Adventures In Legal Tech

Jared Correia

"Adventures In Legal Tech" explores effective solutions to unique technology issues. Each episode provides actionable steps to solve everyday problems lawyers encounter. It's kind of like "This Old House" — but with way more law.

  1. 2h ago

    Forward Lateral: How AI Is Impacting Legal Recruiting

    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, and why the real signal in lateral hiring isn't who a firm hires, it's who actually stays. If you've been wondering whether AI can touch a business this relationship-driven, this conversation has the answer. KEY TAKEAWAYS Traditional lateral recruiting has always run on relationships first, and that's exactly where the risk lives: a partner's promised book of business doesn't always fully travel with them. General AI tools aren't built for a market this specific. Verification, not raw intelligence, is what recruiting actually needs, since two partners can share the same name at different firms. Real growth and churn can look identical on paper. Tracking a firm's actual hires and departures, not just its hiring announcements, is the only way to tell them apart. AI doesn't replace a recruiter's judgment, it removes the weeks of manual dossier-building so that judgment has something accurate to work from. The pandemic proved lateral moves don't need a year and a dozen in-person meetings; verified data is what lets that faster pace hold up. LINKS AND RESOURCES Lateral IQ: lateraliq.app Gold Street Legal Search: goldstreetlegal.com Red Cave Law Firm Consulting: redcavelegal.com Adventures in Legal Tech Podcast: Available on Apple Podcasts, Spotify, Amazon Music, and YouTube. KEYWORDS AI legal recruiting, lateral partner recruiting, legal recruiting software, AI hallucinations in law, Lateral IQ, Gold Street Legal Search, law firm lateral hiring, legal tech software, law firm growth, AI adoption in legal, verified AI data, law firm private equity, legal industry mergers, law practice management, Red Cave Law Firm Consulting, Raj Selvadurai, Jared Correia, AI for law firm recruiting, partner recruiting technology, Adventures in Legal Tech EPISODE HIGHLIGHTS [00:03:04 - 00:03:58] Raj lays out the core risk in lateral recruiting: partners who promise a book of business that shrinks the moment the move is final. [00:04:03 - 00:04:58] Why hallucinations and name collisions make general AI tools a poor fit for a market this specific. [00:09:04 - 00:09:32] The $10 million lateral hire that closed entirely over Zoom, with no in-person meeting except to pick up a laptop. [00:14:09 - 00:15:10] The line that reframes the whole episode: hiring 50 partners and losing 49 isn't growth. [00:17:01 - 00:17:59] Raj's own account of building Lateral IQ with zero coding background, and why owning the code mattered. [00:29:24 - 00:30:15] Raj's case for law firms building their own private equity arm instead of ceding control to outside investors.

  2. 3d ago

    Outside Providence: How to Fire Up a Growing Solo Law Firm

    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 never needed before. We also get into hallucination risk, the malpractice argument for using AI at all, and how Michael turned a deeply personal passion into a growing corner of his practice. Key Takeaways Run every draft through AI before it goes out. Michael caught over twenty typos in a single complaint once he started running documents through AI, and in his book, typos in 2026 read as laziness, not just error. Using AI to rework a sentence or a closing argument isn't cheating, it's the same move as using a thesaurus or asking a colleague at the water cooler. AI can get you to an unfamiliar rule fast, but it can't replace reading the cases yourself. Hallucinated citations have already gotten lawyers sanctioned. If you've never touched AI, start small: feed ChatGPT an email you already wrote and see what it changes. Think of it as a curator, not a mystery box. Solo and small firms without in-house IT can still build real AI infrastructure with off-the-shelf add-ins for Microsoft, Adobe, and Lexis. Links and Resources Santomaro Law: https://santomarolaw.com Red Cave Law Firm Consulting: https://redcavelegal.com Keywords legal tech, legal technology, AI for lawyers, legal AI tools, solo practitioner, small law firm, law practice management, law firm technology, ChatGPT for lawyers, AI hallucinations, legal ethics AI, client confidentiality, law firm marketing, personal injury law, legal research AI, document automation, shadow AI, Jared Correia, Adventures in Legal Tech, Red Cave Law Firm Consulting, AI malpractice risk Episode Highlights [00:02:00 - 00:04:00] Michael explains Ernie DiGregorio's Providence College basketball legacy and his own family connection to him. [00:05:00 - 00:06:00] Michael shares the malpractice warning that pushed him to adopt AI: skip it, and you're falling behind opposing counsel. [00:07:00 - 00:08:00] Michael describes running a redacted complaint through AI and catching over twenty typos his staff missed. [00:08:00 - 00:09:00] Michael uses AI to find unfamiliar federal court rules on his first case removed from state court. [00:09:00 - 00:11:00] Michael pushes back on the idea that using AI to write is cheating, comparing it to a thesaurus or a colleague's input. [00:10:00 - 00:11:00] Michael flags the real risk: hallucinated case law and the sanctions lawyers have already faced for not checking it. [00:13:00 - 00:15:00] Michael's advice for AI beginners: run an email you already wrote through ChatGPT and see what changes. [00:20:00 - 00:23:00] Michael opens up about his personal connection to plant medicine and his work with the Psychedelic Bar Association. [00:26:00 - 00:30:00] Michael breaks down how referral relationships, not big ad spend, drive his caseload.

