The Millionaire Dentist™

In this episode, Casey and Jarrod explore the surprising crossover between the chaos of March Madness and the daily realities of dentistry. From upsets and unexpected losses to preparation, analytics, and strategy, they reveal how lessons from the court apply directly to running a successful practice. Even the heartbreaks—like tax surprises or unpredictable growth—mirror the shock of a top seed getting knocked out early. They also break down how data, teamwork, and having the right “support staff” (whether coaches or advisors) can make or break your season. Whether you’re a die-hard basketball fan or just someone who appreciates a good analogy, this episode offers practical, eye-opening takeaways for thriving in dentistry—on and off the court.

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Casey and Jarrod sit down with Steve Levy, CPA & JD, to uncover what really happens when a tax surprise hits your practice. From sudden five-figure balances to misleading refunds, the trio breaks down the financial strain, penalties, and stress these surprises create—and why they’re almost always preventable with the right strategy. They also expose how reactive CPAs, poor planning, and outdated “safe harbor” estimates set practice owners up for trouble year after year. With clear examples and practical insight, this episode gives dentists a roadmap to avoid surprises, stay proactive, and finally take control of their tax destiny.

Interested in more info on how to: Earn More, Save More, and Retire Early



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Casey and Jarrod unpack what really happens after a private practice is sold to a DSO—from how patient relationships shift to whether your staff culture survives the transition. They dive into the subtle but significant ways corporate ownership can reshape the ethos of a practice, long after the ink on the contract has dried. They also explore why “easy” sales aren’t always the best ones, and how strengthening your financials before selling opens up better options, better valuations, and better outcomes. Whether you’re years from selling or actively considering it, this episode offers the clarity every practice owner needs before making a career-defining decision.

Interested in more info on how to: Earn More, Save More, and Retire Early



Upcoming Tour Dates: Go to our EVENTS page for info

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Casey and Jarrod reveal details about Four Quadrants’ upcoming national tour—an event series designed to help dentists understand and fix the most common financial pain points in private practice. From overhead problems to insurance adjustments to income frustrations, they break down exactly what practice owners can expect at these intimate, high-impact CE dinners and Topgolf sessions. Unlike large conference lectures, these events get straight to the real issues that hold dentists back. The guys discuss why Four Quadrants isn’t a volume shop, how they identify the right fit, and what happens after a dentist raises their hand for deeper help.

Interested in more info on how to: Earn More, Save More, and Retire Early



Upcoming Tour Dates: Go to our EVENTS page for info

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In this episode, Casey and Jarrod team up with Stacy Phillips, CFP®, to break down why practice transitions succeed—or fall apart. From timing to profitability to the emotional side of letting go, they explore why owners often wait too long, how declining production can tank a future sale, and what buyers really look for when evaluating a potential practice. The conversation also sheds light on the reality of associate buy-ins: most don’t work out, timelines are longer than owners expect, and profitability must look good for both parties. Whether you’re 10 years out or just beginning to think about a sale, this episode highlights why early planning protects your income, widens your options, and leads to a smoother, more profitable transition.

Interested in more info on how to: Earn More, Save More, and Retire Early



Upcoming Tour Dates: Go to our EVENTS page for info

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Casey and Jarrod sit down with Christopher Howard, a seasoned voice in dental consulting and education, to explore the gap between how a practice looks from the outside and what’s really happening behind the scenes. With 15+ years in the field, Christopher unpacks why so many dentists master clinical excellence but quietly struggle with leadership, profitability, staff dynamics, and the business systems needed to support a multimillion-dollar practice. He also dives into how burnout, high overhead, insurance pressure, and unclear financial planning seep into culture, relationships, and morale—and why addressing the business side holistically changes everything.

Interested in more info on how to: Earn More, Save More, and Retire Early



Upcoming Tour Dates: Go to our EVENTS page for info

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Casey and Jarrod sit down again with Dr. Brent Habecker to unpack the moment he realized his external finance team simply wasn’t cutting it—and why making a change transformed both his clarity and his practice. Dr. Habecker explains how unclear advice, vague answers, and too much DIY financial work pushed him to seek a true CFO-level partner who could handle the details while empowering him with better information. He also dives into why delegating isn’t about losing control—it’s about freeing up time, mental energy, and focus for the work that actually grows a practice. From efficiency and sanity to patient care and new clinical skills, Dr. Habecker shares candid insights on the impact of surrounding yourself with the right experts.

Interested in more info on how to: Earn More, Save More, and Retire Early



Upcoming Tour Dates: Go to our EVENTS page for info

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Casey and Jarrod sit down with Dr. Brent Habecker, a highly successful young practice owner from Michigan, to talk honestly about how dentistry is changing for the next generation. From shifting attitudes around practice ownership to the rise of corporate dentistry, Dr. Habecker shares what he's seeing among new graduates—and why the traditional ownership path isn’t always the default anymore. They also dig into his own ownership journey, including what it was like growing up with a dentist father, the reality check of corporate dentistry, and the lessons he learned in the first year of running a practice. It’s a candid, insightful look at modern dentistry through the eyes of someone thriving in it right now.

Interested in more info on how to: Earn More, Save More, and Retire Early



Upcoming Tour Dates: Go to our EVENTS page for info

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It’s a new year, and retirement rules are shifting yet again. Casey and Jarrod sit down with CPA Steve Levy to break down the major 2022 Cost-of-Living Adjustments (COLA) that impact retirement contributions, employer matches, and Social Security taxes. From new deferral limits to the rising Social Security wage base, they unpack what practice owners need to know right now. Whether you're planning your own retirement strategy or supporting your team’s savings goals, this episode offers a clear, practical rundown of the changes that will affect your practice’s finances.

Interested in more info on how to: Earn More, Save More, and Retire Early



Upcoming Tour Dates: Go to our EVENTS page for info

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In this episode, Casey and Jarrod dig into the seven uncomfortable realities most practice owners refuse to say out loud. From income that doesn’t match the workload to the quiet fear of under-saving for retirement, they unpack the thoughts dentists keep to themselves—even while juggling clinical care, leadership, HR, taxes, and the never-ending demands of ownership. These are the truths that rarely get discussed at study clubs, but silently weigh on nearly every practice owner. Through candid stories, humor, and a surprising dose of honesty, the hosts explore why dentistry often feels different than what many imagined—and why avoiding these issues only makes them worse.

Interested in more info on how to: Earn More, Save More, and Retire Early



Upcoming Tour Dates: Go to our EVENTS page for info

Facebook: Four Quadrants Advisory

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