The Geek In Review

Paula Reichenberg, a former M&A lawyer turned legal tech entrepreneur who built Hieronymus and now leads Neuron. She talks about legal translation’s shift under machine translation, how mediocre AI outputs shape markets, the move from service to data-driven ML products, and building tools that help experts find and fix AI mistakes faster.

This week, we sit down with two guests from Anthropic, Matt Samuels, Senior Product Counsel, and Den Delimarsky, a core maintainer of the Model Context Protocol, or MCP. Together, they unpack why MCP is drawing so much attention across the legal industry and why some are calling it the USB-C for AI. For law firms long burdened by disconnected systems, scattered data, and the infamous integration tax, MCP offers a shared framework for connecting models to the places where real work and real knowledge live, from iManage and Slack to email, data lakes, and internal tools.Den explains that the promise of MCP is not tied to one model or one vendor. Instead, it creates a standardized way for AI tools to securely interact with many different systems without forcing organizations to build one-off integrations every time they want to connect a new source. The conversation gets especially relevant for legal listeners when Greg and Marlene press on issues like permissions, ethical walls, least-privilege access, and auditability. The answer from Anthropic is reassuring. MCP is built to work with familiar enterprise security concepts such as OAuth and role-based access, meaning firms do not have to throw out their security model in order to explore new AI workflows.Matt brings the legal and operational lens, translating MCP into practical use cases for lawyers, legal ops teams, and security leaders. He describes how AI becomes far more useful once it has access to the systems lawyers already rely on every day, while still operating within carefully defined administrative controls. The discussion highlights a key shift in how firms should think about AI. This is no longer about asking a chatbot a clever question and getting a polished paragraph back. With MCP, firms are moving toward systems where AI can retrieve, correlate, summarize, draft, and support actions across multiple platforms, all while staying inside the guardrails set by the organization.The episode also explores how MCP fits into the rise of agentic workflows, apps, plugins, and skills. Rather than treating AI as a static assistant, Anthropic describes a future where these tools become active participants in legal work, pulling together information from multiple sources, helping assemble case timelines, drafting notes into a shared document, and supporting lawyers in a far more integrated workspace. The conversation around skills is especially useful for firms thinking about standard operating procedures, preferred drafting styles, escalation rules, and repeatable work product. Skills and MCP do different jobs, but together they start to look like the operating system for structured legal workflows.By the end of the conversation, one message comes through clearly. The legal profession is still early in this shift, but the pace is picking up fast. Both Matt and Den encourage listeners to stop treating these tools like abstract future concepts and start experimenting with them now. At the same time, they offer an important note of caution. As much as these systems promise speed and efficiency, lawyers still need to protect the craft of lawyering, their judgment, and the human choices that matter most. For firms trying to make sense of where AI is headed next, this episode offers a grounded and practical look at the infrastructure layer that could shape what comes next.Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.] ⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.comMusic: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

This week we welcome back Niki Black to unpack the findings from the newly released 2026 Legal Industry Report from 8am The conversation centers on a legal profession moving into a new phase of AI adoption, where individual lawyers are embracing general purpose AI tools at a striking pace, while many firms still lack even basic policies or training. Niki explains that this disconnect is especially visible among solo, small, and mid-sized firms, where limited resources often slow formal governance even as day-to-day use rises fast.A major theme of the discussion is the widening gap between personal experimentation and institutional readiness. Niki notes that lawyers are not waiting for permission, and many are already relying on AI to support research, drafting, and routine work. At the same time, firms are struggling to provide guidance, training, and guardrails. The episode highlights the growing risk of shadow AI in legal practice, especially when lawyers and staff turn to unsanctioned tools to keep pace with client demands. For smaller firms, the answer is not elaborate bureaucracy, but practical direction, clear expectations, and a recognition that even a modest policy is better than none.The conversation also turns to client expectations and the economic pressure AI is placing on the traditional law firm model. Greg and Marlene press Niki on whether firms are truly ready to move away from the billable hour as AI compresses the time needed to complete legal work. Niki argues that large firms face deep structural obstacles because compensation systems, staffing models, and internal economics remain tied to hourly billing. Still, she sees pressure building from in-house counsel, boutique competitors, and smaller firms that use technology to deliver comparable work at lower cost. The result is a market that may resist change, but not escape it.Another standout part of the episode explores how AI is reshaping access to justice. Niki points to the promise of generative AI as a force multiplier for legal aid lawyers and public defenders, especially when paired with trusted tools and better funding. She rejects the idea that technology alone will solve the justice gap, but makes a strong case that AI, combined with stronger institutional support, helps lawyers serve more people with better results. At the same time, the hosts and Niki acknowledge the risks of a two-tiered system, where wealthier clients benefit from high quality tools while vulnerable users face lower quality, error-prone outputs.By the end of the episode, the conversation expands from AI tools to a broader structural shift across firms, clients, and law schools. Niki sees the next three to five years as a period of deep change, where pricing, training, competition, and professional expectations all evolve at once. She also shares her own methods for keeping up, including RSS feeds, trusted blogs, and LinkedIn, with a few playful complaints about Substack making life more complicated. The episode leaves listeners with a clear message: the biggest issue is no longer whether AI will affect legal practice. It already is. The real question is whether the profession can adapt fast enough to manage the consequences wisely.Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.] ⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.comMusic: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠Transcript:

