Legal Late Night

For this special episode, Jared Correia is on location at Smokeball's inaugural US user conference, Spark 2026, at the historic Chicago Athletic Association. In the monologue, Jared shares the 19th-century contract law origins behind Smokeball's name, airs a grievance about hotels replacing irons with steamers, and breaks down Smokeball's major product announcements including its context-aware AI assistant Archie, new Archie Apps for bank statement analysis and family law chronologies, Westlaw integration with Thomson Reuters, and the PI Pro suite featuring YoCierge and Supio.   In a two-part interview, Jared first sits down with Smokeball COO Jane Oxley to discuss scaling Spark from Australia to Chicago, why Smokeball integrates with frontier AI models like Anthropic's Claude rather than competing against them, and how internal AI governance committees prevent "shadow AI" risks. Next, Smokeball CEO Hunter Steele joins Jared to talk about staying product-led as a 380-person company, "vibe coding" internal tools, why naming their AI Archie helps attorneys adopt it, the debate over Claude MCP connectors versus built-in legal workflows, and Smokeball's scrappy early days at ABA Techshow.   The episode wraps up in the Counter Program with Smokeball team members Rio Laine and Laurence Colletti going head-to-head in "The Internet Pricing Cavalcade of Fun and Danger."For more about Smokeball, check them out here.And listen to this episode's special Spotify playlist.We're grateful to be supported by Attorney at Work Today, and Lawyer 2 Lawyer.Subscribe to Attorney at Work Today.Subscribe to Lawyer 2 Lawyer.(00:00) - Monologue: Smokeball Spark US 2026 Recap & Carbolic Smoke Ball Lore (03:47) - Archie AI, Archie Apps, Westlaw Integration, & PI Pro Updates (07:19) - Interview Part 1: Jane Oxley, COO of Smokeball (10:43) - Partnering with Frontier AI Models & ISO-Certified Security (14:35) - Australian vs. US Halloween & Preventing "Shadow AI" in Law Firms (19:43) - Interview Part 2: Hunter Steele, CEO of Smokeball (21:39) - Staying Product-Led, "Vibe Coding," & Being a "Chill" CEO (26:55) - Continuous AI Releases, Naming Archie, & The Claude MCP Debate (32:04) - Smokeball's Origin Story: From Small-Firm War Stories to ABA Techshow (35:10) - Counter Program: Rio Laine & Laurence Colletti Join the Show (37:30) - The Internet Pricing Cavalcade of Fun and Danger (Head-to-Head) (52:10) - Outro & The "Smoke and Ball" Spotify Playlist Click here to view the episode transcript.

Jared Correia opens the show by breaking down why every law practice needs an artificial intelligence usage policy—even if the firm doesn't intentionally use AI. Without clear rules, staff inevitably turn to free, ungoverned AI tools that train on sensitive client data. Jared details the five essential pillars of a bulletproof law firm AI policy: educational preambles, designated policy managers and training schedules, whitelists of firm-approved tools and accounts, clear mechanisms for vetting new tools, and human gatekeeping protocols to catch hallucinations and remediate data breaches.   In the interview, Suresh Khanna, the new CEO of Smith.ai, joins Jared to diagnose the widespread failures in law firm marketing funnels and intake systems. Drawing on his background leading SMB teams at Google and scaling tech ventures, Suresh explains why law firms are losing revenue by ignoring the 25–40% of calls that occur after hours and failing to close the loop—revealing that only 40% of firms instruct receptionists to book appointments immediately on qualified calls rather than transferring leads to empty voicemails. He also explores the balance between human empathy and AI automation across different practice areas, his journey opening the acclaimed San Francisco restaurant Casa, and how he uses personal AI agents to streamline everyday workflows.   The episode wraps up in the Counter Program with the return of "The Wheel of Justice," where Jared and Suresh spin for impromptu topics ranging from corporate AI governance confessions and childhood Jose Canseco posters to raising prices to maximize profitability, AGI sentience timelines, and authentic home-cooked Indian cuisine.Learn more about Smith.ai.Check out this week's Spotify playlist!We're grateful to be supported by Attorney at Work Today, and Lawyer 2 Lawyer.Subscribe to Attorney at Work Today.Subscribe to Lawyer 2 Lawyer.(00:00) - Monologue: Why Every Law Firm Needs an AI Usage Policy (02:44) - The 5 Pillars of a Firm AI Policy: Education, Managers, & Approved Tools (05:39) - Human Gatekeeping, Remediation, & Stopping AI Hallucinations (08:34) - Interview: Meet Suresh Khanna, New CEO of Smith.ai (11:53) - The Origins of Smith.ai & The Evolution of Voice AI (13:27) - Modern Intake: Combining Human Empathy with AI Automation (18:23) - The Broken Legal Funnel: 24/7 Answering & The 40% Booking Problem (22:58) - Suresh's Background: Digitizing Small Businesses at Google & Founding Casa (26:30) - Cannabis Tech at Treez & Daily AI Workflows with Instinct (38:12) - Building an AI-Forward Culture & Claude Code (40:46) - Counter Program: "The Wheel of Justice" with Suresh Khanna (42:21) - AI Governance Realities & The #1 Intake Rule (46:27) - Streaming TV, The Bash Brothers, & Raising Prices to Maximize Profits (52:11) - Is AI Sentient? & Authentic Indian Cuisine (55:01) - Outro & The Thanksgiving Spotify Playlist Click here to view the episode transcript.

