The Tech Savvy Lawyer

Michael D.J. Eisenberg

The Tech Savvy Lawyer interviews Judges, Lawyers, and other professionals discussing utilizing technology in the practice of law. It may springboard an idea and help you in your own pursuit of the business we call "practicing law". Please join us for interesting conversations enjoyable at any tech skill level!

  1. TSL Labs 🧪 Bonus: Deep Dive on our April 27, 2026, Editorial, MTC: Smart Recording, Client Secrets, and HeyPocket: What Every Lawyer Needs to Know in 2026 📱⚖️

    6D AGO

    TSL Labs 🧪 Bonus: Deep Dive on our April 27, 2026, Editorial, MTC: Smart Recording, Client Secrets, and HeyPocket: What Every Lawyer Needs to Know in 2026 📱⚖️

    📌 To Busy to Read This Week's Editorial? Join us for an AI-powered deep dive into the ethical challenges facing legal professionals in the age of generative AI. 🤖 In this episode, we unpack how AI note takers and "always-listening" devices can quietly route client secrets to third-party vendors, why that matters under the ABA Model Rules, and how a 2026 federal decision out of the Southern District of New York turned one defendant's AI chats into discoverable evidence. Whether you are a solo practitioner, in-house counsel, or a tech-curious professional in another field, this conversation will help you balance convenience with confidentiality and avoid turning your favorite AI assistant into your biggest evidentiary risk. 👉 Before your next client meeting, listen to this episode, check out our editorial, and run your current AI tools through the checklist we outline—then subscribe and share with a colleague who is still "just trusting the app." 🎧 In our conversation, we cover the following: 00:00 – The "ambient microphone" problem: phones, smart speakers, wearables, and connected cars as a continuous surveillance layer around client conversations. 01:00 – How technology competence has shifted from locking file cabinets to understanding data custody, cloud routing, and API-driven services. 02:30 – What makes AI note takers like HeyPocket different from passive telemetry and why capturing the spoken "payload" changes the threat model. 04:00 – The invisible "third party in the room": routing privileged audio through external AI models and the malpractice risk of default "Allow" clicks. 05:30 – Applying ABA Model Rules 1.1 and 1.6 to AI workflows: competence, confidentiality, and "reasonable efforts" in a world of automated transcription. 07:00 – Risk-based analysis from ABA Formal Opinions 477R and 498: weighing sensitivity, likelihood of disclosure, and available safeguards before using AI. 08:30 – Why secretly recording clients or opponents with AI tools can implicate Rule 8.4(c), even in one‑party consent jurisdictions. 10:00 – Inside United States v. Heppner (SDNY 2026): how public generative AI platforms destroyed privilege and work-product protections for a criminal defendant. 12:00 – How AI training and tokenization work, why "military‑grade encryption" does not save privilege if terms of service allow internal data use. 14:00 – Treating every AI note taker like an outsourced e‑discovery vendor: NDAs, retention policies, security audits, and data destruction timelines. 16:00 – Practical minimization strategies: defaulting to no recording, segmenting AI-generated content by matter, and restricting access via role‑based controls. 17:30 – Establishing bright-line "no‑AI" categories (criminal defense, internal investigations, sensitive family/immigration, high‑value trade secrets). 18:30 – Counseling clients not to "prep their case" with public chatbots after Heppner and why this is now part of competent representation. 19:30 – Building a simple vendor-vetting checklist for law firms and professional practices adopting AI note takers. 20:00 – Looking ahead: when failure to use secure, vetted AI may itself become a competence issue due to inefficiency and overbilling. 21:00 – Rethinking privilege in a world where an algorithmic "third party" is always in the room and devices are never truly off RESOURCES Mentioned in the episode ABA Formal Opinion 477R – "Securing Communication of Protected Client Information" – https://www.americanbar.org/products/ecd/chapter/348777154/ ABA Formal Opinion 498 – "Virtual Practice" – https://www.americanbar.org/content/dam/aba/administrative/professional_responsibility/ethics-opinions/aba-formal-opinion-498.pdf ABA Model Rules of Professional Conduct – https://www.americanbar.org/groups/professional_responsibility/publications/model_rules_of_professional_conduc Pocket / HeyPocket AI note-taking platform – https://heypocket.com/ United States v. Heppner, S.D.N.Y. 2026 – https://storage.courtlistener.com/recap/gov.uscourts.nysd.652138/gov.uscourts.nysd.652138.27.0.pdfHardware mentioned in the conversation

    23 min
  2. Bonus Episode: 📌 TSL Labs "Deep Dive" into our April 20, 2026, editorial - Dynamic Random-Access Memory (DRAM): Why It Matters for Law Firm Performance and Data Security ⚖️💻

    APR 24

    Bonus Episode: 📌 TSL Labs "Deep Dive" into our April 20, 2026, editorial - Dynamic Random-Access Memory (DRAM): Why It Matters for Law Firm Performance and Data Security ⚖️💻

