Inside the market with a broker who’s also a multifamily owner, breaking down real costs, comps, and negotiations from offer through closing in New York City luxury real estate photo provided by contributor
Real Estate Resources

Expert Q&A Interview with Jon Conway, a New York City Luxury Real Estate Broker and Investor

How a New York City luxury broker’s firsthand experience as an investor, landlord, and borrower shapes transparent advice on buying, holding, renting, or selling condos and co-ops

Resident Contributor

Jon Conway is a multifamily investor and New York City real estate broker at Compass with the Vickey Barron Team. This interview is provided for informational purposes and reflects market experience rather than professional tax, legal, or investment advice. Individual circumstances vary. Jon Conway can be reached at 914-462-9145.

Most people who advise on New York real estate have never owned any property. They have shown it, listed it, marketed it, and negotiated it, but they have not signed the mortgage, set the rent, filled the vacancy, or carried the month when the apartment sat empty.

Jon Conway is one of the exceptions. A multifamily investor and New York City real estate broker at Compass with the Vickey Barron Team specializing in condos, co-ops, and new development, he owns and operates multifamily rental property in New York, Westchester, and Connecticut, and has since 2017. We asked him what changes when the person advising you has been the principal.

Who are you, and what do you do?

I am a multifamily investor and a New York City real estate broker at Compass with the Vickey Barron Team, specializing in condos, co-ops, and new development. I represent buyers, sellers, and investors who buy and sell condos and co-ops in Chelsea, Hudson Yards, Tribeca, SoHo, the West Village, Greenwich Village, Flatiron, and NoMad. I also work with clients looking to rent, helping them find luxury condos and co-ops in New York City. Separately from the brokerage, I own and operate several multifamily buildings in New York, Westchester, and Connecticut, and have since 2017.

What does it mean that you have been on both sides of the table?

Most New York City brokers have never purchased real estate themselves. In my opinion that is a red flag. How can someone advise on a process, and charge for performing it, when they have never been through it themselves?

That is not hypothetical for me. When I represent a client I am not describing a process I have read about, I am describing one I have been through with my own money on the line.

The other side matters just as much. I have been a New York renter and I am a New York landlord. I have set rents, filled units, and eaten the months when a unit sat empty.

Does owning property actually change how you advise a buyer?

It gives me a clearer basis for the part of the analysis most buyers look at last, which is what an apartment costs to hold rather than what it costs to acquire.

Those figures vary more than people expect. Two comparable apartments in different buildings can carry very differently, because common charges and management costs are set building by building and the tax picture is not uniform. A building with a large staff, an active capital plan, or an abatement approaching its end produces a different monthly obligation than one without, and none of that appears on a listing sheet.

The numbers tell the story, and they matter well past the closing. A client who buys a condo and later needs to move has to decide whether to rent it out or sell it, and that decision runs on the same figures: the carrying cost, the achievable rent, and the realistic sale price. If those were modeled honestly at acquisition, the decision years later is straightforward. If they were not, the client is guessing with a significant asset.

Having bought and held property myself, I have had to live with those numbers rather than simply present them. So I model the carrying costs before an offer goes in, not after, and give a client a clear picture of the full cost while they can still act on it.

There is a practical dimension worth stating plainly. Owning income-producing property means my livelihood does not ride on any one transaction closing. That is an unusual position for a broker to be in, and it changes what I am able to tell a client. Advising someone to wait, or to walk away from an apartment that does not work, costs me nothing I depend on. What I want out of this work is for people to end up somewhere they are genuinely happy, with numbers that still hold up a year after they move in.

What is the difference between describing a market and underwriting one?

Describing is what a listing sheet does. Underwriting is deciding what a specific unit is worth to a specific buyer at a specific price, and committing to that view rather than hedging it. When I underwrite, that includes telling my client when the numbers do not work. Transparency is key, and a broker who only ever confirms what a client already wants to hear is not adding anything.

How do you build a comparable sales analysis?

Comps are not a list of nearby sales. Two apartments in the same building, one line apart, can be worth materially different amounts because of light, floor, layout, and condition. A sale down the block with a different exposure, or one that closed after a full renovation, is not a comparable to an unrenovated unit, even though both will turn up in the same search.

That gap is where most disagreements begin. An owner will often believe their apartment is worth more on the strength of a sale that is not genuinely comparable to theirs. The answer is not to argue with the conclusion. It is to walk the client through the analysis, so they can see which sales carried weight, which were set aside, and the reasoning behind both.

