Sympathy for the Rich Man

Stern spent Opening Night 2004 at the Palace in Detroit. It was a logical place to be. The Pistons had won the previous season's title, knocking off the favored Lakers. But Stern had other business too. Dan Gilbert had expressed interest in buying the Cavaliers. Stern wanted to meet him.

Two years later, it's odd that Gilbert's reign as Cavaliers owner began in the Palace, the very building where his team was bounced from the playoffs last spring. But for Gilbert, it made perfect sense.

He had grown up in Southfield, a working-class Detroit suburb. As a boy, if he wasn't fooling with the adding machine in the basement of his father's bar, he was at the old Cobo Hall, watching Bob Lanier and Dave Bing. The hometown teams -- Pistons, Tigers, Lions, Red Wings -- were among his chief providers of joy and angst. "I got excited about two things as a kid," he says. "Sports and business."

But it was his "golden gut" for business that earned the eye, and the ire, of adults. At 12, Gilbert built a home pizza delivery store, using kids on bikes to hustle store-bought pizzas to neighborhood families. Only when the real pizza shops alerted the health department was he forced out of business.

In high school, Gilbert says, his entrepreneurial spirit landed him in the principal's office; the school didn't appreciate his cutting into their candy-sales business. At Michigan State, that same spirit landed him in even hotter water when he was arrested for running a football-betting pool. He said later that no money changed hands; the cops thought otherwise. Gilbert was sentenced to 100 hours of community service.

In college, he studied sports journalism, then spent six months as a reporter for a Kalamazoo TV station. But sports were something he could only watch, think about, talk about. Gilbert needed something he could do.

He enrolled in law school at Wayne State and started selling real estate on the side. He started by putting a for-sale sign on his parents' home. That the house wasn't for sale was only a small obstacle, easily hurdled with Gilbert's wit and natural gift for sales. He just shook their hands and showed them to a home that was.

But after a few months, Gilbert realized the real money wasn't in selling houses. It was in lending the money to pay for them. So with savings and a $5,000 bank loan, Gilbert founded Rock Financial, a one-room mortgage company.

It turned out that hustling mortgages was a lot like hustling pizzas. Gilbert hunted down young, eager Detroiters and promised they would succeed if they followed his lead. Athletes were particularly receptive to his message: Patrick McInnis, who played football at Eastern Michigan, and Bill Emerson, who played on a national championship football team at Penn State, started on the same day. Both are now executives with the company and speak of Gilbert like they might a beloved coach. "He had a strong desire and will to win," Emerson says. "He was very motivated. Very high energy."

Shawn Krause, another Quicken employee, was working at a rival mortgage company when Gilbert decided he wanted her. "Dan called me up three times, and I kept hanging up on him," she recalls. "I'm happy where I'm at, dude," she would say. He finally pursuaded her to come see the office, and he sealed it by inviting her on a company outing: a nasty game of WhirlyBall. She's been working there ever since.

From his one-room operation, Gilbert built Quicken into a monster. The company's sales floors in Livonia, Michigan, now hold hundreds of people, divided into teams like the Senior Tour and A League of Their Own. Scoreboards hang above the floor, tracking the length, volume, and result of their calls.

"They have a very 'rah-rah' internal culture," says Cindy Goodaker, editor of Crain's Detroit Business. "Not everybody likes that. But if in you're sales . . . you usually do."

The ones who succeed talk about the place as devotees, not employees. "They have a very cultish mentality over there," Harry Glanz, a former Quicken employee who runs his own Michigan mortgage company, once told Crain's. "It works very well for them . . . but don't drink the Kool-Aid."

Employees learn quickly whether or not they'll fit. The job begins with a day-long orientation led by Gilbert. That's where he introduces his charges to his book of "isms," a manual filled with axioms peeled from the pages of Howard Schultz biographies and Tony Robbins speeches.

"Numbers and money follow; they don't lead," it proclaims, and "Responding with the sense of urgency is the ante to play."