  3. Aug 10

    Inside In-House: What It's Really Like to Be In-House Counsel for a Legal Tech Vendor

    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't assume a vendor's security is handled just because they signed a service level agreement. Push for a zero-day retention agreement, and ask about the LLMs your vendor is built on, not just the vendor itself. SOC 2 Type 2 certification means a company's controls held up over a full year. SOC 2 Type 1 only proves a single snapshot in time. Not all training is created equal. Aggregated usage data is usually fine. Your client's confidential content should never go into a model. New billing ethics guidance says you can only charge for the time you actually spent, not the time an AI tool saved you. About the Guest Carly Savar is general counsel at Steno, a litigation support and court reporting technology company. She spent years litigating before founding her own legal recruiting company and eventually moving in-house. Carly now negotiates AI and data agreements from both sides of the table, as counsel to a legal tech vendor and as a buyer evaluating other vendors herself. Links and Resources Steno: steno.com Red Cave Law Firm Consulting: redcavelegal.com Keywords legal tech, legal technology, AI for lawyers, AI vendor vetting, legal AI vendor contracts, data security for law firms, zero-day retention agreement, SOC 2 Type 2, SOC 2 certification, ISO 27001, shadow AI, in-house counsel, legal tech general counsel, court reporting technology, Steno, AI training data, law firm AI policy, small law firm technology, technology competence rule, Red Cave Law Firm Consulting Episode Chapters 00:00:00 Cold open and show intro 00:02:00 Meet Carly Savar and the vexing AI vendor problem 00:03:00 Zero-day retention and why training on your data is the real risk 00:06:00 What to actually ask vendors before you sign 00:08:00 SOC 2 Type 1 vs Type 2 and other certifications 00:10:00 Life as GC inside a legal tech vendor 00:13:00 Clients who want cool tech vs clients who ask the right questions 00:15:00 Not all training is created equal 00:16:00 Keeping up with shifting ethics rules and regulations 00:18:00 Tech competence and billing for time spent, not time saved 00:22:00 Advice for lawyers going in-house at startups 00:24:00 Carly's path into law and out of Big Law litigation 00:27:00 Finding Steno and the frog-in-water approach to tech adoption 00:33:00 Going to law school too soon and learning to fail 00:37:00 Women in legal tech today 00:39:00 Wrap-up and where to find Carly and Steno

