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Adventures In Legal Tech

"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. 188

    Launch Protocol: How Law Firms Are Adopting AI in Real Time

    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: how to use Westlaw's Quickcheck as a verification loop, why lawyers overestimate what AI will do for them on the first try, and how to find the early adopters inside a firm and turn their discoveries into firm-wide workflows. Sean also looks ahead at what AI means for the billable hour model and why the legal profession can't afford to stay in the way. About the Guest Sean McTigue is a partner at Bartko Pavia LLP in San Francisco, where he handles complex litigation with a particular focus on integrating AI into the practice of law. He has been following the development of large language models closely since GPT-4's launch and has led the firm's rollout of Anthropic for Enterprise. Sean studied philosophy at the University of Utah and earned his law degree at Berkeley Law. Key Takeaways Hallucination risk in AI outputs is a solved problem, using tools like Westlaw's Quickcheck as a verification flywheel alongside AI drafting, not a reason to avoid AI entirely. Legal-specific tools rarely add value beyond a general foundation model; the wrapper around the model matters less than most vendors claim. Direct enterprise deployment of a foundation model lets firms ride the frontier rather than being stuck on whatever model a SaaS vendor last tested. The billable hour model is under pressure, and firms that build internal AI capital now are better positioned to shift toward fixed-fee and alternative-fee arrangements. Adoption inside a firm starts with finding the heavy users, learning what they figured out, and distributing those workflows to everyone else. Links and Resources Red Cave Law Firm Consulting Bartko Pavia LLP Westlaw CoCounsel Westlaw Quickcheck - available inside your Westlaw subscription Anthropic for Enterprise Keywords AI adoption in law firms, legal AI tools, Westlaw Quickcheck, AI hallucinations legal, foundation models for lawyers, Anthropic for Enterprise, billable hours AI, legal tech vendor evaluation, Sean McTigue, Bartko Pavia, Jared Correia, Adventures in Legal Tech, CoCounsel Westlaw, AI verification legal, small firm AI, legal workflow automation, enterprise AI deployment, AI research tools lawyers, prompt engineering legal, alternative fee arrangements AI Episode Highlights [00:02:01 - 00:04:54] Sean introduces Westlaw Quickcheck as the underused verification tool that turns hallucination risk into a manageable step in the workflow. [00:05:00 - 00:07:57] Sean explains why lawyers who try AI once, find it imperfect, and dismiss it are missing the workflow question entirely. [00:08:13 - 00:09:28] The hammer-and-nail analogy: being handed a tool and told to use it without any guidance on what the full project actually looks like. [00:19:14 - 00:23:27] Sean describes the frustration of vetting legal AI vendors who can't tell you what model they're running, including an e-discovery platform using Haiku 3 on million-document reviews. [00:24:54 - 00:28:05] The case for direct foundation model deployment over legal-specific SaaS wrappers, and what you can do with a generalist model that a niche tool will never offer. [00:36:44 - 00:40:43] The future of legal billing: from the billable hour back toward fixed-fee engagements, and why firms that build AI capital now are better positioned. [00:41:50 - 00:47:23] Sean's starter recommendation: Westlaw citing references downloaded in bulk and fed to an LLM, plus why Google AI Overview is already AI whether lawyers know it or not.

  2. 187

    The Ontological Argument: What's Real & Not in Artificial Intelligence in LegalTech

    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?

  3. 186

    First Light: Structural Intelligence Must Come Before Artificial Intelligence

    🧾 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 flows of value. Yet, the tools used to map these structures haven't meaningfully evolved in decades. Tim introduces the concept of structural intelligence, explaining how visual models and semantic data layers can transform diagrams into powerful interfaces for both humans and machines. The conversation explores how diagrams function as "context-loading mechanisms," why AI needs structured foundations to be effective, and what the future of legal interfaces might look like—hint: think Minority Report. This episode blends legal tech, cognitive science, and AI strategy into a compelling argument: if you don't structure your data properly, AI might accelerate your work—but in the wrong direction. 🔗 Links & Resources StructureFlow: https://structureflow.co redcavelegal.com 🔑 Keywords legal tech legal innovation structural intelligence information architecture AI in law legal workflows data visualization diagramming corporate law litigation strategy knowledge management graph data RAG systems legal AI StructureFlow productivity tools legal design ⏱️ Episode Highlights 00:00–01:18 – Introduction to the podcast and the problem of structural complexity in legal work 01:18–02:09 – Why outdated tools (PowerPoint, spreadsheets) still dominate legal workflows 02:09–03:12 – Defining the problem: increasing complexity in professional and personal contexts 03:12–04:16 – Historical roots of diagramming—from early businesses to modern law firms 04:16–05:33 – Why visualizing relationships is essential to understanding structure 06:09–07:20 – What StructureFlow does and how it differs from traditional diagram tools 07:20–08:14 – The power of semantic meaning behind diagrams (data + visuals) 08:14–09:00 – Use cases across law firms, accounting, and corporate environments 10:11–11:02 – Diagrams as knowledge assets and tools for rapid context recall 15:30–16:08 – Diagrams as "context-loading mechanisms" for the human brain 16:08–17:08 – Visual processing vs. text: why diagrams accelerate understanding 17:08–18:14 – Graph structures explained and their role in representing relationships 18:14–19:22 – RAG systems and how AI retrieves and processes structured knowledge 21:01–22:09 – Why AI needs structure: "acceleration without direction" risk 24:51–26:27 – The "Minority Report" vision for the future of legal interfaces

  4. 185

    Slow Your Roll: How to Adopt AI in a Small Firm At a Reasonable Pace

    🧠 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 complex private equity deal documents to drafting contract provisions, AI has dramatically increased efficiency—sometimes reducing work time by up to 90%. However, the conversation makes one thing clear: AI is not a replacement for legal expertise. Instead, it functions best as a "junior associate"—powerful but requiring oversight, context, and verification. They also dive into the ripple effects of AI on billing models, client expectations, firm structure, and the future of junior lawyers. The episode ultimately reframes AI not as a threat, but as a tool that enables lawyers to work smarter, deliver more value, and deepen their strategic role. 🔗 Links & Resources redcavelegal.com Home www.redcavelegal.com 🔑 Keywords legal tech AI law firms artificial intelligence lawyers small law firms legal automation document drafting legal innovation billing models AI productivity legal workflows AI adoption law practice management legal AI tools 🎯 Episode Highlights 00:00–01:00 – Introduction to the podcast and the problem: AI adoption in small law firms 01:00–02:00 – Meet Jane Freedman and the central question: can small firms use AI? 02:00–03:30 – Jane's transition from casual AI use to professional implementation 03:30–05:30 – First real-world use case: leveraging AI in complex private equity deals 05:30–07:00 – Using AI tools like Copilot and Litera strategically 07:00–08:00 – Treating AI like a "junior associate" 08:00–09:30 – Efficiency gains: completing work in 10% of the usual time 09:30–11:30 – Jane's career journey and founding her own firm 11:30–13:00 – Building a team and scaling a legal practice 13:00–14:30 – The importance of precise prompting in AI usage 14:30–16:30 – Risks of AI: hallucinations and the need for verification 16:30–18:30 – Will AI replace junior lawyers? The structural dilemma 18:30–20:30 – Managing AI tools within a legal team 20:30–23:00 – Rethinking billing models in the age of AI 23:00–27:00 – Client behavior shifts and AI-generated legal documents 27:00–31:00 – Practical use cases: drafting, redlining, and document review

