The David Holt Show

Here’s How to Legally Hire a 1099 Contractor in Healthcare


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In this episode of The David Holt Show, host David Holt sits down to tackle one of the most misunderstood and risky areas in healthcare business: independent contractor vs. employee classification. If you’re a healthcare entrepreneur, clinic owner, or medical professional, the way you structure your team could decide the future of your business. Misclassification isn’t just a paperwork issue, it can cost you taxes, penalties, lawsuits, and your professional reputation.

The conversation begins with David sharing his own early experiences working on a farm before he became an attorney. Like many new business owners, he once thought classifying everyone as an independent contractor (1099) was a simple and smart way to avoid payroll headaches. But over time, he learned that what seems like an easy solution often backfires in devastating ways. And in healthcare, where oversight and compliance are non-negotiable, the risks are magnified.

Throughout the episode, David explains the multi-factor test, the actual legal framework used by the IRS, Department of Labor, and state boards to decide whether someone is truly an independent contractor or an employee. He breaks down factors like behavioral control, financial control, and contractual intent, showing why simply having a “contractor agreement” isn’t enough to protect you.

Listeners will walk away with clarity on:
  • Why misclassification can financially destroy a clinic.
  • The myths around independent contractor agreements that too many owners believe.
  • How behavioral and financial control are red flags for regulators.
  • Why even if both parties want a contractor relationship, the government can still step in.
  • The “smart way” top clinics structure roles, contracts, and day-to-day management.

David also shares practical solutions: defining roles clearly, writing airtight contracts, avoiding employee-like behavior in managing contractors, and setting up systems that protect the business. He even outlines a compliance checklist that listeners can apply immediately to safeguard their clinics.

What makes this episode powerful is David’s ability to turn complex legal jargon into straightforward advice. Instead of vague warnings, he gives specific, actionable strategies for staying compliant while scaling a healthcare business. He also teases future episodes, where he’ll dive into even riskier territory; like aesthetics, injectables, and why cash-pay services can be a regulatory minefield.

By the end of this episode, it’s clear: whether you’re hiring your first provider or running a growing clinic, getting contractor vs. employee classification wrong is one of the most expensive mistakes you can make. But with the right knowledge and systems, you can protect your business, your license, and your reputation.

This isn’t just about legal compliance. It’s about building a healthcare business that can scale without fear. For any provider or clinic owner navigating the confusing world of 1099s, W-2s, and labor laws, this episode is a must-listen.
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The David Holt ShowBy Sweet Fish