    Join us for an AI-powered deep dive into the ethical challenges facing legal professionals in the age of generative AI. 🤖 In this episode, we break down our April 20, 2026, Tech‑Savvy Lawyer editorial on how a global DRAM shortage and AI data center demand are driving up PC prices, pushing many legal professionals toward Apple hardware, and redefining what technological competence really means. We explore how unified memory, on‑device AI, and long‑term support lifecycles are changing the Mac vs. Windows calculus, and why "cheap but weak" laptops may now create serious competence and confidentiality risks for your clients. In our conversation, we cover the following: 00:00 – Why upgrading your work laptop in 2026 feels like buying a luxury vehicle, not a routine office expense. 00:45 – Setting the stage: a "seismic shift" in hardware pricing hitting professional industries, with a focus on the legal field.01:30 – Introducing Michael D.J. Eisenberg's Tech‑Savvy Lawyer editorial and its core thesis about a tech hardware crisis. 02:15 – The global DRAM crunch: how AI data centers are buying up memory like airlines hoard jet fuel, and why PC OEMs are getting squeezed. 03:30 – Microsoft's April 2026 Surface price hikes and the end of the "Windows is cheaper" assumption for law firms. 05:15 – The "value inversion": when high‑end Windows laptops now cost more than roughly comparable MacBooks. 06:30 – Why this isn't a normal tech price cycle and how it breaks 20 years of corporate IT purchasing assumptions. 07:15 – Apple's structural advantage: vertical integration, unified memory, and shielding itself from spot‑market DRAM volatility. 08:30 – The M‑series (M5) advantage: performance per watt, thermal behavior, battery life, and running local AI plus heavy legal workloads. 09:45 – Yes, Apple prices are rising too—why the relative "security‑to‑cost" and performance story still favors Macs for many professionals. 10:45 – When "cheap but weak" hardware crosses the line: connecting underpowered laptops to ABA Model Rule 1.1 (competence) and Comment 8 on tech competence. 12:00 – From annoyance to ethical exposure: how sluggish systems cripple eDiscovery, AI‑driven research, and document automation. 13:00 – Why laptop purchasing is now core client‑service strategy, not just a back‑office procurement task. 13:45 – On‑device vs. cloud AI: where computation happens, why that matters, and how it ties into ABA Model Rule 1.6 (confidentiality). 14:30 – The role of Apple's Neural Engine and local processing in reducing reliance on external AI APIs and third‑party servers. 15:30 – Clarifying the security nuance: Windows is not inherently less secure, but comparable on‑device AI capability often costs more. 16:30 – Redefining security in 2026: it's not just antivirus and passwords; it's where the AI thinking physically happens. 17:15 – Building a documented purchase matrix: price, performance, storage, memory, security, lifecycle, and critical software compatibility. 18:15 – When you can't leave Windows: legacy legal software, state e‑filing systems, and the hidden costs of moving to macOS. 19:00 – Survival strategies for Windows‑locked practices: non‑Surface OEMs, staggered refresh cycles, and buying fewer but higher‑quality machines. 19:45 – Treating laptops as long‑term infrastructure instead of disposable commodities. 20:15 – Big‑picture recap: DRAM shortages, unified memory, ethical duties, and shifting hardware norms in law practice. 20:45 – The closing question: will AI‑driven hardware requirements quietly raise the price of access to justice? RESOURCES Mentioned in the episode ABA Model Rule 1.1 – Competence – https://www.americanbar.org/groups/professional_responsibility/publications/model_rules_of_professional_conduct/rule_1_1_competence/ ABA Model Rule 1.6 – Confidentiality of Information – https://www.americanbar.org/groups/professional_responsibility/publications/model_rules_of_professional_conduct/rule_1_6_confidentiality_of_information/ Hardware mentioned in the conversation Microsoft Surface Pro (2026 lineup) – https://www.microsoft.com/surface Microsoft Surface Laptop (2026 lineup) – https://www.microsoft.com/surface Apple MacBook Air (M‑series) – https://www.apple.com/macbook-air/ Apple MacBook Pro (M‑series) – https://www.apple.com/macbook-pro/ Apple "MacBook Neo" (M5‑class device referenced in editorial context) – https://www.apple.com/mac/ Software & Cloud Services mentioned in the conversation eDiscovery / AI‑driven review platforms (category reference) – https://www.logikcull.com / https://relativity.com (illustrative vendors) AI‑driven legal research tools (category reference) – https://casetext.com / https://www.lexisnexis.com / https://www.westlaw.com (illustrative vendors) Complex document automation (category reference) – https://www.lawyaw.com / https://www.smokeball.com (illustrative vendors) Parallels Desktop (virtualization for Windows on Mac) – https://www.parallels.com Remote desktop / virtual desktop infrastructure (VDI) tools (category reference) – https://www.teamviewer.com / https://azure.microsoft.com/en-us/products/virtual-desktop (illustrative) If you want your next laptop purchase to strengthen—not weaken—your ethical obligations, client security, and AI‑powered workflows, hit play now and learn how to build a smarter, future‑proof hardware strategy. 🎧💡

    24 min
  3. APR 14

    TSL.P Podcast, Special Ep. - Podcasting for Lawyers: The Truth Behind the Mic – ABA TECHSHOW 2026 (Special Audio‑Only Episode) 🎙️⚖️