  5. 184

    Good Vibrations - How Vibe Coding Is Infiltrating Legal

    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 opportunities, risks, and economic shifts driven by this movement—along with practical advice for getting started. From democratizing legal tech to reshaping law firm business models, this episode provides a clear look at how AI is changing who builds legal solutions—and how fast it's happening. Links & Resources www.redcavelegal.com www.bryter.com www.vibecode.law LegalQuants   Keywords vibe coding AI legal tech legal innovation no-code tools law firm automation productization legal AI workflows access to justice shadow AI legal startups legal tech trends Episode Highlights (with timestamps) 00:00–01:05 – Introduction to the podcast and its mission 01:05–02:20 – Defining vibe coding and its role in legal tech 02:20–04:00 – Why legal is primed for innovation despite being a late adopter 04:00–05:20 – Natural language as a bridge between lawyers and AI tools 05:20–07:10 – Risks of vibe coding: security, compliance, and infrastructure 07:10–08:50 – Identifying ideal use cases: repetitive, high-volume tasks 08:50–10:05 – Real-world example: lawyers experimenting with app-building 10:05–11:40 – Innovation hours inside law firms 11:40–13:00 – The rise of "shadow AI" and unsanctioned experimentation 13:00–15:00 – Max's background and entry into legal tech 15:00–18:00 – What Brighter does and how it integrates AI 18:00–20:30 – Economic shifts: productized services and new billing models 20:30–23:00 – New players entering legal tech: investors, founders, consumers 23:00–25:30 – Access-to-justice opportunities and unmet legal demand 25:30–28:00 – Best tools, communities, and mindset for vibe coding

  6. 183

    The Future Is Now - Why & How Law Firms Are Adopting Tech Like Never Before

    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 of innovation. Joe shares his journey from litigator to legal tech leader, insights on why legal tech companies are thriving, and how AI is expanding—not shrinking—the legal market. The conversation also dives into emerging trends like managed service organizations (MSOs), private equity in law, and the maturation of the legal tech buying process. Ultimately, Joe argues for a more optimistic future: one where technology enhances legal work, increases access, and creates new opportunities across the industry. Links & Resources redcavelegal.com lexfusion.com Keywords legal tech generative ai law firms innovation legal industry AI adoption legal startups lexfusion legal transformation legal services automation legal workflows legal ai tools corporate counsel legal operations future of law legal business models msos private equity law firms legal innovation trends. Episode Highlights (with timestamps) 00:00–01:03 – Introduction to the podcast and the episode's core problem: legal tech overwhelm for in-house counsel 01:03–02:20 – Framing the challenge: too many tools, not enough clarity or bandwidth 02:20–03:16 – Start with identifying pain points before choosing technology 03:50–05:45 – Joe Borstein's background: from litigator to legal tech entrepreneur 05:45–07:01 – The shift from labor-based services to tech-driven innovation 07:01–09:01 – Founding LexFusion and pivoting to advising legal tech companies 09:01–10:31 – Growth of legal tech valuations and emergence of billion-dollar companies 10:31–12:00 – Generative AI expands the total addressable market for legal services 13:12–14:22 – Law firms are finally adopting structured, mature buying processes 14:22–16:08 – Why legal tech and law firms are now partners instead of competitors 16:08–17:03 – Lower costs per task increase overall legal spending and demand 18:27–19:43 – Why AI adoption is different: it's familiar, accessible, and widely used 21:55–23:41 – What MSOs are and how they could reshape law firm structures 23:41–26:15 – The need for new business models in legal to improve satisfaction and access 28:22–30:20 – Legal Week reflections: more focus needed on innovators and builders

  7. 182

    Upselling: An Associate's Take on How Law Firms Should Implement Artificial Intelligence

    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. Harshita shares a practical framework based on her firm's experience, including the creation of an AI committee, slow adoption strategies, and the importance of transparency across teams and clients. The discussion goes deeper into the unintended consequences of AI adoption—especially for junior associates. From "shadow AI" usage to declining critical thinking skills, Harshita highlights the risks of over-reliance on automation and the importance of preserving foundational legal training. This episode offers a balanced perspective: AI is neither a threat nor a silver bullet. Instead, its success depends on thoughtful implementation, strong mentorship, and a commitment to ethical practice. Links & Resources redcavelegal.com Environmental, Insurance & Real Estate Defense - Boston, MA CMBG3 Law Keywords Legal AI AI in law firms Legal technology Shadow AI Law firm management Junior associate training Legal ethics AI policy Legal research tools E-discovery Work-life balance in law Legal innovation AI risk management Critical thinking decline Law firm culture Episode Highlights 00:00–00:40 – Introduction to the podcast and its mission to solve legal tech challenges 00:00:40–01:20 – The core problem: a new associate wants to implement AI in a resistant firm 01:20–02:03 – Introduction of Harshita Ganesh and her perspective on AI adoption 03:10–04:09 – The real concerns attorneys have about AI in legal workflows 05:07–06:17 – The rise of "shadow AI" and why associates use it under pressure 07:31–08:46 – Risks of AI misuse, including hallucinated cases and legal consequences 10:12–11:13 – Why transparency about AI use is currently lacking in law firms 12:14–13:20 – Examples of AI tools being vetted: Lexis AI and Everlaw 14:31–15:28 – The danger of replacing foundational legal work with AI 16:20–17:40 – The long-term risk: weaker lawyers due to over-reliance on AI 17:40–18:53 – New roles emerging in law firms (AI compliance, legal data analysts) 20:15–21:34 – The decline of critical thinking in law students 21:34–22:52 – How AI is changing learning habits and reducing information retention 24:08–25:21 – AI bias and its impact on legal reasoning 25:21–26:44 – Accountability in AI usage: lawyers remain fully responsible 28:07–29:20 – Practical use cases for AI (e.g., document review) vs. risky applications 30:33–31:33 – The role of mentorship and firm culture in responsible AI adoption 33:17–34:30 – Building trust between partners and associates 35:20–37:06 – Closing thoughts and a lighthearted discussion on favorite cities

