Jill Allen & Associates Blog

Navigating Legal Terrain for Young Orthodontists with Rob Montgomery

Written by Jill Allen | Thu, Sep 11, 2025 @ 03:15 PM

Legal talk doesn’t usually make the highlight reel for young orthodontists, but it should. In this week’s episode of the Hey Docs! Podcast, Jill Allen sits down with Rob Montgomery (aka Your Dental Lawyer) to unpack the hidden legal traps that can derail a doctor’s career. From lease negotiations to associate contracts, Rob makes one thing crystal clear: understanding the fine print isn’t optional. It’s essential to protecting your future.

Meet Rob Montgomery

Rob isn’t just any attorney. He’s a go-to legal guide for dentists and orthodontists. With decades of experience helping doctors through startups, acquisitions, and partnerships, he knows exactly where the blind spots hide and how to steer clear of costly mistakes.

Why Contracts Deserve More Respect

Rob’s advice? Stop thinking of contracts as “just paperwork.” These are career-defining documents like leases, associate agreements, and partnerships that carry real weight. If you’re not reading (and fully understanding) what you’re signing, you’re putting your practice and your future on the line.

Lease Landmines Every Startup Should Watch

Starting your first practice? Your lease is one of the most important contracts you’ll ever sign. Rob highlights two big red flags:

  • Protect Your Buildout – You’re investing serious money into your office space. Relocation clauses or sneaky stipulations can wipe out that investment in an instant.

  • Think Ahead to Resale – Make sure your lease is transferable if you sell your practice, and ensure personal guarantees get released when you do.

The Truth About Associate Agreements

That “partnership track” you were promised? Without binding terms in writing, it may never happen. Rob calls out the risks of non-compete clauses and vague promises that keep associates strung along without real opportunity. His advice: don’t wait until you’re burned. Get legal counsel before you sign.

Ownership vs. Partnership: What’s Really on the Table

DSO partnerships can look shiny from the outside, but they rarely offer the same autonomy and long-term satisfaction as true ownership. Rob encourages young orthodontists not to sell themselves short. Ownership is still very possible, and incredibly rewarding, when done with the right guidance.

Rob’s Pearls of Wisdom

  • Don’t underestimate contracts. They shape your career.

  • Surround yourself with a strong legal and financial team.

  • Don’t let the DSO narrative scare you away from ownership.

Why This Episode Matters

If you’re a young orthodontist navigating big career decisions, this conversation with Rob Montgomery is a must-listen. It’s packed with practical, no-nonsense advice that could save you from years of headaches and financial loss.

👉 Connect with Rob at yourdentallawyer.com
👉 Check out The Dental Amigos Podcast for even more legal and business insights.

Stay smart, stay protected, and most importantly, keep building the career (and life) you want.