Legal Late Night

The Legal Broadcasting Company
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Nov 13, 2025 • 58min

Taylor Swift, Law Firm Automation, & Emmy-Winning Voiceover (Feat. Daleele Alison & Michelle Falanga)

First, Jared shares his monologue on Taylor Swift's 12th studio album, The Life of a Showgirl. He breaks down why he's a "True Swifty," critiques the Jack Antonoff production, and presents his complete Top 12 Track Ranking—from his least favorite song about the Blake Lively drama to his #1 pick, the title track.Then, Daleele Alison, CEO of Rooks DM, joins the show. Daleele explains his company's goal ("to go far") and how they help law firms tackle pain points like onboarding and data collection by implementing AI and automation. He stresses his "process first, technology second" philosophy and gives a rundown of the Microsoft Power Platform tools (Power BI, Power Automate) that firms underutilize.Finally, Michelle Falanga, an Emmy-winning voiceover actress, shares her unique career path, which involved 23 years of improv and murder mystery shows. Michelle discusses her favorite niche projects (like narrating Drum Corps world championships), her thoughts on AI voice cloning, and the emotional "gut punch" of having clients replace her with AI.Learn more about Daleele and RooksDM.And follow Michelle's career on her website.Tune in to our latest Spotify Playlist!Subscribe on YouTube.Thanks to those supporting this episode:Assembly Neos. Visit assemblysoftware.com to learn more and schedule your consultation today.Captain Compliance.  Visit captaincompliance.com to easily manage your company's privacy compliance.Attorney at Work. Head to Attorney at Work for your one really good idea each day.  Check out their new podcast Attorney at Work Today on Apple, Spotify, or wherever you listen to podcasts.(00:00) - Intro & Monologue: Jared, The True Swifty (02:03) - Taylor Swift's Discography: Folklore to Reputation (18:54) - Introducing Guest: Daleele Alison, CEO of Rooks DM (19:34) - What Does "Rooks DM" Mean? (21:05) - Rooks DM's Service: AI & Automation for Law Firm Efficiency (23:26) - Advisory Services: Current State, Future State, and Virtual Work (24:57) - Philosophy: "Process First, Technology Second" (26:54) - Underutilized Microsoft Tools (28:55) - Deep Dive: The Microsoft Power Platform (Power BI, Automate, Apps) (30:17) - Copilot Use Cases: Work Data vs. Web Data (32:13) - Custom AI Agents for SOPs and New Hires (35:44) - Why Attorneys "Keep F***ing Up Their Technology" (36:24) - How to Find a Good Legal Tech Consultant (38:04) - Introducing Guest: Michelle Falanga, Emmy-Winning Voiceover Actress (39:44) - Michelle's Connection to Daleele Alison (40:25) - Michelle Shows Off Her Emmy (42:54) - The Path to Voiceover: Improv and Murder Mysteries (44:35) - Getting Voiceover Parts (Pay-to-Play Sites and Direct Marketing) (46:10) - Favorite Projects: Narrating Drum Corps Monologues (49:41) - The AI Problem: Voice Cloning and Emotional Delivery (53:05) - Michelle's Other Work: Children's Book Author (54:17) - Michelle's Podcast: Real Talk Tuesdays (56:44) - Conclusion & Outro Click here to view the episode transcript.
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Oct 30, 2025 • 1h 6min

Evergreen Retainers, Revenue Leakage & Holidays on Holiday (with Jonathon Fishman)