    This special episode features the audio‑only release of an ABA TECHSHOW 2026 panel I was excited to be part of: "Podcasting for Lawyers: The Truth Behind the Mic," with moderator Ruby Powers and fellow panelists Gyi Tsakalakis and Stephanie Everett. 🎧 Instead of our usual one‑on‑one format, you will hear a live, conference‑style conversation about how lawyers can use podcasting, video, and modern legal technology to build authority, strengthen client and referral relationships, and stay aligned with legal‑ethics and professionalism rules. Join Ruby, Gyi, Stephanie, and me as we discuss the following three questions and more! How can lawyers design and sustain a podcast that supports their practice goals and speaks to a clearly defined audience? What practical tech stacks—microphones, recording platforms, hosting services, and workflow tools—are realistic for busy attorneys and legal professionals? How do podcasting, video, and short‑form content contribute to SEO, GEO, and long‑term business development for law firms? In our conversation, we cover the following 00:00 – Welcome to ABA TECHSHOW 2026 and introduction of the panel: Ruby Powers (moderator), Gyi Tsakalakis, Stephanie Everett, and Michael D.J. Eisenberg. 🎙️ 02:00 – Each panelist explains their podcast, ideal listener, and why they chose podcasting as a medium. 06:00 – Publishing cadence: weekly, bi‑weekly, and how consistency drives listener trust and download growth. 10:00 – Adding video and YouTube to audio‑only shows and how video clips improve discovery on social media. 14:00 – DIY production vs. using producers, internal teams, or podcast networks, including time and cost trade‑offs. 18:00 – Core tech stacks in practice: microphones, Zoom, Riverside, StreamYard, Descript, Libsyn, Calendly, Buffer, and other essentials. 💻 24:00 – Guest selection, outreach, and sound checks; when to decline an appearance or reschedule due to poor audio or bad fit. 30:00 – Using podcast hosting analytics and social‑platform insights to understand who is listening and what resonates. 35:00 – Podcasting as networking and "virtual coffee": building relationships with lawyers, experts, and vendors. ☕ 40:00 – SEO and GEO benefits: how episodes create long‑tail visibility in search, and why attribution still matters. 45:00 – Ethics and professionalism: confidentiality, bar‑advertising rules, disclaimers, and avoiding client‑identifying facts. ⚖️ 52:00 – Final advice for lawyers on the fence about starting a podcast and how to improve with each episode instead of waiting for perfection. RESOURCES Connect with the panel ABA TECHSHOW 2026 session: "Podcasting for Lawyers: The Truth Behind the Mic" – https://www.techshow.com/sessions/podcasting-for-lawyers-the-truth-behind-the-mic/ Gyi Tsakalakis – Lunch Hour Legal Marketing – https://lunchhourlegalmarketing.com Ruby Powers – Power Strategy Group – https://powersstrategygroup.com 😊 Stephanie Everett – Lawyerist / The Lawyerist Podcast – https://lawyerist.com Mentioned in the episode (non‑hardware / non‑software) ABA TECHSHOW – https://www.techshow.com Clio Cloud Conference – https://www.cliocloudconference.com The Lawyers' Guide to Podcasting by Michael D.J. Eisenberg – https://www.amazon.com/dp/B0GGX32DZH?ref=cm_sw_r_ffobk_cp_ud_dp_03CBA2XX7NC03AP4K2DK&ref_=cm_sw_r_ffobk_cp_ud_dp_03CBA2XX7NC03AP4K2DK&social_share=cm_sw_r_ffobk_cp_ud_dp_03CBA2XX7NC03AP4K2DK&bestFormat=true 📘 Podcast Movement - https://podcastmovement.com/ Podfest Expo - https://podfestexpo.com/ Power Up Your Practice by Ruby Powers – https://powerupyourpractice.com/ Prenups.com – https://www.prenups.com Hardware mentioned in the conversation PlexiCam camera mount – https://www.plexicam.com Shure MV7 microphone – https://www.shure.com/en-US/products/microphones/mv7 🎙️ Software & Cloud Services mentioned in the conversation Buffer – https://buffer.com Calendly – https://calendly.com Descript – https://www.descript.com Facebook – https://www.facebook.com GarageBand – https://www.apple.com/mac/garageband Libsyn (podcast hosting) – https://libsyn.com LinkedIn – https://www.linkedin.com Riverside – https://riverside.fm StreamYard – https://streamyard.com YouTube – https://www.youtube.com Zoom – https://zoom.us

    47 min
  4. 🎙️ Ep. #134 — AI-Powered Legal Writing: How BriefCatch Helps Lawyers Write Smarter, Not Harder with Ross Guberman.

    MAR 31

    🎙️ Ep. #134 — AI-Powered Legal Writing: How BriefCatch Helps Lawyers Write Smarter, Not Harder with Ross Guberman.