  8. 181

    Didn't We Almost Have It All - Law Firm IT Is All About Compromises

    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 friction. Guest Mike Maschke, President and CEO of Sensei Enterprises, breaks down practical cybersecurity strategies tailored for law firms, explaining why resistance to security tools often stems from misunderstanding rather than actual inconvenience. The conversation covers essential topics including multi-factor authentication, encrypted communication, compliance frameworks, AI governance, change management, and emerging cybersecurity trends shaping the legal industry. Rather than presenting cybersecurity as a technical burden, the episode reframes it as a strategic business function — one that protects firms, clients, and long-term operational stability. LINKS & RESOURCES redcavelegal.comsenseient.com [email protected] KEYWORDS Legal cybersecurity Law firm data protection Cybersecurity for lawyers Multi-factor authentication law firms Encrypted email legal practice Legal tech security compliance Law firm cybersecurity policy AI governance for law firms Legal technology risk management Cloud security law firms Zero trust security model Legal compliance cybersecurity Law firm IT strategy Change management legal tech Cyber insurance requirements Legal data privacy AI policy law firms Legal practice cybersecurity best practices EPISODE HIGHLIGHTS 00:00–01:15 – Introducing a new approach to solving legal tech problems 01:15–01:49 – The core challenge: security vs convenience in law firms 01:49–03:28 – Why cybersecurity adoption has historically been slow in legal 03:28–04:18 – Multi-factor authentication myths and realities 04:18–04:58 – Why lawyers resist security measures 04:58–06:29 – Email encryption and protecting sensitive client data 06:29–07:13 – Legacy email habits and evolving communication risks 07:13–09:37 – Compliance requirements across state, federal, and industry rules 09:37–10:45 – Productivity concerns when implementing cybersecurity controls 10:45–12:25 – Change management strategies for technology adoption 12:25–13:37 – Why law firms struggle with operational change 13:37–14:48 – Planning technology decisions three to five years ahead 14:48–15:50 – Transition into AI discussions and industry hype 15:50–16:49 – Risks of unstructured AI adoption ("shadow AI") 16:49–20:21 – Building firm-wide AI policies and governance frameworks 20:21–20:55 – Creating formal AI usage policies for law firms 20:55–22:16 – Early adoption of AI automation workflows 22:16–23:15 – Automating legal processes using AI integrations 23:15–25:41 – Future legal tech trends beyond AI hype 25:41–26:55 – Zero Trust security explained simply 26:55–28:55 – Proactive cybersecurity monitoring and incident response 28:55–31:07 – Building collaborative relationships with IT vendors 31:07–32:56 – Leadership transition lessons from Sensei Enterprises 32:56–33:28 – Episode wrap-up and key takeaways

  9. 180

    Good Counsel - How to Launch a Law Firm from Scratch

    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 systems, tools, and strategic choices lawyers actually need when starting a modern practice. Rather than focusing on flashy software, the discussion emphasizes practical foundations — collaboration tools, workflow management, AI adoption, pricing models, marketing experimentation, and the realities of transitioning from in-house counsel to entrepreneurship. The episode also explores: Why Google Workspace may outperform traditional setups for small firms How cloud technology has lowered the barrier to starting a law practice The evolving role of AI in legal workflows Subscription and flat-fee pricing models replacing hourly billing Marketing experimentation and networking as growth drivers Burnout risks in in-house roles and the motivation to go independent Building partnerships and fractional legal services practices LINKS & RESOURCES redcavelegal.comembeddedcounsel.com [email protected] KEYWORDS Legal tech for startups Starting a law firm Legal technology stack Google Workspace for lawyers Law firm technology basics Fractional general counsel Flat fee legal pricing Subscription legal services AI for lawyers Legal research technology Cloud law practice Legal entrepreneurship In-house counsel transition Law firm marketing strategy Legal networking Practice management tools Law firm automation Legal business development EPISODE HIGHLIGHTS 00:00–01:14 - Introducing a new approach to legal tech conversations 01:14–02:23 - The problem: starting a firm with zero technology knowledge 02:23–03:13 - Why Google Workspace became the foundation of a modern law firm 03:13–04:01 - Microsoft vs Google ecosystems and integration simplicity 04:01–05:11 - Project management challenges in legal practice tools 05:11–06:14 - AI tools lawyers are experimenting with today 06:14–06:57 - Guardrails and risks when using general AI platforms 06:57–07:24 - Cloud technology lowering startup costs for law firms 07:24–08:19 - The minimal tech stack needed to launch a practice 08:19–09:12 - John Pothier's unconventional path into law 09:12–10:08 - Entrepreneurship before traditional legal careers 10:08–11:10 - The reality of working as in-house counsel 11:10–12:19 - Burnout, workload pressure, and limited time off 12:19–13:41 - Why lawyers leave stable roles to start firms 13:41–15:00 - Choosing the right business partner in legal practice 15:00–17:00 - Balancing entrepreneurship with family life and risk 17:00–19:24 - Designing pricing models without industry transparency 19:24–20:37 - Flat fee vs hourly billing and client psychology 20:37–22:30 - The rise of fractional legal services 22:30–23:26 - Marketing experiments that didn't work 23:26–24:47 - Networking as the most reliable growth strategy 24:47–26:22 - Lessons learned from running AI-driven marketing ads 26:22–28:26 - Professional development while managing a law firm

  10. 179

    Compare & Contrast: Modern Drafting & Revision Tools for Law Firms

    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 document comparison in legal tech. 00:10:18 - Caspar's transition from product team to general management. 00:13:43 - The importance of customer feedback in product development. 00:16:40 - Caspar's unexpected journey from agriculture to legal tech. 00:19:57 - Tech overload in law firms and renewal cycles explained. 00:24:58 - Balancing off-the-shelf solutions versus building bespoke tools. 00:28:35 - Navigating pricing and honest cost structures in legal software.   Episode Resources Resources mentioned in the podcast: www.redcavelegal.com www.draftable.com Binge Thinking   Keywords Adventures in Legaltech Legaltech conversations Technology issues Law practice technology Red Cave Law Firm Consulting Legal software solutions Document comparison software Draftable Legal tech commentary Real estate, banking, finance, M&A Podcast professional Vibe coding AI in legal tech Vendor-law firm relationship Legal tech automation Law firm tech overload Software renewal cycles Legal tech pricing AI technology features  

  11. 178

    For Profit - Running a More Effective Law Firm through Efficiency, AI & Planning with Jess Birken

    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 marketing in law. 12:50 - The rise of podcasting for marketing. 16:05 - Transition to nonprofit law. 18:41 - Vetting AI tools for legal use. 21:00 - Balancing innovation with caution in AI. 23:48 - Prioritizing intentions over rigid plans.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Jess Birken https://birkenlaw.com/  [email protected]   

