Note: While reading a book whenever I come across something interesting, I highlight it on my Kindle. Later I turn those highlights into a blogpost. It is not a complete summary of the book. These are my notes which I intend to go back to later. Let’s start!

  • Over time, Herbie turned the tricks he learned in coastal Brooklyn—he’s from Bensonhurst, looks like it, and talks like it—into a philosophy, a kind of Jewish Buddhism. He preaches engaged detachment, characterized as “caring, but not that much.” More than a business strategy, he considers this a way of life. “Don’t get fixated on a particular outcome,” he says. “Always be willing to walk away—from the car, from the house, from the property. Once you see your life as a game, and the things you strive for as no more than pieces in that game, you’ll become a much more effective player.”

  • This experience let Herbie test a theory he’d been working on since his crossing guard days: life is a game, and to win, you must consider other people as players with as much at stake as yourself, if not more. If you understand their motivations, you can control the action and free yourself from every variety of jam. Focus less on yourself and more on others. Everyone has something at stake. If you address that predicament, you can move anyone, even a junior high principal, from no to yes.

  • Here’s what Herbie learned in New Haven: if you say something long enough and loud enough and with enough confidence—“No one has worked harder for this campaign than Zeke”—people will believe you, and once they believe you, you can take as many donuts as you want.

  • Herbie’s version is more fantastic. Ellen was sensible, committed to the literal truth. To Herbie, there is truth, and then there is truth, or, as he says, “You see things not as they are, but as you are.” He believes in founding myths and fairy tales, in giving people a story, a poetic reality that supersedes the facts on the ground.

  • People loved him in Libertyville, and he loved them right back. He was a character, a small-town celebrity, the sort of oddball you went to with a problem. He helped neighbors work out their purchases and closings. His art of the deal was never about tricking an opponent. It was about making the other person feel respected, getting a good deal while letting the other guy feel he’d done the same. Win-win. “And it isn’t because I want to be a good person,” he’d explain. “It’s because I want to be effective. If the other guy walks away feeling bad about what happened, the deal is going to fall apart and you’re going to end up with nothing.”

  • Herbie speaks of the rule of three. If someone sees your name three times—initial publication, murder, movie—they feel as if you’re everywhere, so must be famous, and, if people think you’re famous, you’re famous.