
Adventures In Legal Tech
Think of this weekly podcast as the main-stage panel of our Adventures In Legal Tech podcast, focused on how technology can benefit your bottom line and geared for an audience of luddite-leaning lawyers. “Fun” may even ensue — within reason, of course.
Latest episodes

May 9, 2025 • 30min
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 jared@redcavelegal.com 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/

Apr 28, 2025 • 30min
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 jared@redcavelegal.com 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/ JCary@dwmlaw.com https://dwmlaw.com/profile/justin-b-cary/

Apr 21, 2025 • 30min
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 jared@redcavelegal.com 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/

Apr 14, 2025 • 29min
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 jared@redcavelegal.com https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Kim Bookout kbookout@opus2.com https://www.opus2.com/ https://www.linkedin.com/in/kim-bookout-496a8193/

Apr 7, 2025 • 37min
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 jared@redcavelegal.com 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/

Mar 28, 2025 • 35min
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 jared@redcavelegal.com https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Michael Pratt michael@execuservices.net https://getwaas.io/

Mar 14, 2025 • 47min
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 jared@redcavelegal.com 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 stephanie.corey@uplevelops.com shaun.sethna@lsuite.co https://uplevelops.com/ https://www.lsuite.co/ https://linkforlegal.com/

7 snips
Mar 7, 2025 • 42min
Match Point - Are Point Solutions All They're Cracked Up To Be? with Cain Elliott and Keegan Chapman
Cain Elliott, Chief Legal Futurist at Filevine, and Keegan Chapman, CMO at Filevine, dive into the complexities of legal tech. They discuss the overwhelming nature of multiple tech solutions and the critical need for unified platforms. Humorously comparing software decisions to leap year birthdays, they explore the pitfalls of using email for storage and the importance of auditing tech tools. The duo emphasizes proactive change management and the promising role of AI in creating more efficient legal practices, ultimately aiming for predictability and enhanced operations.

Feb 28, 2025 • 29min
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 jared@redcavelegal.com 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/

Jan 27, 2025 • 30min
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 jared@redcavelegal.com https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.linkedin.com/in/jaredcorreia/ Connect with Franklyn Jones franklyn@rizeware.com https://rizeware.com/leadership/
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