The Tech Savvy Lawyer

My next guest is Alan Klevan, a veteran personal injury lawyer and Chair of the ABA Law Practice Division's Legal Technology Resource Center (LTRC), known for running one of the first paperless practices in New England and for his clear-eyed approach to AI in law. In this live episode recorded at the ABA Spring Conference in San Diego, Alan and I dig into how solos and small firms can use AI, case management platforms, hardware, and workflows to practice more efficiently while honoring their ethical duties and protecting client confidentiality.

Join Alan Klevan and me as we discuss the following three questions and more!

• What are the top three ways Alan uses AI and other tech tools to control discovery and document management at scale, protect client confidentiality, and communicate complex case progress to clients who only care that it is accurate and on time?
• As Chair of the ABA Law Practice Division's Legal Technology Resource Center, what top three technology practices does Alan wish every small or solo lawyer would adopt in the next 12 months?
• What were the three most important technology decisions Alan made early in his career around paperless workflows, practice management, automation, and AI‑powered research—and how can today's practitioners follow that lead?

In our conversation, we covered the following

• [00:00:00] Live from the ABA Spring Conference in San Diego, introducing Alan Klevan and the setting of the conversation 🌴
• [00:00:30] Alan's mirrored bi‑state setup: two Lenovo i7 laptops in Massachusetts and Florida, dual 24" HP HD monitors, two ScanSnap iX1600 scanners, laser printers, and Microsoft OneDrive syncing between offices 💻📠
• [00:01:10] Traveling with a third "road warrior" Lenovo laptop, iPhone as primary smart device, and using the reMarkable 2 tablet for handwritten notes that sync into client and ABA files ✍️
• [00:01:45] Early impressions of the Plaud (AI wearable) device, background-noise muting, and why Alan limits it to non‑critical meetings due to privilege concerns 🎧
• [00:02:20] Judicial skepticism about AI recording tools in court; motion practice, privilege issues, and a New York judge flatly banning AI recorders in the courtroom 🚫
• [00:03:10] AI hallucinations in legal practice, roughly 1,300 known hallucination incidents, and why the real problem is lawyers not checking citations—highlighted by a recent Oregon sanctions case 💸
• [00:04:00] The Oregon lawyer who tried to "fix" hallucinated citations with a motion to refile instead of candor to the court and opposing counsel, and how that became a fraud‑on‑the‑court issue under the Oregon Rules of Professional Responsibility
• [00:04:45] Using Google Scholar as an AI‑prompting "hack" to verify every citation and case suggested by AI tools 🔍
• [00:05:20] Question 1 restated: top three ways Alan uses AI and tech to (1) control discovery, (2) protect confidentiality and ethical duties, and (3) communicate complex case progress to clients
• [00:05:45] Drafting AI and social media policies directly into contingency‑fee agreements so clients do not post about their case or use open‑source AI on case‑related issues 📜
• [00:06:30] Hepner and Warner: open‑source vs enterprise AI, attorney–client privilege, work product concerns, and emerging discoverability questions for public‑facing AI platforms
• [00:07:20] Trap for the unwary: why Alan insists clients notify him before using AI on their case and why he prefers enterprise versions of AI for better protection and governance 🧠
• [00:08:10] The Nippon life Insurance case: client uploads attorney communications into ChatGPT, asks if her lawyer is gaslighting her, then files 44 AI‑drafted motions—raising product liability and disclaimer questions for AI vendors 🏛️
• [00:09:30] Court pushback on AI disclaimer language, defective product theories, and the infancy of AI‑related legal liability
• [00:10:10] Alan's big personal‑injury "Aaron Brockovich‑type" case with a deep‑pocket defendant and using AI to level the playing field on litigation management and motion practice ⚖️
• [00:11:00] Feeding facts, parties, defense counsel names, and pleadings into a case management system with a built‑in, highly accurate legal AI component (VL) and generating 50‑state case research for negligent infliction of emotional distress claims 📂
• [00:12:00] Running the same matter through two AI platforms (case management AI and Claude) to compare outputs, reduce hallucination risk, and mold responses to Alan's writing style and Massachusetts practice
• [00:13:00] Using Claude (enterprise tier) to draft an opposition to a motion to dismiss seven emotional‑distress claims, followed by manual review and cross‑checking in the case management AI—leading to the defendant's motion being denied ✅
