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 sitting on a tractor for ten or 12 hours at a stretch. Saturdays often brought the chores nobody wanted: cleaning manure sheds. Baling hay.

“That wasn’t much fun,” Workman says, admitting the experience snuffed out any interest he might have had in farming.

College was the first step away from the farm. Workman began at Olney Central College, a community college about 20 miles from home. He thought about becoming a chiropractor. A doctor he knew suggested dentistry instead.

He was already studying science, so the switch required no change in coursework. Workman transferred to Southern Illinois University, where he completed his degree in biological science in 1977 and went on to dental school.

In 1980, Workman opened his first practice in Effingham, about 40 minutes from the family farm. He found a basement location, borrowed $35,000 (the equivalent of $150,000 today) from his parents and grandparents and set up a two-chair office. His advertising budget was a $15 hand-painted sign on the front of the building. His goal for the first year was ambitious, but reasonable. “Twenty-five thousand dollars,” he says, which was 20% more than the national median family income at the time.

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Growth came quickly. By the next year, Workman realized he was seeing a couple dozen patients a month from a town 25 miles away. One of those patients was a banker who offered him a loan on favorable terms if he would open an office there. Workman accepted. Soon he was running two practices and employing another young dentist. It was a lot of work: about 55 hours a week treating patients and another 30 hours handling the business side.

In 1982 he opened a third office in a different town. More practices followed. Over time the group grew to 29 locations across Illinois under a company called Workman Management Group, employing 21 dentists.

In 1997, at age 42, Workman sold all but four of those practices for $15.8 million, leaving him personally with nearly $11 million in proceeds. But instead of hitting the golf course, Workman, seeing a bigger opportunity, opened Heartland Dental the same year.

For decades, dentistry was dominated by small practices run by individual doctors. Twenty-five years ago, two-thirds of dentists worked in solo offices, according to the American Dental Association’s Health Policy Institute. In the 1990s, dental support organizations (DSOs) were created as a workaround to state laws that prohibit corporations from owning medical practices. Under that model, the dentist owns the clinical practice while the DSO owns the business infrastructure. This paved the way for private equity ownership. Today only one-third of practices are solo offices.

Heartland Dental began as a management company built around this simple idea: Let dentists treat patients and let someone else handle the business. Heartland bought cotton rolls and recruited assistants while doctors retained control of clinical care.

Another key was real estate and infrastructure. Early on, Workman founded a real estate development company called WMG Development, which purchased the land and built the physical buildings in choice locations, then leased them to Heartland Dental, which recruited the dentists. All told, Winter Garden, Florida–based WMG has developed $1.4 billion in real estate in more than 30 states. For an industry accustomed to dental practices being run from basements, Workman’s corporate approach was both revolutionary and disruptive.

Not everyone liked it.

The American Dental Association (ADA) has long guarded the independence of the profession—or, to a cynic like Workman, the license to run dental practices as lifestyle businesses between rounds of golf. A 2007 New York Times investigation into a national shortage of dentists noted that the ADA disputed the idea of a shortage and fought efforts to expand the number of providers. When Workman began expanding and using metrics to measure the business, many dentists saw it as a threat.

Even post-Workman, dentistry has remarkably few performance standards. One dentist might find reasons to drill and fill numerous cavities on every patient. Another might take a less vigilant approach, merely suggesting more flossing. Gum disease could be treated aggressively in one office and barely assessed in another.

“Dentistry is the only industry you can think of that has no metrics,” Workman explains. “You can do whatever you want as long as you’re happy.”

That approach never sat well with him. At Heartland, the answer was data. Dentists follow standardized clinical protocols that spell out what conditions justify treatments like fillings, crowns or root canals. The company tracks routine benchmarks such as how many new patients receive full exams, including periodontal checks and X-rays, and whether diagnoses fall within expected ranges across populations of patients. If a dentist gives full exams to only 84% of new patients, offering little more than a teeth cleaning, for example, Heartland’s internal reporting flags the gap and asks why it wasn’t 100%.

Heartland dentists earn a base salary, which works like an advance on the money they generate treating patients. Once dentists produce more than four times their base salary in revenue, they begin earning a 25% share of it. As production rises, that percentage increases. On average it climbs to about 32%. Dentists can also qualify for quarterly profit-sharing payments based on how profitable their individual office is. The company claims the average Heartland dentist earns $318,000 a year, versus about $208,000 for general practitioners, according to the ADA.

Given that dentistry is large ($180 billion in domestic revenue), fragmented and steady—people get their teeth cleaned whether the economy is booming or not—it didn’t take long for Wall Street’s savviest investors to take notice. In 2012, 15 years after Workman started Heartland and built it into 375 dental offices in 21 states, the Ontario Teachers’ Pension Plan made a large investment, valuing Workman’s operation at $1.3 billion. Six years later, after Workman had built the firm to 800 offices in 36 states, KKR bought control from the Ontario pension fund at a $2.8 billion valuation.

Since he sold out, vintage cars and philanth­ropy have become Workman’s focus. He’s a well-known presence at the Pebble Beach Concours d’Elegance automobile show. His 1937 Bugatti Type 57S won Best in Class in 2016. In 2023, Workman and his wife donated $32 million to create the Workman School of Dental Medicine at North Carolina’s High Point University.

Workman’s real estate business, WMG Development, has expanded beyond dental offices. Recent projects include Chipotles, Mavis Tire, the Waldorf Astoria Residences in Sarasota, Florida, and a large KFC in Sanford, Florida. In 2025, he added another asset to the portfolio, buying about 10% of the Tampa Bay Rays as part of a deal that valued the baseball franchise at $1.7 billion.

Workman says he still spends much of his time thinking about Heartland and coaches younger dentists who come through the company with new ideas and plenty of ambition. “You’re probably going to make the same mistakes I made ten years ago,” he says. “You don’t have to.”

“Dentistry done normally is reasonably profitable,” he adds. “There are a lot of ways a dentist can go bankrupt. But it’s hard. You’ve got to make more than one bad decision.”

© Forbes