SUMMARY

Teo Doremus traded a litigation desk in China for a startup in San Francisco, and along the way he became convinced that the legal industry's AI moment is right now. On this episode, Teo makes the case for starting an AI-native law firm, walks through how he thinks about hallucination risk, and explains the "digital desk" concept behind Advocacy, a platform built to connect the narrative silos of litigation that have historically lived in Microsoft Word and nowhere else.

Teo also shares what he got wrong about law practice, why he thinks lawyers misunderstand what AI actually does when it "helps" them, and draws the most useful analogy you will hear about what lawyers get paid for in an AI world. The pilot and the autopilot are not enemies. Neither are lawyers and AI. The question is figuring out who does what.

KEY TAKEAWAYS

Start building your AI-native practice now. The advantage goes to whoever gets comfortable with the technology first, not whoever waits for it to be perfect.
Before deploying AI in your firm, learn what it actually is and what it is not. Understanding its fundamental limitations is your best defense against hallucinations.
AI adoption in law is high on subscriptions and low on genuine daily use. Real adoption means using AI regularly enough that it changes how you work, not just having a login.
Specialized legal AI tools and general AI tools are not competitors. Use both strategically depending on how much precision your task requires.
The lawyer's value in an AI-assisted practice looks like the pilot who no longer holds the stick for seventeen hours: rested, prepared, and ready for whatever the automation cannot handle.

WHO IS THE GUEST?

Teo Doremus is the CEO and co-founder of Advocacy, a litigation-focused AI platform built around what he calls the "digital desk," a place where all the narrative silos of a case live together and AI connects them. Before founding Advocacy, Teo practiced law in China and the United States as both a litigator and a transactional attorney. He studied law in France after picking it almost by accident at 18, fell in love with it along the way, and eventually made his way to San Francisco, where a deep dive into AI convinced him the legal industry needed something that did not yet exist. Advocacy can be found at advocacy.ai.

LINKS AND RESOURCES

Advocacy:

advocacy.ai

Red Cave Law Firm Consulting:

redcavelegal.com

Adventures in Legal Tech Podcast:

Available on Apple Podcasts, Spotify, Amazon Music, and YouTube.

KEYWORDS

AI-native law firm, legal AI, artificial intelligence for lawyers, AI hallucinations in law, litigation AI tools, Advocacy AI, legal tech software, law firm technology, AI adoption in legal, legal software selection, AI-powered litigation, law practice management, Red Cave Law Firm Consulting, Teo Doremus, Jared Correia, AI governance for lawyers, digital desk litigation, specialized legal AI, general AI for law firms, Adventures in Legal Tech

EPISODE HIGHLIGHTS

[00:02:02 - 00:02:48] Teo's immediate, unhedged answer on the AI-native firm question: do it, do it now, and do it because the technology rewards early commitment.
[00:04:35 - 00:06:03] Why the hallucination conversation needs multiple angles at once, and why no single answer is going to hold.
[00:06:04 - 00:06:44] What lawyers fundamentally misunderstand about AI: it does not actually understand you. When it does not know the answer, it just agrees with you.
[00:10:37 - 00:11:26] Teo describes the moment AI went from a five-minute curiosity to a full obsession that changed the direction of his career.
[00:13:55 - 00:14:28] The origin of the "digital desk" concept and why Microsoft Word from 1984 is still, technically, the competition.
[00:21:40 - 00:23:11] The pilot analogy: if planes have flown themselves for twenty years, what exactly are pilots for? And what does that tell us about lawyers?