Why Did This Deal Come to Me? — On Why the Good Ones Sit Unsold

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Say you spot a used car on the lot in unusually good shape. Low mileage for its age, priced under the going rate. Your pulse quickens. But there’s a question you can’t afford to skip: “If this car is this good, why is it still here?” A truly great car would have sold already. The fact that it’s still sitting there might itself be a signal — that people who saw it before you noticed something and walked away.

Real estate can’t dodge the same question. The moment an attractive property lands in front of you, the first thing to ask isn’t “what’s the price,” but “why did this deal come to me, of all people?”

The Other Side Always Knows More

Economics has a concept that describes this phenomenon precisely: the “market for lemons.” The economist George Akerlof used the used-car market to lay it out, and the core idea is simple. The seller knows the true condition of the goods; the buyer doesn’t. Under that information asymmetry, sellers holding good merchandise (“peaches”) struggle to get fair value, and the market ends up disproportionately stocked with defective goods (“lemons”) that linger longer. Buyers, unable to tell a peach from a lemon on sight, will only pay an average price — which drives peach-holding sellers out of the market altogether.

In real estate transactions, this asymmetry runs far more extreme. The seller already knows the building’s plumbing needs a full replacement within three years, that the largest tenant is showing signs of not renewing, that a new elevated highway going in on the adjacent lot will hurt access. The buyer doesn’t. When you come across a property with unusually attractive terms, the first instinct should be suspicion, not excitement.

The Habit of Asking “Why Me?”

William Poorvu, who taught real estate practice at Harvard for decades, has said that whenever a deal came his way, he made a habit of asking himself: “Why me?” — and that pinning down the seller’s real motive is a gate every negotiation has to pass through before anything else.[1] Good properties simply don’t sit on the market long. If something is genuinely attractive, a local investor who already knows the neighborhood cold, or an institutional buyer with a dense information network, has probably already snapped it up. So if a property is still drifting your way, one of two things is usually true: either you hold some specific edge nobody else has — experience handling that tenant type, a local network in that neighborhood — or there’s a problem that everyone who looked before you already spotted, and you just haven’t found it yet.

The first case is a gift. One real estate firm’s acquisition of a large office portfolio was exactly that. The seller, an insurance company, had announced it would negotiate only with the top two or three bidders. This firm judged that the portfolio’s management complexity — nineteen buildings, a large roster of individual tenants — would scare off most of the competition. And because the firm had actually managed comparable assets in the Washington, D.C., area before, that complexity became a negotiating edge rather than a deterrent.[2] The answer to “why did this come to me?” was “because I’m the only one who can handle this mess.”

Why the Second and Third Owner Are Often the Happier Ones

The trouble is the second case. Real estate has an old saying: “There are more happy third owners than happy first owners.”[3] The person who first develops or buys a building is usually blinded to its problems by emotional attachment to their own plan and by the sunk costs already poured in. The second or third owner to take title often picks up an asset that earlier owners have already worked the kinks out of, at a coldly discounted price. If the answer to “why did this property make its way to me?” turns out to be “because the two owners before me already wrestled with the headaches and sold,” that’s not a red flag — it’s information. But it’s a good signal only for the buyer who recognizes it and prices accordingly.

Cross a Border, and the Question Becomes a Matter of Survival

Skip this question in a cross-border deal, and the cost of skipping it comes back far harsher — because the information asymmetry runs several times larger than in a domestic transaction.

The presale scam pattern that keeps recurring across popular Southeast Asian resort destinations is a textbook case. Units get sold on terms like “guaranteed 10 percent yield, ten-year buyback” — far above what the market actually supports. When a deal’s terms look unusually generous next to the market’s real rental yields, that premium is typically baked into the purchase price already, or funded through a Ponzi-style structure that pays early investors with new investors’ money.[4] Investors who skipped the question “why is this generous an offer coming to me?” have repeatedly found themselves watching yields get cut in half once the guarantee period ends, or watching the developer simply vanish.

In Bali, a foreign-national developer who had built trust through a large social-media following used that trust to raise substantial sums from investors across multiple countries, then went dark without building the promised villas.[5] Behind the glossy marketing and the generous terms was a question worth asking: “why would this person offer terms this good to a foreigner like me?” Asking it would have bought at least one more round of due diligence. In markets like Dubai or parts of Europe, where escrow regulation and development-guarantee regimes are well established, good properties are far less likely to be left to fester like this. Where regulation itself narrows the market’s information asymmetry, the lemons get weeded out faster.

Turning Suspicion into Leverage

One thing worth being clear about here. The point of asking “why did this come to me?” isn’t to reflexively avoid every good deal. Quite the opposite — being able to answer that question yourself is exactly what earns you the right to step into the deal. If the market’s suspicion has a clear cause, and that cause happens to be your particular strength — a problem you know how to fix, a complexity you’re equipped to handle — then you’re the one capturing an opportunity everyone else passed on. But if you walk in seduced by the terms, never able to explain why the deal landed on your desk, you’re no different from the buyer at the used-car lot who signed the contract without ever asking, “why is it this cheap?”

Closing Out Part One

Part One of this book has built the game’s basic conditioning — mapping the grammar of numbers onto the human body, negotiation onto courtship, due diligence onto a credit check. And what this final piece points to is an attitude that has to come before every number and procedure covered so far. The habit of pausing, the instant a property catches your interest, to take a breath and ask: “If this is this good, why has it been waiting for me?” Only once you can answer that question yourself are you ready for the next stage — Part Two, where the game turns to money crossing borders.

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Sources [1] (Poorvu, The Real Estate Game, chap. 3) — the “Why me?” self-check and the principle of identifying the seller’s true motive before negotiating. [2] Brief 03 — JBG’s acquisition negotiation for the Twinbrook Metro portfolio, in which management complexity screened out competing bidders. [3] Brief 09 (Poorvu, The Real Estate Game, chap. 9) — citing the saying “there are more happy third owners than happy first owners.” [4] the mechanics of “guaranteed yield” marketing in Southeast Asia and Dubai’s RERA regulatory response. [5] the Bali influencer-driven villa presale fraud case (loss totals and victim counts vary widely across press accounts and are not specified here; related coverage includes Izvestia, The Bali Times, and others).