Tim O'Reilly O'REILLY HOSPITALITY MANAGEMENT, SPRINGFIELD

By the time Tim O’Reilly finished college, the family business in Springfield—
you know it for auto parts—was flourishing, and not small. “The company is very efficient, very good at what it does, but by necessity it has a lot of layers of control, and I had a more entrepreneurial spirit,” says O’Reilly. After law school, he still thought he might end up at the corporate headquarters before a new realization hit him: “I really started enjoying the practice of law, doing it and having some success.” And then the entrepreneurial side kicked in. Seizing on the opportunity to buy the Doubletree Hotel in Springfield in 2006, he discovered a business-development yen that spawned O’Reilly Hospitality Management. A love for hotels stemming from travels in his boyhood, and an admiration for what hotel legend John Q. Hammons had done for Springfield, helped produce a natural fit. Today, in addition to the law practice at O’Reilly and Jensen, his O’Reilly Hospitality Management provides third-party management for a series of hotels and restaurants from southern Missouri into Texas. O’Reilly and his wife, Brooke, have four children, ages six to 15, and he says it would be hugely satisfying
if his own kids would follow him into the next O’Reilly family enterprise.

Bob Clark CLAYCO CONSTRUCTION, ST. LOUIS

Bob Clark has a very simple outlook on business ownership: Work hard. Be fair. Treat people the way you’d like to be treated. And do what you say you’ll do. That, folks, is how you go from starting a construction company with $1 million in revenues in 1986 and getting it to $800 million—and counting—as of 2010. In Clark’s case, it’s Clayco of St. Louis.

Although the privately held company is one of the biggest builders in the U.S., it also specializes in real-estate development, engineering, architecture and construction—enough of it to cover 4,000 acres of land if you could jam it all into one location. Aggregate value of all that? More than $9 billion. The father of four, Clark is on the executive committee for the trustees at Saint Louis University, and he sits on the scientific advisory council for Washington University’s School of Medicine.

Jerry O'Neal CONTINENTAL SIDING, INDEPENDENCE

Jerry O’Neal came to Kansas City from his native Tulsa 32 years ago to help an acquaintance right the finances of her struggling siding company. As is often the case, Kansas City got its hooks into the newcomer—but good. “I turned the company around, got it profitable and hired somebody to take my place,” O’Neal recalls. “But in the meantime, I just fell in love with Kansas City. It has something about it that’s just different, with the people here, and the city.”

Before long, O’Neal decided that rather than pursue an early retirement, he’d get back into business here. That’s how Continental Siding came to be, and 29 years later, the company is still going strong with four locations, including its headquarters in Independence.

Construction was always in O’Neal’s blood; he first picked up a hammer at 16 as a carpenter’s assistant, something that helped pay the bills for a young newlywed. He’s been married for 54 years now, has five children to show for it and figures that retirement just isn’t something very appealing.

“I knew in 1980 after I sold my carpet business that I had an emptiness in my stomach that couldn’t seem to go away,” he says. “I figure now, I’ll probably work my entire life.”

Diane Sullivan BROWN SHOW CO., ST. LOUIS

You can boil Diane Sullivan’s leadership philosophy down into this nugget she threw out, assessing the challenges facing Brown Shoe Co. when she became CEO a year ago: “If it was that simple, it would have been done a long time ago.” Heading up the $2.6 billion company based in Clayton, Mo., Sullivan is one of only three female chief executives at public companies in the St. Louis region.

Her challenge with Brown Shoe, she said, would be scaling back the vast inventory of 70 shoe brands that fell under the company’s umbrella when she took the reins.

Sullivan, 56, has been with the company since becoming its president in 2004. She oversees all of Brown’s operating divisions and worldwide marketing. Brown also operates the Famous Footwear retail chain, with more than 1,100 stores nationwide.