Jared is joined by Jonathon Fishman, CEO & Co-founder of LeanLaw, to talk about law firm finances, retention, and defunct holidays.First, Jared shares his monologue on law firm retention strategies. He argues that the market is too tight to run your firm on "vibes" and offers seven tips to keep your best people, including the need for transparent incentives, financial clarity, and more frequent payouts. He also offers a strong argument for why lawyers love bullsh*t titles.Then, Jonathon Fishman discusses the founding of LeanLaw and its mission to help small firms be better businesses. He delves into his three major areas of focus: the power of LeanLaw's deep QuickBooks integration for compensation tracking, how to stop "revenue leakage" in your firm, and his strong take on trust accounting, which he argues should drive the universal adoption of evergreen retainers.Finally, stick around for our fun and utterly unhinged Counter Program segment, "Holidays on Holiday." Jonathon is quizzed on whether bizarre, defunct holidays—like the "Festival of the Whispering Wax" and "Old Clem's Night"—are real or fake.For more on Jonathon Fishman and LeanLaw, check out LeanLaw here.And tune into this week's Spotify playlist to keep the party going.Thanks to those supporting this episode:Assembly Neos. Visit assemblysoftware.com to learn more and schedule your consultation today.Captain Compliance.  Visit captaincompliance.com to easily manage your company's privacy compliance.Attorney at Work. Head to Attorney at Work for your one really good idea each day.  Check out their new podcast Attorney at Work Today on Apple, Spotify, or wherever you listen to podcasts.(00:00) - Intro & Monologue: How to Keep Your Best Employees (03:05) - Tip 1: Clear, Transparent Incentives (Hourly Tiers, Project Bonuses, etc.) (07:38) - Tip 2: Regular Incentives (Weekly/Monthly Payouts) (09:21) - Tip 3: Titles (And Why Lawyers Love Them) (11:01) - Tip 4: Professional Development (12:23) - Tip 5: Marketing Opportunities (14:04) - Tip 6: Financial Transparency (15:22) - Tip 7: Flexibility (Working in the Dining Room) (18:41) - Introducing Guest: Jonathon Fishman of LeanLaw (20:41) - The LeanLaw Founder Story: From Silicon Valley to Boise, Idaho (22:52) - The Joy of Helping Small Firms Be Better Businesses (26:28) - Why Law Firms Are "Unbelievably Slow to Adopt" Tech (27:40) - LeanLaw's Core Focus: Financial Workflows & QuickBooks Integration (29:43) - The Four Phases of Legal Tech (and the Rise of Niche Tools) (32:34) - Supercharging Reporting with QuickBooks Data (35:49) - Sophisticated Compensation Tracking (and the Black Box Problem) (38:11) - The Biggest Problem: Stopping Revenue Leakage (40:31) - Hourly Billing vs. Value-Based Pricing (The Hybrid Approach) (43:39) - Trust Accounting & The Power of Evergreen Retainers (46:21) - AI's Role in Law Firm Finance (50:57) - Are Lawyers Asking About AI Yet? (54:58) - Counter Program Intro: Holidays on Holiday (01:06:47) - Conclusion & Outro Click here to view the episode transcript.
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Oct 23, 2025 • 57min

Micro-Hard for Microsoft: AI, Copilot & The Future of Legal Tech (Feat. Ben Schorr)

Welcome back, late nighters! Make sure the kids are asleep, because we're going hard this week.  Or kinda of micro-hard, specifically.  This week, Jared is joined by Ben Schorr, Innovation Strategist at Affinity Consulting, who spent nine years working at Microsoft.First, Jared shares his monologue on the seminal sci-fi anthology series, The Twilight Zone. He discusses creator Rod Serling's history as a WWII paratrooper and his commitment to addressing taboo subjects like fascism and war. Jared then lists his Top 10 Twilight Zone Episodes—from "Time Enough at Last" to "The Monsters Are Due on Maple Street"—without spoilers, of course!Then, Ben Schorr takes us deep into the world of Microsoft. He clarifies the confusing reality of Microsoft 365 Copilotlicensing and explains why lawyers are slow to ditch desktop apps. Ben shares his thoughts on the broader AI landscape, advising lawyers to be monogamous with their two or three best tools to avoid "tech paralysis". He also offers clear answers on the difference between OneDrive ("me files") and SharePoint ("we files").Finally, stick around for our Counter Program segment, "Ben Rates the 80s." Ben shares stories from his early career, including working for Alex Trebek, and then rates 80s staples like hair styles, movie soundtracks (hello, Top Gun!), his favorite movie (Real Genius!), and which defunct store he misses most.Be sure to connect to with Ben Schorr on LinkedIn.And learn more about Affinity Consulting.And don't think we're not giving you that sweet, sweet Spotify love this week.  Check out our playlist here.Thanks to those supporting this episode:Assembly Neos. Visit assemblysoftware.com to learn more and schedule your consultation today.Captain Compliance.  Visit captaincompliance.com to easily manage your company's privacy compliance.Attorney at Work. Head to Attorney at Work for your one really good idea each day.  Check out their new podcast Attorney at Work Today on Apple, Spotify, or wherever you listen to podcasts.(00:00) - Intro & Monologue: The Fifth Dimension of The Twilight Zone (02:25) - Rod Serling's WWII History & Fight Against Censorship (06:09) - Rules for Jared's Top 10 Twilight Zone Episodes (07:00) - Jared's Top 10 (12:15) - More Obscure Twilight Zone Selections (The Beholder, The Invaders) (15:34) - The Singular Power of Rod Serling’s Closing Narration (18:01) - Introducing Guest: Ben Schorr of Affinity Consulting (18:40) - Ben’s Career Path: From Law Firm Admin to Consulting to Microsoft (20:01) - Working for Alex Trebek (The Jeopardy! Story) (22:57) - The Move from Microsoft to Affinity Consulting (24:26) - Ben’s Role as Innovation Strategist & AI Beyond Copilot (25:33) - Microsoft 365 Copilot Licensing Explained (29:04) - The Broader AI Landscape: Why You Need Multiple Tools (31:02) - AI Research: Tuning vs. Data Sets (32:19) - Practice-Specific AI: Medical Chronologies (34:19) - Custom GPTs & The Daily News Briefing Use Case (35:53) - Notebook Tools (Copilot Notebooks & Google Notebook) (37:36) - Why Lawyers Still Use Desktop Apps (The Add-in Problem) (38:56) - Jared Hates Microsoft Teams: The Debate (42:11) - OneDrive vs. SharePoint Explained (45:30) - Counter Program Intro: "Ben Rates the 80s" (46:38) - Best 80s Hairstyle (47:45) - Favorite 80s Movie Soundtrack (49:41) - Favorite 80s Movie (52:05) - Favorite 80s Tech Device (54:23) - Favorite Defunct 80s Store (55:50) - Conclusion & Outro Click here to view the episode transcript.
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Oct 16, 2025 • 47min