Anastasia Boyko joins us this week for a wide-angle conversation about AI adoption, leadership, and the uncomfortable truth behind “we are watching what peer firms do.” A Yale-trained tax lawyer with experience spanning Axiom, legal education, and innovation leadership, Boyko argues that precedent-driven instincts are turning into a liability when the underlying rules of the market are shifting in real time.The episode opens with lessons from the Women + AI 2.0 Summit at Vanderbilt and the “AI competence penalty” narrative. Boyko’s central principle for law firm leaders is simple, stop copying the competition and start operating with intention. Strategic planning matters more than tool shopping, especially when uncertainty makes leaders freeze, over-index on fear, or chase noise instead of outcomes.From there, the conversation sharpens into client reality. Boyko shares what she is hearing from in-house leaders, and it is not comforting for firms. Legal departments are working to reduce dependence on outside counsel, business partners inside companies often accept “good enough,” and the models keep improving. The risk is not losing to a peer firm; it is losing the client relationship because the work stops feeling necessary.A major theme is talent and the apprenticeship gap. Boyko argues firms underinvest in people, even as they spend aggressively on software stacks. AI can help junior lawyers with coaching and confidence, but it does not replace mentorship, judgment-building, or context. The skills that matter now include client advisory, operational thinking, critical judgment, and the ability to solve problems across a complex system, not only perform discrete tasks in a vacuum.The episode closes on legal education and the future value of the JD. Boyko urges students to be selfish about learning AI, especially when faculty guidance comes from avoidance or philosophy rather than experimentation. Looking ahead, she predicts the JD’s value shifts upward, away from rote production and toward proactive advisory work, relationships, anticipatory counsel, and wisdom-driven judgment. In other words, fewer fire drills, more looking around corners.PLI - How to Navigate Law School PodcastPower Paradox webinarListen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.comMusic: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

This week we go “talk show mode” for a special episode where Marlene recaps her trip to the Women + AI 2.0 Summit at Vanderbilt Law, hosted by Cat Moon, and shares why the event felt different from the standard conference grind, more energy, more structure, and yes, a DJ.The summit’s core focus sits right on a tension point in the wider AI conversation. There’s a persistent narrative that women use AI less than men. Cat Moon’s framing, if it’s true, it’s a problem, and if it’s false, it’s also a problem, sets the tone for a day built around participation and peer connection. The format uses “spark” cards, mini, midi, and maxi prompts, to push attendees into small conversations, deeper reflection, and a final takeaway.Marlene also highlights sobering research shared during the opening, including an “AI competence penalty” dynamic where identical work is judged differently depending on whether evaluators believe a man or a woman used AI. The discussion lands on why these biases matter inside legal workplaces, and what leaders and peers can do to reduce the social cost of being open about AI usage.Interspersed throughout are short interviews with attendees and speakers. Nicole Morris (Emory) captures the day’s purpose, expanding AI knowledge, talking risks, and connecting across roles. Sabra Tomb (University of Dayton School of Law) reframes AI as a leadership amplifier, moving from day-to-day management overload toward strategy and vision. Adele Shen (Vanderbilt) offers a funny but sharp taxonomy of AI “experts,” including “technocratic oracles,” “extinction alarmists,” and “touch grass humanists,” which sparks a candid side conversation about self-promotion, authority vibes, and who becomes “the story” in AI discourse.The episode closes with a look at how education and training can work better. Marlene and Greg lean into peer show-and-tell sessions, leadership modeling, and safe spaces, both governance-safe and learning-safe. A two-person segment from Suffolk Law (Chanal Neves McClain and Dyane O’Leary) adds a teaching twist, integrating AI tools into skills instruction without isolating “AI week” from real lawyering judgment. The final note comes from Stephanie Everett (Lawyerist) on the power of stories, and the reminder that people do not need to internalize the narrative someone else hands them.Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack [Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.comMusic: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

Stefan Ciesla, co-founder and CEO of Ayora, blends finance and decision science to build pricing and matter management tools. He discusses revenue leakage, the $36B value gap, how metadata and tooling replace partner moonlighting, and why AI is forcing a rethink of the billable hour and pricing workflows.

Otto von Zastrow, founder and CEO of MidPage AI, builds legal research data and integrations that put case law and citator tools into chat platforms. The conversation covers why structured legal data still matters. It explores systems of record versus new chat interfaces, how AI scales normalization and editorial work, and the integration bet of embedding legal research into Claude and ChatGPT.

