The Redline

Mike Whelan

The Morning Show for Lawyers Who ❤️ AI

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August 22 · 30 min
The Hank Green Problem for Lawyers: Why Disclosing AI Use is So Complicated | Nika Kabiri
Nika Kabiri is a decision scientist who has spent 20+ years studying how consumers pick who to trust, including for legal tech companies like Clio and Avvo. In this conversation, Nika and Mike discuss what happens in clients' heads when a lawyer discloses using AI, why it often erodes trust instead of building it, why Gen Z calls AI images "boomer art," and what lawyers should actually signal if they want disclosure to help. 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ https://www.spellbook.legal/newsletter 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆's 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/nikakabiri/ 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝗠𝗶𝗸𝗲 𝗪𝗵𝗲𝗹𝗮𝗻: https://www.linkedin.com/in/mikewhelanjr/ 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:13 - The Hank Green AI backlash 2:55 - Why law is a credence good 3:48 - How consumers really pick a lawyer 8:29 - Why AI reads as a cheap signal 13:57 - Why disclosing AI erodes trust 17:16 - Where AI use is fine, and where it’s not 19:55 - How to disclose AI use 25:00 - Billing, ethics, and the AI price question 29:37 - Connect with Nika
- Transcript
July 31 · 28 min
Why Lawyers Are Working More but Billing Less (Based On 10 Years of Data) | Joshua Lenon
Joshua Lenon is the Legaltech hype man and Lawyer in Residence at Clio, where he's spent a decade turning Clio's data across 400k accounts into the industry's most-cited look at what's really happening inside law practices. In this conversation, Joshua and Mike walk through what 10 years of the Legal Trends Report reveal, including what clients are really annoyed by, why $400/month is the affordable-legal price point hiding in the data, what the "$27K at risk from AI" number actually means and why solo lawyers are surprisingly slow to adopt AI. 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆's 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/joshualenon/ https://bsky.app/profile/joshualenon.bsky.social https://www.clio.com/resources/legal-trends/ 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝗠𝗶𝗸𝗲 𝗪𝗵𝗲𝗹𝗮𝗻: https://www.linkedin.com/in/mikewhelanjr/ 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 0:21 - Meet Joshua Lenon 1:59 - What the Legal Trends Report measures 5:30 - The 24-hour rule for landing new clients 6:00 - The async vs. synchronous communication mismatch 7:18 - Why clients feel relief (and lawyers miss it) 8:32 - Payment plans and the $400/month price point 10:50 - Utilization rate: 26% to 33% in 10 years 12:21 - Value creation vs. value capture in non-billable time 13:32 - Flat fees are getting more complex and more expensive 15:51 - What the "$27K at risk from AI" number really means 17:18 - The Jevons paradox and the latent legal market 21:00 - Are lawyers doing better work now? 23:33 - Why solos are slow to adopt AI 27:02 - Connect with Joshua
- Transcript
July 16 · 24 min
What Does "Legal Judgment" Actually Mean in the AI Era with Brian Powers | The Redline
Brian Powers is the CEO and co-founder of Markups AI, creators of Agent Marco - an AI that negotiates routine contracts end-to-end, backed by a team of legal engineers who translate each client's expertise into rules the agent can dependably apply. During the episode, he takes on the biggest question in legal-AI discourse: what is "judgment” really? He splits it into two parts (the rules you set up front and the ad hoc calls you didn't see coming), makes the case for humans as a premium asset, and works through what happens to young lawyers when the low-level work that used to build judgment stops existing. 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆's 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/brian-powers-41465662/ https://www.markups.ai/ 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝗠𝗶𝗸𝗲 𝗪𝗵𝗲𝗹𝗮𝗻: https://www.linkedin.com/in/mikewhelanjr/ 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 0:22 - Meet Brian Powers 0:56 - Markups AI and Agent Marco 1:26 - What "agentic" actually means 2:36 - The two types of judgment 5:09 - Where humans fit in the workflow 7:52 - AI judges and the trust gap 11:35 - Waymo, and how trust is built 13:46 - Is legal judgment an information problem? 16:05 - Why humans become a premium asset 17:07 - How young lawyers develop judgment without low-level work 20:01 - Pointing lawyers straight at the hard problems 20:42 - Marco's theory: apply the playbook, flag the rest 24:03 - Connect with Brian