Jared Live! at Lex Summit: AI, LinkedIn Hell, & Dumb and Dumber

Welcome to our first ever episode recorded LIVE in front of an audience! Host Jared Correia, on stage at Filevine's Lex Summit user conference, is joined by a massive panel from Filevine to discuss the future of legal tech and the genius of Jim Carrey.First, Jared shares his monologue on his worst-ever LinkedIn messages, naming and shaming spammers who used terrible emojis, asked for sex toy sales, and didn't even bother to read his title. He argues that his inbox is the "10th circle of hell."Then, Dr. Cain Elliott, Filevine's Chief Legal Futurist, joins us to discuss his "skunkworks" development team, the "too many outputs" problem with AI, and the strong suite of AI products they offer, including their proprietary Deposition AI. He also reveals the single most overlooked technology application for lawyers: Process Mining.Finally, we're joined by Erik Bermudez and Mary Lyon for a panel review of the classic 1994 film Dumb and Dumber. The panel debates who is "dumb" and who is "dumber," who the MVP is, the best one-liners, and the surprising amount of the movie that was filmed in Utah. Dr. Cain also shares an insane piece of Filevine history: the company's first office had a double toilet with no dividing wall.Watch the show on our YouTube channel.Thanks to those supporting this episode:Assembly Neos. Visit assemblysoftware.com to learn more and schedule your consultation today.Captain Compliance.  Visit captaincompliance.com to easily manage your company's privacy compliance.Attorney at Work. Head to Attorney at Work for your one really good idea each day.  Check out their new podcast Attorney at Work Today on Apple, Spotify, or wherever you listen to podcasts.(00:00) - Intro & Monologue: The Hellscape of the LinkedIn Inbox (04:11) - Naming and Shaming: Jared’s Worst LinkedIn Messages (08:56) - Introducing Guest: Dr. Cain Elliott, Chief Legal Futurist at Filevine (10:46) - What Does a "Chief Legal Futurist" Do? (11:55) - Lex Summit: The Annual User Conference (14:11) - Public Service: Hydration at Altitude (15:44) - Shouting Out Filevine's Integration Partners (17:17) - The Futurist Lounge & Legal-Only Networking (18:25) - Filevine's AI Strategy: The "Too Many Outputs" Problem (19:53) - The Power of Deposition AI (21:03) - Jared's Robot Law Firm Dream (and the Robot Trash Cans) (22:33) - The Most Overlooked Tech for Lawyers: Process Mining (23:56) - Counter Program Intro: Dumb and Dumber Panel (26:22) - Who is Dumb and Who is Dumber? (29:30) - Who is the MVP of the Movie? (32:59) - The Best One-Liner / Scene (35:41) - Filevine Lore: The Infamous Double Toilet (39:29) - Jim Carrey Ad-Libs & Fun Facts (42:41) - Favorite Jim Carrey Movie (43:57) - Final Fun Facts & Conclusion Click here to view the episode transcript.
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Oct 9, 2025 • 47min

