The Redline
The Redline is a morning show for lawyers who love AI. Hosted by Mike Whelan, it covers the intersection of law and artificial intelligence, providing insights and discussions tailored to legal professionals interested in technology.
Episodes
What Anthropic’s $1.5B Settlement Means for AI Copyright with Damien Riehl | The Redline Podcast
Damien Riehl is a lawyer, coder, musician, and legal technologist at Clio. He joins Mike Whelan to unpack Anthropic’s $1.5 billion copyright settlement and what it means for AI, creators, and lawyers. They discuss the distinction between training on bo...
1,200 OpenAI Agents Went Rogue. Here’s What Lawyers Need to Know | Kevin Frazier, Texas School of Law
Kevin Frazier teaches at the University of Texas School of Law and studies how we govern emerging technology, with AI now at the top of the list. In this conversation, he and Mike unpack the Hugging Face OpenAI breakout incident, where 1,200 agents coo...
Is AI Making Lawyers Dumber? The Skills Atrophy Problem with Michael Bloom | Michael Bloom, CEO of Praktio
Michael Bloom is the founder and CEO of Praktio, the training platform law firms use to enable new associates to develop practical skills through training that feels like doing the work. Before that, he ran the Transactional Lab & Clinic at University ...
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 disclo...
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...
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. Dur...
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...
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-...
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...
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 mo...
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 ...
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...
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...
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 b...
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 w...
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 exp...
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 checkli...
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 cy...
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 1...
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 e...
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 in...
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 client...
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