- Transcript
July 2 · 22 min
Everyone's Wrong About AI and Access to Justice | Natalie Knowlton
Natalie Knowlton has spent 20 years working on what everyone in legal calls "access to justice", a phrase she calls "the buzzword to end all buzzwords." Now as the Associate Director of Legal Innovation at the Center on the Legal Profession at Stanford, she's focused on civil justice reform, family court, and the middle-market clients most lawyers forget are locked out too. During this conversation, Mike and Natalie discuss what AI can and can't do for access, why self-help isn't the fix everyone wants it to be, why the adversarial system was already broken before ChatGPT showed up, and what practitioners themselves would have to change for anything to actually improve. 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆's 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/natalieanneknowlton/ Bluesky/X: natalalleycat 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝗠𝗶𝗸𝗲 𝗪𝗵𝗲𝗹𝗮𝗻: https://www.linkedin.com/in/mikewhelanjr/ 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 0:37 - Meet Natalie Knowlton 1:07 - What "access to justice" actually means 6:07 - Self-help and its limits 7:23 - Why pro se filings are flooding the courts 9:37 - The three functions of lawyers and where AI fit 10:46 - AI in the adversarial system 13:13 - The emotional good of being seen and heard 14:16 - The Nippon Life / OpenAI case 15:37 - Law as a credence good problem 16:41 - Small legal AI vs. big general AI on accountability 18:30 - Regulation and the trust vs. capability question 20:03 - What practitioners need to do next 22:11 - Bottlenecks surfacing older problems 22:33 - Connect with Natalie
- Transcript
June 15 · 26 min
Why Every Legal Team is About to Be Restructured with Alex Su (Latitude Legal)
Alex Su talks to the people who hire lawyers. As Chief Revenue Officer at Latitude, an alternative legal services provider that builds on-demand teams for firms and in-house departments, he sees the resourcing decisions, the AI pressure, and the trade-offs play out in real time. During our conversation, we spoke about why in-house teams keep growing, why "judgment" isn't something you type into a chatbot, and what lawyers need to underline when their bosses ask what humans still do. 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝘀𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘁𝗼 𝗔𝗜 𝗶𝗻 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗲: Spotify: https://open.spotify.com/show/1RqIrtq... Apple: https://podcasts.apple.com/us/podcast... 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆's 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/alexander-su/ https://www.alexofftherecord.com/ 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal
- Transcript
May 28 · 22 min
The Client Side of Legal AI with Hilary Bowman
Hilary Bowman built Querious to solve the most frustrating moment in legal practice - when something unexpected comes up in a client meeting and the lawyer has to say "let me research and follow up." After more than a decade as a healthcare attorney at law firms and in-house at enterprises like IBM, she founded Querious to sit inside attorney-client conversations on Zoom, Teams, or phone and surface issues, questions, and follow-ups in real time. In this conversation, she flips the usual AI for lawyers script and asks what these tools actually do for clients - why most clients want a relationship partner instead of a black box, why timely follow-ups beat fancy portals, and how language tools finally let lawyers meet clients where they are. 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆's 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/hilarybowman/ https://www.querious.ai/ 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 0:50 - Meet Hilary 2:03 - What Querious does in a client meeting 2:45 - From healthcare law to founding a startup 4:10 - What clients actually want from a lawyer 5:21 - The lawyer as relationship partner and traffic cop 6:55 - The black box problem of hourly billing 7:30 - Bridging asymmetries between lawyer and client 8:03 - Why law can't have a Domino's Pizza tracker 10:36 - The most powerful LLM unlock for clients 12:38 - Where AI ends and creative lawyering begins 14:22 - Change costs and tool adoption 15:55 - Speed to value: narrowing the scope 17:45 - Building feedback loops with clients 20:18 - One thing to implement on Monday 22:15 - Connect with Hilary
