Didn't We Almost Have It All - Law Firm IT Is All About Compromises
Release Date: 02/26/2026
Inside In-House: What It's Really Like to Be In-House Counsel for a Legal Tech Vendor
Adventures In Legal Tech
Executive Summary Jared sits down with Carly Savar, general counsel at Steno, to unpack what actually happens when a law firm signs up with an AI vendor. Carly explains why reading the fine print matters more than any feature list, and what separates a vendor you can trust from one that's just telling you what you want to hear. Key Takeaways Read the actual data processing agreement yourself. Don't assume a vendor's security is handled just because they signed a service level agreement. Push for a zero-day retention agreement, and ask about the LLMs your vendor is built on, not just the...
info_outline
Immaculate Vibes - Building an AI-Literate Organization
Adventures In Legal Tech
Executive Summary On this episode of Adventures in Legal Tech, Jared Correia talks with Phillip Greer, CEO of Best Lawyers, about how AI is rewriting the rules of legal search and firm operations. Greer breaks down the real differences between SEO, AEO, and GEO, then explains how he turned his own company into a shop full of vibe coders. It's a practical look at getting found online and getting comfortable with AI at the same time. Key Takeaways SEO isn't dead. It's the foundation that feeds AEO and GEO, the practices that get law firms found inside AI search tools and chatbots. Quality,...
info_outline
Mind Map - The Intersection of Artificial Intelligence & Knowledge Management
Adventures In Legal Tech
Summary Law firms are drowning in scattered knowledge, and AI can't fix disorganized data on its own. Rachel Shields Williams, Director of AI and Knowledge Management at Bass, Berry & Sims and President of the Legal Marketing Association, joins Jared Correia to explain why structured data has to come before any AI rollout, and how firms can build the human relationships that make AI adoption safe. Key Takeaways AI can't structure your data for you. A firm's data represents its relationships and intellectual property, and only humans understand that context well enough to organize it. ...
info_outline
Grand Central Station - The Value of Case Management Software in the Age of Artificial Intelligence
Adventures In Legal Tech
Summary “Attorney Matt Damon” needs to draft a demand letter, but the facts he needs are scattered across medical records, deposition transcripts, case notes, and email threads. Jared Correia brings in Claude Simpson, Vice President of Client Operations at Smart Advocate, to unpack why that scattered data problem is nearly universal in legal practice. Claude explains that documents, not buzzwords, still run the practice of law, and that AI only works well when it is pulling from a structured case management system. They cover client portals, the real costs of switching platforms, data...
info_outline
Skills Acquisition: How One Litigator Uses Claude to Build His Case Strategy
Adventures In Legal Tech
Summary Jared Correia sits down with Luis Vargas Rivera, head of litigation at Embedded Counsel, to unpack a problem most solo and small firm litigators never get to solve: a real moot before a hearing. Luis built a Claude skill called Adversarial Review that simulates a three-judge panel, each with a different mindset, to attack his motions before a judge ever does. From there, the conversation covers AI accountability and Rule 11, Luis's move from big law to a boutique firm, why marketing to referral sources beats paid ad spend, and how cross-practice litigation experience wins cases other...
info_outline
Voyage of Discovery: Why Managing ESI for Lawyers Is Easier Than Ever
Adventures In Legal Tech
Summary Law firms and legal departments sit on mountains of electronically stored information, and most have no real system for dealing with it. Warren Parrino, Regional Vice President of Solution Sales at TrustPoint.One, has a clear starting point: email threading, date filters, and search terms. From there, an early case assessment environment can cut review costs before a single document hits a reviewer's queue. Warren and Jared also cover modern attachments, audio and video redaction, and when AI actually earns its place in the workflow. The bottom line: AI only pays off after you...
info_outline
Search Engine: How to Create Content for the New Algorithm
Adventures In Legal Tech
Summary Alan Alda runs his own firm and figured AI tools would make content creation easy. He was half right. Jared Correia sits down with David Arato, founder of Lexicon Legal Content, to unpack why mass AI publishing is triggering Google penalties, what compliance risks law firms are ignoring in their marketing content, and how the rise of AI overviews is reshaping the entire game. David explains the EEAT framework, breaks down a three-level compliance review process for AI-generated content, and outlines what law firms should actually be doing to get cited in AI search results. The...
info_outline
Launch Protocol: How Law Firms Are Adopting AI in Real Time
Adventures In Legal Tech
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...
info_outline
The Ontological Argument: What's Real & Not in Artificial Intelligence in LegalTech
Adventures In Legal Tech
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...
info_outline
First Light: Structural Intelligence Must Come Before Artificial Intelligence
Adventures In Legal Tech
🧾 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...
info_outlineEPISODE 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
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