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The Tech Savvy LawyerAuthor: 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! Language: en Genres: News, Tech News, Technology Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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🎙️ Ep. 139, From MyCase to Claude: Building a Secure, AI-Ready Tech Stack for Solo and Small Law Firms.
Episode 139
Tuesday, 23 June, 2026
My next guests are Gabriella "Gabby" Cabero, Senior Vice President of Product at 8am — the legal tech company behind MyCase, LawPay, CASEpeer, and DocketWise — and Majo Castro, founder and managing attorney at CastroMand Legal in Austin, Texas. 🌟 Gabby brings over 16 years of legal tech experience, including co-founding CASEpeer, and today leads product strategy for one of the most widely used law practice management ecosystems in the country. Majo is a Venezuelan-born cybersecurity and AI attorney whose firm helps growing companies navigate AI implementation, data management, and cybersecurity — and she's also the voice behind The Cyber Law Gal on Substack. 🔐 Together, they deliver a frank, peer-level conversation about building a tech stack that's both AI-ready and genuinely secure — without the hype and without the hand-holding. Join Gabriella Cabero, Majo Castro, and me as we discuss the following three questions and more! What are the top three integrations or workflows a solo, small, or midsize firm should expect from a modern cloud-based LPM platform like 8am — and what's missing that signals a real red flag around efficiency, cash flow, or security? As AI gets baked into cloud LPM tools like 8am, what are the top three day-to-day tasks that will change most for solo and small firm lawyers — and what basic security or ethical guardrails should they put in place to use those AI features without putting client data at risk? For solo and small firms without a CISO or CTO, what are the top three cybersecurity mistakes you see over and over again? In our conversation, we cover the following: [00:00:00] 🪝 Show Hook — Gabby's critical warning: if your firm hasn't "adopted" AI, your employees probably already have — on free consumer tools [00:00:00] Title read — Episode 139 [00:01:00] Host intro: why this conversation goes tactical on AI, security, and LPM workflows [00:02:00] Guest introductions — Gabriella Cabero (8am/MyCase) and Majo Castro (CastroMand Legal / The Cyber Law Gal) [00:03:00] Majo celebrates 1.5 years as a solo practitioner 🎉 [00:03:00] Ad: Five-star review request for The Tech-Savvy Lawyer.Page [00:03:30] Tech setups — Gabby's MacBook Air (M4 chip), iPhone Max, Slack, Zoom, Google Drive, Claude Enterprise [00:06:00] Gabby's portable USB-C external monitor for travel (Amazon, highest-rated) [00:09:00] Majo's MacBook Pro 14" M4 (16GB RAM), performance issues, upgrade path discussion [00:10:00] Michael recommends Onyx (free Mac maintenance utility); Michael's Mac Studio M3 Ultra with 256GB [00:11:00] Mac Mini and Mac Studio as desktop alternatives; MacRumors Buyer's Guide tip [00:13:00] Apple Business Account benefits — small discounts + white-glove service [00:15:00] Majo's full setup: iPhone 16 Pro Max, Google Workspace + Gemini (team account with DPA), DJI Osmo Pocket 3, Hollyland wireless mic [00:16:00] Q1: Top three LPM workflows — intake, secure client communication (client portal), and getting paid (trust accounting + automated invoicing) [00:19:00] Majo on switching from QuickBooks to MyCase after discovering QuickBooks mishandles trust accounting [00:20:00] 🎉 Gabby announces: AI case summary features are now LIVE in 8am/MyCase [00:21:00] Cloud vs. local access debate — SaaS uptime, SLAs, and asking vendors for proof [00:23:00] Michael's redundant backup strategy: Backblaze + Dropbox + local Mac Mini [00:25:00] Cautionary tale: ransomware attack converts a server-based firm to the cloud overnight [00:28:00] Majo's Google Drive third-party backup