  12. 177

    Get Busy Growing, or Get Busy Shrinking: Law Firm Growth by Acquisition & Technology Adoption with Jack O'Donohue

    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 initiatives. 10:57 - Decision-making and organizational charts. 13:35 - Featuring the human side of business with events. 17:33 - Approach to business and acquisitions. 19:12 - Opportunities in legal and closing business models. 27:17 - Decision on adopting Qualia for business. 31:43 - Using AI in legal practices. 34:35 - Future for lawyers in AI integration.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Jack O'Donohue https://touchstoneclosing.com/  https://touchstonelawoffices.com/  https://www.youtube.com/@DonutDigest  [email protected]   

  13. 176

    Master of the CRM Universe: A Paralegal's Perspective on Intake & Customer Service with Vanessa Reynolds

    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 use of answering services. 16:13 - Importance of metrics and lead tracking. 19:45 - Training clients for law firm communication expectations. 22:15 - Simplifying software usage in law firms. 25:01 - Exploring artificial intelligence in legal practices.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Vanessa Reynolds gmrodriguezlaw.com  [email protected]   

  14. 175

    Stay of Execution: AI May Not Kill Us All, But It Will Change Legal Practice & Legal Education Like Nothing Else Before It with David Colarusso

    I spoke with a lawyer, developer, educator & data scientist about how AI is disrupting law practice & legal education.   Episode Highlights 03:33 - AI revolution challenge for law firms. 05:57 - What is agentic AI? 11:41 - Custom GPTs in practice. 19:52 - Bias in AI and its implications. 25:52 - Tackling AI fairness and justice. 32:57 - Star Trek's predictive view on AI. 36:01 - The concept of P-Doom. 45:20 - Role-playing in AI and law education. 48:30 - The promise of AI in education. 54:41 - Legal students' interaction with AI tools.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with David Colarusso https://suffolklitlab.org/  https://lawrpg.org/  [email protected] 

  15. 174

    Practical Magic: How AI WIll Really Impact Law Firms with Jordan Furlong

    I spoke with Jordan Furlong, of Law21, a legal futurist, about what impact AI is having (and, will have) on lawyers.   Episode Highlights 04:51 - Large language models and ChatGPT in law. 05:39 - General-purpose technology's ubiquity. 07:39 - The empowerment potential of AI. 09:57 - Rethinking legal tasks and roles. 16:59 - AI adoption in law firms: Challenges and opportunities. 19:04 - Billable hours and changing legal pricing. 37:11 - Law21 consulting focus: Adaptation in legal services. 39:59 - The need for legal industry transformation. 54:12 - Reflecting on societal and historical responsibilities.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Jordan Furlong [email protected]  https://www.law21.ca/   

  16. 173

    Automators, Assemble! How to Manage with Quinten Steenhuis

    I spoke with a consultant who builds document automation tools for private law firms & legal aid agencies, among others.   Episode Highlights 01:21 - Problem of slow document generation. 03:10 - Automating documents with DocAssemble. 07:11 - Open source vs. commercial software. 08:52 - Potential and barriers of document automation. 11:01 - Challenges in automating complex documents. 12:02 - Logic and formatting complexity. 14:09 - Customization in legal tech. 15:51 - Impact of budget cuts on Legal Services Corporation. 16:52 - Legal aid's critical role for community stability. 18:56 - AI's impact on the legal intake process. 20:14 - AI tools for legal outreach. 22:16 - Environmental concerns regarding AI. 23:52 - Upcoming legal innovation conference in Boston.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Quinten Steenhuis https://lemmalegal.com/  https://suffolklitlab.org/  [email protected]   

  17. 172

    Transfer Station: Success at Succession Planning and a LegalTech Adoption Update with Donna Brown and Jaclyn McDuffey

    I spoke to a member of a legaltech implementation & customization firm - the former owner & the new owner, as we spoke about the state of legal software & AI.   Episode Highlights 03:29 - Donna and Jackie offer tech solutions. 04:01 - Importance of customized tech stacks. 06:01 - Evolution from limited to vast legal tech. 09:17 - Jackie on internal transitions and recruitment. 11:48 - The growing allure of Oklahoma City. 14:44 - Shift towards alternative legal billing. 20:51 - AI's role in law firm billing discussions. 25:15 - Automation's impact on billing approvals. 29:37 - Consolidation trends in Legal Tech.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Donna Brown and Jaclyn McDuffey https://www.beyondsquareone.com/   

  18. 171

    Zen and the Art of Crisis Litigation Management - Tricks for Running a Successful Solo Law Firm with Adam Hersh

    I spoke with a business attorney who works for corporations and handles crisis litigation about his practice.   Episode Highlights 03:06 - Importance of technology in managing court deadlines. 06:43 - Evolution and significance of docket calendaring. 08:52 - Insights into selecting travel bags for lawyers. 09:36 - Recommendations for travel gadgets and mice. 10:28 - Sports memorabilia collecting insights. 12:07 - Favorite sports memorabilia pieces. 14:05 - Concept of crisis litigation explained. 17:11 - Handling chaotic legal situations. 19:07 - Working with corporations and honest communication. 21:37 - Key to maintaining lawyer-client relationships. 23:14 - Personal management style advice for lawyers.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Adam Hersh https://bluechip.law/ourteam/adam-hersh/ 

  19. 170

    Risky Business - Managing Technology for Ethical Competence with Rio Laine

    I talked with my guest about adopting and managing legal technology with an eye toward law firm ethics.   Episode Highlights 03:51 - Essential Legal Tech Tools 06:00 - Vendor Partnership Program at alps 06:51 - Wire Fraud and Its Risks 07:59 - Deepfake Scams in Transactions 09:23 - Technology Integration Challenges 10:05 - Importance of Tech Training 13:23 - Tech Adoption Barriers for Lawyers 15:28 - Vetting Tech Vendors for Security 18:11 - Younger Lawyers and Tech Challenges 19:29 - Importance of Processes and Workflows 20:47 - Vetting Software for Risk Reduction 25:51 - Selecting Malpractice Insurance 27:59 - Necessity of Cyber Insurance   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Rio Laine https://www.alpsinsurance.com/   

  20. 169

    A Brand New Protege: The Latest Update in AI Legal Research with Simon Weierman

    I spoke with a long-time employee of LexisNexis, about where AI search is, and where it's going.   Episode Highlights 02:51 - Google or general AI tools vs. Lexis AI for legal research. 03:53 - Generative AI assistant "Protege" by LexisNexis. 05:08 - Lexis Plus AI's approach to addressing hallucinations. 09:08 - Evolution of legal tech over the years. 10:32 - Legal industry's AI adoption increases. 12:14 - Simon's personal journey at LexisNexis since 1999. 18:28 - Importance of user-focused AI tools at LexisNexis. 20:03 - AI-driven workflow strategies in legal research. 24:09 - Less known Lexis features: Search-tree explanation.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Simon Weierman https://www.linkedin.com/in/simonweierman/   

