🎙️ Ep. 139, From MyCase to Claude: Building a Secure, AI-Ready Tech Stack for Solo and Small Law Firms.

My next guests are Gabriela "Gabby" Cubeiro, 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 Gabriela "Gabby" Cubeiro, 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 — Gabriela "Gabby" Cubeiro (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 Gabriela "Gabby" Cubeiro 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