    My next guest is Ross Guberman — founder of BriefCatch, nationally recognized legal writing trainer, and author of several acclaimed books on persuasive legal writing. Ross has trained thousands of lawyers and judges across the country. After years of teaching the craft of legal writing, he channeled that expertise into building BriefCatch — a purpose-built AI writing tool that lives right inside Microsoft Word and Outlook, scanning your legal documents using roughly 17,000 rules to help you write cleaner, sharper, and more persuasive work product. Whether you're a solo practitioner or part of a large firm, Ross brings insights that are immediately practical — no matter your tech comfort level. 🚀 Join Ross Guberman and me as we discuss the following three questions and more! 🏆 From your vantage point — having trained thousands of lawyers and judges and now running BriefCatch — what are the top three ways lawyers can leverage AI-driven writing tools like BriefCatch inside Word and Outlook to measurably improve the quality and persuasiveness of their briefs without sacrificing their own voice or judgment? ⚖️ For a tech-curious but time-strapped practitioner, what are the top three everyday workflows beyond traditional brief writing where lawyers are leaving the most value on the table by not using tools like BriefCatch and other legal tech? 🔮 Looking ahead five years, what are the top three technology competencies every lawyer must develop — not just "nice to have" skills — to collaborate effectively with AI, stay ethically compliant, and turn technology into a genuine competitive advantage rather than a source of risk? In our conversation, we cover the following: [00:30] 💻 Ross's current tech setup — MacBook Pro M4 Max, macOS, and iPhone 16 [01:30] 🔄 Why keeping your OS updated matters — security and performance [03:00] 🖥️ External monitors, portable screens, and traveling with tech [07:00] 📱 Using your iPad as an external monitor via Apple Sidecar [08:30] 🎪 Bonus Question #1 - Ross's experience in the ABA TECHSHOW Startup Alley [11:00] ✍️ Question #1 — Top 3 ways to use AI writing tools to improve briefs without losing your voice [12:00] 🧑‍⚖️ Using AI to role-play as a skeptical judge or opposing counsel to pressure-test your brief [13:00] 📊 Transforming fact sections into timelines and case law into comparison charts [14:00] 📝 Using AI as a self-check for hyperbole, redundancy, and tone [15:30] 📲 How judges now read briefs on iPads — and what that means for your writing style [17:00] 📂 Using Text Expander to store and deploy your best prompts [18:30] 🎙️ Google Notebook LLM as a learning and podcast creation tool [20:00] 🧩 Bonus Question #2 — What is BriefCatch and why use purpose-built legal AI over general tools? [21:00] 🚀 The origin story of BriefCatch — from side hustle in 2018 to funded legal tech startup [22:30] ⚙️ Workflow, ethics rules, and attorney-specific conventions — why legal-specific AI wins [24:30] 📋 Question #2 — Top 3 underused everyday workflows for lawyers using AI [25:00] 📧 Using AI with your email to surface unanswered messages and unresolved threads [25:45] 📁 Mining your past work product for patterns, style, and reusable language [26:30] 📅 Having AI review your calendar and correspondence for efficiency insights [27:00] 🔒 Data privacy, security settings, and the risks of default AI configurations [28:30] 🏛️ New York State's data protection approach and what more states should do [29:30] 🤖 Question #3 — Top 3 technology competencies every lawyer must master in the next five years [30:00] 🧠 Understanding how LLMs actually "think" — reading the AI's reasoning chain [30:45] 🖊️ Making AI output sound like you — the human voice in an AI-generated world [31:30] 🔧 Integrating AI into your daily workflow while preserving human judgment [32:00] 👏 Closing thoughts and where to find Ross and BriefCatch Resources 🔗 Connect with Ross Guberman 📧 Email: ross@briefcatch.com 🌐 Website: https://www.briefcatch.com 💼 LinkedIn: Search "Ross Guberman" on LinkedIn at https://www.linkedin.com 📌 Mentioned in the Episode 🎤 ABA TECHSHOW — Annual legal technology conference hosted by the American Bar Association: https://www.techshow.com/ 🎤 ABA TECHSHOW Startup Alley — Competition for early-stage legal tech startups at ABA TECHSHOW: https://www.techshow.com/sessions/startup-alley/ ⚖️ Anthropic / Defense Department data privacy discussion — https://time.com/article/2026/03/16/your-data-pentagon-battle-with-anthropic/ 🗒️ Google Notebook LLM — AI-powered note-taking and audio podcast generation tool: https://notebooklm.google.com 📰 Legal Week New York — Premier legal industry conference: https://www.event.law.com/legalweek 🎙️ Mac Geek Gab Podcast (Dave Hamilton, Pilot Pete & Adam Christiansons): https://www.macgeekgab.com 🎙️ Mac Power Users Podcast (David Sparks): https://www.relay.fm/mpu 🌐 MacRumors.com Buyer's Guide — Track Apple product release cycles before you buy: https://buyersguide.macrumors.com 📝 Text Expander — Text snippet and macro expansion tool for power users: https://textexpander.com 🖥️ Hardware Mentioned in the Conversation 📟 Apple iPad — https://www.apple.com/ipad/ 📱 Apple iPhone 16 — https://www.apple.com/iphone-16/ 💻 Apple MacBook Pro 16" (2024, M4 Max chip) — https://www.apple.com/macbook-pro/ ⌚ Apple Watch — mentioned (Ross humorously declines to use one): https://www.apple.com/apple-watch/ ☁️ Software & Cloud Services Mentioned in the Conversation 🍎 Apple macOS Tahoe (latest OS at time of recording): https://www.apple.com/macos/ 🪟 Apple Sidecar — Built-in macOS feature for using iPad as external display: https://support.apple.com/en-us/HT210380 ✍️ BriefCatch — AI-powered legal writing tool for Word and Outlook: https://www.briefcatch.com 🤖 ChatGPT (OpenAI) — https://chat.openai.com 🤖 Claude (Anthropic) — https://claude.ai 🎧 Descript — Audio/Video editing tool used by the host for podcast production: https://www.descript.com 📧 Gmail — https://mail.google.com 📓 Google NotebookLM — https://notebooklm.google.com 🛠️ GitHub — Code repository mentioned as part of BriefCatch's tech stack: https://github.com 📨 Microsoft Outlook — https://www.microsoft.com/en-us/microsoft-365/outlook/email-and-calendar-software-microsoft-outlook 🪟 Microsoft Word — https://www.microsoft.com/en-us/microsoft-365/word 🐍 Python — Programming language referenced by Ross in context of BriefCatch's development — https://www.python.org/ 🗒️ Text Expander — https://textexpander.com