with 2-hour recovery window [00:29:00] Q2: How AI changes daily workflows — drafting, case summaries, surfacing critical info fast [00:30:00] Why reading vendor Terms of Service and activating Data Processing Agreements (DPAs) is non-negotiable [00:31:00] 8am's SOC 2 Type 2 compliance; updated AI terms and opt-in controls coming [00:32:00] SOC 2, HIPAA, end-to-end encryption as baseline vendor security requirements [00:34:00] AI as the great equalizer — leveling the playing field for solo firms vs. BigLaw [00:35:00] Majo's real data: ~12 hours saved last month across 27 consultations using Gemini for proposals [00:36:00] Plaud and Pocket AI recording devices — data retention, PII, and DPA concerns [00:37:00] Majo's stance on wearable AI recorders; Apple Watch comparison; one-party vs. two-party consent [00:39:00] Plaud's terms say no AI training — but it's not a DPA; terms can change without notice 🚨 [00:40:00] Google Workspace DPA must be manually activated — most users don't know; creating user friction around protection [00:41:00] Q3: Top cybersecurity mistakes — shadow AI, no MFA, undertrained employees [00:42:00] Majo's checklist: DPA + no model training on client data + enterprise/team-tier subscriptions + MFA [00:43:00] Gabby: employees are the #1 security risk; fractional IT and CISO options for small firms [00:44:00] AI-powered phishing attacks on law firms will only intensify [00:45:00] Majo's training method: positive AI policies + 45-second staff video explainers 🎬 [00:46:00] 🚨 Gabby's shadow AI reminder (Show Hook 🪝 callback): audit your tech stack — your team already has [00:47:00] Episode originally recorded at ABA Techshow; re-recorded after a technical snafu 😅 [00:47:00] Where to find Gabby: LinkedIn, X, 8am.com, Kaleidoscope conference (September — banner at 8am.com) [00:48:00] Where to find Majo: LinkedIn (Majo Castro), CastroMand Legal, Substack: The Cyber Law Gal [00:48:30] Outro — michaeldj@thetechsavvylawyer.page | next episode in ~two weeks Resources Connect with Gabriella "Gabby" Cabero LinkedIn: https://www.linkedin.com/in/gabriela-cubeiro/ Connect with Majo Castro CastroMand Legal (Austin, TX): https://www.castrolandlegal.com/ The Cyber Law Gal Substack: https://www.linkedin.com/in/majocastro/ LinkedIn: https://www.linkedin.com/in/majocastro/ Mentioned in the Episode ABA Techshow — https://www.techshow.com/ Apple Business Account — https://www.apple.com/business/ Apple Trade-In Program — https://www.apple.com/shop/trade-in Model Rules 1.1, Comment 8 — https://www.thetechsavvylawyer.page/search?q=comment%208 MacRumors Buyer's Guide — https://buyersguide.macrumors.com Hardware Mentioned 8am.com — https://www.8am.com Apple iPad — https://www.apple.com/ipad/ Apple iPhone 16 Pro Max — https://www.apple.com/iphone-16-pro/ Apple iPhone Max — https://www.apple.com/iphone/ Apple Mac Mini — https://www.apple.com/mac-mini/ Apple Mac Studio — https://www.apple.com/mac-studio/ Apple MacBook Air — https://www.apple.com/macbook-air/ Apple MacBook Pro 14 — https://www.apple.com/macbook-pro/ Apple Watch — https://www.apple.com/apple-watch/ Backblaze — https://www.backblaze.com CASEpeer — https://www.casepeer.com ChatGPT (OpenAI, Enterprise referenced) — https://chat.openai.com Claude (Anthropic, Enterprise) — https://www.anthropic.com/claude DJI Osmo Pocket 3 — https://www.dji.com/osmo-pocket-3 DocketWise — https://www.docketwise.com Dropbox — https://www.dropbox.com Google Drive — https://drive.google.com Google Workspace + Gemini — https://workspace.google.com Hollyland wireless mic — https://www.hollyland-tech.com LawPay — https://www.lawpay.com MyCase — https://www.mycase.com Onyx (free, Mac) — https://www.titanium-software.fr/en/onyx.html Plaud AI recorder — https://www.plaud.ai Pocket AI recorder — https://heypocket.com/pages/ QuickBooks (referenced as insufficient for trust accounting) — https://www.quickbooks.intuit.com Slack — https://www.slack.com Zoom — https://www.zoom.us