- Transcript
May 14 · 26 min
Why AI Won't Fix Your Broken Workflow with John Grant
AI tools won't solve your overwhelm if your processes are the problem. John Grant is a fourth-generation lawyer turned workflow consultant. He spent a decade in tech before practicing law, and another eleven years helping firms fix how work actually moves. In this conversation, he breaks down the "magical thinking" behind AI adoption, why the real bottleneck is almost never where lawyers think it is, and how speeding up the wrong step actually makes everything worse. He also explains the concepts of "definition of done" and "definition of ready," why legal has an immature relationship with quality assurance, and what courts are already seeing as AI-assisted filings flood systems that aren't built to handle them. 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/johnegrant/ https://agileattorney.com https://greenlinelegal.com 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 0:42 - Meet John Grant 2:13 - What is Greenline? 3:18 - AI hasn't reduced work 4:30 - The optimism bias and the planning fallacy 6:00 - AI and the last mile problem 7:09 - Output vs. productivity: the developer study 8:06 - Effort is not value 9:21 - Reimagining what value actually means 10:00 - There's only one bottleneck 11:16 - Why improving the wrong step makes things worse 12:10 - AI-assisted pro se filings are flooding courts 13:45 - More but worse vs. less but better 14:00 - Where bottlenecks actually form in legal 15:27 - Legal's immature relationship with quality assurance 16:15 - Quality control is chosen friction 17:21 - Definition of done and definition of ready 18:06 - Failure demand and rework 19:29 - Lawyering is a caregiving profession 22:39 - The board game analogy: multiple ways to lose 23:32 - The Agile Attorney 101 podcast series 25:04 - Takeaway: AI won't solve overwhelm without design 25:38 - Connect with John
- Transcript
#12
April 25 · 16 min
Are AI Notetakers Ethical for Lawyers? with Wendy Meadows & Michael Eisenberg
In this episode, Mike walks through the New York City Bar's recent opinion on using AI to record, transcribe, and summarize client conversations, and boils it down to four duties you probably already follow. Then mediator Wendy Meadows shares her full workflow, including Fathom for capture, Clio for document production, Spellbook for quality control, and how it turned a two-hour MOU into a 20-minute job. Michael Eisenberg breaks down consent rules, one-party vs. two-party states, and why none of this is actually new. 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal https://www.linkedin.com/company/spellbookai/posts/?feedView=all https://www.linkedin.com/in/mikewhelanjr/ https://www.linkedin.com/in/scottas/ 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:46 - The New York City Bar opinion (Formal Opinion 20256) 2:45 - Risk 1: Consent and one-party vs. two-party states 4:48 - Risk 2: Confidentiality and ABA Rule 1.6(c) 6:06 - Risk 3: What if the client records the call? 8:46 - Why these rules aren't new 9:05 - Wendy's practice: mediator on Zoom all day 10:00 - Turn off the defaults 10:51 - Using it like an associate 12:27 - Drafting direct examination from a transcript 13:08 - Spellbook as the quality control layer 14:48 - Predicting the future: insights in context 16:01 - Why the good outweighs the bad 16:37 - Connect with Wendy and Michael
- Transcript
#11
April 10 · 32 min
How a Business Lawyer Reviews a 56-Page Contract with AI with Chris Brown
