Oliver Gentile, MD · Hampton Roads, Virginia
Buy well.
Operate carefully.
Reinvest. Repeat.
Recursive Real Assets is the commercial real estate practice of Oliver Gentile, an anesthesiologist who buys and operates small income property across the seven cities of Hampton Roads. Each acquisition is underwritten with what the last one taught and funded by what it earns — that is the recursion.
Why Hampton Roads
1.7 million people
The largest metro between Washington and Charlotte, spread across seven cities that share one labor market.
Naval Station Norfolk
The largest naval base in the world. Military housing allowances put a floor under rents that most markets don't have.
Port, shipyard, hospitals
The Port of Virginia, Newport News Shipbuilding, and Sentara anchor employment that doesn't move with the national cycle.
The method
Four steps, in order, every time.
Anesthesia and property have the same shape: careful setup, constant monitoring, and margins of safety for the moment something drifts.
- 01
Screen
Every deal goes into the same model: price, rent roll, expenses, debt. Below 1.25× coverage, or a going-in cap under the cost of debt, it stops here.
- 02
Underwrite
Sensitivity before conviction. Price and exit cap are stressed together; a deal has to survive the bad corner of the grid, not just the base case.
- 03
Verify
The trailing twelve is a claim, not a fact. Rent roll against leases, expenses against invoices, capex against a walk-through with a contractor.
- 04
Operate
Monitoring is the job. Monthly actuals against the underwriting, the way a case is watched minute to minute — small drifts caught early.
Buy box
What I’m looking for.
Specific on purpose. A deal that fits gets a real answer fast; one that doesn’t saves us both a week.
- Where
- Hampton Roads — Norfolk, Virginia Beach, Chesapeake, Portsmouth, Suffolk, Hampton, Newport News. I live here and walk every property myself.
- What
- Small multifamily, five to forty units, and medical office. I've been the tenant on the other side of a medical lease.
- Size
- $1M to $10M total capitalization.
- Debt
- Local bank or agency, 65–70% loan-to-value, coverage of 1.25× or better on in-place income.
- Hold
- Five to ten years. Refinance over sale when the numbers allow.
- Not
- Ground-up development, hospitality, or anything that needs rent growth to work.
Portfolio
Every acquisition, with the numbers that bought it.
Deals are listed here as they close — the underwriting going in, and later, how they actually performed against it.
In underwriting
First acquisition.
Brokers and owners with a fit for the box above: send it.
About
Oliver Gentile, MD
Oliver is an anesthesiologist practicing in Hampton Roads. Outside the operating room he built locu.ms, a locums marketplace for physicians, CRNAs, and anesthesiologist assistants; trades index options around dealer positioning; and writes the software he analyzes deals with — including the underwriter on this site.
The name is the strategy. Each property is underwritten with what the previous one taught, and bought with what it earned. The function calls itself.
The underwriter
One model, every deal.
NOI, DSCR, cash-on-cash, levered IRR, and a price × exit-cap sensitivity grid — software I wrote and run every submission through. Send a deal and you get the output, not a feeling.
Send a deal
An OM, a rent roll, and a trailing twelve are enough.
That’s what it takes for a yes or no within a week. Off-market and direct from owners is welcome.
hello@recursiverealassets.com