Negotiation · 4 min read

When the Deal Gets Large

Small deals are about price. Large deals are about structure, and about everyone else who now has a say: lenders, lawyers, tax rules and the other side's own risks.

By Jeev Trika

A small purchase is a conversation between two people. Somewhere above a few hundred thousand dollars it stops being one. The price is still there, but it is now surrounded by financing, tax, title, contracts and the other side’s own constraints, each with somebody representing it.

These are the deals in my records where that change was visible.

2012: counsel, a broker, an escrow agent

The office purchase in Naples in 2012 was not large by most standards, but the cast was already bigger than two people. The seller was reviewing the draft with his counsel. I had a broker reviewing it with me. My notes that day were about the mechanics only a larger deal has: whether the escrow agent was legitimate, who was obliged to prove title, and whether the contract could be assigned.

Each of those people protects one part of the deal. None of them sets the commercial terms. That stays with the principal.

2018: the structure was the offer

In October 2018 I was negotiating for a piece of development land in Naples. The seller, through his broker, offered two options: a higher price with half paid at closing and the rest in three annual instalments, or a lower cash price paid in full at closing.

I took the lower price and asked for the instalments. My final offer was one line:

Final offer. I am offering 5.3M. 2M, 1.3, 1, 1.

That is the cash price, with two million down and the balance over three years. The seller agreed to the price. Then he withdrew the financing. Having looked at the federal tax rules on interest for seller-held loans, and at how long foreclosure takes in Florida if a buyer stops paying, he wrote that “it will not be in our best interest to hold the loan,” and that he would rather the banks did it.

His broker thought he had been badly advised and offered to keep trying. She also mentioned another opportunity I had been shown. I had an alternative. My reply was one line:

Tell [the seller] to enjoy his life.

What I did not do

Reading the thread now, the seller told us exactly what his problem was. It was not the price; he had agreed to the price. It was the risk of being a lender: the tax treatment of the interest and the cost of foreclosing if something went wrong. Those are specific, and some of them are solvable: a larger down payment, a shorter term, a bank loan for part of the balance, security that made default less painful for him.

None of that was tested. I walked. With an alternative in hand that may have been the right call, but it was a decision about the deal, not a discovery that there was no deal. On a large transaction, the other side’s constraint is often more negotiable than its price.

2022: counsel after the price, not before

The purchase of two residences in Bangkok in 2022 ran on a long clock. I had Thai counsel looking at projects from early 2021. I spent more than a year asking the developer questions about the lease term, payment plans, financing for foreign buyers, price escalations and timelines, and I made a due diligence trip. When the commercial terms were settled, I handed over:

The price has been negotiated. Pls have your team ready to review, edit, and then have me sign off.

The large-deal pattern, in one sentence: I negotiate the terms myself, then the professionals turn them into a document and look for what I missed.

What changes with size

More people represent more risks. Brokers, lawyers, title, lenders. Each protects one piece. Someone still has to own the whole.
Structure matters more than price. How and when the money moves, who carries the risk if it does not, and what happens on delay or default.
The other side’s constraints are real. Tax, lenders, partners, timing. They are often the actual obstacle, and they are often negotiable.
Time becomes a term. Large deals take months. Diligence periods, deposits and closing dates are negotiated as hard as price.
Tone gets expensive. A short reply costs nothing on a small purchase. On a large one, it can close a door that a better answer to the other side’s problem might have opened.

I work on deals of this size alongside the people whose deals they are, behind the scenes or at the table.