Jared Correia kicks off the episode with an in-depth dissection of the Dexter television universe—tracing the series from its peak Season 4 showdown with the Trinity Killer and the infamous lumberjack finale, to its revitalized modern renaissance across Dexter: New Blood, Dexter: Original Sin, and Dexter: Resurrection.   In the interview, Jeremy Poock, founder and principal of Senior Attorney Match, breaks down the rapidly shifting market for law firm mergers and acquisitions. Jeremy explains the critical differences between "Law Firm Sales 1.0" (relying strictly on a book of business, earnouts, and personal trust transfer) and "Law Firm Sales 2.0" (building real enterprise value through brand equity, trade names, multichannel digital marketing, and repeatable client acquisition). He cautions firm owners against the "Random Tuesday" risk when relying on associates for succession, unpacks how Management Services Organizations (MSOs) allow private equity to invest in law practices while navigating ethics rules, and explains why attorneys must understand corporate finance metrics like EBITDA, Quality of Earnings, and CAC.   We wrap it up with "Unlikely Pookies with Jeremy Poock," testing Jeremy on famous history and pop-culture friendships—from Doc Brown and Marty McFly to Salvador Dalí and Alice Cooper, and Bobby Fischer and Boris Spassky.Click here for more about Jeremy Poock and Senior Attorney Match.Listen to our latest Spotify playlist.We're grateful to be supported by Attorney at Work Today, and Lawyer 2 Lawyer.Subscribe to Attorney at Work Today.Subscribe to Lawyer 2 Lawyer.(00:00) - Monologue: The Evolution of Dexter (From Miami to NYC) (03:47) - Season 4 Peaking, The Lumberjack Finale, & The Franchise Renaissance (06:40) - Dexter: New Blood, Original Sin, & Dexter: Resurrection (12:38) - Interview: Meet Jeremy Poock, Founder of Senior Attorney Match (14:35) - Brokering Law Firm Sales for Baby Boomer Attorneys (19:35) - Law Firm Sales 1.0: Books of Business, Earnouts, & "Trust Transfer" (23:48) - The "Random Tuesday" Risk: Why Associates Don't Buy Law Firms (25:47) - Law Firm Sales 2.0: Brand Equity, Digital Rainmakers, & Trade Names (34:37) - Private Equity & MSOs (Management Services Organizations) in Law (40:30) - Platforms, Roll-Ups, EBITDA, & Quality of Earnings for Firms (44:03) - MSO Deal Structures: Upfront Cash, Earnouts, & The Second Bite of the Apple (48:16) - Counter Program: "Unlikely Pookies" Trivia with Jeremy Poock (01:02:00) - Outro & "The Pookies Playlist" (Best Duets) Click here to view the episode transcript.