  21. 168

    Deep Impact: AI Deposition Technology for Law Firms & the State of AI in Law Practice with Joe Stephens

    I spoke with a lawyer and clinical law professor about the impact of AI in the deposition space & elsewhere in legal.   Episode Highlights 05:02 - Frictionless deposition process with AI. 08:48 - Educating lawyers beyond law school. 11:50 - Introducing Transcript Genius: AI in depositions. 16:13 - AI's potential to revolutionize legal education. 21:08 - Balancing traditional skills and AI enhancement. 25:25 - Next-gen law firms empowered by AI. 29:39 - The future impact of AI on the legal industry.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Joe Stephens https://steno.com/   

  22. 167

    Beads of Wisdom: Ernie the Attorney's Got LegalTech Takes with Ernie Svenson

    I spoke with a legaltech consulting veteran, who has lots of thoughts about the current state of technology implementation in law firms + how AI is changing the way attorneys operate.   Episode Highlights 02:00 - Effective solutions for technology issues. 05:35 - Solo attorney overwhelmed by marketing success. 06:09 - Embracing AI before hiring staff. 07:40 - Advancing legal tech adoption. 09:23 - Big firm inefficiencies as a small firm advantage. 10:56 - Past the paperless office era. 12:19 - The significance of the cloud for AI advancement. 14:00 - Encouragement to explore beyond generative AI. 16:34 - Custom GPTs for tailored tasks. 18:17 - Perspective on cruises and travel. 20:15 - Utilizing smartphones to the fullest. 23:22 - Psychology of technology resistance. 25:29 - Disciplined technology adoption. 28:00 - Digital nomad lifestyle for lawyers. 30:15 - Importance of password managers.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Ernie Svenson https://ernietheattorney.net/  https://www.linkedin.com/in/ernieattorney/   

  23. 166

    Deep Research: How A Real Lawyer Deploys AI in An Actual Law Practice with Josh Noffke

    I spoke with an attorney who aggressively implements AI in his law firm, and teaches other lawyers to do the same.   Highlights 09:03 - AI and Prompt Engineering 18:46 - Perplexity and AI Search Engine 21:03 - Perplexity Partners with Legal Zoom 24:02 - Federal Regulations on AI 28:36 - Tools to Start with AI in Legal Practice   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Josh Noffke https://www.brasstacksai.com/  https://www.linkedin.com/in/joshnoffke/   

  24. 165

    Outstanding in Our Field(s): Transitioning Into & Out of Case Management Software with Adriana Linares

    I talked with an expert in the space about how law firms adopt and customize or transition between case management software.   Highlights 02:07 - Importance of addressing people and technology roadblocks. 03:10 - Modern to modern case management transition. 06:56 - The role of bookkeepers as roadblocks. 11:13 - Addressing partners who resist tech adoption. 15:50 - The critical first step in evaluating software. 17:45 - Adriana's unexpected journey into owning a perfume shop. 24:25 - Increasing efficiency with case management systems. 26:32 - The necessity of using Microsoft 365 and Copilot. 31:33 - Exploring new PDF tools with Adobe AI. 35:39 - Integrating AI smartly into legal practices. 36:47 - The potential of AI for administrative tasks.   Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Adriana Linares https://www.lawtechpartners.com/  https://madameaucoinperfume.com/ https://madameaucoinperfume.com/   

  25. 164

    This is IT: All About Managed Service Providers for Law Firms with Darragh Fitzpatrick

    I talked with an expert on managed IT services for law firms about the state of the industry.   Episode Highlights 04:02 - The emergence of managed service providers. 05:02 - Affordable tech solutions for law firms. 06:39 - Three essential aspects of law firm tech: functionality, accessibility, security. 07:59 - Legal industry survey insights. 09:19 - Law firms' cautious adoption of AI. 12:39 - Irish cultural discussion: Playwrights and sports. 13:56 - Description of the sport of Hurling. 17:39 - Importance of strategic IT planning for law firms. 21:40 - Encouragement for proactive IT management. 27:07 - AI in managed service providers. 31:41 - Creating policies around AI use in law firms. 35:39 - Growing risks of cybersecurity due to AI advances. 39:49 - Current investments in cybersecurity. Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Darragh Fitzpatrick https://www.tabush.com/  https://www.linkedin.com/in/darraghfitzpatrick/   

  26. 163

    Above & Beyond the 8-Bit: A Discussion Around Modern Document Assembly Software with Samuel Smolkin

    I spoke with the founder of a document assembly program about the latest software upgrades in the space.   Episode Highlights 05:40 - Eric Burdon's document drafting woes 09:47 - Genesis of Office and Dragons 18:52 - Importance of tailored document automation 21:22 - Limitations and role of AI in law 23:30 - Ensuring accuracy with AI-assisted processes 28:17 - Future of document assembly and legal tech Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Samuel Smolkin [email protected]  https://www.officeanddragons.com/  https://www.litera.com/ 

  27. 162

    Trust the Process (Management): All About the Modern World of CRM with Wendy Wylde

    I talked with an implementation consultant about how to best leverage your law firm CRM.   Episode Highlights 03:32 - Wendy Wylde's approach to problem-solving. 05:26 - Transition from Lawmatics to independence. 06:33 - From chemistry teacher to legal tech consultant. 09:36 - Importance of starting with simple automations. 11:02 - Overcoming resistance to automation in law firms. 13:47 - Documenting processes for a predictable outcome. 16:46 - The significance of CRMs for law firms. 19:04 - Using data for better firm reporting. 21:40 - Business versus legal-specific CRMs. 23:35 - Standard operating procedures as business assets. 25:05 - Potential AI innovations in CRMs. Episode Resources Connect with Jared Correia [email protected]  https://redcavelegal.com/  https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/  Connect with Wendy Wylde https://www.linkedin.com/in/wendy-wylde/  https://matterflowadvisors.com/   

  28. 161

    Revolutionary: Why AI Will Rewrite Legal Institutions with Justin Cary

    I spoke with an attorney about how AI is changing, and will continue to change, the practice of law. Episode Highlights 03:29 - Trust issues with AI at law firms. 05:50 - Tribal law insights. 08:36 - AI in law: Career impact. 11:06 - Challenges of upskilling with AI. 14:10 - Data preparation importance. 18:34 - Dangers of premature regulation. 23:18 - AI agents in legal practice. 26:41 - Potential destabilization by AI. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Justin Cary https://dwmlaw.com/ [email protected] https://dwmlaw.com/profile/justin-b-cary/ 