    34 min
  5. 🎙️ Ep. #133 | AI Search, GEO & Legal Marketing Tech: How Small Law Firms Win Cases — Not Just Clicks!

    MAR 17

    🎙️ Ep. #133 | AI Search, GEO & Legal Marketing Tech: How Small Law Firms Win Cases — Not Just Clicks!

    My next guest is Nick Cohen, Chief Operating Officer of Matador Solutions — a legal marketing think tank and agency — and a newly minted partner at Cohen Injury Law Group. Nick brings a rare dual perspective: he lives the daily grind of running a law firm AND helps over 170 firms across the country use technology and marketing strategy to grow their practice. With more than $1 billion in case value generated for clients, Nick knows what separates the law firms that thrive from the ones that spin their wheels. 🚀 Whether you are just hanging out your shingle or you have been practicing for years and feel overwhelmed by the alphabet soup of SEO, GEO, PPC, and AI, this episode breaks it all down in plain language. Nick shares actionable steps — some of which cost nothing — to help your firm show up where your next great client is already looking. ⚖️ Join Nick Cohen and me as we discuss the following three questions and more! 🤔 What are the top three ways a small or mid-size law firm can leverage AI-driven search — like Google AI Overviews and ChatGPT — to reliably generate better cases, not just more clicks? 💡 For firms that feel overwhelmed by SEO, paid search, and social media, what are the top three pieces of marketing technology or automations they should implement first to turn their website into a true new case acquisition system? 🏆 Looking across $1 billion+ in case value generated for over 170 law firms, what are the top three technology habits the most successful firms share — and what are their less successful peers simply not doing? In our conversation, we cover the following: [0:00] 🎤 Introduction & five-star review shoutout [0:45] 👨‍💼 Nick's background: Matador Solutions, Cohen Injury Law Group, and tech stack overview (Jira, Google Suite, Claude, ChatGPT, WordPress, Slack) [1:30] 💻 Hardware setup: MacBook Pro M4, desktop, HDMI monitor — what Nick runs on daily [3:00] 📱 iPhone, planned obsolescence, and the Apple ecosystem slowdown conversation [4:00] ❓ Question 1: Leveraging AI-driven search (Google AI Overviews, ChatGPT) to get better cases — not just traffic [5:00] 🔍 GEO vs. SEO explained — what is Generative Engine Optimization and why it matters for your law firm right now [6:30] 📖 The difference: SEO = Google ranking; GEO = getting cited by ChatGPT, Claude, Perplexity, and Grok [8:00] 🤖 Schema markup, robots.txt, and opening your website to LLM crawlers — practical steps any firm can take [9:00] 📋 Attorney directory listings (Avvo, Super Lawyers, FindLaw) — are they worth the money in 2026? [10:30] ✍️ Tip #2: High-quality thought leadership content as a GEO and SEO powerhouse [11:30] ⭐ Tip #3: Reviews, reviews, reviews — the single highest-ROI, zero-cost activity for any law firm [12:00] 📲 The "one-click review link" strategy: why text beats email every time [13:00] 😬 How to handle negative reviews — call first, respond professionally, and why a 4.9 rating beats a perfect 5.0 [15:00] ❓ Question 2: Top three marketing tech tools/automations for overwhelmed firms — CallRail, case management software, and understanding your channels [17:30] ❓ Question 3: The technology habits that separate high-growth firms from stagnant ones — intake systems, engagement, and growth mindset [19:30] 🗺️ How Matador Solutions walks a brand-new firm from zero to a steady stream of cases — step by step [22:00] 📬 Where to find Nick Cohen Resources 🔗 Connect with Nick Cohen 📧 Email: nick@matadorsolutions.net 💼 LinkedIn: https://www.linkedin.com/in/nickecohen/ 🌐 Website: matadorsolutions.net 📚 Mentioned in the Episode (Non-Hardware / Non-Software) 🎙️ Apple Podcasts — podcasts.apple.com ⚖️ Matador Solutions — Legal marketing agency — matadorsolutions.net 📋 Avvo — Attorney directory — avvo.com ⚖️ Cohen Injury Law Group — Nick's law firm — https://cohenandcohen.net/⭐ Facebook Reviews — facebook.com 📊 GEO (Generative Engine Optimization) — The emerging discipline of optimizing for AI-driven search engines ⭐ Google Reviews — google.com/business 📋 FindLaw — Attorney directory — findlaw.com 📋 Super Lawyers — Attorney directory — superlawyers.com ⭐ Yelp — yelp.com 💻 Hardware Mentioned in the Conversation 📱 Apple iPhone 15 — Nick's smartphone (approximate model) — apple.com/iphone 📱 Apple iPhone (latest, annual upgrade) — Michael's smartphone — apple.com/iphone 🖥️ Apple Mac Studio (M3 chip) — Michael's desktop — apple.com/mac 🖥️ Apple MacBook Pro (M4 chip) — Nick's primary laptop — apple.com/macbook-pro ☁️ Software & Cloud Services Mentioned in the Conversation 📞 CallRail — Call tracking & marketing ROI — callrail.com 🤖 ChatGPT (OpenAI) — AI assistant & AI search — chatgpt.com 🤖 Claude (Anthropic) — AI assistant — claude.ai 🤖 Google AI Overviews — AI-powered search summaries — google.com 📊 Google Business Profile — Local SEO & reviews — business.google.com 🔍 Google Workspace / Google Suite — Productivity & search — workspace.google.com 🤖 Grok (xAI) — AI assistant — x.ai/grok 📋 Jira — Project management — atlassian.com/software/jira 🎙️ Libsyn — Podcast hosting — libsyn.com 🤖 Perplexity — AI search engine — perplexity.ai 💬 Slack — Team communication — slack.com 🌐 WordPress — Website platform — wordpress.org 🎧 Enjoy the episode? Please leave us a ⭐⭐⭐⭐⭐ five-star review on Apple Podcasts or wherever you get your podcast feeds!