Jared Correia kicks off the episode by breaking down why solo and small law firms hold a massive competitive advantage when recruiting associates away from BigLaw. He details the three core pitches small firm owners can leverage: superior lifestyle autonomy, hands-on substantive work style with direct client contact, and achievable, quarterly incentive structures.   In the interview, Kelley Brubaker, CPA and owner of Profit, Scale, Thrive, joins Jared to dive into law firm financial management. Kelley recounts her journey from the grind of Big Four accounting and bank executive roles to running a specialized financial consultancy for law firms. She explains why obsessing over top-line revenue is a dangerous trap, outlines the "Rule of Thirds" for firm spending, and introduces the concept of "Cash Lockup" (unbilled WIP plus uncollected A/R). Kelley also tackles law firm fraud and embezzlement, sharing wild stories from the audit trenches—including an $86,000 Amazon credit card scam by an executive assistant—and explains why managing partners must practice "trust but verify".   The episode wraps up in the Counter Program with "The Internet Pricing Cavalcade of Fun and Danger," where Kelley guesses prices on bizarre web oddities, including the Stranger Things Creel house, a Freddy Krueger fire pit, and disposable emergency toilet ponchos.Learn more about Kelley Brubaker.Check out this week's Spotify playlist.We're grateful to be supported by Attorney at Work Today, and Lawyer 2 Lawyer.Subscribe to Attorney at Work Today.Subscribe to Lawyer 2 Lawyer.Click here to view the episode transcript.

Jared Correia takes over both sides of the mic in a self-described "identity crisis" episode of Legal Late Night. In the monologue, Jared digs into artificial intelligence in the arts, dissecting an AI-generated Beatles cover of Oasis's "Don't Look Back in Anger," contrasting corporate AI efficiency with genuine human creativity, and explaining why machine learning struggles to recreate artistic "happy accidents" like the alarm clock on A Day in the Life.   For the interview, Jared dons a faux mustache to interview himself, costume changes and everything, as the founder and CEO of Red Cave Law Firm Consulting. He walks through his origin story from college debate and state legal assistance to founding Red Cave in 2016, discusses launching the new redcavelegal.com website, and shares practical business advice on prioritizing firm goals, solving legal talent acquisition/retention issues, and tackling AI governance protocols.   The show wraps up in the Counter Program with a brand-new segment, "Number Five Is Live," where Jared challenges Google Gemini to generate a live, rapid-fire trivia quiz spanning astrophysics, thermodynamics, art history, and British monarchs.Check out this episode's Spotify playlist.We're grateful to be supported by Attorney at Work Today, and Lawyer 2 Lawyer.Subscribe to Attorney at Work Today.Subscribe to Lawyer 2 Lawyer.(00:00) - Monologue: AI in the Arts & The AI Beatles Covering Oasis (03:50) - Can AI Replicate True Human Creativity & "Happy Accidents"? (07:13) - Interview: Jared Correia Interviews... Jared Correia (08:43) - From College Debate to Launching Red Cave Law Firm Consulting (10:51) - Launching the New Red Cave Website & Designing an AI Logo (12:19) - The Vision for the Legal Broadcasting Company (13:38) - The First Steps in Law Firm Business Consulting & Managing Growth (14:25) - Law Firm Talent Acquisition, Retention, & Childhood Fears (16:45) - AI Governance Protocols: The Biggest Hurdle for Law Practices (18:27) - Counter Program: "Number Five Is Live" — Quizzing Live with Google Gemini (24:25) - Outro & "The Identity Crisis Playlist" Click here to view the episode transcript.

Jared Correia kicks off the episode exploring the collision between frontier AI vendors (Anthropic's Claude legal connectors, OpenAI's Astra4Legal) and traditional legal tech case management systems. Jared breaks down the existential crisis facing legal software vendors—whether to gatekeep their ecosystems or let the "Trojan horse" in.In the interview, Thomas Kranz, Director of Sales at ProfitSolv, shares his journey from SDR to sales director. Thomas outlines how ProfitSolv and CosmoLex approach AI security with SOC 2 compliance, highlights new embedded features like AI intake and document summarization, and details ProfitSolv's 12-product "a la carte" legal tech suite. He also offers actionable advice for law firm growth, including immediate lead response strategies, why lawyers must track non-billable time even on flat-fee cases, and why generic tools like QuickBooks struggle with IOLTA trust accounting.We lose out with a brand-new trivia game, "Thomas's Time Loops," testing Thomas on time-travel escape scenarios in iconic movies like Back to the Future Part III, Groundhog Day, and Avengers: Endgame.Learn more about ProfitSolv.Take a listen to our latest Spotify playlist.We're grateful to be supported by Attorney at Work Today, and Lawyer 2 Lawyer.Subscribe to Attorney at Work Today.Subscribe to Lawyer 2 Lawyer.Click here to view the episode transcript.