  4. Aug 4

    Immaculate Vibes - Building an AI-Literate Organization

    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 comfortable with AI at the same time. Key Takeaways SEO isn't dead. It's the foundation that feeds AEO and GEO, the practices that get law firms found inside AI search tools and chatbots. Quality, well-structured content and citations from reputable third-party sites matter more than backlink farming ever did. Legal consumers across every generation are shifting from typed search terms to conversations with AI tools, often without realizing it. Building an AI-literate firm starts with a safe, governed environment where non-technical staff can experiment without touching client data. Start small. Pick something fun, not a client matter, to learn how an AI tool handles data before you roll anything out firmwide. Links and Resources Red Cave Law Firm Consulting: redcavelegal.com Best Lawyers: bestlawyers.com Keywords AEO, GEO, AI search optimization, legal SEO, AI Overview, ChatGPT for lawyers, shadow AI, vibe coding, AI-literate law firm, Best Lawyers, legal directory marketing, law firm content strategy, AI governance, legal tech podcast, Jared Correia, Phillip Greer, structured data for lawyers, AI search engines, law firm AI adoption, legal marketing strategy Episode Highlights [00:02:29 - 00:04:31] Greer lays out his top SEO pitch: keep doing SEO, treat it as the foundation feeding AIO. [00:04:56 - 00:08:38] Greer defines SEO, AEO, and GEO and explains why all three belong in a firm's strategy. [00:09:32 - 00:11:59] Greer traces shadow AI from a guilty secret to standard practice at nearly every firm. [00:12:56 - 00:16:39] Greer argues authenticity beats generic AI-written content and backlink farming for standing out. [00:27:48 - 00:32:20] Greer describes building the Best Lawyers internal app store that turned employees into vibe coders. [00:32:48 - 00:36:13] Greer explains how he handled data governance and change fears before rolling AI out company-wide. [00:36:20 - 00:39:08] Greer's advice: start vibe coding with something fun and low-stakes before touching firm data.

  5. Aug 3

    Mind Map - The Intersection of Artificial Intelligence & Knowledge Management

    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. Key Takeaways AI can't structure your data for you. A firm's data represents its relationships and intellectual property, and only humans understand that context well enough to organize it. Treat AI as the "middle layer" between two things you control: your structured data and your firm's unique expertise. You can't control LLM pricing or availability, so keep those other two pieces solid. Shadow AI risk isn't just about lawyers pasting client data into a chatbot. It also includes open-source code pulled from GitHub that can carry hidden backdoors. Change management works better in small, steady steps. A firm that gets 1% better most weeks of the year ends up roughly 48% better, without blowing up anyone's workflow. A new "translator" role is emerging in law firms: someone who can move between lawyers, IT, and business leadership to explain why data structure matters and what AI can realistically deliver. Links and Resources Red Cave Law Firm Consulting: redcavelegal.com Bass, Berry & Sims: bassberry.com Legal Marketing Association: legalmarketing.org Keywords knowledge management, legal AI, AI in law firms, shadow AI, structured data, law firm data management, legal technology, Bass Berry Sims, Legal Marketing Association, LMA, change management, law firm innovation, AI governance, legal knowledge management, AI as junior associate, law firm technology adoption, data governance law firm, AI risk management, legal marketing, law firm AI strategy Episode Highlights [00:03:00 - 00:04:00] Rachel introduces her "Fibber McGee's closet" metaphor for law firm data chaos. [00:06:00 - 00:06:30] Rachel says if AI could structure firm data on its own, she'd be retired. [00:07:00 - 00:08:00] Rachel frames AI as the uncontrollable "middle layer" between structured data and firm expertise. [00:12:00 - 00:12:30] Rachel warns that open-source code from bad actors is a bigger shadow AI risk than most firms realize. [00:13:30 - 00:14:00] Rachel compares vetting AI use to letting a niece use a safety knife instead of a chef's knife. [00:17:00 - 00:17:30] Rachel argues a firm that's 1% better most weeks ends the year roughly 48% better. [00:27:30 - 00:28:00] Rachel describes the emerging "translator" role bridging lawyers, IT, and business needs. [00:31:00 - 00:31:30] Jared and Rachel joke about AI's "Uber Black" pricing phase before costs rise.

