2008 Minnesota Business Hall of Fame

Gary Holmes has always had a talent for making money—big money.

He was in high school when he bought his first rental property. At 21, he was a millionaire. Today, at 61, he is CEO and sole owner of Minneapolis-based CSM Corporation, the $800 million real-estate development and management firm that he founded in 1976, with a portfolio comprising more than 200 projects: residential, commercial, industrial, retail, and hotel properties in 16 states.

But when Holmes graduated from Southwest High School in Minneapolis, he was ranked 392 out of 396 students. He had severe attention-deficit disorder. He was profoundly dyslexic. He was literally tongue-tied—a physical impairment anchored his tongue to the bottom of his mouth and mangled his speech. He was left-handed, but forced to use his right.

“To this day, you can’t read my handwriting,” he says with a grin. He remembers the embarrassment of waiting for the so-called dumb bus that carried him to special classes. And he hasn’t forgotten the frustration of his teachers: “They’d keep drilling and drilling,” he says. “They’d be spitting, they were so mad! They’d say, ‘You’re smart. Why can’t you do this?’”

Their frustration was understandable, given what they knew Gary Holmes could do. By junior high, his entrepreneurial talents were well known.

When the dad of a fellow Boy Scout enlisted the troop to sell some chrome cleaner he had in his garage, Holmes sold the most—and was hooked. He found his next product advertised in a magazine: long-burning light bulbs. At age 12, he bought them wholesale and his scout troop sold them door to door. Eventually, Holmes had almost 50 troops in the Twin Cities selling light bulbs—and a novelty toilet-bowl cleaner (when you went to the bathroom, the water turned green).

“I can say two things about Gary,” says Ralph Hegman, a buddy from 50-plus years ago. “First, there is nothing he’s not interested in. Second, he has incredible focus. When he’s engaged, when he has a plan, there’s nobody I’d put against him.”

The light bulb company came out with a commercial line, and Holmes donned his Sunday suit to call on downtown Minneapolis businesses after school. Business owners were won over by the gangly (6-foot-3, 145 pounds), likable teenager, and by age 16, Holmes had enough money to buy an apartment building in south Minneapolis.

Within a few years, he owned properties that were making him about $400,000 a year. He applied to the University of Minnesota to avoid Vietnam, was accepted (on probation), and studied business administration while managing his real estate on the side. His assets were so substantial by the time he was 21 that his accountant advised him to draw up an estate plan and share it with his parents.

“I’m thinking, ‘This is a great moment—I can show them how successful I can be.’ But they just had the worst looks on their faces. They said I must have been doing something illegal, because nobody honest makes money like that. Talk about devastated,” Holmes recalls. “That taught me a good lesson. I already was low key—but from then on, I was even more low key.”

After college, he went to work for mortgage banker H. & Val. Rothschild. “I wanted to see how the big guys did real estate,” he says. “I took a $7,800-a-year job that was worth a million dollars a year in education.” Clients there became his mentors and partners.