• [00:14:15] Alan's process for verifying AI outputs: second set of "AI eyes," Google Scholar citation checks, and lawyer‑level review of every filing
• [00:15:00] Advice for new attorneys: try AI platforms before buying, choose a tool that fits your workflow, avoid shiny‑object syndrome, and do not over‑commit to annual plans while the market is moving fast 🧩
• [00:16:00] Michael's caution about yearly plans, vendor lock‑in, and ensuring your data is nimble enough to move between AI platforms without costly migrations
• [00:16:45] Alan's rule: do not chase every AI; become a master of one platform, learn it deeply, and resist the temptation to constantly switch 🧠
• [00:17:10] Both hosts stress "review, review, review"—AI as a law librarian or 3L intern, not as your practicing lawyer, and the concept that AI does not have a JD 🎓
• [00:18:00] Anecdote from 1990: Alan is sent to court unprepared, gets sent out of the courtroom to learn his file, and how that story frames his modern view of AI oversight and responsibility
• [00:19:10] Question 2: as LTRC Chair, Alan's top three technology practices every small or solo lawyer should adopt in the next 12 months
• [00:19:30] Tech Practice #1: invest in a fast machine (Windows or Mac) with as much RAM and storage as you can reasonably afford, and strip the "crapware" off box‑store Windows machines 🖥️
• [00:20:10] Discussion of Apple vs Windows pricing, the need for more than 16 GB of RAM, multi‑core processors, and why Alan buys Lenovo laptops with 32 GB RAM and expects 3–4 year laptop lifespans 💾
• [00:21:30] Backups and storage: redundant cloud backups, redundant hard drives, using external 5 TB drives from Staples, and keeping active machines "clean" for better AI performance
• [00:22:30] Tech Practice #2: immerse yourself in what is happening with AI and law practice, become a master of one AI platform, and continuously read ethics and disciplinary decisions about AI use 📚
• [00:23:15] Tech Practice #3: your head is your most important piece of technology—using judgment, stepping back to assess risks, and making sure anything submitted to court or client is accurate
• [00:24:00] Economic access, hardware costs, and why Alan still believes lower‑resource attorneys can get workable hardware by being strategic about purchases, specs, and lifecycles
• [00:25:10] Michael's storage philosophy: lots of local SSD, multiple backups, and revisiting older briefs and arguments (e.g., mailbox‑rule analysis) to build new work more efficiently
• [00:26:10] Disk space versus backup strategy, internal vs external drives, cloud vs local files, and disaster recovery considerations
• [00:27:20] Question 3: top three early technology decisions Alan made around paperless practice, automation, and AI‑powered research
• [00:27:40] Answer #1: going fully paperless in 2005—the first paperless practice in New England—and eliminating almost all postage costs by sending encrypted electronic communications and demand packages ✉️
• [00:28:15] Answer #2: becoming a power‑user of Adobe Acrobat and PDF workflows so he can respond to massive production requests (e.g., 10,000 pages) in seconds instead of hours 📑
• [00:29:00] Answer #3: adopting case management platforms with AI‑driven workflows that automatically assemble record requests, HIPAA authorizations, and certifications for medical providers
• [00:29:45] Dusty hardware: why Alan's printer and ScanSnap are seeing less use, yet scanners remain necessary for partners who still prefer paper and non‑electronic delivery 🖨️
• [00:30:20] Michael's own shrinking paper consumption, stamps.com, and transitioning to PDF‑based workflows with secure electronic delivery
• [00:31:00] Adobe Acrobat as "gold standard" for lawyers, why every attorney must understand PDFs deeply, and Alan's "learn it, love it, live it" mantra 📄
• [00:31:40] Bonus segment: what the ABA Legal Technology Resource Center (LTRC) is, its role as a "delivery board," and how it serves both the Law Practice Division and the broader ABA membership 🏛️
• [00:32:20] LTRC's four pillars of law practice management—marketing, technology, practice, and finance—and how it delivers content via Law Technology Today, webinars, podcasts, and roundtables
• [00:33:10] 2024–25 LTRC theme: AI‑centric content from intake through trial, and why Alan believes LTRC may become the ABA's most important board for practitioners navigating AI
• [00:34:00] Using AI for law‑firm marketing, content creation, case‑law recaps, and SEO—along with warnings about legal advice, PII, and AI‑generated "SEO articles" that sound inauthentic
• [00:35:00] Call to action: join the ABA Law Practice Division and LTRC, become one of roughly 30 tech‑focused thought leaders, and help shape AI guidance for the profession 🙌
• [00:36:00] Where to find Alan: why he is minimizing social presence during a major move and high‑stakes case, and the best way to reach him on LinkedIn