Contract review is tedious, but missing something can be expensive. In this episode, Chris Brown of Pixel Law shares his screen as he reviews a 56-page Asset Purchase Agreement using Spellbook. See how effective AI tools can help you: - Surface unknown risks, - Draft clauses like indemnification and delivery terms, and - Update you on substantive legal issues within a contract. Chris also shares how he uses Spellbook for a "second opinion," and why he believes AI will change the practice of law. 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/thepixellawyer/ 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 0:37 - What contract review looked like before AI 1:52 - The document: a 56-page asset purchase agreement 2:11 - High-level risk overview 4:18 - Diving into indemnification 8:25 - Non-compete analysis and Florida law 10:46 - Breaking down the purchase price 15:08 - Reps and warranties review (35 issues in 9 pages) 17:52 - Running the same prompt twice for a second opinion 18:24 - Closing deliveries and what's missing 22:08 - Catching missing terms across the document 24:44 - Compare to Market feature 28:35 - What stood out most from the process 29:51 - When to trust AI vs. your own judgment 31:00 - How to get started with AI tools 32:09 - Wrap up
- Transcript
#10
March 27 · 33 min
Is Your Client's AI Chat Discoverable? with Leslie Bender & Craig Linton
What happens if your client asks ChatGPT for advice about their case? Is that discoverable? Is it your fault if you didn't warn them it might be? Leslie Bender and Craig Linton join the show to unpack two cases: Heppner and Warner v Gilbarco, that seem to reach opposite conclusions as judges try to draw lines around privilege, work product, and AI in an area where the rules haven't caught up to the tools. 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝘀𝘂𝗯𝘀𝗰𝗿𝗶𝗯𝗲 𝘁𝗼 𝗔𝗜 𝗶𝗻 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗲: Spotify: https://open.spotify.com/show/1RqIrtqTgbng2BGuzr4aAq Apple: https://podcasts.apple.com/us/podcast/ai-in-practice/id1846506529 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁𝘀: https://www.linkedin.com/in/lescbender/ https://www.linkedin.com/in/craigalinton/ 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal https://www.linkedin.com/company/spellbookai/posts/?feedView=all https://www.linkedin.com/in/mikewhelanjr/ https://www.linkedin.com/in/scottas/ 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:49 - Meet Leslie Bender 2:31 - Meet Craig Linton 3:31 - Attorney-client privilege and work product 101 5:54 - Clients have always gone rogue with case info 8:00 - The Heppner case: a CEO, AI, and a 31-point memo 11:21 - Does it matter if the lawyer directed it? 13:00 - Warner v Gilbarco: the pro se counterpoint 16:08 - What discoverability means for pro se litigants 19:21 - Assume your AI self-help is discoverable 21:37 - The engagement letter hack 23:19 - Should we encourage or discourage client AI use? 25:06 - Lawyers as AI consumers: is Claude enough? 28:10 - Reasonable privacy expectations vs. the fine print 30:49 - Three predictions for the next 10 years 33:06 - Connect with Leslie and Craig
- Transcript
January 22 · 24 min
How to Run a Law Firm Like a Tech Startup with Kyle Westaway
Kyle Westaway has run his firm for 17 years without ever tracking a billable hour. In this conversation, he breaks down why he believes 75% of a lawyer's value has nothing to do with documents—and why that makes AI a tailwind, not a threat, for firms built around outcomes instead of time. He also shares how he prices work without defaulting to hourly estimates, why clarity with clients takes courage, and what it means to design a law firm from first principles. 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal https://ca.linkedin.com/company/spellbookai https://www.linkedin.com/in/mikewhelanjr https://ca.linkedin.com/in/scottas 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:14 - Meet Kyle Westaway 2:30 - Starting a firm fresh out of law school 4:00 - Designing a firm for startups from first principles 5:00 - What do lawyers actually sell? 7:00 - Why the billable hour persists 10:45 - Flat fees only: How Kyle prices work 13:00 - Why clarity with clients takes courage 15:00 - Why they've never tracked a single hour 17:00 - The "market for lemons" problem in legal 19:30 - Why AI helps flat-fee firms (and hurts hourly ones) 22:00 - Purpose and the future of law practice 23:30 - Connect with Kyle
- Transcript
#8
Dec 11, 2025 · 34 min
How to Build a Subscription-Based Law Practice Fueled by AI with Ryan Juliano