Jared Correia opens with three broad, practical AI use cases for attorneys who aren't sure where to start: data collation, interactive/iterative search, and creative brainstorming.In the interview, NetDocuments Director of Product Management Nate Ruiz shares his journey from self-teaching web development to building an AI startup acquired by NetDocuments. Nate breaks down NetDocuments' "Next Gen Experience," detailing their new UX/UI architecture, automated "Doc Intelligence," and the "Legal Context Graph". He also explains the concept of "ambient AI"—AI that works passively in the background without needing prompts—and demystifies Model Context Protocol (MCP) and developer vibe-coding with Claude.The episode concludes in the Counter Program with the return of "Holidays on Holiday," where Nate tests his historical knowledge against Jared on defunct ancient and medieval holidays.Learn more about Nate Ruiz and NetDocuments.Check out this week's Spotify playlist.We're grateful to be supported by Attorney at Work Today, and Lawyer 2 Lawyer.Subscribe to Attorney at Work Today.Subscribe to Lawyer 2 Lawyer.(00:00) - Monologue: 3 Practical AI Use Cases for Lawyers (01:48) - Use Case 1: Collating & Aggregating Large Datasets (03:10) - Use Case 2: Interactive & Iterative AI Search (04:34) - Use Case 3: Creative Brainstorming & Revision Partnering (06:53) - Interview: Meet Nate Ruiz, Director of Product Management at NetDocuments (07:41) - Learning to Code, Bootcamp Life, & The Termscout / Screens AI Startup (11:39) - Transitioning to NetDocuments & Managing Customer Feedback (15:01) - Re-Architecting NetDocuments: The "Next Gen Experience" (18:08) - Unpacking the Legal Context Graph & Automated Doc Intelligence (22:46) - Ambient AI: AI That Works Without Asking (26:42) - Integrating Legal Authorities, Citations, & CourtListener (29:55) - How Developers Use AI Coding Agents & Claudecode (31:17) - What Is Model Context Protocol (MCP)? (34:14) - Data Cleanliness, Security, & AI Governance Best Practices (37:20) - Counter Program: "Holidays on Holiday" Defunct Holiday Trivia (47:58) - Outro & "Songs About Going on Trips" Spotify Playlist Click here to view the episode transcript.

Jared starts off by heavily criticizing the toxicity of John Morgan's employee surveillance policies at Morgan & Morgan.Next, Andrea Cannavina joins us to explain how the push-pull mechanics of early mobile tech shaped modern digital addiction.  Andrea advises lawyers to thoroughly read software Terms of Service to avoid becoming the product, breaks down why AI output degrades over time, and shares her triad of office processes (DAFT, Control Journal, and Uncalendaring) to tame email and protect mental capacity. She also previews her unique, live-streaming, screen-free podcast, From Paper to Portals.Learn more about Andrea Cannavina.Subscribe to Andrea's new podcast From Paper to Portals.Check out our latest Spotify playlist.We're grateful to be supported by Attorney at Work Today, and Lawyer 2 Lawyer.Subscribe to Attorney at Work Today.Subscribe to Lawyer 2 Lawyer.(00:00) - Monologue: Law Firm Spy Games & Morgan & Morgan's Remote Work Surveillance (07:07) - Interview: Meet Andrea Cannavina, "The Law Firm Therapist" (08:08) - The 2007 Tech Landscape: Palm Pilots, WebOS, & Push vs. Pull Technology (11:38) - Digital Disconnect Days & The Addiction of Modern Smartphones (14:22) - Cloud Computing, Private Equity, & Reading Your Tech Terms of Service (23:27) - The Reality of AI: Why ChatGPT Degrades and the Truth About Tokens (27:57) - Becoming the Law Firm Therapist: Why Attorneys Need Process Consulting (32:42) - How Email "Push" Tech Destroyed Work-Life Boundaries for Lawyers & Staff (36:43) - The 3-Step Process: DAFT, Control Journals, & Uncalendaring (39:05) - Announcing the "From Paper to Portals" Screen-Free Podcast (40:40) - Counter Program: Regional Slang ("StuffLong Islanders Say") (42:30) - "Chopped Meat," "Waiting Online," & The First US Supermarket (50:47) - Up Island vs. Down Island & The Economics of Long Island (54:24) - The "Bag Speck" Deli Order & The Secret to NY Bagels (56:26) - Outro & "Boomers (Songs About Explosions)" Spotify Playlist Click here to view the episode transcript.