Hardware mentioned in the conversation

• Fujitsu ScanSnap iX1600 scanners – https://www.pfu-us.ricoh.com/scanners/scansnap/ix1600
• HP HD monitors – https://www.hp.com/us-en/shop/slp/hp-monitors/hp-series-3-pro?jumpid=ma_accy_button_na_2_260304
• HP LaserJet printers – https://www.hp.com/us-en/shop/vwa/printers/prnttyp=Laser?jumpid=ma_pr_featured_na_1_250511
• iPhone – https://www.apple.com/iphone
• Lenovo laptops – https://www.lenovo.com/us/en/laptops/
• Mac mini – https://www.apple.com/mac-mini
• reMarkable 2 tablet – https://remarkable.com/store/remarkable-2

Software & cloud services mentioned

• Adobe Acrobat – https://www.adobe.com/acrobat
• ChatGPT – OpenAI ChatGPT – https://chatgpt.com
• Claude – Anthropic Claude – https://www.anthropic.com/claude
• Dropbox – https://www.dropbox.com
• Microsoft OneDrive – https://www.microsoft.com/en-us/microsoft-365/onedrive/online-cloud-storage
• Stamps.com – https://www.stamps.com
• Zoom – https://zoom.us

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. 🎧💡

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!

1. How can lawyers design and sustain a podcast that supports their practice goals and speaks to a clearly defined audience?
2. What practical tech stacks—microphones, recording platforms, hosting services, and workflow tools—are realistic for busy attorneys and legal professionals?
3. 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

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!

1. 🏆 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?
2. ⚖️ 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?
3. 🔮 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: [email protected]
• 🌐 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

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!

1. 🤔 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?
2. 💡 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?
3. 🏆 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: [email protected]
• 💼 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!

Join us for an AI‑powered deep dive into the ethical challenges facing legal professionals in the age of generative AI. 🤖 We stress‑test the dream of a wallet‑free future against the hard realities of courthouse security, fragile connectivity, and ABA ethics rules.

In this episode, we unpack how digital wallets, mobile IDs, and peer‑to‑peer payment apps interact with Model Rules 1.1, 1.3, 1.6, 1.15, and 5.3—and why "biometric fortress" security is not enough if a deputy at the metal detector still wants to see plastic. ⚠️

You'll learn:

• Why cash and a physical bar card can still save your hearing date 🏛️
• How Venmo‑style metadata can silently broadcast your litigation strategy 🕵️
• What every firm should know about BYOD and mobile device management 🔐
• A practical hybrid model that combines ultra‑slim physical wallets with thoughtfully configured digital wallets 🪂

👉 Call‑to‑action: Listen now, then audit your payment‑app privacy settings and wallet setup, and forward this episode to one colleague who thinks they can safely go "all‑digital" today. 🎧📤

📌 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?

