Dr. Rick Workman sits in his wood-paneled home office in a gated golf community outside Orlando, Florida. The room has a clubby old-money vibe. Floor-to-ceiling windows draped in royal blue curtains frame an ornate golden chandelier, and a large silver statue of Ferrari’s horse prances on his desk. Outside, in the driveway of the estate, sits an even bigger statue of the famous Cavallino Rampante, a tribute to his large collection of exotic sports cars.

Workman leans back in his chair and begins talking about the cold reception he has received from others in his profession. “I’ve had people walk up to me at a conference and want to get in a fistfight with me,” he says.

At 71, Workman has the energy of someone who expects an argument and welcomes it. His voice carries the blunt rhythm of rural southeastern Illinois, where he grew up on a farm and learned early that work was something you did whether you liked it or not. On this day, he’s wearing a satiny navy button-down shirt that catches the light whenever he moves. It’s a fashion choice flashier than you might expect from a dentist.

Then again, no other dentist made a billion dollars treating teeth. Workman has spent the last four decades creating the largest dental operation in the United States. His Effingham, Illinois–based Heartland Dental has 1,900 practices with some 3,100 dentists across 39 states. Among some dentists, Workman is persona non grata, as they believe dental conglomerates like his prioritize productivity and profits over patient care and have made their once-cushy profession hyper­competitive.

“I learned the Chicago way,” he says, nodding to the city’s reputation for bare-knuckle politics. The fights over corporate dentistry and private equity often get loud and personal. But Workman’s solution is what he calls staying “underneath the cabbage patch.” Keep your head down. Keep building.

In 2024, Heartland Dental generated about $3.6 billion in revenue and $455 million in earnings handling the business side of dentistry: payroll, staffing, marketing and supplies. The dentists focus on treating patients, an approach that helped reshape a profession long dominated by solo practices. Private equity firm KKR, which manages $744 billion in assets, bought a 58% stake in the company in 2018 at a $2.8 billion valuation. Today Heartland is worth $6 billion, giving Workman, who serves as chairman, an estimated net worth of $1.6 billion.

Workman grew up on a farm outside Clay City, Illinois. His grade school had three classrooms and six students in his class. His mother was his teacher. The family farm grew corn and soybeans. Work started early. His first job was gathering eggs when he was 4 years old. By age 7 he was milking cows. Summer days meant........

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