    24 min
  6. MAR 6

    TSL.P Labs 🧪 Initiative: Why 96% AI Accuracy Still Fails Lawyers: Ethics, Hallucinations, and the Future of the Billable Hour ⚖️🤖

    📌 To Busy to Read This Week's Editorial? Welcome to the TSL Lab's Initiative. 🤖 This weeks episode builds on my March 3rd, 2026, editorial "Even Though AI Hallucinations Are Down: Lawyers STILL MUST Verify AI, Guard PII, and Follow ABA Ethics Rules ⚖️🤖" is a misleading comfort blanket for lawyers, and how ABA Model Rules on confidentiality, competence, diligence, candor, supervision, and client communication must govern every AI prompt you run. Our Google LLM Notebook hosts translate the theory into practical workflows you can implement today—from document grounding and tokenization to vendor due diligence and line‑by‑line verification—so you can leverage AI confidently without sacrificing ethics, privilege, or your professional license. You will hear how document grounding changes what LLMs actually do, why uploading active case files to cloud AI tools can quietly trigger Rule 1.6 problems, and how cross‑border data flows, vendor training rights, and retention policies can erode privilege if you do not negotiate them carefully. 🔐 We also unpack practical safeguards like tokenization, internal sandbox testing, and bright‑line "danger zones" where AI must never operate unsupervised—especially on open‑ended research, choice of law, and any task that turns statistical text into real‑world legal risk. Finally, we confront the economic paradox: when AI can compress 100 hours of document review into seconds, but partners must still verify every line to protect their licenses, what exactly are clients paying for—and how does the billable hour survive? 💼 👉 Tune in now to learn how to stay tech‑forward without becoming the next ethics cautionary tale, and start designing AI policies that actually protect your clients, your firm, and your bar license. In our conversation, we cover the following 00:00 – Why "96% fewer hallucinations" is still not good enough in law ⚖️ 01:00 – How the remaining 4% error rate can trigger malpractice, sanctions, and ethics violations 02:00 – From IT issue to ethics issue: ABA Model Rules as the real constraint on AI adoption 03:00 – Document grounding 101: turning a free‑floating LLM into a reading‑comprehension engine 04:00 – The hidden danger of "just upload the file": how Rule 1.6 confidentiality is instantly implicated 05:00 – Cloud AI architecture, cross‑border data transfers, GDPR, and privilege risk 🌐 06:00 – Model training nightmares: when your client's trade secrets leak back out through someone else's prompt 07:00 – Negotiating no‑training clauses and ring‑fencing vendor data use (before you upload anything) 08:00 – Tokenization explained: turning John Doe into "Plaintiff 01" without losing legal meaning 🔐 09:00 – What AI does well today: grounded summarization, clause extraction, and playbook‑based redlines 10:00 – The "danger zone" of tasks: open‑ended research, choice of law, and abstract legal reasoning 11:00 – Phantom case law: how LLMs manufacture perfect‑looking but fake citations (and Rule 3.3 candor) 12:00 – Sandboxing AI tools internally and measuring real‑world failure rates against known outcomes 🧪 13:00 – Building bright‑line firm policies around forbidden AI use cases 14:00 – Verification as a workflow, not a suggestion: what Model Rules 5.1 and 5.3 demand from supervisors 15:00 – The efficiency paradox: when partner‑level verification erases associate‑level time savings ⏱️ 16:00 – Making AI verification as routine as a conflict check in your practice 17:00 – Falling hallucination rates, rising risk: why better AI can still make lawyers more vulnerable 18:00 – Client communication under Rule 1.4: when and why clients may be entitled to know you used AI 19:00 – "You can delegate the task, not the liability": Rule 1.2 and ultimate responsibility for AI‑assisted work 20:00 – Treating every AI prompt and ToS as a potential ethics document 📝21:00 – The existential question: if AI drafts in seconds, what exactly are clients paying lawyers for?

