Adventures In Legal Tech

Jared Correia
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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.

  1. Oct 22

    Universal Joint: How to Bridge Law Firm Software Siloes

    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 Takeaways Map where your people re-key data between intake, matters, documents, signatures, and billing, because those hand-offs are where the time goes. Look at back office automation before billable-work automation, since saving operational time puts money in your pocket without changing what you bill. Constrain AI agents to the steps you've taught them, set permissions through IT, test before anything goes live, and require an audit log of every action. Set firm-wide rules for agents, such as agents can draft client emails but never send them on their own. Start with a low-risk experiment, like an agent that sorts your email into folders, and move off on-prem systems that limit what agents can do. About the Guest Alejandro Castellano is the CEO and co-founder of Caddi, an AI back office platform for law firms and other professional services firms. Born in Peru, he spent more than 10 years implementing technology in professional services, including real estate and financial services, before focusing on legal over the last three to four years. He studied electrical engineering in Peru, earned his master's at Cornell Tech in New York, and was accepted into the Allen Institute for AI Incubator in Seattle. He's the guest who comes to Brad Pitt's rescue in this episode's opening scenario. Links and Resources Caddi: trycaddi.com Red Cave Law Firm Consulting: redcavelegal.com Listen: Apple Podcasts, Spotify, Amazon Music, Deezer, YouTube, RSS Keywords law firm software integration, siloed systems, law firm automation, back office automation, AI agents for law firms, AI agents, legal AI tools, AI governance, law firm technology, legal tech, legal technology, practice management software, vibe coding, law firm operations, small law firm, solo practitioner, flat fee billing, Caddi, Jared Correia, Adventures in Legal Tech Episode Highlights [00:01:00 - 00:02:00] The vexing problem: intake, matters, documents, signatures, and billing live in separate tools, and people re-key data between them. [00:03:00 - 00:04:00] Alejandro says roughly half of an expert's time, plus staff time, goes to clicking things around between systems. [00:04:00 - 00:06:00] How Caddi works: a Discover agent finds automation opportunities, and Automate agents learn your process like a new employee. [00:05:00 - 00:07:00] Time entries began as a way to measure capacity for everyone at the firm, and firms lost visibility into staff operations. [00:06:00 - 00:08:00] Why automating the back office fits a law firm's business model better than automating the work you bill for. [00:08:00 - 00:09:00] Flat fees and subscriptions: clients push prices down, yet distrust fixed pricing, and one attorney's subscription offer got a no from every client. [00:09:00 - 00:11:00] Governance: agents constrained to the steps you teach them, plus oversight across departments and practice areas. [00:14:00 - 00:16:00] Vibe coding horror stories: thousands of dollars burned on a job a $20 tool could do, and 2,000 records updated the wrong way. [00:16:00 - 00:18:00] Permissions, workarounds, and testing before launch, plus a low-risk first experiment: sorting your email. [00:26:00 - 00:29:00] No big clean-up needed first, the on-prem problem, and why Caddi now maps AI opportunities and ROI.