Transparency is one of the most important traits a broker can have. A number a client understands is a number they can act on with confidence. A number they are simply handed is one they will second-guess at the worst possible moment.

What does it actually mean to take a deal from start to finish?

It is worth spelling out, because the phrase gets used loosely. A purchase is not one process, it is several, and they call for different skills. A written offer or letter of intent. The negotiation to an accepted offer. Contract review with counsel. A board package, if the building requires one. Due diligence. A lender's underwriting and appraisal. Then the closing itself.

Most residential agents are genuinely active for the first two and hand the rest to the attorney and the mortgage broker. That is the industry norm and it is not laziness, it is how the job is usually structured. But it means the person who advised you on the decision is not in the room for most of what determines whether the deal survives.

I have run the full sequence as the principal, which is the only way I know it. I have sat across from lenders, worked through attorney comments line by line, and answered diligence questions myself, because on my own acquisitions there was nobody to hand them to. I have also taken clients through condo and co-op board approval, which is its own discipline and the stage where transactions most often stall.

I firmly believe a broker's job does not end when a contract is signed. It is my responsibility to carry a client through due diligence and to be reachable, from the first apartment we walk through to the day they close. That stretch is the easiest part of the job to quietly stop doing, and it is the part that decides whether a deal reaches the closing table.

How does financing experience help a client?

I have negotiated my own mortgages and refinanced buildings I own, so I have sat on the borrower's side of that table and signed for the debt. When rates move I do not need a headline to tell me what it does to a buyer's budget. I can show them the payment, and what the change does to the monthly cost they will actually carry.

How do you approach a negotiation?

Price is what clients care about most, which is exactly why I do not open with it. The leverage that actually moves a price comes from understanding what the other side needs, and you cannot find that out by leading with a number.

So I work out the terms first and use them to get the price. Timing, contingencies, the closing date, what the seller's next move depends on. A seller who needs to close by a particular date will often trade real dollars to get it, and you only learn that by asking questions most people skip in the rush to get an offer in.

I negotiate for clients on the same terms I use when the money at risk is my own.

A client owns an apartment they do not live in. Should they sell it or lease it?

That is a modeling question before it is a listing question, and it deserves an honest answer rather than a convenient one. The comparison is the achievable rent against the achievable sale price, net of what it costs to hold, over a realistic time horizon.

I can build both sides of that number because I have done both. When a client asks what their apartment would actually lease for, that is not a guess I outsource to a rental agent.

Many practices are only equipped to answer half of that question, and it tends to be the half that results in a listing.

What makes a co-op board package difficult?

A board package is an underwriting file. Liquidity, post-closing reserves, debt to income, and how an applicant's money is actually documented. I have assembled that same category of file for lenders many times, and I have taken clients through condo and co-op board approval, so I know where a package draws questions before a board opens it.

The mistake I see most often is treating it as paperwork to complete rather than a case to argue. A board is underwriting the applicant. The package should answer the question the board is going to ask before it gets asked.

What should someone ask a broker who says they invest in real estate themselves?

Ask what they have personally financed rather than what they have sold. Ask whether they have carried a vacancy. Ask whether they stay in a transaction through financing and closing, or step back at contract.

Those three answers separate someone who has been the principal from someone who has been standing next to one.

Why did you build your practice this way?

I got into brokerage because I was on the client side of the table and the service was not good enough. Too much pushing, too little math, too much interest in the next commission. I built my practice as the opposite. 

How do people reach you?

Directly. I am always reachable at 914-462-9145, or through my page at Compass. Calls come to me rather than to an associate.

Buyers weighing a specific line or floor, owners deciding between selling and leasing, and investors who want a purchase underwritten before an offer goes in are all worth a conversation before anything is committed to.

Inspired by what you read?
Get more stories like this—plus exclusive guides and resident recommendations—delivered to your inbox. Subscribe to our exclusive newsletter

The products and experiences featured on RESIDENT™ are independently selected by our editorial team. We may receive compensation from retailers and partners when readers engage with or make purchases through certain links.

Why Luxury Watches Remain the Ultimate Legacy Asset

Mytheresa Brings a Mobile Airstream Boutique to the Hamptons This Summer

Shinola's Mackinac Night Race Brings a Sailing Legend to the Wrist

Rodeo Star Rocker Steiner Signs as Rock & Roll Denim's Newest Brand Ambassador

Delano Miami Beach and The Paradise Suite Score a Football Capsule for the World Cup