  6. Jul 31

    Grand Central Station - The Value of Case Management Software in the Age of Artificial Intelligence

    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, still run the practice of law, and that AI only works well when it is pulling from a structured case management system. They cover client portals, the real costs of switching platforms, data ownership disputes with cloud vendors, and how to measure ROI beyond time saved. Key Takeaways AI is only as good as the data feeding it, and case management software is what gives that data structure. Client portals are underused by most firms, even though clients already expect 24/7 self-service access from their bank and doctor. Centralizing case data beats stacking disconnected point solutions, even when integration with existing tools is required. Switching case management systems is harder than adopting one for the first time, and change management is the real obstacle. ROI on case management software shows up in turnaround time, error rates, client satisfaction, and staff retention, not just hours saved. About the Guest Claude Simpson is the Vice President of Client Operations at Smart Advocate, a case management platform built for law firms. He has been with the company since 2013, bringing a background as a practicing trial attorney, including medical malpractice litigation, along with early technology experience dating back to building one of the first local area networks at the New York State Supreme Court's Appellate Division in the 1980s. Links and Resources Red Cave Law Firm Consulting: redcavelegal.com Smart Advocate: smartadvocate.com Keywords case management software, legal technology, law firm AI, Smart Advocate, legal case management system, AI in law firms, client portal, law firm client experience, legal tech ROI, law firm technology adoption, cloud case management, law firm data security, legal ethics technology, change management law firm, law firm staff retention, demand letter drafting, personal injury case management, law firm KPI, legal AI adoption, shadow AI Episode Highlights [00:03:03 - 00:03:45] Claude Simpson explains that despite AI hype, documents, physical or electronic, still control the practice of law. [00:05:37 - 00:06:04] Jared and Claude agree AI needs structured data, and case management software provides that backbone. [00:10:38 - 00:11:24] Claude Simpson makes the case for client portals: clients expect 24/7 access the same way they get it from their bank or doctor. [00:13:14 - 00:14:03] Claude Simpson warns that disjointed systems create frustration and increase the risk of missed information. [00:16:53 - 00:17:34] Claude Simpson on convincing a 30-year veteran attorney to switch systems: show them they can be even more successful. [00:26:53 - 00:27:44] Claude Simpson flags a real risk: what happens if a firm and its cloud host end up in a contract dispute over data access. [00:29:19 - 00:30:31] Claude Simpson breaks down ROI beyond time saved: turnaround, error rate, client satisfaction, and staff retention. [00:33:00 - 00:34:00] Claude Simpson predicts AI bots listening in on firm discussions to suggest case values in real time.

  7. Jul 29

    Skills Acquisition: How One Litigator Uses Claude to Build His Case Strategy

    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 covers AI accountability and Rule 11, Luis's move from big law to a boutique firm, why marketing to referral sources beats paid ad spend, and how cross-practice litigation experience wins cases other lawyers can't see. They close on a shared obsession with a concept album about The Odyssey. Key Takeaways A Claude skill can run a three-persona Adversarial Review panel, a fact-focused judge, a procedural judge, and a pragmatist judge, that pressure tests a motion before oral argument. Citation tools like Lexis and Westlaw confirm your sources are accurate; they don't tell you where your argument is weakest. That's a different job. AI hallucinations are an accountability problem, not a technology problem. Rule 11 already requires lawyers to investigate what they sign, AI just removes the excuse for skipping that step. Marketing to other lawyers as referral sources can outperform paid ad spend aimed directly at clients, especially in crowded practice areas. Cross-practice litigation experience, moving ideas from civil litigation into a probate case, for example, can produce solutions opposing counsel doesn't see coming. Links and Resources Red Cave Law Firm Consulting: redcavelegal.com Embedded Counsel: embeddedcounsel.com Keywords Claude skills for lawyers, AI legal tech podcast, adversarial review AI skill, moot court AI simulation, AI argument testing for litigators, AI judge personas, legal AI ethics, Rule 11 AI hallucinations, boutique law firm AI, small firm litigation technology, AI referral marketing for lawyers, LinkedIn marketing for attorneys, cross-practice litigation strategy, probate litigation technology, AI generated evidence, deepfake chain of custody, Claude versus Westlaw, legal tech for solo practitioners, AI in law school, shadow AI in law firms Episode Highlights [00:02:10 - 00:04:00] Luis explains the Adversarial Review Claude skill and its three AI judge personas. [00:05:00 - 00:05:50] Luis contrasts a custom Claude skill with citation-checking tools like Lexis and Westlaw. [00:12:00 - 00:12:30] Luis estimates judges ask him questions his AI panel already raised 20 to 40 percent of the time. [00:13:10 - 00:14:05] Jared and Luis agree AI hallucinations are a lawyer accountability problem, not a technology problem. [00:14:10 - 00:16:00] Luis explains why he left big law for a boutique litigation practice at Embedded Counsel. [00:17:00 - 00:18:10] Luis lays out his thesis on marketing to referral sources instead of paid client acquisition. [00:21:00 - 00:22:20] Luis tells the story behind his $75,000 retainer LinkedIn hook. [00:25:30 - 00:27:00] Luis describes a cross-practice motion strategy that won a probate intervention in 15 minutes. [00:29:00 - 00:31:00] Luis and Jared discuss AI-generated evidence and chain-of-custody verification for deepfakes.

