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...
Jun 25, 2025•35 min•Ep. 166
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 jared@redcavelegal.com https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/RedCaveLegal www.l...
Jun 13, 2025•33 min•Ep. 165
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 eff...
Jun 10, 2025•40 min•Ep. 164
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 - ...
Jun 03, 2025•39 min•Ep. 163
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 jared@redcavelegal.com https://redcavelegal.com/ ht...
May 14, 2025•29 min•Ep. 162
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 ...
May 09, 2025•30 min•Ep. 161
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://...
Apr 28, 2025•30 min•Ep. 160
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 m...
Apr 21, 2025•30 min•Ep. 159
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...
Apr 14, 2025•29 min•Ep. 158
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 wor...
Apr 07, 2025•37 min•Ep. 157
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 emphas...
Mar 28, 2025•35 min•Ep. 156
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 t...
Mar 14, 2025•47 min•Ep. 155
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 stor...
Mar 07, 2025•42 min•Ep. 154
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...
Feb 28, 2025•29 min•Ep. 153
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 commu...
Jan 27, 2025•30 min•Ep. 152
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...
Dec 27, 2024•39 min•Ep. 151
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 favo...
Dec 18, 2024•33 min•Ep. 150
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 con...
Dec 13, 2024•32 min•Ep. 149
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. ...
Dec 02, 2024•39 min•Ep. 148
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 p...
Nov 29, 2024•30 min•Ep. 147
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 te...
Nov 22, 2024•31 min•Ep. 146
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 wi...
Nov 15, 2024•26 min•Ep. 145
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 pract...
Nov 12, 2024•25 min•Ep. 144
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:...
Oct 30, 2024•45 min•Ep. 143
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....
Oct 25, 2024•26 min•Ep. 142
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 jared@redcavelegal.com https://redcavelegal.com/ https://www.linkedin.com/in/jaredcorreia https://twitter.com/...
Oct 11, 2024•24 min•Ep. 141
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 Firm...
Oct 05, 2024•44 min•Ep. 140
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 ef...
Oct 04, 2024•27 min•Ep. 139
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 c...
Sep 18, 2024•31 min•Ep. 138
For the eighth episode of our special series with ProfitSolv, we talk about how law firms can switch into new case management software, alongside ProfitSolv’s Joyce Brafford & Beyond Square One's Donna Brown. (It's not impossible!) [SPONSORED BY COSMOLEX] Episode Highlights 05:50 - Introducing cryptid corner: intriguing and fun. 07:45 - Donna’s pick: Oklahoma octopus legend. 13:10 - Jared’s clue for software trouble: frustration triggers. 13:52 - Reason for frustration: pricey, slow, ineffec...
Aug 23, 2024•49 min•Ep. 137