  29. 160

    Take Off: Launching a Technology-Focused Personal Injury Law Firm with Rob Hartigan

    I spoke with a personal injury attorney, who has started a technology-first law practice. Episode Highlights 04:26 - Discussion on AI tools for document referencing. 07:00 - Rob discusses starting a successful law practice. 10:28 - Experimenting with legal tech as a new law firm. 11:59 - Efficient management of PI medical records. 13:34 - Use of AI in settlement demands. 16:10 - Deposition software evolution. 20:46 - Market opportunity for case strength analysis software. 22:32 - Discussion on managing practice in different states. Episode Resources Connect with Jared Correia [email protected]   https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Rob Hartigan https://lionhartlaw.com/  

  30. 159

    Trial by Fire - Artificial Intelligence as a Competitive Advantage for Litigation Firms with Kim Bookout

    I spoke with an expert in the technology space about how law firms can better leverage AI for a competitive advantage. Episode Highlights 02:14 - Defining this week's challenge: AI effectiveness in law firms. 03:50 - Guest introduction: Kim Bookout, Director at Opus2. 05:10 - Opus2's approach to AI integration. 09:40 - Legal Week insights: AI adoption trajectory. 12:00 - Lawyer's biggest AI fear: confidentiality breach. 14:22 - Practical AI use in personal life for beginners. 19:14 - Low-risk AI use in law: summarizing deposition transcripts. 22:23 - Urgency of adopting AI in law practices. 23:23 - Will AI replace lawyers? Kim's perspective. 26:56 - Using AI to enhance, not replace, legal expertise.   Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal  www.linkedin.com/in/jaredcorreia/ Connect with Kim Bookout [email protected] https://www.opus2.com/ https://www.linkedin.com/in/kim-bookout-496a8193/  

  31. 158

    Artificial Flavor - How AI Has & Will Irrevocably Change the Practice of Law with Stephen Embry

    I talked with a legaltech journalist about the many ways in which artificial intelligence will impact the legal vertical. Episode Highlights 01:04 - Unique tech solutions for law firms. 01:43 - Generative AI's impact on law practice. 03:00 - Stephen Embry joins as guest expert. 05:55 - Threat to the traditional law firm model. 09:40 - Shifting from billable hours to value-based fees. 14:51 - Tech Law Crossroads blog origin. 18:19 - Stephen's South by Southwest experience. 21:08 - Valuing law work by outcome, not hours. 24:14 - Law automation: Replacing non-productive work. 27:40 - The challenge of AI in trial law.   Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Stephen Embry https://www.techlawcrossroads.com/  

  32. 157

    Site Unseen - How to Build & Maintain a Quality Law Firm Website with Michael Pratt

    I talked with an expert in the space about how to create + keep updated a law firm website. Episode Highlights 01:21 - Real-life law firm scenarios. 02:04 - Building and maintaining law firm websites. 05:50 - Subscription model for websites. 06:56 - Website as a service (WaaS) strategy. 07:50 - Transitioning from trades to tech. 13:03 - Modern website design trends. 15:08 - Dealing with outdated websites. 16:12 - AI's impact on SEO and content quality. 18:59 - The shift to quality content emphasis. 20:39 - AI in automating client onboarding. 25:11 - Convincing skeptics of AI benefits. 27:55 - Importance of personal branding online. 31:50 - Ensuring website security and compliance. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Michael Pratt [email protected] https://getwaas.io/ 

  33. 156

    Team Up - How General Counsel & Legal Ops Can Work Together; LINK Acquired by L Suite with Stephanie Corey and Shaun Sethna

    I spoke with general counsel and a legal operations professional about how those two disparate sets of professionals can work better together! Episode Highlights 04:22 - Miscommunication: every problem looks like a nail. 06:06 - Bridging gaps with strategic operations. 18:36 - Origin story of Link and L Suite. 28:50 - Reality check: Legal Ops vs tools mismatch. 37:36 - AI's seismic impact in legal operations. 41:06 - Legal professionals' growing interest in AI tools. 42:04 - Changing attitudes towards AI in law. 44:42 - Empathy and networking as keys to success. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Stephanie Corey and Shaun Sethna [email protected] [email protected] https://uplevelops.com/ https://www.lsuite.co/ https://linkforlegal.com/  

  34. 155

    Match Point - Are Point Solutions All They're Cracked Up To Be? with Cain Elliott and Keegan Chapman

    I spoke with two experts in the legaltech space about the value of unified software platforms for attorneys. Episode Highlights 03:17 - Overwhelmed by numerous tech solutions. 05:09 - Impact of AI on tech-business convergence. 06:06 - The cable-cutting analogy for software solutions. 07:16 - Merging law firms' tech stacks. 08:54 - Change management: making tough decisions proactively. 10:29 - Humor on leap year births. 16:57 - Data silos in law firms and inefficiency. 18:02 - Email is not a storage solution. 20:02 - Importance of auditing tech tool usage. 21:54 - Importance of tool adoption and training across generations. 24:20 - Evaluation process when choosing a unified software platform. 31:34 - Potential of diffusion models for AI in legal tech. 37:06 - AI's power is maximized within a platform. 38:11 - Legal tech should enhance predictability and efficiency. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Cain Elliott and Keegan Chapman https://www.filevine.com/ [email protected] [email protected]  

  35. 154

    Full Circle - The Benefits of Contract Lifecycle Management Software for Law Firms and Legal Departments with Kristin Riviello

    I spoke with an expert in the contract lifecycle management software space, about how the software helps lawyers.  Episode Highlights 02:52 - Problem of the Week: Missing Contract Deadlines 04:43 - Guest Introduction: Kristen Riviello 05:49 - Automating the Contract Process 07:54 - Definition: Contract Lifecycle Management 09:55 - Importance of Post-Contract Execution Management 11:34 - Benefits of Contract Management Software 16:00 - Integration with Other Tools 22:19 - Adoption of Automation in Law Firms 26:44 - Impact of Artificial Intelligence in Contract Management 33:40 - Developing AI Features for Contract Management 35:57 - Chatbots and AI: Enhancing Legal Processes Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Kristin Riviello https://www.cobblestonesoftware.com/ https://www.linkedin.com/in/kristin-riviello/  