Jared Correia opens with an in-depth retrospective on the legendary Marvin Gaye. He traces Gaye's multi-faceted career from his early days as an aspiring jazz crooner and Motown hitmaker to his iconic duet era with Tammi Terrell, his groundbreaking protest album What's Going On, his sexy late-period reinventions, and his tragic death.  In the interview, Author and True Worth Expert Vanessa Ugatti joins host Jared Correia to explore the psychology behind lawyers’ fee conversations and client boundaries and how self-worth affects what they charge, the boundaries they set, and ultimately the revenue they generate.Then it's time for the Counter Program with "The Internet Pricing Cavalcade of Fun and Danger," where Vanessa guesses prices for absurd online products ranging from a James Bond Florida mansion to dinosaur chicken nugget throw pillows.Learn more about Vanessa Ugatti.Check out her book.Listen to this episode's Spotify playlist.We're grateful to be supported by Attorney at Work Today, and Lawyer 2 Lawyer.Subscribe to Attorney at Work Today.Subscribe to Lawyer 2 Lawyer.(00:00) - Monologue: The Life, Art, and Legacy of Marvin Gaye (Part 1: Jazz Singer) (06:32) - Motown Hits, Songwriting, & Hitsville USA (09:20) - The Duets Era & Tammi Terrell's Tragic Story (14:33) - What’s Going On: The Birth of a Protest Album (19:26) - Let’s Get It On, Sexual Healing, & Late Career (21:33) - Personal Struggles, Tragic Death, & Reprise (25:43) - Interview: Meet Legal Pricing Expert Vanessa Ugatti (28:32) - Mindset & Self-Worth: The Psychology Behind Fees (33:46) - The True Worth Formula & Eliminating "PITA" Clients (46:45) - Setting Client Boundaries & Charging Premium Rates (52:58) - Fee Adjustments, Inflation, & How to Get Paid Your True Worth (56:26) - Counter Program: "The Internet Pricing Cavalcade of Fun and Danger" (01:09:01) - Outro & "Marvin Gaye Favorites" Spotify Playlist Click here to view the episode transcript.

Jared Correia opens with a strategic breakdown of why managing attorneys must practice at the top of their law license. He details a three-tier task delegation framework—Administrative, Low-Level Substantive, and High-Level Substantive—explaining how structured workflows and non-attorney incentive systems maximize revenue and employee satisfaction.  For the interview, Case Compass CEO Joey Organisciak reflects on his career, spanning Apple during the launch of the iPad, composing marching band music, and scaling MedTech startups. Joey explains why legal intake is an underserved discipline in practice management, how Case Compass focuses exclusively on pure intake and landlord-tenant automation, and why he views current AI valuations as an overinflated bubble.  We wrap it up with the Counter Program, where Joey spins "The Wheel of Justice."Click here to learn more about Joey Organisciak and Case Compass.Check out this episode's Spotify playlist.We're grateful to be supported by Attorney at Work Today, and Lawyer 2 Lawyer.Subscribe to Attorney at Work Today.Subscribe to Lawyer 2 Lawyer.(00:00) - Monologue: Practicing at the Top of Your Law License (02:38) - The 3 Tiers of Law Firm Tasks & Workflow Delegation (07:05) - HR, C-Suite Staffing, & Non-Attorney Incentive Structures (09:35) - Interview: Meet Joey Organisciak, CEO of Case Compass (10:33) - Working at Apple (2008–2013) & The Launch of the iPad (13:31) - Music Composition, Computer Science, & Marching Band Scoring (17:24) - Transitioning into MedTech, Telehealth, & Digital Health Startups (25:40) - Co-Founding Sandbox Union & Knowledge-Sharing Leadership Lessons (29:53) - What Case Compass Does: Pure Intake OS & Landlord-Tenant Tech (35:47) - Overinflated AI Valuations, Compute Costs, & Legal Tech Hype (45:08) - Counter Program: "The Wheel of Justice" Trivia & Random Q&A (58:05) - Outro & "Alliterative Songs" Spotify Playlist Click here to view the episode transcript.