A "Gateway" to AI: Why Lawyers Need to Get Creative with Tech (with Ernie Svenson)

Ernie Svenson, founder of Law Firm Autopilot and creator of Ernie the Attorney, shares his insights on AI in law. He highlights top AI tools like ChatGPT Plus, positioning them as accessible entry points for lawyers. Ernie discusses AI's role in amplifying staff productivity while reducing the need for hiring. He offers a candid take on ethics, arguing that the real issue lies in human incompetence, not AI itself. Listeners are also treated to travel anecdotes and a fun segment where Ernie tries to guess Jared's current location.
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Oct 3, 2025 • 46min

Vetting AI for Law Firms, Drunk Business Advice & Celebrity Shenanigans (Feat. Kristin Kenzy)

Kristin Kenzy, creator of the Drunk Business Advice newsletter and a former commercial real estate professional, joins the conversation to share her unique journey into media. She reveals the importance of learning from failures and how her personal anecdotes shaped her writing cohorts. Amid laughs, Kristin delves into bizarre networking experiences, including a neighbor's odd pitch for a sex toy pyramid scheme. Plus, she showcases her celebrity trivia prowess in a fun drinking stories quiz!
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Sep 25, 2025 • 46min

Why Law Firm Customer Service Sucks (and the Technology That Can Fix It)

Matt McClellan and Manny Griffiths, co-founders of Hona, share insights into transforming legal customer service with innovative tech. They discuss their journey to create 'Domino's tracker' for legal cases, aiming to streamline client communication. The duo highlights the struggles lawyers face in customer service, comparing expectations with giants like Amazon. They reveal cutting-edge tools like AI chatbots and virtual receptionists designed to automate redundant tasks and address the evolving landscape of legal practice.
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Sep 18, 2025 • 59min

Getting Paid; Leslie Witt of 8am; and Dazed & Confused with Gyi Tsakalakis

In honor of 8am's recent Kaleidoscope Conference in Austin, Texas, Jared's joined not by one, but TWO guests.  Leslie Witt of 8AM and Gyi Tsakalakis of AttorneySync.First, Jared shares his monologue on law firm collections, explaining the two best ways to get paid: having a structured, escalating collection process and, even better, avoiding collections altogether by using alternative fees and credit card authorization forms. He discusses how to put yourself at the top of the "bill drawer" and why that's so important for your firm's cash flow.Then, Leslie Witt, the Chief Product Officer at 8AM (the company behind LawPay and MyCase), shares her background and discusses the company's rebrand and new product initiatives. She gives us the rundown on Smart Spend for cash flow and 8AM IQ, their new AI-powered service for case management. She also explains why lawyers are so slow to adopt new payment models and how AI is acting as a catalyst for change.Finally, Gyi Tsakalikis joins us for the Counter Program to review the classic 1970s movie "Dazed and Confused." They talk about the MVP, the demented hazers, and the actors who should have been bigger stars. Plus, they dive into the movie's classic soundtrack and iconic "needle drops" that you already use every day.This week's Spotify Playlist: https://open.spotify.com/playlist/03QqCmubwd3EoXX1nSaElA?si=2nZYQxadQFql3CSp0VqrnQ&nd=1&dlsi=74109d9341144b99For more on our guests:Leslie Witt8am.comLinkedInGyi Tsakalikis:AttorneySyncLunch Hour Legal Marketing (podcast and summit)LinkedInThanks to those supporting this episode:Assembly Neos. Visit assemblysoftware.com to learn more and schedule your consultation today.Captain Compliance.  Visit captaincompliance.com to easily manage your company's privacy compliance.Attorney at Work. Head to Attorney at Work for your one really good idea each day.  Check out their new podcast Attorney at Work Today on Apple, Spotify, or wherever you listen to podcasts.(00:00) - Intro & Monologue: The Law Firm Collections Game (01:45) - The First Species: Have a Collection Process (03:58) - The Second Species: Avoid Collections Altogether (04:57) - Evergreen Retainers & Subscriptions (06:06) - The Bill Drawer Problem: The Power of Credit Card Authorization Forms (07:33) - The 8AM Product Family (LawPay, MyCase, etc.) (09:17) - Introducing Guest: Leslie Witt of 8AM (10:47) - Leslie's Background: From Architect to CPO at 8AM (13:07) - The 8AM Rebrand & The "8AM Clock" Joke (15:13) - New Products: Smart Spend & 8AM IQ (AI with Cases) (19:04) - The Future of AI and Payments (22:32) - Why Lawyers Are Slow to Adopt Alternative Fees (24:59) - The Role of a Chief Product Officer (26:22) - Leslie's Music Recommendations: Maynard Ferguson and Vinyl (27:41) - Counter Program Intro: Gyi Tsakalikis & "Dazed and Confused" (56:03) - Conclusion & Outro Click here to view the episode transcript.
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Sep 11, 2025 • 56min

