Adventures In Legal Tech

Brad Pitt's firm doesn't have a missing-tool problem. It has a tools-that-don't-talk problem, and a person sits between every pair of systems re-keying the same client data. Alejandro Castellano of Caddi joined me to unpack how AI agents can take over that back office work, and how to keep them on a short leash. If your team spends its week clicking between systems, this one's for you. Key Takeawa...

Diana Prince's firm just hit 75 lawyers, and the infrastructure behind those lawyers didn't grow with them. Beth Thompson of Actionstep joined me to unpack how a firm of any size can grow with software, clean processes, and better numbers instead of just more headcount. If your pre-bill queue is a mess and your reports only tell you what already happened, this one's for you. Key Takeaways Write do...

Chance Shifflett, head of product at Rev, joins Jared to unpack how solo and small-firm criminal attorneys can get a handle on the flood of evidence, body cam footage, jail calls, depositions, and thousands of documents, that discovery throws at them. He explains what makes an investigative platform different from a generic discovery tool, why verbatim transcription and accurate speaker diarizatio...

Raj Selvadurai, founder of Gold Street Legal Search and Lateral IQ, has spent nearly twenty years placing lateral partners the old-fashioned way: relationships, referrals, and a lot of judgment calls about who actually fits where. On this episode, Raj explains why general AI tools like ChatGPT fall short for recruiting, how he built Lateral IQ to give partners and firms verified, self-service data...

This week's vexing problem: solo attorney Ernie DiGregorio has no IT department and no fractional vendor to help him weigh AI tools against data security and client confidentiality. Michael Santomaro, principal of Santomaro Law in Providence, walks through how he actually uses AI across his personal injury and criminal law practice, from proofreading pleadings to finding federal court rules he'd n...

Executive Summary Jared sits down with Carly Savar, general counsel at Steno, to unpack what actually happens when a law firm signs up with an AI vendor. Carly explains why reading the fine print matters more than any feature list, and what separates a vendor you can trust from one that's just telling you what you want to hear. Key Takeaways Read the actual data processing agreement yourself. Don'...

Executive Summary On this episode of Adventures in Legal Tech, Jared Correia talks with Phillip Greer, CEO of Best Lawyers, about how AI is rewriting the rules of legal search and firm operations. Greer breaks down the real differences between SEO, AEO, and GEO, then explains how he turned his own company into a shop full of vibe coders. It's a practical look at getting found online and getting co...

Summary Law firms are drowning in scattered knowledge, and AI can't fix disorganized data on its own. Rachel Shields Williams, Director of AI and Knowledge Management at Bass, Berry & Sims and President of the Legal Marketing Association, joins Jared Correia to explain why structured data has to come before any AI rollout, and how firms can build the human relationships that make AI adoption safe....

Summary "Attorney Matt Damon" needs to draft a demand letter, but the facts he needs are scattered across medical records, deposition transcripts, case notes, and email threads. Jared Correia brings in Claude Simpson, Vice President of Client Operations at Smart Advocate, to unpack why that scattered data problem is nearly universal in legal practice. Claude explains that documents, not buzzwords,...

Summary Jared Correia sits down with Luis Vargas Rivera, head of litigation at Embedded Counsel, to unpack a problem most solo and small firm litigators never get to solve: a real moot before a hearing. Luis built a Claude skill called Adversarial Review that simulates a three-judge panel, each with a different mindset, to attack his motions before a judge ever does. From there, the conversation c...

Summary Law firms and legal departments sit on mountains of electronically stored information, and most have no real system for dealing with it. Warren Parrino, Regional Vice President of Solution Sales at TrustPoint. One, has a clear starting point: email threading, date filters, and search terms. From there, an early case assessment environment can cut review costs before a single document hits...

Summary Alan Alda runs his own firm and figured AI tools would make content creation easy. He was half right. Jared Correia sits down with David Arato, founder of Lexicon Legal Content, to unpack why mass AI publishing is triggering Google penalties, what compliance risks law firms are ignoring in their marketing content, and how the rise of AI overviews is reshaping the entire game.   David expla...

