Tax Day is coming fast, and CPA/JD Steve “Pipes” Levy joins Jarrod to break down one of the most misunderstood topics in dentistry finance: tax extensions. They tackle the biggest myths—like whether extensions trigger audits or delay payment deadlines—and explain when filing one is not only okay but actually smart. From missing documents to brokerage statements that always show up late, Steve shares the real reasons people extend (and the costly mistakes many make when they do). He also spills a few insider tips on keeping your records tight, avoiding penalties, and staying far away from that dreaded box of year-old receipts.

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CFP® Stacy Phillips joins Casey and Jarrod to break down one of the most confusing parts of money management: the difference between an investment advisor and a true financial planner. She explains why dentists often get targeted with questionable “opportunities,” what red flags to watch out for, and why having a comprehensive plan—not just someone picking your investments—is the real game-changer. From hilarious March Madness bragging rights to Ponzi schemes, FINRA BrokerCheck, and why your crazy uncle should not be your financial guru, this episode is packed with practical tips and eye-opening insights.

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Casey and Jarrod sit down with CFP® Colin Holmes to break down the recent headlines around Silicon Valley Bank and explain why it’s got everyone in the financial world talking. From bank runs to treasury troubles, they unpack what happened in a way that makes sense—even if you’re not a Wall Street expert. They also dive into how smaller banks can struggle compared to the big players, the role of regulation (or deregulation), and why ESG initiatives can sometimes distract from the basics of banking. Whether you’re a dentist, business owner, or just curious about your money, this episode gives you the insight you need to stay savvy and avoid financial surprises.

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Casey and Jarrod dive into one of the most surprising stats in dentistry: dentists retire, on average, seven years later than everyone else. They explore why a profession known for high income often struggles to produce early—or even on-time—retirement. Spoiler: it’s not just debt… and it’s not just burnout. From tangled finances to skewed income perceptions, rising stress, and the mental load of running a practice, they break down the real reasons many dentists work well past the national average. Whether retirement feels decades away or right around the corner, this episode sheds light on what’s holding dentists back—and how to change the story.

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Casey is back in the studio and ready to stir the pot with Jarrod as they dive into a universal pain point for dentists: terrible cash flow. From “cooking the books” to outdated fees, hidden tax surprises, and being booked out months because insurance is eating your margins, they break down why so many practice owners feel stuck, stressed, and constantly behind. Together, they peel back the layers on the real reasons cash flow suffers, and the small, practical fixes that start turning everything around. Whether you’re drowning in overhead, clueless about your true numbers, or convinced the only escape is selling to a DSO, this episode reminds you that good cash flow isn’t magic… it’s management.

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CEO and Founder Jason Smith joins Jarrod to tackle one of the loudest—and most misleading—ideas circulating in dentistry: that the only way to become wealthy is to own a string of practices. Jason breaks down the hype, the hidden risks, and the real-world disasters no one talks about, from bad locations to burned-out doctors barely keeping all the plates spinning. With blunt honesty and real numbers, he walks through why most dentists don’t need multiple practices to get rich—what they actually need is one well-run practice and the right guidance behind it. If you’ve ever wondered whether expansion is ambitious or unnecessary chaos, this episode will have you rethinking what success in dentistry really looks like.

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Casey and Jarrod welcome Four Quadrants Regional Sales Rep Chad Tothero to pull back the curtain on what really happens at our Topgolf CE events. From young associates to seasoned dentists on the brink of retirement, Chad shares what surprised him most: no matter the city, stage of career, or personality—practice owners across the country are wrestling with the exact same business challenges. From honest questions whispered after the presentation to conversations about taxes, transitions, and whether someone’s accountant is truly helping, this episode dives into the unfiltered reality of dentistry today. Plus, Casey recounts his turbulent flight, emotional movie choices, and what Boston and Nashville practice owners oddly have in common.

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Casey and Jarrod ring in the sixth anniversary of The Millionaire Dentist™ with a special guest: Four Quadrants COO and original episode alum, Baxter Brogan. Together, they look back at the humble beginnings of the show—tiny tables, nerves, and questionable marketing advice included—and reflect on how far both the podcast and the profession have come. From pre-COVID norms to today’s rising costs, staffing battles, and changing financial pressures, the trio breaks down the biggest shifts they’ve witnessed in dentistry. This milestone episode blends nostalgia, humor, and hard-hitting insights—and proves that even after 150 episodes, they’re just getting started.

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Casey and Jarrod serve up a spicy comparison between perfecting a chili recipe and running a thriving dental practice. From unexpected ingredients to personal preferences, they explore why no single trick, hack, or “secret sauce” can make a practice truly successful. Like great chili, it takes the right blend of details, discipline, and creativity. They also dive into real workshop stories, tax frustrations, upcoming events, and why practice owners often inherit a “half-cooked” recipe they never chose. Whether you like your chili sweet, spicy, or tear-inducing, this episode will make you laugh, and rethink what’s simmering in your own practice.

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Casey and Jarrod take a cross-country look at dentistry, exploring whether the place you practice really changes the pressures you face. From big-city bustle to small-town calm, they dig into what’s myth, what’s real, and why most practice problems are more universal than you’d think. Through candid stories from the road, honest conversations with dentists, and a few hilarious detours, they reveal why owners everywhere struggle with the same insecurities, surprises, and financial hurdles, no matter their ZIP code. If you’ve ever wondered whether other dentists “have it all figured out,” this episode sets the record straight.

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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