    24 min
  7. TSL.P EP# 132 (Special Episode): AI, Deepfakes, and Metadata: Guest-Hosting Capital University Law School's First Law Library Podcast Club with Professor Jennifer Wondracek 🎙️⚖️

    MAR 3

    TSL.P EP# 132 (Special Episode): AI, Deepfakes, and Metadata: Guest-Hosting Capital University Law School's First Law Library Podcast Club with Professor Jennifer Wondracek 🎙️⚖️

    In this special episode, I join Professor Wondracek virtually to guest-host Capital's very first Podcast Club session for a live conversation about AI, legal ethics, deepfakes, and metadata. We talk candidly with law students about how AI-generated evidence, consumer AI tools, and digital footprints are already impacting sanctions, privilege, and professional responsibility, then translate those issues into practical safeguards for everyday practice. Whether you are in law school, running a small firm, or managing litigation for a larger organization, this inaugural Podcast Club episode shows how to stay competent, secure, and credible when AI and technology are part of your case strategy. Questions section Join Professor Jennifer Wondracek and me as we discuss the following three questions and more! How do deepfakes and manipulated digital evidence challenge a lawyer's ethical duties under core rules on competence, candor to the tribunal, and honesty? What can we learn from recent cases involving deepfake videos, privilege risks in consumer AI tools, and sanctions for hallucinated citations when designing our own AI workflows? How can lawyers and law students build realistic, sustainable practices for reviewing metadata, using VPNs and secure Wi‑Fi, and choosing secure legal AI and eDiscovery tools? Timestamps In our conversation, we covered the following: 00:00 – Welcome to Capital University Law School's first Podcast Club: live recording and today's focus on AI and ethics 🎓 01:00 – Introducing Michael D.J. Eisenberg as guest host and his work with veterans, and The Tech-Savvy Lawyer.Page blog and podcasting 📚 02:30 – What is a deepfake, and how a staged "Bethesda incident" highlights the real-world risk of fake video evidence 🚨 04:00 – Applying competence rules to technology: why "I didn't know" is not a sustainable defense for lawyers 05:00 – Everyday tech risks: public Wi‑Fi, airports, coffee shops, and why lawyers must use VPNs when client information is involved 🌐 06:30 – Discussing NordVPN, ExpressVPN, and how unsecured sessions can compromise client portals, trust accounts, and email 🔐 07:30 – First steps in vetting digital evidence: what to look for in image files and when to call in a forensic expert 08:30 – Lessons from deepfake litigation and obviously altered video: shadows, color-in-black-and-white, and credibility with the court 🎥 10:00 – Candor to the tribunal and rules against dishonesty, fraud, and misrepresentation in the AI era 11:00 – Student question: can you rely on built-in operating system tools to review metadata, or do you need specialist software? 🖼️ 13:30 – Live demo: opening file properties, reading timestamps, device info, and geotags to validate or challenge evidence 16:00 – When scrubbed metadata makes sense, when it doesn't, and how to request original metadata in discovery 18:00 – Five practical safeguards for new and experienced lawyers: education, protocols, client transparency, updated letters, and constant monitoring of AI changes ✅ 20:00 – Why refusing to learn AI and tech is itself a risk to your bar license and your clients' interests 21:00 – Student Q&A: low-resource firms, large volumes of data, and using sampling plus AI to stretch limited budgets 22:30 – Using legal AI to surface anomalies in documents and metadata while still protecting privilege 23:00 – How consumer AI terms and conditions can put privilege and work product at risk, and what to look for in safer options ⚠️ 24:00 – Free vs paid AI accounts: retention, training, and why personally identifiable information doesn't belong in general chatbots 25:00 – Evaluating legal AI vendors: zero retention, encryption, prompt confidentiality, and subpoena requirements 26:00 – Using tightly controlled legal research platforms and "vault" environments to access models like GPT or Claude securely 🧠 27:00 – Documenting prompts and AI use so that, if questioned by a court or bar, you can show reasonable diligence 28:30 – Reasonable metadata review in practice: random sampling, documenting your process, and knowing when to bring in eDiscovery tools 30:00 – How modern eDiscovery platforms surface metadata and support deeper analysis at scale 📂 31:00 – Staying current on AI and tech: newsletters, bar alerts, court updates, and following The Tech-Savvy Lawyer 32:30 – AI hallucinated citations and sanctions: how one New York matter became a warning to the entire profession 💸 34:30 – Firm-wide consequences when AI misuse becomes a pattern: reputational damage, client impact, and even firm dissolution 36:00 – Owning mistakes, repairing trust with judges, and why transparency matters more than perfection 37:00 – Live giveaway of The Lawyer's Guide to Podcasting during the first Podcast Club session 🎲 38:00 – Inviting students to Capital's upcoming summit/bootcamp and to dinner at the Red Door Tavern, plus closing thoughts on the future of tech competence 🍽️ Resources Connect with Professor Jennifer Wondracek: LinkedIn: https://www.linkedin.com/in/jennifer-wondracek E-Mail: jwondracek@law.capital.edu Software & Services: NordVPN - https://nordvpn.com/ ExpressVPN - https://www.expressvpn.com/ Lexis - https://www.expressvpn.com/ Westlaw - https://legal.thomsonreuters.com/en/westlaw