Ryan Juliano runs Darwin Legal, a subscription-based fractional general counsel practice serving early-stage tech startups. After 15 years moving down the legal food chain from IPOs to pre-seed companies, he's built a model that replaces the crushing wave of hourly billing with committed capacity—and he's using AI across every part of his practice. In this conversation, he shares what it means to use tools "promiscuously," why lawyers need to get comfortable chopping with blunt axes, and how AI helps him think through not just legal problems but business model design. 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/ryan-juliano-b3833124 https://darwinlegal.com/ 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:12 - Meet Ryan Juliano 2:15 - From IPOs to early-stage startups 5:34 - The subscription fractional GC model 8:34 - Who manages legal before you arrive 11:01 - Running everything through AI 16:19 - Good enough vs. perfect 17:55 - Will tools consolidate or stay fragmented? 20:29 - How Ryan spends his time now 24:37 - Shifting from inputs to outputs 27:23 - Capturing knowledge to repurpose 32:57 - Defining "good enough" in legal services 34:04 - Connect with Ryan
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#7
Nov 27, 2025 · 24 min
Why AI Is Stalled At Your Firm (And How to Fix It) with Colin Lachance
Colin Lachance helps law firms implement AI without the paralysis. As founder of LawQi and former Innovator in Residence at the Ontario Bar Association, he's developed a practical framework: start with tasks, not processes. In this conversation, he explains why most firms aren't ready for full process redesigns, what infrastructure you actually need before experimenting, and how to build the skills that prevent expensive mistakes. 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗪𝗵𝗲𝗿𝗲 𝘁𝗼 𝗳𝗶𝗻𝗱 𝘁𝗼𝗱𝗮𝘆'𝘀 𝗴𝘂𝗲𝘀𝘁: https://www.linkedin.com/in/colinlachance https://lawqi.com/ 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:30 - Meet Colin Lachance 4:15 - Working inside a real law firm 6:00 - The messy garage problem 11:30 - Tasks vs. processes: which comes first 14:00 - What infrastructure you actually need 17:30 - Why start with tasks, not whole processes 21:30 - How lawyers should learn AI 24:15 - Connect with Colin
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#6
Nov 20, 2025 · 26 min
Using AI to Compete with BigLaw: The Small Firm Playbook w/ Shavon J. Smith
Washington, DC attorney Shavon J. Smith runs a small firm that serves growing businesses as their fractional general counsel. In this episode, she explains how AI helps her compete with larger firms – from mapping workflows to drafting contract checklists, improving client alerts, pressure-testing assumptions, and crafting clearer redline comments during negotiations. She also shares where AI meaningfully improves efficiency, where it simply improves quality, and where human judgment still matters most, especially in negotiation and client counseling. 📌 𝗧𝗵𝗲 𝗥𝗲𝗱𝗹𝗶𝗻𝗲 𝗡𝗲𝘄𝘀𝗹𝗲𝘁𝘁𝗲𝗿: Get the latest news, trends, and tactics in legal AI—straight to your inbox. ➞ join free: https://www.spellbook.legal/newsletter 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 2:15 - Meet Shavon J. Smith 3:32 - What is fractional general counsel? 4:00 - AI for process mapping and improvement 6:03 - Using AI as a brainstorming partner 7:46 - Marketing and client communication 8:25 - How clients find the firm (including through AI) 10:06 - Email overwhelm and client management 13:12 - AI for contract drafting and review 16:06 - Being a better strategic advisor 18:00 - Understanding clients' businesses 19:48 - Managing people and processes 22:35 - Where AI can't help: settlement psychology 24:17 - Learning from other lawyers 24:35 - Connect with Shavon
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#5
Nov 13, 2025 · 30 min
AI Readiness: The IT Infrastructure Lawyers Need Before Adopting AI with Olivia Anderson
Olivia Anderson helps law firms build the IT infrastructure they need before adopting AI. As Principal at Framework IT, a managed service provider working with legal practices of all sizes, she's seen what happens when firms rush into AI without the cybersecurity foundations in place. In this conversation, she walks through shadow AI, the $5.5 million problem most firms don't know they have, and why managing partners need to own AI governance whether they like it or not. 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:21 - Meet Olivia Anderson 2:11 - Shadow AI and the $5.5M problem 6:09 - IT readiness for solo lawyers 10:16 - Consumer AI vs. legal-specific tools 13:15 - Creating a responsible AI policy 17:22 - Who owns AI governance at your firm 21:45 - Risk tolerance culture in law 28:56 - Quantifying your firm's risk profile 31:00 - Connect with Olivia