  36. 153

    AI's Impact on Law Firms in 2025 with Franklyn Jones

    I talked with a legal marketer about the impacts of artificial intelligence on law practices in the coming year. Episode Highlights 05:50 - Coldest temperatures experienced 07:30 - Exploring the lawyer's brain 10:05 - Overcoming aversion to tech change 12:32 - Modular law practice management 15:20 - AI vs. traditional billing methods 17:25 - Younger lawyers lean alternative billing 20:47 - ROI calculator for AI efficiency 24:54 - AI as a client expectation 26:17 - Customizing client-lawyer communication with AI 30:15 - AI impacting talent recruitment at firms 34:40 - Developing training programs for AI 36:20 - Need for AI training in law schools 38:38 - Brain chemistry and learning from mistakes 44:20 - Hallucinations in AI: a caution 45:10 - How lawyers can mitigate AI risk 48:55 - Cultural shift towards AI in law firms 55:40 - AI transformation of document management Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Franklyn Jones [email protected] https://rizeware.com/leadership/  

  37. 152

    A TimeSolv Festivus - Airing of Grievances, Feats of Strength, the Festivus Pole, Festivus Miracles & Festivus Dinner with Joyce Brafford and Scott Clasen

    For the twelfth & final episode of our special series with ProfitSolv, we've got a Festivus extravaganza, with all the fixin's.  But, don't worry - we found a way to smuggle in some legaltech & law firm management talk!  So, get some hot chocolate & snuggle up to this very special podcast episode. Featuring guest host Joyce Brafford & guest Scott Clasen, both of ProfitSolv. [SPONSORED BY TIMESOLV] Episode Highlights 00:15 - Legal Tech Adoption Challenges 02:12 - ProfitSolv! Product Line Overview 04:47 - Festivus Origins and Seinfeld Reference 18:52 - Importance of Software Testing Before Deployment 20:10 - Challenges with Onboarding and Software Adoption 22:58 - Underutilized Tools: Workflow and Process Automation 24:15 - Effective Use of Legal Accounting Features 31:24 - Law Firm Collection Practices and Soft Collections 36:20 - Making Credit Card Acceptances Common in Firms 38:40 - Recommended TimeSolv Features: Project Management Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Joyce Brafford and Scott Clasen [email protected] [email protected] https://www.profitsolv.com/ https://www.timesolv.com/  

  38. 151

    Why Lawyers Should Read Fiction Books & Other Tales with Kim Velk

    I spoke with a bar association executive about reading works of fiction & how her state bar serves attorney members. Episode Highlights 03:38 - Kim Velk's role at Vermont Bar Association. 04:53 - Snowy Vermont weather experience. 06:08 - Transition from practicing lawyer to education role. 08:15 - Importance of reading for relaxation and communication. 11:12 - Discovering and enjoying Hilary Mantel's historical fiction. 12:44 - Discussing historical fiction and its appeal. 16:55 - Kim's favorite authors and books. 18:11 - Bookstore vs. online book buying. 21:07 - Discussing current projects at Vermont Bar Association. 24:48 - Technology and AI education at bar associations. 27:15 - Low volume in media on technology discussions lately. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia  https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Kim Velk [email protected] https://www.vtbar.org/  

  39. 150

    Building a 2025 Law Firm Marketing Plan with Gyi Tsakalakis

    I spoke with a law firm marketing expert about how to build a marketing program for the upcoming year. Episode Highlights 01:14 - Legal marketing rebuilding. 01:32 - Introducing Gyi Tsakalakis. 05:55 - Favorite Christmas gift memory. 07:00 - Importance of annual planning for law firms. 09:08 - Metrics and law firm identity. 10:32 - Affinity audiences explained. 11:30 - Google de-indexing explanation. 13:13 - AI impacting search results. 15:30 - Google's AI challenges. 16:50 - Strategy for AI content placement. 19:50 - Rise of AI search engines. 23:15 - Importance of brand vs. direct response. 26:10 - CRM's role in marketing. 28:05 - Owning your marketing data. 30:38 - Practicing gratitude daily. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Gyi Tsakalakis [email protected] https://www.attorneysync.com/ https://legaltalknetwork.com/podcasts/lunch-hour-legal-marketing/  

  40. 149

    Dashboard Confessional - How LegalTech Displays Data Now with Joyce Brafford and JD Robinson

    For the eleventh episode of our special series with ProfitSolv, we talk about the usefulness of dashboards in modern software - including how law firms can deploy them to effectively and regularly surface practice data, alongside ProfitSolv's Joyce Brafford & Cosmolex's JD Robinson. [SPONSORED BY COSMOLEX] Episode Highlights 44:41 - Importance of dashboard flexibility and customization. 49:00 - Financial metrics and productivity insights. 53:36 - Key challenges firms face in capturing data. 53:41 - Role of passive time tracking for time capture. 01:16:03 - Next-gen tools in ProfitSolv's lineup.   Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Joyce Brafford and JD Robinson [email protected] [email protected] https://www.cosmolex.com/ https://www.profitsolv.com/ 

  41. 148

    Growing a Law Practice with the Right Staff & Technology with Chris Strang

    I spoke with a construction lawyer, who built his niche practice, with shrewd moves around marketing, hiring & technology. Episode Highlights 04:25 - Chris Strang's origin as a New York Jets fan. 05:54 - Most traumatic Jets moment: Vinnie Testaverde injury. 06:25 - Best Jets moment: Beating the Patriots in 2011. 09:05 - Chris Strang: Mastering personal networking. 13:07 - Critical view on lawyer referral sites. 18:13 - Post-pandemic changes in commercial office space. 19:56 - Importance of proactive hiring strategies. 23:54 - Challenges with current legal technology. 27:02 - Chris' love for bourbon and recommendations.   Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Chris Strang [email protected] https://www.strangscott.com/  

  42. 147

    Starting a Law Firm with Alternative Tech with Faith Alvarez

    I talked to a lawyer who launched a law firm with lesser-known technology, and a unique practice mix. Episode Highlights 03:06 - Thanksgiving food dislikes. 05:13 - Faith Alvarez's legal career journey. 09:12 - Launching a business during a recession. 11:17 - Challenges as a state prosecutor. 12:49 - Transitioning to personal injury law. 16:01 - Wise business strategy advice. 21:28 - Hiring flexible, part-time staff. 25:01 - Using social media for firm marketing. 28:36 - Innovative use of CRM technology. 30:07 - Community engagement and outreach. 32:36 - The Lady Justice Foundation. 35:26 - Future growth plans for the firm.   Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Faith Alvarez [email protected] https://faithalvarez.com/ 

  43. 146

    Building a Successful Intellectual Property Law Firm with Scott Sisun

    I talked with an IP attorney about how he started & grew his law firm. Episode Highlights 01:01 - How to build a successful IP law firm. 02:17 - Favorite fall activity: apple picking. 05:50 - Journey into trademark law amidst economic downturns. 12:26 - The pivotal role of vision boards and focus. 15:20 - Leveraging technology like Alt Legal for firm management. 18:09 - Hiring talent globally with virtual structures. 24:26 - Exciting client roster with pop culture links. 27:01 - Marketing with pop culture references. 29:40 - Reflecting on childhood interests shaping career. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Scott Sisun [email protected] https://www.sisunlaw.com/ 

