that they face the same kinds of challenges in relating to their children that immigrants to any new country face. Someone like the Hollywood mogul grew up in the Old Country of the middle class, where scarcity was a great motivator and teacher. His father taught him the meaning of money and the virtues of independence and hard work. But his children live in the New World of riches, where the rules are different and baffling. How do you teach “work hard, be independent, learn the meaning of money” to children who look around themselves and realize that they never have to work hard, be independent, or learn the meaning of money? That’s why so many cultures around the world have a proverb to describe the difficulty of raising children in an atmosphere of wealth. In English, the saying is “Shirtsleeves to shirtsleeves in three generations.” The Italians say, “Dalle stelle alle stalle” (“from stars to stables”). In Spain it’s “Quien no lo tiene, lo hance; y quien lo tiene, lo deshance” (“he who doesn’t have it, does it, and he who has it, misuses it”). Wealth contains the seeds of its own destruction.
    “A parent has to set limits. But that’s one of the most difficult things for immigrants to wealth, because they don’t know what to say when having the excuse of ‘We can’t afford it’ is gone,” Grubman said. “They don’t want to lie and say, ‘We don’t have the money,’ because if you have a teenager, the teenager says, ‘Excuse me. You have a Porsche, and Mom has a Maserati.’ The parents have to learn to switch from ‘No we can’t’ to ‘No we won’t.’”
    But “no we won’t,” Grubman said, is much harder. “No we can’t” is simple. Sometimes, as a parent, you have to say it only once or twice. It doesn’t take long for the child of a middle-class family to realize that it is pointless to ask for a pony, because a pony simply can’t happen.
    “No we won’t” get a pony requires a conversation, and the honesty and skill to explain that what is possible is not always what is right. “I’ll walk wealthy parents through the scenario, and they have no idea what to say,” Grubman said. “I have to teach them: ‘Yes, I can buy that for you. But I choose not to. It’s not consistent with our values.’” But then that, of course, requires that you have a set of values, and know how to articulate them, and know how to make them plausible to your child—all of which are really difficult things for anyone to do, under any circumstances, and especially if you have a Ferrari in the driveway, a private jet, and a house in Beverly Hills the size of an airplane hangar.
    The man from Hollywood had too much money. That was his problem as a parent. He was well past the point where money made things better, and well past the point where money stopped mattering all that much. He was at the point where money starts to make the job of raising normal and well-adjusted children more difficult. What the parenting graph really looks like is this:
     

     
    That’s what is called an inverted-U curve. Inverted-U curves are hard to understand. They almost never fail to take us by surprise, and one of the reasons we are so often confused about advantages and disadvantages is that we forget when we are operating in a U-shaped world. 2
    Which brings us back to the puzzle of class size: What if the relationship between the number of children in a classroom and academic performance is not this:

    or even this:

    What if it’s this?

    The principal of Shepaug Valley Middle School is a woman named Teresa DeBrito. In her five-year tenure at the school, she has watched the incoming class dwindle year by year. To a parent, that might seem like good news. But when she thought about it, she had that last curve in mind. “In a few years we’re going to have fewer than fifty kids for the whole grade coming up from elementary school,” she said. She was dreading it: “We’re going to struggle.”

5.
    Inverted-U curves have three parts, and each part follows a different logic. 3 There’s the left side, where doing more or having more makes things better. There’s the flat middle, where doing more doesn’t make much