    40 min
  8. TSL Labs 🧪 Initiative: Attorney-Client Privilege vs. Public AI: The Hoeppner Decision Lawyers Need to Understand in 2026 ⚖️🤖

    FEB 27

    TSL Labs 🧪 Initiative: Attorney-Client Privilege vs. Public AI: The Hoeppner Decision Lawyers Need to Understand in 2026 ⚖️🤖

    Join us for an AI-powered deep dive into the ethical challenges facing legal professionals in the age of generative AI. 🤖 We unpack the February 23, 2026, editorial AI may not be your co‑counsel—and a recent SDNY decision just made that painfully clear. ⚖️🤖.  Our Google Notebook LLM hostsbreaks down why a single click on a public AI tool's Terms of Use can trigger a privilege waiver, and what "tech competence" really means in 2026—especially after United States v. Hoeppner and Judge Jed Rakoff's wake-up-call analysis of confidentiality and third-party disclosure risk. 🔗 Read the full editorial on The Tech-Savvy Lawyer.Page and share this episode with a colleague who is experimenting with AI in client matters. In our conversation, we cover the following 00:00 — The "superhuman assistant" promise, and the procedural nightmare risk. 🧠⚖️ 00:01 — The core warning: AI use can "blow a hole" in privilege. 00:02 — Editorial overview: "The AI Privilege Trap" by Michael D.J. Eisenberg. 00:02 — The case: United States v. Hoeppner (SDNY) and why it matters. 00:03 — Why Judge Jed Rakoff's opinion gets attention (tech-literate, influential). 00:03 — The facts: defendant drafts with a public AI tool, then sends outputs to counsel. 00:04 — The court's conclusion: no attorney-client privilege, no work product protection. 00:05 — Privilege basics applied to AI: "confidential + lawyer" and why AI fails that test. 00:06 — The Terms-of-Use problem: inputs/outputs may be collected and shared. 🧾 00:07 — The "stranger on the street" analogy: you can't retroactively make it confidential. 00:08 — PII and client facts: why pasting sensitive data into public AI is high-risk. 00:08 — ABA Model Rule 1.1: competence includes understanding tech risks. 00:09 — ABA Model Rule 1.6: confidentiality and waiver risk with public AI. 00:10 — "Reasonable safeguards": read policies, adjust settings, and know training/logging. 00:11 — Public vs. enterprise AI: why contracts and "walled gardens" matter. 00:11 — Legal research AI examples discussed: Lexis/Westlaw-style AI offerings. 00:12 — ABA Model Rules 5.1 & 5.3: supervise AI like a nonlawyer assistant/vendor. 00:13 — Redefining "tech-savvy lawyer" in 2026: judgment and restraint. 🧭 00:14 — The "straight-face test": could you defend confidentiality after a judge reads the policy? 00:15 — Client-side risk: clients can sabotage privilege before contacting counsel. 00:16 — Practical takeaway: check settings, read the fine print, keep true secrets offline (for now). 🔒 RESOURCES Mentioned in the episode ABA Model Rules of Professional Conduct (Rules 1.1, 1.4, 1.6, 5.1, 5.3) Software & Cloud Services mentioned in the conversation Lexis (Lexis+ AI category mentioned) — https://www.lexisnexis.com/ Microsoft Word — https://www.microsoft.com/microsoft-365/word Public generative AI "chatbot" tools (general category) — https://en.wikipedia.org/wiki/Chatbot Westlaw (Westlaw AI category mentioned) — https://legal.thomsonreuters.com/en/products/westlaw

    19 min
5
out of 5
15 Ratings

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The Tech Savvy Lawyer interviews Judges, Lawyers, and other professionals discussing utilizing technology in the practice of law. It may springboard an idea and help you in your own pursuit of the business we call "practicing law". Please join us for interesting conversations enjoyable at any tech skill level!

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