  44. 145

    Signs Your Firm Has Outgrown Its Current Tech Stack with Matt Orlinsky

    I talked with a legaltech expert about how law firms can outgrow their tech stacks & what to do about it. Episode Highlights 00:13 -  Simplifying legal tech access. 04:18 - Challenges in tech adoption for lawyers. 10:06 - Transition to cloud-based solutions. 15:49 - Bottlenecks: Identifying inefficiencies. 21:30 - Importance of client feedback. 24:09 - Streamlining software use in firms. 27:10 - Integration of software applications. 34:02 - Automation and workflows. 40:23 - Winding down practices with tech. 46:11 - Building firm value through tech.   Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Matt Orlinsky  [email protected] https://www.practicepanther.com/ https://www.linkedin.com/in/mattheworlinsky  

  45. 144

    Shake Your Money Maker - Law Firm Billing & Financial Management Strategies with Joyce Brafford and Brooke Lively

    For the tenth episode of our special series with ProfitSolv, we talk about forward-looking financial management strategies used by top law firms - including how AI and data are affecting law firm billing tactics, alongside ProfitSolv's Joyce Brafford & Cathedral Capital's Brooke Lively. [SPONSORED BY ROCKETMATTER] Episode Highlights 15:41 - Introducing the "Sticklefish" metaphor for work. 39:26 - Brooke's five essential AR puzzle pieces. 58:53 - Discussing individualized law firm metrics. 1:04:39 - Customizable dashboards for law firms.   Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Joyce Brafford and Brooke Lively [email protected] [email protected] https://cathcap.com/ https://www.profitsolv.com/ https://www.rocketmatter.com/  

  46. 143

    Revamping an Immigration Law Firm on the Fly with Ellen Sullivan

    I talked with an immigration attorney who executed a plan to grow her law firm from a solo practice. Episode Highlights 01:08 - Revamping an immigration law firm. 03:39 - Favorite cold-weather drinks. 06:06 - Transition from nonprofit to for-profit law. 07:52 - The influence of "the patriarchy" in career decisions. 10:33 - Challenges of constructing a work-life balance with a partner. 13:10 - The journey from solo practice to a larger firm. 14:59 - Importance of team and roles in firm expansion. 19:59 - Decision to rebrand and create a new website. 22:12 - Transitioning from lawyer to business owner. 25:41 - Selecting the right technology tools for law practice. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Ellen Sullivan [email protected] https://cambridgeimmigrationlaw.com/  

  47. 142

    Contract Lifecycle Management & the Impact of Artificial Intelligence with Kristin Riviello

    We explored the viability of contract lifecycle management software in the legal space, including AI features and integrations. Episode Highlights 18:00 - Expansion beyond legal teams. 24:00 - AI's role in contract management. 30:00 - Automatic redlining feature. 36:00 - Importance of integration. 49:00 - Generative AI's potential and limits. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Kristin Riviello http://cobblestonesoftware.com/ https://www.linkedin.com/in/kristin-riviello  

  48. 141

    Back to Law (Practice) School: Everything Law School Didn't Teach You with Joyce Brafford

    For the ninth episode of our special series with ProfitSolv, we talk about all the business management instruction you missed in law - including how to use software to run a better law firm, alongside ProfitSolv's Joyce Brafford. [SPONSORED BY TIMESOLV] Episode Highlights 10:41 - Challenges Lawyers Face with Money. 12:00 - Importance of Fee Schedules for Lawyers. 14:30 - Engagement Agreements as Client Relationships. 19:52 - Need for Passive Timekeeping. 27:40 - Technology Platforms for Law Firms. 31:43 - Effective Use of Software for Lawyers. 37:11 - Comprehensive Marketing Plans for Legal Practice. 40:36 - CRM's Role in Legal Marketing. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Joyce Brafford [email protected] https://www.profitsolv.com/ https://www.timesolv.com/ 

  49. 140

    Effectively Implementing Artificial Intelligence in Law Practice with Jennifer Poon

    I talked with an expert in the space about how to utilize and implement AI to use more effectively generate and manage law firm documents. Episode Highlights 10:55 - AI-related skills for lawyers. 13:30 - Importance of prompt building. 16:15 - Comparison to Lexis and Westlaw innovations. 19:45 - Necessity of AI usage policies in law firms. 24:05 - Security protocols for AI use in law firms. 28:00 - Client-driven demand for AI. 32:15 - AI's potential impact on legal professionals' workload and efficiency. 36:50 - Document management systems' role in AI integration. 38:00 - Benefits of a metadata-enriched environment. 43:20 - Workflow automation for repetitive tasks. 46:00 - Positive outcomes from AI adoption in legal fields. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Jennifer Poon https://www.netdocuments.com/ https://www.linkedin.com/in/jennifer-poon-4638392a/  

  50. 139

    Solos, Women-Owned Law Firms & AI - Oh, My! With Carolyn Elefant

    I spoke with legendary solo & small firm lawyer advocate Carolyn Elefant, about how solo practice has changed, how attorneys should be using AI & how ethics rules may be holding them back + the impact of women-owned law firms in the legal ecosystem. Episode Highlights 13:08 - Discussion on the complexities and training required for energy regulatory work. 14:11 - Evolution and challenges of running a solo practice in the energy sector. 19:32 - Reflection on how starting a firm provided control and flexibility, especially for women. 26:20 - Innovations brought by solo and small firm practices through technology. 28:10 - Elevated importance of entrepreneurial skills in legal practice. 30:45 - The impact of women-owned firms on the legal ecosystem and work culture. 35:00 - Advocacy for better models in law practice to support women in leadership roles. 39:46 - Legal tech revolution: Professionalization of solo and small firms through technology. 41:59 - Role of AI in enhancing legal work efficiency and managing tasks. 45:39 - Practical barriers preventing lawyers from adopting AI tools. 48:33 - Discussion on current bar rules around AI ethics and the limitations they impose. 53:10 - Future outlook: Increased handling of marginal cases and higher quality services through AI. Episode Resources Connect with Jared Correia [email protected] https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Carolyn Elefant https://lawofficesofcarolynelefant.com/ https://myshingle.com/ 

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ABOUT THIS SHOW

"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.

HOSTED BY

Jared Correia

Produced by Breaking Media

CATEGORIES

Frequently Asked Questions

How many episodes does Adventures In Legal Tech have?

Adventures In Legal Tech currently has 50 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Adventures In Legal Tech about?

"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.

How often does Adventures In Legal Tech release new episodes?

Adventures In Legal Tech has 50 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to Adventures In Legal Tech?

You can listen to Adventures In Legal Tech on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Adventures In Legal Tech?

Adventures In Legal Tech is created and hosted by Jared Correia.
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