  2. Oct 19

    Take the Next Step: Law Firm Growth via Software

    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 down your growth plan and map every step a matter takes, including who touches the file and how often the client hears from you, before you add people or software. Don't onboard new hires onto technology and processes that no longer serve you, because you're setting them up to fail. Grow without adding headcount by making your current people more effective, taking on new practice areas, and sometimes skipping the backfill when someone leaves. Make your firm earn AI: clean data, defined processes, and automation first, and check which tools you already pay for have added AI before you buy anything new. Review your metrics regularly, meet about them, and act on them. A monthly report nobody can explain is just paper. Links and Resources Actionstep: actionstep.com Red Cave Law Firm Consulting: redcavelegal.com Listen: Apple Podcasts, Spotify, Amazon Music, Deezer, YouTube, RSS Keywords law firm growth, law firm growth strategies, legal tech, legal technology, practice management software, law firm workflows, law firm automation, law firm SOPs, law firm metrics, AI for lawyers, legal AI tools, small law firm, solo practitioner, scaling a law firm, continuous improvement, non-billable time, Actionstep, Actionstep Intelligence, Jared Correia, Adventures in Legal Tech Episode Highlights [00:01:00 - 00:02:00] The vexing problem: Diana Prince's firm hits 75 lawyers, and pre-bill queues, intake, and reporting start to crack. [00:03:00 - 00:05:00] Beth's first move: analyze your growth plan and map every step a matter takes before you onboard anyone new. [00:06:00 - 00:08:00] Growing capacity without headcount: make current people more effective and consider new practice areas. [00:09:00 - 00:10:00] The three assets in a law firm, and why you need an honest baseline of where you are today. [00:10:00 - 00:12:00] A Melbourne firm grows from four attorneys to 60 and hires a continuous improvement officer. [00:13:00 - 00:14:00] Non-billable work as money down the drain, and why you map workflows before you automate them. [00:14:00 - 00:15:00] Beth's case that a firm has to earn AI, and why you check your current tech stack first. [00:19:00 - 00:21:00] Actionstep Intelligence: AI built inside the platform so you don't add another tool or login. [00:22:00 - 00:24:00] Designing law firm metrics: capture your time, find the bottlenecks, and know what to do with the data. [00:25:00 - 00:26:00] Why firms should meet about their metrics, and the monthly report nobody can explain.

  3. Sep 18

    Final Examination: What Does a Modern Investigative Platform Look Like for Law Firms?

    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 diarization are non-negotiable in criminal cases, and why running privileged evidence through a generic AI tool is a real risk. He also lays out how to actually pilot legal AI before you trust it with a case. Key Takeaways An "investigative platform" is built to help you interrogate a body of evidence and find the truth, not just search a document set, and that is a different job than most discovery software does. Verbatim transcription, capturing every stutter, false start, and "mm-hmm," matters in criminal cases because a polished transcript can smooth over the details that end up mattering to the outcome. Speaker diarization is still the hardest problem in legal transcription, especially on body cam footage and jail calls, where bad mics and background noise make it worse. When you pilot an AI tool, put your skeptics on it instead of your AI enthusiasts. They are the ones who will tell you what will actually break at your firm. AI can help draft documents and process evidence faster, but it cannot read a jury's emotions or tell a case's story, so the courtroom skills that make a great trial lawyer are not going anywhere. Links and Resources Rev: rev.com Red Cave Law Firm Consulting: redcavelegal.com Listen: Apple Podcasts, Spotify, Amazon Music, YouTube Keywords legal tech, legal technology, AI for lawyers, legal AI tools, e-discovery, investigative platform, evidence review, speaker diarization, verbatim transcription, legal transcription, body cam footage, jail calls, criminal defense technology, small law firm, solo practitioner, shadow AI, AI hallucinations, Rev, Red Cave Law Firm Consulting, Jared Correia Episode Highlights [00:01:00 - 00:02:00] The vexing problem: Emma Stone's team is drowning in body cam footage, jail calls, depositions, and documents during discovery. [00:09:00 - 00:10:00] Chance calls speaker diarization the hardest problem in the market, especially on body cam and jail call audio. [00:11:00 - 00:12:00] Rev's own transcription workforce pushed back the first time the company built an AI model. [00:14:00 - 00:15:00] Rev paused all production for several weeks to rebuild its internal process around AI. [00:15:00 - 00:16:00] Why running privileged legal data through a generic AI tool is a real risk, not a shortcut. [00:21:00 - 00:22:00] Chance's pilot advice: put your AI skeptics on the test, not your true believers. [00:23:00 - 00:24:00] The adoption gap: a 25-person firm where five lawyers using AI jump from 95 cases to 130. [00:29:00 - 00:31:00] Why courtroom skills, like telling a story a jury will feel, cannot be automated.

  4. Sep 11

    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.

  5. Sep 8

    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.

  6. 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

  7. 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.

  8. 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.

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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.

Information

  • Creator
    Jared Correia
  • Years Active
    2021 - 2026
  • Episodes
    200
  • Rating
    Explicit
  • Copyright
    © 2025 Breaking Media. All Rights Reserved.
  • Show Website
    Adventures In Legal Tech

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