  8. Jun 24

    Voyage of Discovery: Why Managing ESI for Lawyers Is Easier Than Ever

    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 a reviewer's queue.   Warren and Jared also cover modern attachments, audio and video redaction, and when AI actually earns its place in the workflow. The bottom line: AI only pays off after you have already done the basics. Crawl, walk, then run. About the Guest Warren Parrino is Regional Vice President of Solution Sales at TrustPoint.One, an e-discovery and legal services company. A former practicing attorney in Birmingham, Alabama, he most recently co-led the company's project management team before moving into his current role, giving him a view from both the operational and client-facing sides of a project. He still holds his bar license, attributing that decision entirely to how hard the exam was. Key Takeaways Start with email threading, date filters, and search terms before anything else. These three basics narrow your data set before you spend a dollar on document review. Early case assessment (ECA) databases are the single most effective way to cut e-discovery costs, yet most firms skip them because they have never heard of the approach, not because of cost. Modern attachments (hyperlinked files stored in OneDrive or SharePoint rather than attached directly to email) are the biggest current landmine in discovery, though workable solutions are emerging. Audio and video redaction that once cost thousands of dollars and required a production team can now be done at a desk in minutes using off-the-shelf tools. AI in e-discovery only delivers real savings after you have already cut your data set down. Throwing AI at a terabyte of raw data inflates your bill, it does not shrink it. Links and Resources TrustPoint.One: trustpoint.one Red Cave Law Firm Consulting: redcavelegal.com Keywords e-discovery, ESI, electronically stored information, early case assessment, ECA, email threading, modern attachments, hyperlinked files, data management, RelativityOne, shadow AI, legal technology, law firm data, e-discovery costs, solo practitioner, small law firm, audio video redaction, document review, TrustPoint.One, e-discovery consultant Episode Highlights [00:03:49 - 00:04:46]  Warren lays out the three starting points for any firm overwhelmed by data: email threading, date filters, and search terms, in that order, before anything else. [00:05:56 - 00:08:13]  Warren explains early case assessment, how it works in RelativityOne, and why communications analysis often surfaces the witness you never knew you needed. [00:08:13 - 00:09:02]  The reason most firms skip ECA is not cost. It is lack of knowledge, because if cost were the issue, everyone would already be doing it. [00:09:08 - 00:10:44]  Email threading today means reviewing one file instead of 15. It is not the labor-intensive process it once was, and the savings in time and cost are significant. [00:11:19 - 00:12:54]  Modern attachments (hyperlinked files in SharePoint or OneDrive) create versioning, custodian, and association problems that traditional e-discovery workflows were not built to handle. [00:14:59 - 00:17:28]  Audio and video redaction that once required a production team and thousands of dollars can now be done with off-the-shelf software at a desk. Warren shares a real transit authority case. [00:20:33 - 00:22:14]  There is no minimum data threshold for engaging an e-discovery consultant. The only question is whether the hassle of managing the data yourself outweighs your willingness to deal with it. [00:24:33 - 00:28:06]  AI in e-discovery is real and capable, but it only delivers savings after you have already cut the data set down. Warren describes what Relativity's AIR tools can do once the groundwork is done.

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6 Ratings

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"Adventures In Legal Tech" explores effective solutions to unique technology issues. Each episode provides actionable steps to solve everyday problems lawyers encounter. It's kind of like "This Old House" — but with way more law.

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