Billy Joel's Pain = Perfection, The Death of Litigation, and Those "Majestic" Horses

In this jam-packed episode, we tackle Billy Joel's tortured past, a corporate fraud scandal that's straight out of a movie, and the future of law itself. Jared Correia kicks things off with his "Perfect Albums" monologue, adding two classics from Billy Joel's back catalog—the under-appreciated "Streetlife Serenade" and the technically perfect "An Innocent Man"—to the list. Along the way, he gives a raw, unfiltered look into Billy Joel's personal life, from his family's dark history to his struggles with mental health. Then, Collin Williams, founder of New Era ADR, joins us to tell an unbelievable true story of his career. He recounts how he was the attorney at a startup that became known as the **"Theranos of Chicago," leading to an FBI subpoena and a stint as a witness at trial. Collin explains how this experience led him to found New Era ADR, a company designed to fix the broken legal system by focusing on storytelling over procedure and aligning incentives with a flat-fee model. Finally, stick around for our new Counter Program segment, "Travels with Jared and Child," where Jared's daughter Gracie describes a truly wild trip to a horse show that included a very sketchy Wendy's, a horse show injury, and a driver's grave in the drive-thru.For more on Collin and New Era ADR, check out: https://www.neweraadr.comCheck out this episode's Spotify playlist: https://open.spotify.com/playlist/6kKXlmAziLv4oBtQ9wcqzs?si=47ARWb7zTtaq0qXTnXaHVQThanks to those supporting this episode:Assembly Neos. Visit assemblysoftware.com to learn more and schedule your consultation today.Captain Compliance.  Visit captaincompliance.com to easily manage your company's privacy compliance.Attorney at Work. Head to Attorney at Work for your one really good idea each day.  Check out their new podcast Attorney at Work Today on Apple, Spotify, or wherever you listen to podcasts.
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Sep 4, 2025 • 41min

AI Can't Replace Your Content Writer: Tips for Lawyers + How to Write a Book (Feat. Adam Kosloff)

Jared  and special guest Adam Kosloff of Virtuoso Content are here to discuss everything from content marketing and AI to the truly bizarre (and disgusting) world of Urban Dictionary. First, Jared hits the three things you need to be a content marketing monster, focusing on anchor content, a content calendar, and learning how to write for AI. Then, Adam discusses his new book, The Treasure Map, and offers a project management-focused approach to translating your experience into a book worth reading. Finally, stick around for Suburban Dictionary, this week's Counter Program segment, where Jared and Adam put their dad-hood to the test by trying to guess the definitions of the Internet's best and worst slang.To learn more about Adam Kosloff, check out:His book: https://www.amazon.com/Treasure-Map-Write-Turns-Expertise-ebook/dp/B0FNGYGWLG/His website: https://virtuosocontent.com/Or email him at adam@virtuosocontent.comCheck out this episode's Spotify Playlist here: https://open.spotify.com/playlist/0EaqIPBPLMw2dAlFW6GzI6?si=zPrkc6UWTXGsb-LXtw_l9gThanks to those supporting this episode:Assembly Neos. Visit assemblysoftware.com to learn more and schedule your consultation today.Captain Compliance.  Visit captaincompliance.com to easily manage your company's privacy compliance.Attorney at Work. Head to Attorney at Work for your one really good idea each day.  Check out their new podcast Attorney at Work Today on Apple, Spotify, or wherever you listen to podcasts.

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