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: [email protected]

Software & Services:

• NordVPN - https://nordvpn.com/
• ExpressVPN - https://www.expressvpn.com/
• Lexis - https://www.expressvpn.com/
• Westlaw - https://legal.thomsonreuters.com/en/westlaw

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

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 discuss our February 16, 2026, editorial, "Lawyers and AI Oversight: What the VA's Patient Safety Warning Teaches About Ethical Law Firm Technology Use! ⚖️🤖" and explore why treating AI-generated drafts as hypotheses—not answers—is quickly becoming a survival skill for law firms of every size. We connect a real-world AI failure risk at the Department of Veterans Affairs to the everyday ways lawyers are using tools like chatbots, and we translate ABA Model Rules into practical oversight steps any practitioner can implement without becoming a programmer.

In our conversation, we cover the following:

• 00:00:00 – Why conversations about the future of law default to Silicon Valley, and why that's a problem ⚖️

• 00:01:00 – How a crisis at the U.S. Department of Veterans Affairs became a "mirror" for the legal profession 🩺➡️⚖️

• 00:03:00 – "Speed without governance": what the VA Inspector General actually warned about, and why it matters to your practice

• 00:04:00 – From patient safety risk to client safety and justice risk: the shared AI failure pattern in healthcare and law

• 00:06:00 – Shadow AI in law firms: staff "just trying out" public chatbots on live matters and the unseen risk this creates

• 00:07:00 – Why not tracking hallucinations, data leakage, or bias turns risk management into wishful thinking

• 00:08:00 – Applying existing ABA Model Rules (1.1, 1.6, 5.1, 5.2, and 5.3) directly to AI use in legal practice

• 00:09:00 – Competence in the age of AI: why "I'm not a tech person" is no longer a safe answer 🧠

• 00:09:30 – Confidentiality and public chatbots: how you can silently lose privilege by pasting client data into a text box

• 00:10:30 – Supervision duties: why partners cannot safely claim ignorance of how their teams use AI

• 00:11:00 – Candor to tribunals: the real ethics problem behind AI-generated fake cases and citations

• 00:12:00 – From slogan to system: why "meaningful human engagement" must be operationalized, not just admired

• 00:12:30 – The key mindset shift: treating AI-assisted drafts as hypotheses, not answers 🧪

• 00:13:00 – What reasonable human oversight looks like in practice: citations, quotes, and legal conclusions under stress test

• 00:14:00 – You don't need to be a computer scientist: the essential due diligence questions every lawyer can ask about AI

• 00:15:00 – Risk mapping: distinguishing administrative AI use from "safety-critical" lawyering tasks

• 00:16:00 – High-stakes matters (freedom, immigration, finances, benefits, licenses) and heightened AI safeguards

• 00:16:45 – Practical guardrails: access controls, narrow scoping, and periodic quality audits for AI use

• 00:17:00 – Why governance is not "just for BigLaw" and how solos can implement checklists and simple documentation 📋

• 00:17:45 – Updating engagement letters and talking to clients about AI use in their matters

• 00:18:00 – Redefining the "human touch" as the safety mechanism that makes AI ethically usable at all 🤝

• 00:19:00 – AI as power tool: why lawyers must remain the "captain of the ship" even when AI drafts at lightning speed 🚢

• 00:20:00 – Rethinking value: if AI creates the first draft, what exactly are clients paying lawyers for?

• 00:20:30 – Are we ready to bill for judgment, oversight, and safety instead of pure production time?

• 00:21:00 – Final takeaways: building a practice where human judgment still has the final word over AI

RESOURCES

Mentioned in the episode

• American Bar Association Model Rules of Professional Conduct

• Interview by Terry Gerton of the Federal News Network of Charyl Mason, Inspector General of the Department of Veterans Affairs, "VA rolled out new AI tools quickly, but without a system to catch mistakes, patient safety is on the line".

Software & Cloud Services mentioned in the conversation

• ChatGPT — https://chat.openai.com/

• Lexis - https://www.lexisnexis.com

• Westlaw - https://legal.thomsonreuters.com