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Never Call The Name On The Sign — And Other Lease Lessons From A Dental Lawyer

Rob Montgomery III makes rooms full of startup dentists stand up, raise a hand, and repeat after him: I promise not to call the name on the sign.

Then he tells them the punchline: even after the pledge, three of the twenty of you will do it anyway.

Montgomery has been practicing law for 30 years and running his own firm — known in the industry as Your Dental Lawyer — for 28, with dentists as the near-exclusive focus for the last fifteen: acquisitions, startups, leases, real estate purchases, buy-ins, partnership and employment agreements. He also co-hosts The Dental Amigos podcast, which is how he knows how to make an hour about legal documents genuinely fun. We had him on the Dentelligentsia podcast, and the conversation kept returning to one theme: these are once-in-a-career transactions, and nothing about them can be undone. “You can’t give back a practice. You can’t unsign a lease. It’s the old Fram oil filter commercial — pay me now or pay me later.” (Our amendment: pay once now, or twice later.)

The sign, and the two deals

Start with the pledge, because the economics behind it explain everything else. When a dentist sees a space they love and calls the leasing number on the sign, two things happen. First, the landlord’s agent now controls the conversation — and there are two versions of every deal: “There’s the deal for the represented party, and the deal for the unrepresented party. They do not look the same.” Montgomery has watched unrepresented dentists negotiate themselves into shopping-center leases without knowing tenant improvement allowances exist — money the landlord had budgeted, never requested, never received.

Second, and less understood: that phone call can lock your own advocate out. Once the landlord’s broker claims the deal, they typically refuse to recognize or compensate a tenant rep who shows up afterward — so the structure that normally pays for your representation is gone, and you’re alone against a professional. “You’ve totally shot yourself in the foot,” Montgomery said, “with no upside.” See a space you love on a Friday drive? Text your broker the address. That’s the whole discipline.

The clause that decides what your practice sells for

Asked what he actually fights for in a lease, Montgomery didn’t start with rent. He started with the exit. “The number one deal killer in a practice transition is an uncooperative landlord.”

His firm handles transitions constantly, and the pattern repeats: a dentist builds value for a decade, finds a buyer, and then discovers the landlord holds a veto — because the lease’s assignment clause requires consent the landlord can withhold, or hedges with the word “reasonable,” which Montgomery calls punting: “What Remy thinks is reasonable, what Rob thinks is reasonable, what a judge thinks is reasonable, and what a landlord thinks is reasonable could be five different things.”

His cautionary tale is brutal. A disabled specialist needed to sell. A buyer was found; everything came together. The landlord reviewed the buyer’s financials — $350,000 in student debt, negative net worth, which is to say: a completely normal practice buyer whom a bank was happily financing — and demanded a ten-month security deposit to approve the assignment. Roughly $60,000 that existed in nobody’s deal. The sale died; the seller defaulted on her loan. All of it preventable with one paragraph negotiated ten years earlier.

What he wants instead: the right to assign to a purchaser of all or substantially all of the practice’s assets — with the selling dentist released from the lease and their personal guarantee extinguished at assignment. And he wants it raised in the letter of intent, not the lease. His numbers on that: terms that make it into the LOI survive into the lease nineteen times out of twenty, because at the LOI stage you’re negotiating with business people who want a deal. Wait for the lease draft and you’re negotiating with the landlord’s lawyer, whose job is to protect their client — and the odds fall to one in five. This is also where he was generous about our profession’s role, so we’ll quote rather than paraphrase: the broker’s job is to educate the landlord on what a dental tenant is — a decade-plus, near-zero-default, evergreen tenant whose practice will occupy the space for a generation. “If the table’s not set right, everything we’re asking for gets a lot harder.”

Employment agreements: enforceability is the wrong question

For associates, Montgomery’s message starts blunt: you’ve spent your life signing apartment leases and Subaru contracts — consumer documents with protection laws baked in. “These are grown-up contracts now. There’s no telling what’s in there, and there’s no such thing as a standard agreement.”

On non-competes, he dismantles the advice associates actually receive — “I read on Facebook they’re not enforceable; my attending said don’t worry.” His response: the only way to find out if a non-compete is enforceable is a lawsuit — complaint, depositions, trial, easily six figures and a year of your life. And even a laughably broad covenant binds you in practice, because banks won’t fund a startup that could be shut down on opening day: a 50-mile non-compete nobody would ever enforce can still kill your $700,000 loan. “For all economic and business purposes, they are enforceable. Sign them as though they are.”

Which makes the analysis personal, not legal: the associate spending two years in one city while a spouse finishes residency may not care about a non-compete there; the orthodontist whose referral network lives in one neighborhood cares enormously. And on Nick’s technical question — can you sign a lease and build out during the restricted period as long as you’re not practicing? — Montgomery’s lawyerly, correct answer: usually yes, but it depends entirely on how that specific document is drafted. Which is the whole argument for having someone read it.

Buying the building: the work is everything around the documents

On real estate purchases, his pitfall list starts with zoning and permitted use — never assume dental is allowed, and never assume the approval timeline is zero; bake it into the deal instead of discovering it after closing. Then the physical and environmental diligence, then title, survey, and encroachments: confirming that what you think you’re buying is what you’re buying.

And he flagged a misconception worth its own paragraph: first-time legal consumers think the lawyer’s job is the documents. “That’s the commodity part. What’s really important is everything we do to get you to closing — making sure the conditions are satisfied and nothing comes up as a surprise. To be limited to just the document, and then something goes wrong on a ship we were on but had no control over — I’d rather not be in that position.” His firm declines document-only engagements, and that’s the reason.

Cheap lawyers cost the most

His hiring advice generalizes to every professional on a dental project. Legal work has no minimum deliverable standard the way a crown does — “you’re buying time” — so the lowball flat fee usually means one thing: less time spent on your deal. “People quoting lowball flat fees are just not putting in the time to make sure it’s done right. Those are the deals where problems come up after the fact.” The fix isn’t paying blindly; it’s due diligence and trust — and if your fear is that an attorney will run up the bill on you, the problem isn’t attorneys, it’s that you’ve hired one you don’t trust.

The best moment of the hour was his description of why he’s still at this after 30 years, borrowing from his podcast partner Paul Goodman: being part of a startup or a practice purchase is like being there when the baby is delivered — present at the defining moment of someone’s career, with the experience to make sure it goes right. Add his other borrowed line — Arthur Brooks’s question of whether you’re working on your résumé or your eulogy — and you get a pretty good picture of the kind of advisor worth having.

Assemble the team, use the team, and put the hard terms in the LOI. The full conversation with Rob Montgomery, “Why Do Dentists Need a Lawyer? Find Out!,” is on the Dentelligentsia podcast. And the next time a building with a sign catches your eye — text us the address. Don’t call the number.

And follow Rob Montgomery on Linked In or check out the Your Dental Lawyer website.