A Manhattan-based broker who also owns and finances his own rental buildings says the two roles rarely overlap in the industry — and that the gap explains a lot about how deals are handled from offer to closing.

According to a Q&A published by Resident, Jon Conway, a Compass broker with the Vickey Barron Team who covers condos, co-ops and new development across neighborhoods including SoHo, Tribeca and Hudson Yards, says he has personally negotiated and refinanced mortgages on multifamily buildings he owns in New York, Westchester and Connecticut since 2017. That borrower-side experience, he says, means he does not need a headline about rate movements to know what they do to a client’s monthly budget — he can calculate the payment directly.

Negotiation itself, Conway argues, should never start with price. He first establishes a seller’s timing pressures and contingencies, since a seller racing toward a particular closing date will frequently give up real money in exchange for certainty. He says he applies identical scrutiny to his own transactions and to client deals alike, treating price as something extracted from terms rather than opened with.

That same principle carries into comparable sales analysis. Rather than pulling a list of nearby closings, Conway weighs differences in floor, light, layout and renovation status, since two apartments in the same building can differ significantly in value despite appearing identical in a basic search. When a seller disputes a valuation based on a sale that is not genuinely comparable, he says the fix is walking through the reasoning, not arguing the number.

Ownership experience also shapes how he handles co-op board packages, which he describes as underwriting files rather than paperwork — documents built to answer a board’s questions about liquidity, reserves and income before they are asked. He says the same is true of decisions about whether to sell or lease a vacant property: the choice comes down to modeling achievable rent against achievable sale price net of holding costs, a calculation he can run on both sides having been both landlord and seller.

Conway’s advice to buyers vetting a broker who claims investment experience is direct: ask what mortgages they’ve actually signed for, whether they’ve personally carried a vacancy, and whether they remain in a deal through financing and closing or exit once a contract is signed.