How Contract Superintelligence came to be
Jim Vanderpool began practicing law in 2000, and the two kinds of work he took to were estate work and real estate. Both made sense to him: a family, a house, a set of papers, and a day when everything has to be right.
One thing about the real estate side bothered him from the start, and it still does. The day a contract was signed, the file already held almost everything a buyer or a seller needed to know about their closing: the price, the earnest money, who pays for what, the closing date, and from those, the taxes, the title insurance, the recording fees, and the two figures a family actually cares about, what the buyer brings to closing and what the seller walks away with. And yet nobody saw a settlement statement until the day before closing, or the day of. Nobody was hiding anything. Dozens of people touch a real estate file between contract and closing; each one sends in their piece when they get to it, and the statement waits for the last of them.
What he saw, almost from his first closings, was a pattern of surprise. Buyers brought more than they expected. Sellers walked away with less. The reason is human: a person hears the sales price and that number sticks. A seller with a $500,000 contract thinks of $500,000, and forgets the $10,000 in closing costs they agreed to pay for the buyer, and the two loans that have to be paid off, and that a payoff is always a little higher than they remembered. Buyers are caught by the fees that ride with the services they need, the lender’s first among them. Realtors were in a hard spot: the contract was signed, the seller wanted to know what they would net, and all the realtor had was rules of thumb.
So his office did something few offices do. Whenever a contract came in, the staff built a settlement statement, incomplete because the third-party fees were not in yet, and sent it to the client right away. Buyers liked knowing roughly what they would need. Sellers liked seeing the bottom line early. Realtors, more than anyone, liked being able to give a client a real answer the day the contract was signed. But it cost real hours, and some of those contracts never closed; an inspection went badly or the financing fell through, and the work was done for nothing. That went on for years.
On September 1, 2017, he had had enough of what he called contract ignorance. He sat down with a pen and one sheet of paper, wrote the date at the top, and boxed a title that was the opposite of that phrase. That handwritten page is where the name comes from, and he still has it. It lists three things. One, the problem: “When we get a contract we have all the info we need except 3rd party fees, which we should be able to estimate closely.” Two, the facts behind a solution: “There are patterns in the contract. All real estate contracts have the same fundamentals: sales price, contingencies, property address, terms, responsibilities, language.” Three, starred, the solution: build it. The whole plan, on one page, on the first day.
He is not a programmer and had never written a line of code. But after more than 15,000 contracts he could see the patterns the page talked about, and he set out to teach a computer to see them. He learned from videos and articles, much of it over his head at first. There was nothing to ask in 2017; ChatGPT, Claude and Grok did not exist. You learned it or you did not.
In April 2018, just before his birthday, the first contract went through the program and came out the other side as a settlement statement. It was rough, by his own account, and he checked it line by line, but no one had typed a number. It was the proof that it could be done.
From 2018 the firm ran it, which the office simply called CSI, alongside full human review on every file: a person read the contract, the program read it too, and the two were compared. Its accuracy was good from the start, but not ready for prime time, because the numbers turn out to be the easy part. The hard part is the rules: what happens when a term changes in an amendment, or in a counter, or when two pages of the same file disagree. He wrote those rules one at a time, and that was the real work. Sixteen years of closings had taught him what the rules were; he only had to teach them to the program.
In 2019 he founded two companies on it, both kept inside the firm at first: Realestart, for buyers, sellers and the realtors who want to show them what a contract means, and Realestart, for the title industry. All of it, the page in 2017, the first statement in 2018, the rules, the two companies, came before ChatGPT, Claude, Grok or any of the programs people now use to write code. Behind it stood what he brought to the table in the first place: twenty-five years of practicing law, more than 15,000 closings, and a working knowledge of every way a contract can go wrong and what the law does about it when it does. A program can be taught to read a contract. What a closing attorney knows only gets into it if a closing attorney is the one teaching it. His edge was not a computer skill. It was that he knows contracts.
Even the people who were told about it did not believe it. In 2019 the owner of a title company asked him how his office handled so much volume with so few employees; did they not burn out? He asked if she wanted to know what they used, and she said yes, tell me. So he told her: a program he had written, called Contract Superintelligence, that worked through closing files and got the information to consumers, realtors and lenders. She laughed and said he was such a joker. He said he was serious. She laughed again. She did not believe him.
Contract Superintelligence has been around for almost a decade, and for most of that time hardly anyone outside the firm knew it existed, because it lived in one law office. It made the firm faster and let the same people handle more files, and the two companies he founded on it in 2019 stayed inside the office with it. Then, somewhere in 2024 or 2025, the thought arrived and would not leave: this is something everyone could use. Every buyer and seller deserves to know their numbers. That is when the office tool became a product.
Today Contract Superintelligence runs inside Realestart and Realestart, open to every Tennessee buyer and seller.
Jim Vanderpool tells this story in his own words at vanderpoollaw.com.