Ninety-eight percent of small practices believe they're HIPAA compliant. Far fewer actually are — and that gap tends to sit quietly until an audit, a complaint, or a breach forces it open.

In this SNACK episode, Miranda Dorta turns the mic on Tracy Cherpeski for an unscripted conversation about the compliance question providers ask quietly after everything else has been covered: how do I actually know if I'm in compliance?

They talk through why so many providers wait until something goes wrong, the one area practices most often assume they've got covered (and usually haven't), and why “better safe than sorry” beats “no news is good news” every time.

Tracy also shares a simple, low-cost first step any provider can take today — no big budget required.

Read the full show notes, memorable quotes, and key takeaways.

Podcast Episode With Compliance Expert Dr. Natasha Guess: Don’t Wait for the Audit: Three Compliance Gaps Hiding in Your Practice Featuring Dr. Natasha Guess, EP 270

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Will a patient check-in kiosk cost your practice the human touch, or give it back? In this episode, Tracy Cherpeski talks with Aaron Westphal, president of Kiosk Group, about self-service technology for independent healthcare practices.

Aaron started in professional kitchens, and he explains why a good kiosk setup works like a well-run line: many stations, one plate. He and Tracy cover how kiosks connect with your EHR, why you still need a great front desk, the difference between automation and AI, and why fear of technology can quietly cost a practice time and money.

You will also hear how to decide whether your problem is about people, systems or tools, why modular technology can grow with you, and the first question Aaron asks every prospective customer.

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What's the most important financial document a practice owner will ever have? It's not a mutual fund, a will, or a trust — according to this episode's guest, it's a written financial plan. Tracy Cherpeski sits down with Mike Milligan, founder of One Oak Financial, a B Corp certified firm that works with high-income earners, especially physicians and practice owners.

Mike spent his early career on Wall Street before building a firm around impact over profit. In this conversation, he draws a sharp line between practices that are thriving and practices that are just surviving, and explains why some people own a business while others just own a job.

They also dig into money scripts, why taxes may be the biggest expense practice owners never address, and how a written plan can keep you from making decisions out of fear when the market gets shaky. If you've been meaning to have the money conversation but keep putting it off, this one's for you.

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Exhausted practice owners tend to wait for the holiday break to plan next year, or rush a purchase just to feel like they moved something. Both come from the same place, and both cost more than they seem to. In this solo episode, Tracy Cherpeski shares a year-end order of operations built on one idea: don’t wait, but don’t rush.

You’ll hear five steps you can start in November: know your numbers, name whether you have a people, systems, or tool problem, clean up the process before you automate it, choose your tools and partners with a clear head, and give time back to your team and yourself. Tracy also shares a client story about making space for planning first, and previews two November gatherings, including the first look at the Bottleneck Diagnostic.

It is also a big month on the show, with Aaron Westphal, Jeremy Hummer, and Ginger Hilton joining Tracy one per week.

November Gatherings

Community of Practice Gathering: Tuesday, November 10, 2026, 7:00 to 8:30 p.m. Eastern. A structured 90 minutes with questions submitted in advance (or asked in the moment), hot seat coaching, and conversation with fellow practice owners. The Bottleneck Diagnostic is introduced at this gathering. Click to register.

MasterMind Gathering: Friday, November 20, 2026, 9:00 to 10:00 a.m. Eastern. A popcorn-style conversation with no presentation and no advance questions, led by Tracy. It is a good place to ask about Thriving Practice Community programming and get a feel for how the community works. Click to register.

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Ask a practice owner when they last took two weeks off without checking in once, and you'll usually get a long pause. In this SNACK episode, Miranda Dorta puts Tracy Cherpeski in the interview seat to talk about what it takes to step away from your practice, with the holidays close enough to make it urgent.

A 2024 JAMA Network Open study found that about 70% of the physicians surveyed worked on vacation, and fewer than half had full inbox coverage. Tracy explains why the inbox is only the visible part, and why time off turns into work from a different location when every decision runs through one person.

In this episode, you'll hear:

• Why decision rights come before coverage

• How to use the ABCD delegation quadrant for team decisions

• How to test time off with a long weekend before you try a week or two

• A 10-minute exercise to start this week

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You earn six figures. But what if your entire financial future depends on being able to work? In this episode, Tracy Cherpeski sits down with Rob Natale, founder of North Square Capital, to explore why high-earning physicians need a "second engine of wealth."

Rob spent over a decade in corporate finance at firms like Morgan Stanley, Merrill Lynch, and UBS before leaving to help physicians build financial security outside their practices. He shares four real estate investment pathways—from direct ownership to passive syndications—and walks you through the returns, tax implications, and which strategy might be right for you.

But here's what makes this conversation so compelling: Rob's personal story. When he was 13, he was diagnosed with chronic fatigue syndrome. That experience—and a team of physicians who truly believed in him—shaped his entire mission. He's publishing a book this month and is deeply committed to helping medical professionals protect themselves and build generational wealth.

Whether you're thinking about passive income, planning for retirement, or wanting to eventually sell your practice for maximum value, this episode gives you the framework to start.

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Most practice owners know their patient volume. Far fewer know their denial rate, cash on hand, or what a credentialing delay is costing them this month. In this episode, Tracy Cherpeski talks with Ginger Hilton, founder of Nautilus Operations Consulting, about the operational foundations that keep an independent medical practice profitable and the owner out of the weeds.

Ginger spent 15 years inside healthcare offices, working every role from medical assistant to office manager before launching her consulting practice. She walks through the numbers every owner should track, what an operational foundation actually includes, the difference between an office manager and a fractional COO, and why you should never automate a workflow you haven't cleaned up first.

You'll also hear the two biggest misconceptions practice owners have about operations, including why more hands don't fix a broken process, and the one condition that has to be true before any operations help can work: a real willingness to delegate.

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What if the reason your practice is burning out isn't broken people—it's a broken system? In this episode, Tracy Cherpeski sits down with Jeremy Hummer, SVP of Strategic Partnerships and Growth at Certified Health, a practice automation platform that's been quietly solving this problem for healthcare systems and group practices for over 12 years.

Jeremy comes from hospitality, not healthcare IT—and that changes everything. Certified Health started by helping enterprises consolidate patient identity across thousands of locations using biometrics. But Jeremy realized the real insight: automation isn't about replacing staff. It's about freeing them from paperwork and repetitive data entry so they can actually connect with patients.

In this episode, you'll hear about the 'training hamster wheel'—the invisible cost of staff turnover that most practices don't calculate—and why the biggest fear about AI and automation completely misses the point. Tracy and Jeremy discuss real implementation challenges, the importance of stakeholder buy-in before deploying any technology, and how to think like hospitality instead of IT when designing patient experience. Plus: how multi-location practices can unify workflows across disparate EMR systems without expensive replacements.

Read the full show notes, memorable quotes, and key takeaways.

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