He taught federal judges how to write. Then he taught a machine to do it - inside the same Microsoft Word everyone already lives in.
The grin of a man who has read more bad sentences than anyone alive - and still believes the next draft can be better.
A lawyer somewhere is staring at a citation, trying to remember whether the comma goes inside the italics. A judge is rereading the same paragraph for the third time, sure it can be tighter but unsure how. Ross Guberman has spent his career standing in that exact moment of doubt - and his current bet is that software can stand there too.
He runs BriefCatch, a legal-writing platform that lives inside Microsoft Word and offers real-time edits, examples lifted from the best legal writers, and analytics that score a draft the way a demanding partner would. In December 2025 the company closed a $6 million Series A led by Full In, a software-focused growth-equity firm. Guberman says more than three dozen funds approached him to lead the round. He chose one - the one whose founding partner, Elodie Dupuy, grasped the technical roadmap on first contact.
The headline number that gets investors leaning forward is not the funding. It is the retention: 99% of customers stay, gross retention among law firms and courts sits at 100%, and net revenue retention runs to 126%. Lawyers, a famously skeptical crowd, try BriefCatch and then refuse to give it back.
Those three figures tell a single story. Gross retention at 100% means the firms and courts that sign on do not leave. Net revenue retention at 126% means the ones who stay spend more each year - more seats, more use, more of the work that used to live in a partner's marked-up margins. For a category that lawyers were supposed to resist, the math reads like a verdict that has already been entered. The $6M round, described as an upround, is the financing that follows that kind of proof, not the thing that creates it.
Even the best lawyers struggle to write clearly and persuasively under pressure.- Ross Guberman, on why BriefCatch exists
Before there was software, there was a book. In Point Made: How to Write Like the Nation's Top Advocates, Guberman did something most legal-writing guides never bother with: he gathered the actual briefs of 50 of the most influential advocates in the country - Barack Obama, John Roberts, Elena Kagan, Ted Olson, David Boies - and took them apart. Not to admire them. To find the repeatable moves underneath. The opening that grabs. The transition that carries weight. The sentence that lands.
Three years later came Point Taken: How to Write Like the World's Best Judges, the same empirical scalpel turned on opinions instead of briefs. He co-authored Deal Struck: The World's Best Drafting Tips. Across all of it runs a conviction that good legal writing is not a gift you are born with. It is a set of techniques you can name, teach, and - this is the leap - encode.
How to write like the nation's top advocates. The brief, dissected.
How to write like the world's best judges. The opinion, dissected.
The world's best drafting tips, for the contracts no one reads twice.
That conviction is what makes BriefCatch different from a generic grammar checker. The suggestions are not pulled from thin air. They are the distilled output of a man who has run thousands of workshops and read tens of thousands of paragraphs written under deadline. When the software flags a flabby phrase, it is channeling a specific point of view about what good looks like.
The empirical habit shows up everywhere in his work. Point Made is not organized around abstractions like "be clear" or "be persuasive." It is organized around named techniques, each one pulled from a real brief that won a real argument, each one demonstrated rather than asserted. The implicit promise is that style is teachable, and the proof is on the page. That same promise is the seed of the software: if a move can be named, it can be detected, and if it can be detected, it can be suggested at the exact moment a writer needs it.
Scale was always the question hovering over the workshops. Guberman conducted thousands of them across the globe - for prominent law firms, judges, agencies, corporations, and bar associations - and worked with attorneys at more than 100 of the world's largest firms. That reach is enormous for one person and tiny next to the number of lawyers who write badly every day. The market for clearer legal writing is, essentially, the entire profession. No amount of frequent-flyer miles closes a gap that size. Software might.
The route here was not a straight line. Before law, Guberman earned a living as a musician, a translator, an editor, and a journalist. He started down a Ph.D. path before pivoting to the University of Chicago Law School. His degrees come from Yale, the Sorbonne, and Chicago - an education that explains both the multilingual ear for rhythm and the appetite for taking complicated things apart.
He practiced at a top firm, taught as a law-school adjunct, and became a Professorial Lecturer in Law at The George Washington University Law School. Somewhere in there he founded Legal Writing Pro and became, by broad agreement, the person American institutions call when they want their lawyers to write better. He was selected to train newly appointed federal judges - the judiciary's choice, as the shorthand goes. He has commented on law and lawyer development for The New York Times, radio, and television.
Training judges is its own kind of credential. Judges write the opinions that everyone else has to read, cite, and live under, and they do it with no editor and no boss. A workshop leader who earns a room full of them has cleared a bar that flattery cannot. It also gave Guberman a vantage point most legal-tech founders never get: he saw, up close and at volume, where good writers stall and where the same problems recur. The catalog of recurring problems is, not coincidentally, a product roadmap.
Legal Writing Pro was the analog version of that insight - a person in a room, a stack of drafts, a finite number of hours. The constraint was obvious. One Ross Guberman can only stand in front of so many lawyers in a career. BriefCatch is the answer to that ceiling: take the part of the work that can be systematized and let it run wherever a lawyer is typing, at any hour, on any draft, without a calendar invite. The workshop ends and the room empties. The software stays open in the next tab.
Chosen to train new federal judges in the craft of writing opinions people can actually follow.
BriefCatch built AI to handle Bluebooking - the copious, confusing citation rules widely held to be the most tedious chore in all of legal writing.
It plugs into Microsoft Word instead of asking lawyers to change how they already work. Friction, removed.
Every book and feature starts the same way: gather what great writers actually did, then name the move so others can steal it.
BriefCatch v4 arrived in 2025 with AI-driven Bluebook correction and a context-aware writing advisor. The Series A money points two directions at once. One is disciplined acquisitions. The other is deeper product. The destination Guberman names is a unified, Word-native AI platform for elite legal writing, editing, and research - the whole arc of a document handled in the place the document already lives.
The Bluebook feature is worth pausing on, because it shows the strategy in miniature. Bluebooking is the dense, exception-riddled system for citing legal authorities, and it is universally disliked precisely because it is mechanical, fussy, and unforgiving. It is also exactly the sort of task that rewards automation: bounded rules, clear right answers, enormous tedium. By aiming AI at the chore lawyers complain about most, BriefCatch buys trust on the easy case and earns the right to advise on the hard one - the argument itself.
This investment lets us accelerate two things at once: disciplined acquisitions and deeper product development.- Ross Guberman, on the 2025 Series A
There is a quiet irony in a legal-writing purist building an AI company in an era awash with machine-generated prose. Plenty of tools will now write a brief for you. Guberman's wager is the opposite: that the scarce thing is not more words, but better ones - and that judgment about what makes a sentence persuasive is exactly the thing worth bottling. He spent decades developing that judgment one workshop at a time. BriefCatch is the attempt to hand it to everyone at once.
The selection of Full In tells you something about how he operates. Three dozen funds came knocking, which is the kind of attention most founders chase for years. He did not run an auction for the biggest check. He picked the partner who understood the roadmap fastest and who had scaled and exited companies like his before. The choice was about fit and judgment, not vanity - which is, fittingly, the same standard he applies to a sentence.
The skeptics in his audience are, conveniently, his customers. Lawyers do not adopt tools out of enthusiasm. They adopt them when something works and keeps working. A 99% retention rate is the verdict of a jury that does not award points for charm. On the strength of that record, the red pen has gone from a single desk to thousands of screens - and it is still, recognizably, his.