Ray Brescia, Associate Dean and author of Lawyer 3.0, explores how technology and AI are reshaping legal practice. He maps historic shifts to a new Lawyer 3.0 era. He uses the milkshake metaphor to reframe client needs as jobs to be done. He discusses productized services, TurboTax-style legal tools, limited-scope programs, and practical AI guardrails for legal work.

Sateesh Nori joins us on The Geek in Review for an episode that flips the usual legal innovation conversation away from law firm efficiency and toward survival-grade help for people stuck in housing courts and legal aid queues. They open with news from Sateesh himself, he has started a new role with LawDroid, working with Tom Martin, and he frames the mission in plain terms. Legal tech should stop orbiting lawyers and start serving the person with the problem, especially the person who does not even know where to begin.Sateesh traces his path into law through debate, literature, politics, and a desire to push back on a family tradition of medicine. He describes his work as a long, continuous pursuit of fairness rather than a single turning point, and he admits the early myth that drew many into the profession, the dream of dramatic courtroom advocacy. The conversation quickly lands on the core tension, the legal system sells itself as rule of law and due process, yet ordinary people experience confusion, delay, and closed doors.From there, Sateesh offers his critique of the current AI gold rush in legal. Too many products promise “faster horses” for lawyers, while the access to justice gap remains untouched because the real bottleneck sits upstream. People need early guidance, clear pathways, and tools that reduce friction before problems metastasize into crises. He argues for technology as “life-preserving tools,” not lawyer toys, and pushes the industry to center tenants, families, and workers navigating high-stakes issues without counsel.The episode gets concrete with Depositron, a tool Sateesh helped bring to life with LawDroid to help renters recover security deposits through a simple, mobile-friendly workflow. He shares back-of-the-napkin math showing how large the problem is in New York, and why small, focused tools matter at scale. Greg ties the theme to earlier Geek in Review conversations about courts as a service, with the reminder that users experience the justice system like a bureaucracy, not a public utility built for them.Finally, Sateesh expands the lens to systemic redesign, triage and intake failures, burnout in legal aid, and the hard truth that the current one-on-one model leaves most people unserved. He explores funding ideas ranging from public investment to small-fee consumer tools that sustain themselves, and he sketches future-facing concepts like AI-assisted dispute resolution to provide faster closure. In the crystal ball segment, he predicts a reckoning for the legal market as AI reshapes client expectations, with major implications for law students, staffing models, and the profession’s sense of purpose.Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack [Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.comMusic: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠LawDroidLawAnswers AIDepositronRoxanne AI (Housing Court Answers)Housing Court AnswersJosef Sateesh Nori, The Augmented Lawyer (Substack)Transcript

Quinten Steenhuis brings a builder’s mindset to legal innovation, rooted in early Indymedia activism where scavenged hardware became community infrastructure. That scrappy origin story carries through a dozen years of eviction defense at Greater Boston Legal Services, with a steady focus on tools that help people solve problems without waiting for a savior in a suit. Along the way, Quinten also lived the unglamorous side of mission tech, keeping systems funded, supported, and usable when budgets get tight and priorities get loud.The conversation then jumps to Suffolk Law’s approach to generative AI education, including a required learning track for first-year students. Quinten frames the track as foundational training, then points to a deeper bench of follow-on courses and the LIT Lab clinic where students build with real tools, real partners, and real stakes. The throughline stays consistent, exposure alone solves nothing, so Suffolk puts reps, projects, and practice behind the syllabus.A standout segment tackles the “vaporware semester” problem, where student-built prototypes fade out once finals end. The LIT Lab fights that decay by narrowing tool choices, standardizing around DocAssemble, and supervising work with a clinic-style model, staff stay close, quality stays high, and maintenance stays owned. Projects ship through CourtFormsOnline, with ongoing updates, volunteer support, and a commitment to keep public-facing legal help online for the long haul.Then the episode turns toward agentic workflows, with examples from Quinten’s consulting work in Virginia and Oregon. One project uses voice-based intake to screen for eligibility, confirm location and income, gather the story in a person’s own words, and route matters into usable categories. Another project speeds bar referral by replacing slow human triage with faster classification and better user interaction patterns, fewer walls of typing, more guided choices, more yes-or-no steps, and fewer dead ends.In the closing stretch, Quinten shares the sources feeding his learning loop, LinkedIn, Legal Services Corporation’s Innovations conference, the LSNTAP mailing list, podcasts, and Bob Ambrogi’s LawSites, plus the occasional spicy Reddit detour. The crystal ball lands on a thorny challenge for both academia and practice, training lawyers for judgment and verification when AI outputs land near-correct most of the time, then fail in the exact moment nobody expects. Quinten’s bottom line feels blunt and optimistic at once, safe workflows matter, and the public already uses general chat tools for legal help, so the legal system needs harm-reducing alternatives that work.Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.] ⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.comMusic: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠Suffolk Lit LabLemma LegalPipe CatLinks (as shared by Quinten):Transcript