Summary Jared Correia sits down with Sean McTigue, a partner at Bartko Pavia LLP and one of the more technically fluent attorneys in practice today. Sean unpacks how his firm navigated the leap from legal-specific AI tools to a direct enterprise deployment of Anthropic's models, and why he thinks that distinction matters a lot more than most firms realize. The conversation covers practical ground:...

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 s...

🧾 Episode Summary In this episode of Adventures in Legal Tech, host Jared Correia sits down with Tim Follett, CEO and co-founder of StructureFlow, to unpack one of the most overlooked yet critical challenges in legal work: structural complexity. From corporate transactions to litigation strategy, legal professionals rely heavily on understanding relationships—between entities, obligations, and fl...

🧠 Episode Summary In this episode of Adventures in Legal Tech, Jared Correia sits down with Jane Freedman to explore a pressing question: Can small law firms effectively use AI? The answer is a clear yes—but with nuance. Jane shares how she transitioned from cautious observer to active AI user, integrating tools like Microsoft Copilot and Litera into her daily legal workflows. From analyzing comp...

Summary In this episode of Adventures in Legal Tech, host Jared Correia sits down with Max Paterson to unpack one of the hottest trends in the industry: vibe coding. They explore how AI-assisted development is lowering the barrier to entry for building legal tools, allowing lawyers, paralegals, and non-technical professionals to actively participate in innovation. The conversation dives into the o...

Summary In this episode of Adventures in Legal Tech, host Jared Correia sits down with Joe Borstein, CEO and Co-founder of LexFusion, to unpack the evolution of legal technology and what's driving its rapid transformation today. They explore how law firms are finally embracing structured tech adoption—largely fueled by generative AI—and why this moment feels fundamentally different from past waves...

Episode Summary In this episode of the Adventures in Legal Tech Podcast, host Jared Correia sits down with attorney Harshita Ganesh to unpack one of the most pressing challenges in modern legal practice: how to responsibly integrate AI into law firms. Using the case of a new associate eager to implement AI in a resistant firm, the conversation explores the tension between innovation and caution. H...

EPISODE SUMMARY In this episode of Adventures in Legal Tech, host Jared Correia tackles one of the most persistent frustrations in modern law practice: balancing cybersecurity requirements with everyday usability. Using a fictional law firm scenario, the discussion explores how attorneys can safeguard confidential client information without sacrificing productivity or creating unnecessary workflow...

EPISODE SUMMARY In this episode of Adventures in Legal Tech, host Jared Correia speaks with John Pothier, managing partner at Embedded Counsel, about one of the most common challenges lawyers face: launching a law firm without understanding technology. Using the fictional scenario of an in-house attorney ready to go solo but overwhelmed by tech decisions, the conversation breaks down the essential...

Summary  Tune into "Adventures in Legaltech" for an engaging talk with Caspar Roxburgh, GM of Draftable. Discover how to tackle the infamous Word doc track changes mishap, get insights on law firm tech overload solutions, and explore fresh paths in legal technology innovation. 📄🎙️.   Episode Highlights 00:05:45 - Introduction to Colin's vexing problem: missing track changes. 00:07:44 -Options for...

I spoke with a solo attorney, who gets a heck of a lot done in her unique practice niche, by leveraging AI + business planning.   Episode Highlights 02:12 - Overwhelming AI solutions in law. 03:56 - Jess Birken recommends note-taking AI. 04:48 - Fathom: AI for virtual meetings. 06:31 - Flat fees vs. hourly billing for AI efficiency. 07:25 - AI in competitive practice areas. 08:55 - Using AI for ma...

I talked with an attorney who owns a law firm and real estate closing company about how he grew his organizations using acquisition as a tool, as well as about how the firm has stayed on track by adopting modern technology.   Episode Highlights 01:04 - Commitment to actionable insights. 02:05 - Creating a fun workplace culture. 06:22 - Impact of culture and dynamics. 07:39 - Using unexpected initi...

I spoke with a senior paralegal about best practice tips for intake + client service.   Episode Highlights 02:45 - Automations in CRM to filter conversations. 04:04 - The "CRM as ATM" concept for law firms. 06:13 - The importance of cultural responsiveness in client communication. 07:46 - The value of short, effective intake forms. 11:03 - Benefits of outsourcing roles in firms. 12:56 - Effective...