Dental practice management looks very different from the inside of a career that has survived a major office fire, embezzlement, a lost lease, a robbery at gunpoint, and over two dozen associate relationships — and Dr. Bill Simon has been through all of it. On this episode of The Technology Evangelist Podcast, host Dr. John Flucke sits down with the Chicago-based practitioner, organized dentistry leader, and passionate mentor to explore what four decades of hard-won experience actually looks like in practice. This conversation is brought to you by Medidenta Digital Solutions, the proud sponsor making this podcast possible.
Key Insights on Dental Practice Management and the Future of Organized Dentistry:
- A Career That Started With a Legal Wake-Up Call: Dr. Simon’s entry into practice ownership was anything but conventional. Three years into his first associate position, he discovered that the practice owner — a dentist by training — was not licensed to practice in the United States, leaving Dr. Simon under investigation for aiding the unlicensed practice of dentistry. After his offer to buy the practice was rejected, he executed one of the boldest moves in dental practice management: he built out a two-operatory office four doors down in complete secrecy, and on a Monday morning, opened his doors with a full schedule of patients from his former employer. He credits that harrowing experience as the foundational lesson in understanding the legal and business infrastructure that dental school never covers.
- The Fire — and Why It Was One of the Best Things That Ever Happened: In 2002, Dr. Simon arrived at his office to find a hook-and-ladder truck with its ladder extending into his second-floor practice. The fire did not result in complete combustion, but it effectively ended operations at that location. Within hours, his team had gathered around a server, confirmed the practice management system was intact, and begun notifying patients. Over the following month, the practice operated as a traveling road show across three shared office spaces before settling into an abandoned five-operatory dental suite eight miles away. The fourth month after the fire, the practice posted its best production month in history. Dr. Simon credits his office manager — who grabbed him by the shoulders in the landlord’s apartment while fire hoses were still running upstairs and told him his team needed him to be strong — as the spark that turned the crisis around.
- Embezzlement and the Dental Practice Management Lessons It Teaches: Dr. Simon also navigated a coordinated embezzlement scheme in which an associate dentist and an office manager worked together to defraud the practice — a particularly difficult situation to detect because he was not physically present at that location on a daily basis. He notes that embezzlement in dental offices rarely looks like dramatic theft; it frequently involves inventory shrinkage, understated collections, and incremental skimming that goes unnoticed because independent practices often lack the oversight infrastructure that larger organizations have. His prescription is straightforward: surround yourself with people whose integrity you trust, build a culture where everyone is genuinely looking out for the practice, and implement monitoring systems that make patterns of dishonesty visible before they become catastrophic.
- Hiring Right — The Working Interview Model: One of the most practical dental practice management principles Dr. Simon shares is his team-based hiring process. After an initial interview, promising candidates are invited for a paid working day before any hiring decision is made. Dr. Simon intentionally steps back and lets the team — not himself — interact with the candidate throughout the day. He also funds a team lunch without him present, where conversations tend to surface both the positives and the concerns that a formal interview setting suppresses. When the team comes back saying they love someone, the hire almost always works. When they come back hesitant, it rarely does. Both hosts agree that the instinct to hold onto a bad hire — driven by empathy, staffing shortages, and the disruption of making a change — is one of the costliest dental practice management mistakes a doctor can make.
- The Medicaid Space and Access to Care: Dr. Simon’s second practice, opened in 1987 in Chicago’s Little Village neighborhood, introduced him to Medicaid dentistry and a patient population whose access to care challenges have stayed with him throughout his career. He eventually became chair of the Illinois State Dental Society’s Access to Care Committee and now serves on Illinois’s Health and Family Services Medicaid Policy Review Committee. He and Dr. Flucke discuss the long-term consequences of removing fluoride from drinking water, particularly for lower-income communities where bottled water has already reduced fluoride exposure and where the dental disease burden is already disproportionately high. Dr. Simon frames the policy argument for access to care in the same terms he used in legislative advocacy: preventive dental care keeps patients out of emergency rooms, and the cost comparison is not even close.
- Organized Dentistry and the Future of Dental Meetings: As Chair of the 2026 Chicago Dental Society Midwinter Meeting program — one of the largest and most respected dental meetings in the country — Dr. Simon offers a nuanced view of where the meetings landscape is heading. Smaller state and regional meetings are consolidating or disappearing, while the major hubs — Chicago, Hinman, CDA, and a handful of others — continue to grow. He sees the future as a combination of consolidation among association meetings and a parallel proliferation of independent niche events targeting specific clinical interests or career stages. His core conviction is that in-person meetings provide something that no online format can replicate: unscripted human connection, spontaneous clinical conversations, and the kind of audience questions that push even experienced speakers to think in new directions.
- Social Media, Fake Reality, and What It Costs the Profession: Both Dr. Simon and Dr. Flucke reflect on the tension between the profession’s digital communication tools and the risks of a dental community — especially younger dentists — anchoring their expectations of success and career satisfaction to curated or AI-generated online images of dental life. Dr. Simon offers a memorable phrase: “There are so many ways to communicate that nobody’s communicating.” His concern is not with technology itself, which his practice uses actively, but with the erosion of face-to-face relationship skills that comes when online engagement substitutes for genuine professional community.
- Mentorship as the Highest Return on Experience: Dr. Simon describes mentorship as the activity that gives him the greatest professional satisfaction — and expresses genuine frustration that so many early and mid-career dentists who could benefit from it never reach out. His speaking portfolio spans dental practice management, technology integration, risk management, associate relationships, specialist partnerships, and laboratory collaboration. He makes his cell phone number and email publicly available specifically so that any dentist facing a challenge he has navigated — a difficult associate relationship, a lease crisis, a staffing breakdown, an unexpected legal issue — has a direct line to someone who has already been through it and come out the other side. Dr. Flucke notes that this kind of accessible, experienced mentorship simply did not exist when he started out, and that its availability now is one of the genuinely underutilized resources in dentistry.
Dr. Bill Simon’s career is a masterclass in dental practice management under real-world pressure — not the idealized version taught in dental school, but the version that includes fires, legal complications, betrayal by trusted team members, and the slow, disciplined work of building a culture that can survive all of it. If you are a dental student, an early-career associate, or a seasoned owner looking for a peer who has genuinely seen it all, he is worth reaching out to. Visit drbillsimon.com to learn more about his speaking topics and mentorship availability, or contact him directly at [email protected].
