Before there was a billion dollar company, there was a hand painted sign. When Rick Workman opened his first dental office in Effingham, Illinois, his entire marketing budget was a $15 sign stuck in the front yard. Fifteen months later he opened a second office and settled into a punishing rhythm: 55 hours a week in the chair and another 30 on the business side. Somewhere in those 85-hour weeks, he had the thought that would eventually reshape American dentistry: there had to be a better way to run the business of a practice, so the dentist could just be a dentist.

Today that idea is Heartland Dental, the largest dental support organization in the United States, and Workman is, by Forbes’s reckoning, the only person who has become a billionaire by practicing dentistry. What he built is genuinely impressive. It’s also incredibly controversial. An honest look at his career has to take both seriously.

The dentist who got tired of being a dentist

Workman grew up on a farm near Ingraham, Illinois, a town of about 247 people; his father farmed, his mother taught. He has said he was certain of two things growing up: he didn’t want to farm forever, and he wanted a red Corvette. He earned an undergraduate degree from Southern Illinois University in 1977 and a dental degree from the SIU School of Dental Medicine in 1980, then opened his first practice in Effingham.

The insight that made him rich wasn’t clinical. It was that the business of a dental practice is largely the same from one office to the next, which means it can be standardized, centralized, and run by specialists, freeing the dentist to do the one thing only a dentist can do. Workman started offering that kind of non-clinical support to other dentists in the early 1980s, refined it across his own growing group of offices through the next decade, and in 1997 formally founded Heartland Dental.

The model: selling dentists their time back

A dental support organization, stripped to its essence, is a company that takes everything that isn’t dentistry off a dentist’s plate. Heartland’s pitch to a supported doctor is straightforward: keep your clinical autonomy and your name on the door, hand us the back office, and get your evenings back. In exchange, the DSO earns fees for those services and, in most arrangements, a share of the economics.

There’s a legal reason it’s structured as a support company rather than a dental chain. In most states, only a licensed dentist may own a dental practice, so investors who want exposure to dentistry create a separate services entity, the DSO, that contracts with the dentist owned practice to handle the business side. Critics call that a workaround; the industry calls it compliance. Either way, it’s the framework the entire sector is built on.

The timing of Workman’s bet looks prescient now. New dentists are leaving school with student debt north of $300,000, equipment and overhead keep climbing, and the technology bar keeps rising. This is exactly the pressures that make a turnkey support partner attractive to someone who can’t easily bankroll a solo startup. The numbers show the shift: per the ADA Health Policy Institute, more than one in four dentists less than a decade out of school are apart of a DSO. Workman didn’t just ride that wave. He helped create it.

Where the money came from: pension funds and private equity

For its first decade and a half, Heartland grew the slow way. The inflection came from outside capital. Just before the close of 2012, Canada’s Ontario Teachers’ Pension Plan took its first majority stake, when Heartland supported 397 offices across 21 states. Over the next five years the company roughly doubled, and supported practice revenues rose about 126%.

Then came the deal that signaled dentistry had arrived as a serious institutional asset class. In 2018, private equity giant KKR acquired a majority interest from Ontario Teachers’, which kept a sizable minority stake. Workman, longtime President, CEO Pat Bauer, and supported dentists all retained shares. At the time Heartland backed roughly 850 offices in 35 states and around $1.3 billion in supported practice revenue. The official terms went undisclosed, though the transaction was widely reported to value the company at about $2.8 billion. Notably, KKR invested through a long hold strategy rather than a typical flip in five year fund — a vote that Heartland was a compounder, not a quick trade.

Workman layered on a second business most dentists never think about: he founded a real estate company. The company named WMG Development which built dental offices and leased them back to Heartland. He now owned the dirt under the chairs as well as the chairs. Add it up and the farm kid got more than the Corvette. In 2026, Forbes placed Workman on its World’s Billionaires List at No. 2,481, with a net worth of $1.6 billion. One of a handful of dental billionaires, and the only one who built the fortune from the practice of dentistry rather than from selling implants or equipment.

How big it is now

Heartland today is the category’s runaway leader. As of mid-2025 it supported more than 3,000 doctors across over 1,800 offices in 39 states and the District of Columbia, with more than 20,000 total team members. Growth hasn’t stalled either, revenue rose about 7.3% in 2025, earning a credit rating upgrade, and the company kept buying, including the 60 office Florida group Smile Design Dentistry. For scale, its nearest DSO rivals, Aspen and PDS, each support around a thousand practices. Heartland leads the field by a wide margin.

The other side of the drill

Here’s where the story gets contested, and where we owe you the uncomfortable half.

The DSO model, and the private equity that now dominates it, draws sustained criticism from clinicians, watchdogs, and a growing number of legislators. The Private Equity Stakeholder Project, which tracks PE across industries, found that 27 of the 30 largest DSOs are private equity owned, and argues that the time pressured returns PE demands can create incentives for over treatment, aggressive marketing, and revenue target pressure on dentists. The fear, in one line: that quantity of care starts to crowd out quality.

The cautionary tales belong to other chains, not Heartland. Benevis, formerly Kool Smiles, paid roughly $24 million in 2018 to settle Justice Department allegations that it billed Medicaid for medically unnecessary procedures on children, with the government claiming dentists were pushed toward more treatment via bonuses and discipline. Aspen Dental has faced its own years of regulatory scrutiny. Heartland has not been the subject of comparable federal findings, and it markets itself, pointedly, on preserving clinical autonomy. Workman’s consistent framing is that Heartland is a group practice built to give doctors “what doctors want,” not a corporation dictating treatment. But the sector’s baggage is why the scrutiny exists, and it’s landing in statute: California’s SB 351, effective January 2026, bars investor interference with dentists’ clinical judgment and outlaws the gag clauses that stop dentists from speaking up about quality. Expect more states to follow.

Heartland points to the other side of its ledger as well with a charitable arm. The Heartland Dental Foundation is an annual Free Dentistry Day that has delivered millions in donated care; and a funding gift behind the new Workman School of Dental Medicine at High Point University. Whether you read all that as genuine mission or reputational ballast probably depends on what you already think about corporate dentistry.

What a solo dentist can take from it

You don’t have to want to build the next Heartland to learn from how Workman built this one. His real move wasn’t clinical brilliance; it was recognizing that the business of dentistry is a separable, standardizable, and scalable product. He refused to treat his own time at the chair as the ceiling on what he could earn. That’s the same insight, scaled up, behind every associate’s decision to eventually own, and every owner’s decision to add a second location.

It also cuts the other way. The consolidation Workman helped unleash is exactly what’s reshaping the math for the next generation deciding whether to associate, buy, or build. Because increasingly there’s a fourth option on the table, which is to sell to, or start under, a DSO. Love the model or distrust it, it’s now a permanent feature of the landscape. A guy with a $15 yard sign made sure of that.