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#4
Nov 6, 2025 · 28 min
AI's Role in the Courtroom with Appellate Lawyer Todd Smith | AI in Practice
Todd Smith is a board-certified appellate lawyer in Texas who consults with trial teams and handles appeals. In this conversation, he explains how AI tools are changing his work—and where they hit their limits. 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:42 - Todd's appellate practice model 6:10 - AI collaboration challenges 9:15 - Analyzing trial transcripts with AI 14:57 - Finding arguments vs. knowing what to do with them 19:03 - Small data sets and judgment calls 24:50 - Why hourly billing is breaking down 28:04 - Flat fee experiments 31:23 - Marketing as an AI quick win 34:19 - Connect with Todd
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#3
Oct 31, 2025 · 30 min
How to Build a Law Firm That Runs Without You with Joey Vitale
Before "AI automation" was a buzzword, Joey Vitale built Indie Law to operate without him. That experience—paired with years helping lawyers scale through virtual assistants—turned him into a quiet expert on systems, delegation, and identity. In this episode, he and host Mike Whelan dig into what happens when the work that once defined you starts running itself, and why the real value of a lawyer might have less to do with tasks and more to do with trust. 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal/ 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 2:15 - Why Joey left litigation 5:34 - The crisis that forced systematization 8:27 - Four stages: doer to strategist 14:44 - Managing VAs prepares you for AI 19:42 - Prompting AI effectively 24:15 - 80% right is 100% awesome 32:51 - Redefining lawyer identity 36:20 - Why clients still need attorneys
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#2
Oct 23, 2025 · 29 min
Teaching Lawyers to Prompt with AI Legal Consultant Alessandra Colaci
Alessandra Colaci helps in-house legal teams figure out how to actually use AI—not just talk about it. As the founder of Legal Plus AI and former founding marketer at Harvey, she's spent years teaching lawyers to prompt, experiment, and integrate AI into their daily work. In this conversation, she breaks down the quick wins that build momentum, the security concerns that keep lawyers up at night, and why most teams need to start smaller than they think. 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.legal 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:10 - Meet Alessandra Colaci 2:34 - The adoption gap: Strategy vs. reality 3:42 - Micro-learning and experimentation 6:04 - Quick wins 6:54 - Using AI as a thought partner 11:32 - The "prompt library" approach 13:48 - What to try on your own vs. with the team 17:18 - What's real vs. what's fear 22:53 - When courts will catch up to AI as standard practice 24:27 - Learning what works for you 27:34 - Connect with Alessandra
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#1
Oct 15, 2025 · 34 min
Fixed Fees, AI Experiments, and The Future of Family Law with Beau Atkins
Beau Atkins runs Evolve Family Law in Saskatchewan, Canada, where he's using AI to reach the 79% of people with legal problems who never hire a lawyer. In this conversation, he shares how he built an AI-assisted tool that guides self-represented clients through court processes — and how he's testing an AI agent to handle intake calls. His end goal? Serve with three lawyers what would normally take 300. 𝗧𝗶𝗺𝗲𝘀𝘁𝗮𝗺𝗽𝘀: 0:00 - Introduction 1:14 - Meet Beau Atkins 2:15 - The journey from frustrated lawyer to entrepreneur 5:34 - AI experiments in family law practice 8:27 - Solving the 79% problem 14:44 - Ethics, disclaimers, and hallucinations 19:42 - What clients really want (and don't get) 27:58 - Product design: Flat fees and AI tools 30:25 - Learning from COVID experiments 32:51 - How Beau uses AI today 33:33 - Connect with Beau 💎 𝗦𝗽𝗲𝗹𝗹𝗯𝗼𝗼𝗸: Draft and review contracts 10x faster ➞ try it free: https://www.spellbook.com
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