🎙️ 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!

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: 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 

🎙️🎁 TSL Labs Bonus: The Ultimate 2025 Tech Gift Guide for Attorneys — Expert-Curated Gadgets, AI Tools, and Must-Have Devices Every Lawyer Needs!

🎯 In this TSL Labs Bonus episode, we are experimenting with Google’s Notebook LLM to do a “Deep Dive” on our November 24th editorial on the ultimate 2025 tech gift guide for attorneys. We use this AI-powered conversation to unpack the key themes, ethical challenges, and actionable recommendations. Whether you're a solo practitioner, big law associate, or tech-curious partner, this episode delivers expert-curated insights on gadgets, AI tools, and must-have devices that support technological competence as a professional obligation.

If you're a busy legal professional seeking practical tech recommendations that enhance daily practice rather than collect digital dust, join us for this insightful conversation that explores how the right technology investments can improve your practice, safeguard your clients, and help prevent unnecessary bar complaints.

🤔 Join Google AI Deep Dive as they discuss the following three questions and more!

1. What are the essential low-cost tech gifts under $25 that can make an immediate impact on an attorney's practice, and why do items like cables and tracking devices matter for professional competence?

2. Which professional-grade tools under $100 deliver the best value for attorneys seeking to fulfill their ethical duty to work smarter and faster through AI integration and productivity enhancements?

3. Why should premium technology investments over $100—including physical infrastructure like ergonomic chairs—be considered essential to an attorney's professional obligation to their clients?

In our conversation, we cover the following:

[00:00:00] — Episode introduction and TSL Labs Bonus overview

[00:01:00] — Navigating the perfect tech gift for attorneys: unique needs like security, portability, focus, and raw power

[00:02:00] — The three seismic forces driving tech choices: AI integration, cloud-based practice management, and heightened ethical duties

[00:03:00] — Target audience: solo practitioners, big law associates, and tech-curious partners who need technology that lasts

[00:04:00] — Essential low-cost gifts under $25: OWC Thunderbolt 4 USB-C cable and Apple AirTag for security and reliability

[00:05:00] — Productivity essentials: Logitech Pebble M350 silent mouse and Anker 7-in-1 USB-C Hub for presentations

[00:06:00] — AI tools for "forced competence": ChatGPT Plus one-month subscription as a low-risk nudge toward AI exploration

[00:07:00] — Professional grade tools under $100: Apple Pencil (1st Gen) for document annotation and Logitech MX Keys Mini keyboard

[00:08:00] — Focus and noise cancellation: Soundcore Space One headphones with 40+ hours battery life

[00:09:00] — Precision document navigation: Logitech MX Master 3S mouse with horizontal scrolling for wide documents

[00:10:00] — Premium mobile computing sweet spots: iPad Air with M3 chip ($599) and MacBook Air M4 ($999)

[00:11:00] — Physical infrastructure as health technology: Herman Miller Aeron chair ($1,351) for sustained high-quality work

[00:12:00] — Ultra-wide monitor benefits: LG 34" 5K 2K ($315) for seamless document comparison and reduced cognitive strain

[00:13:00] — Virtual practice essentials: Logitech Brio 4K webcam ($160) and Samsung T7 SSD ($109) for secure data management

[00:14:00] — The ultimate organizational hub: CalDigit TS3 Plus dock ($280) with 15 ports for cable clutter elimination

[00:15:00] — Strategic gift-giving advice: Understanding ecosystem (Apple, Windows, Android) and workflow considerations

📚 Resources

🖥️ Hardware Mentioned in the Conversation

Under $25:

• OWC Thunderbolt 4 USB-C Cable (~$19.99) — Universal cable supporting 40Gb/s data, 100W power delivery, up to 8K video —(https://www.owc.com)

• Apple AirTag (Single Pack) ($24) — Bluetooth tracking device using Find My network —(https://www.apple.com/airtag)

• Logitech Pebble M350 Wireless Mouse (~$19.99) — Silent click, 90% noise reduction, 18-month battery — (https://www.logitech.com)

• Anker 341 USB-C Hub (7-in-1) (~$19.99) — HDMI 4K@30Hz, USB ports, SD card slots — https://www.anker.com)

• ORICLE 65W USB Travel Power Strip — Flat plug, 4-foot cord, 7-in-1 hub for travel —(https://oricotechs.com)

Under $100:

• Apple Pencil (1st Generation) ($99) — Pressure and tilt sensitive stylus for iPad annotation —(https://www.apple.com/shop/product/myqw3am/a/apple-pencil-1st-generation)

• Logitech MX Keys Mini Keyboard (~$99.99) — Compact wireless keyboard, connects to 3 devices simultaneously — (https://www.logitech.com)

• Soundcore Space One Noise-Canceling Headphones ($69.99) — Adaptive ANC reducing up to 98% noise, 40+ hours battery — [soundcore.com](https://www.soundcore.com)

• Logitech MX Master 3S Mouse (~$99) — Silent clicks, horizontal scroll wheel, 8000 DPI sensor —(https://www.logitech.com)

• Apple AirTag (4-Pack) (~$64-99 during sales from resellers) — Bulk tracking solution for multiple devices/bags — https://www.apple.com/airtag/?afid=p240%7Cgo~cmp-21634151991~adg-175030672529~ad-739792099355_kwd-1231853153907~dev-c~ext-~prd-~mca-~nt-search&cid=aos-us-kwgo-btb-airtag-account-launch-

Premium Over $100:

• iPad Air with M3 Chip (Starting at $599) — 8-core CPU, 9-core GPU, ideal balance of power and portability — (https://www.apple.com/ipad-air)

• MacBook Air M4 (Starting at $999) — 10-core CPU, 10-core GPU, up to 18 hours battery life —(https://www.apple.com/macbook-air)

• Herman Miller Aeron Chair (~$1,351) — Ergonomic office chair with PostureFit SL, three sizes for 1st-99th percentile —(https://www.hermanmiller.com)

• LG 34" Ultrawide 5K 2K Monitor (~$315) — 3440x1440 resolution, curved display for seamless multitasking — (https://www.lg.com/us/monitors)

• Logitech Brio 4K Ultra HD Webcam (~$160) — 4K@30fps, RightLight 3 HDR, adjustable 65°/78°/90° FOV — (https://www.logitech.com)

• Samsung T7 Portable SSD (1TB) (~$109.99) — 1,050MB/s read speed, AES 256-bit encryption, 2m drop resistant — (https://www.samsung.com)

• CalDigit TS3 Plus Thunderbolt 3 Dock (~$280) — 15 ports, 87W laptop charging, dual 4K display support — (https://www.caldigit.com)

💻 Software & Cloud Services Mentioned in the Conversation

• ChatGPT Plus ($20/month) — OpenAI's premium AI assistant with GPT-4 access for research and drafting — (https://chat.openai.com)

• Grammarly Premium (~$96/year on sale; $144/year regular) — AI-powered writing assistant with plagiarism detection —(https://www.grammarly.com)

• Apple Find My — Location tracking app for AirTags and Apple devices — https://www.icloud.com/find

📌 Disclaimer: Prices mentioned throughout this episode and show notes are approximate and based on manufacturer suggested retail prices around the time of the publication date; actual pricing may vary depending on manufacturer availability, retailer promotions, seasonal sales, and geographic location, and we recommend verifying current pricing before making any purchase decisions.