Before the Shovel: The Questions I Ask on Every Land and New Construction Deal

My focus today is on global acquisitions, land and new construction. It's the natural next chapter after credit, capital and a luxury fleet: moving from assets that depreciate to assets that can't be manufactured. But I've learned that land is one of the easiest investments to get excited about and one of the easiest to get wrong.

A beautiful parcel in a growing market is not a deal. It's a starting point. Here are the questions I ask before any opportunity gets serious attention.

Can you actually build what you want to build?

Zoning, entitlements, setbacks, density limits and the local approval process decide what a piece of land can become. I want to know the current zoning, what it would take to change it if needed, how long that process typically takes locally and who has the relationships to move it forward responsibly.

Can you get to it and connect it?

Road access, water, sewer or septic, power and internet are the quiet deal killers. Raw land without utilities can carry costs that surprise even experienced buyers. I ask what it costs and how long it takes to bring each service to the site, in writing, before any number gets modeled.

What's in the ground?

Soil, drainage, flood exposure, environmental history and survey accuracy all matter. Professional reports aren't an expense to minimize. They're the cheapest insurance in the whole project.

Who is the operator?

This is the question I care about most, and it comes from my time at PNC in Pittsburgh. Deals don't execute themselves. People do. I want to know who the developer and builder are, what they've completed before, how they've handled delays and overruns, and whether they've stuck with partners when things got hard.

How is the capital structured?

Where does each dollar sit in the capital stack? What's senior, what's subordinate, and who carries the first loss? What are the fees, and how are decisions made? How is everything documented? Serious partners welcome these questions. People who get defensive about them are telling you something.

What's the downside case?

Everyone shows the upside. I ask for the version where construction runs long, costs climb, rates move the wrong way or the market softens. If the project only works in the best case, it isn't ready.

What's the exit, and when?

Sell after completion? Hold and lease? Refinance? Each path has different timelines and risks. I want a clear, realistic plan for how and when capital comes back, with no promises attached, because nobody can honestly promise a market.

Red flags that make me slow down

Over the years, a few patterns have taught me to slow down, ask more questions or walk away entirely:

• Pressure to commit quickly before documents are ready.
• Projections presented without a downside case or assumptions you can check.
• Vague answers about who controls decisions or how fees are calculated.
• Talk of “guaranteed” outcomes. Nobody can honestly guarantee a market.
• An operator with no completed projects of similar size or type.

None of these automatically kills a deal, but each one deserves a clear, documented answer. The right partners are happy to provide one.

Discipline is the edge

Royal Rentals taught me that time exposes mistakes in a depreciating asset. Land is more forgiving, but it isn't immune. The discipline I built underwriting cars one by one is the same discipline I bring to land: ask the boring questions first, document everything and be willing to walk away.

If you're a land owner, developer or investor who appreciates that approach, I'd welcome a private conversation.