16-17 June 2027 – London, InterContinental O2 | Magazine

LegalTech Diaries Volume 18

Ryan Anderson

CEO
FileVine

LegalTech Diaries Volume 18

Ryan Anderson​

CEO
FileVine

You built the first version of Filevine as a working litigator trying to solve your own problem. What is the last thing you personally built or prototyped, and what did it teach you?

I was running a personal injury practice off a Google Sheet I called my PI Checklist. My co-founder Jim saw it and recognised the workflow problem. That is still how Filevine works: people who have lived the problem working alongside engineers who can build the fix. 

The last thing I got my hands dirty on was anti-hallucination in LOIS. In June, I was at a retreat in Sun Valley with a group of preeminent trial lawyers, and the fear of AI hallucinations in that room was palpable. I walked out convinced we already had most of the pieces to catch the three ways AI gets legal authority wrong: the case that doesn’t exist, the real case that doesn’t say what the brief claims, and the quote that’s in some part of the case but not in the actual opinion. Our machine learning team sprinted for about 90 days. Along the way, we took briefs federal judges had already sanctioned, ran them through LOIS, and checked what it caught against what the court found. 

It taught me two things. 

  1. A real citation isn’t a supported argument. Fake cases make the news. The harder problem is the real case with a paraphrase dressed up in quotation marks, or a line lifted from the dissent instead of the holding. We have to verify more than just existence; we need to know if the court’s reasoning actually supports the argument. 
  2. Verification has to be fast. A few years ago, nobody asked whether a Filevine report was right. It was a database query. Large language models get it right the vast majority of the time, but not every time, and in law that gap matters. So checking has to be one click from the claim to the exact passage. If it’s slow, it won’t happen.

You’ve described your approach as embedded, matter-aware intelligence built for regulated environments. What’s a guardrail you’ve built into the product that most competitors haven’t bothered with, and why does it matter?

Checking that a case exists is the easy part. The question that matters is whether the opinion says what the brief claims it says. 

Every citation gets flagged. Every citation in LOIS gets a status: verified, unverified, suspect, ambiguous, wrong case name, or mischaracterised. When LOIS quotes or relies on an opinion,

one click takes you to the exact passage, highlighted in the opinion itself. We build on the assumption that AI makes mistakes. Real verification layers are hard and expensive to build, and it means admitting something a lot of AI marketing avoids. To be completely transparent: LOIS doesn’t have zero hallucinations. No tool built on large language models does. We designed LOIS so the lawyer catches the error before a judge does. Being honest about the limits is how you earn a lawyer’s trust. 

The lawyer’s name is on the brief. Software can’t take on a lawyer’s professional duty to verify authority, but it can make meeting that duty an easier part of the job. Verification has to be integrated directly into the drafting workspace. 

Tested against real sanctions. We ran LOIS against 68 U.S. federal filings that courts had already sanctioned for fabricated or misused authority. It reviewed 2,073 citations, flagged at least one issue for attorney review in every filing, and identified 174 severe errors: cases that don’t exist or holdings that were mischaracterised. 

Hallucination cannot remain a feature of our justice system. 

If you were starting Filevine today, in this market, what would you build differently in the first six months?

I’d still start with the system of record. That’s unfashionable when so many new companies start with a model and a chat box. AI is great at generating text. What is harder is understanding the context. Uploading documents to a chatbot is one thing. Asking “What’s the history of this matter?” or “What patterns show up across my last ten matters with this client?” is another. That takes real structure underneath, and the database and partner choices you make early are very hard to unwind. 

Here’s what I’d do differently: 

  1. Put the law next to the facts from day one. When I practiced, I’d take a case file home, sometimes thousands of pages, spread it across the kitchen table, and mark what mattered with color-coded Post-it notes. Filevine was built for that part of the job: the facts. The law lived somewhere else. Starting today, I’d build facts and case law together, so the system that already knows the file can also tell you whether the law supports your argument. 
  2. Ship verification in version one. Lawyering has always been shoe-leather work: take the facts, apply the law, draft. Now there’s another step: make sure nothing you relied on is hallucinated. Old software earned trust by being deterministic. AI doesn’t get that trust for free. From the first launch, legal AI needs to be able to show where its answers come from. 
  3. What I wouldn’t change: starting from a real problem in real practice. Lawyers bend the arc of justice toward truth. I’d still build for them first.

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