Lawyers have been reaching out to me about breaking into legal tech for years. Now engineers at some of the biggest tech companies in the world are looking at Harvey too, and I think that's the clearest signal yet that professional services became a hot space to be in, and that just wasn't true a few years ago. Katie Burke spent nearly twelve years at HubSpot before betting on Winston, Gabe and Harvey. She explains why Harvey doesn't want lawyers running from Big Law, what makes someone stand out in an interview, and why top engineers suddenly want to work in legal. And yes, someone still tweets that Harvey is going to zero every six months.

In this episode:

0:00 Zach’s Hot Disruptive Legal Take 4:22 Why Katie Burke Left HubSpot for Harvey 8:48 Betting on Winston and Gabe in Their 20s 11:39 The “Harvey Is Going to Zero” Tweet Cycle 12:54 Is There Actually a Moat in Legal AI? 15:23 Is Harvey Only for Big Law Juniors? 18:01 Can Harvey Compete With the Frontier Models? 20:55 Harvey’s Killer Feature May Be Its SLAs 22:37 Why Top Engineers Suddenly Want to Work in Legal 25:40 How Many Harvey Employees Are Lawyers? 27:34 Who Works Harder: Big Law or Harvey? 30:18 Does Working at Harvey Burn People Out? 32:30 The #1 Way to Stand Out in a Harvey Interview 36:18 Where Harvey Is Hiring Right Now 38:00 The HubSpot Playbook at Harvey 39:50 Should You Even Make a Three-Year Plan? 41:18 Dharmesh Shaw Called It in 2023 42:30 You Don’t Need to Write Code to Use AI 45:08 Where to Find Open Roles at Harvey

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Alex Su is one of those people I need to catch up with every now and then just to see what he's thinking. Since we recorded this, Alex was named President of Latitude Legal. He understands both the people selling lawyers on change and the lawyers they're trying to convince, and those two groups don't always see the same world. We get into Harvey, Legora and Claude, the billable hour, junior associates, where human judgment still matters, why trust may be part of Harvey's moat, and how both of us are using AI differently now than we were in 2023.

0:00 Zach's Hot Disruptive Legal Take 3:22 Harvey vs. Legora vs. Claude 5:58 Can Claude Gobble Up Harvey? 8:00 Why Haven't Junior Associates Been Replaced? 10:30 In-House Is Outpacing Law Firms on AI 12:49 Why Hasn't AI Killed the Billable Hour? 17:49 Why Hourly Rates Could Go Up 20:04 Is Anyone Less Busy Because of AI? 22:39 Where AI-Native Law Firms Could Win 24:28 If NDAs Are Never Litigated, Why Sign Them? 28:06 AI Made My Content More Human 31:11 How We Actually Use AI for Writing 38:28 How Many Lawyers Do You Need With AI? 40:22 When AI Gets Better, Trust Matters More 44:50 Has Harvey Built a Moat? 46:54 How Do You Compete With Harvey? 49:06 Is CLM Dead in the Water?

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Legora just acquired Wexler, and I think it's the clearest signal yet that AI in law is moving from transactional work to litigation. Gregory Mostyn, co-founder and CEO of Wexler, built the company just to the right of discovery. Not doc review, what happens when the documents actually hit the lawyers. He explains why he bet on facts instead of documents, why he stayed a scalpel while Harvey and Legora built Swiss Army knives, and why a company that wasn't for sale sold anyway. I also pushed him on the two questions I get from lawyers every week. Are we in a bubble? And if the models are this good, why buy anything at all instead of building it yourself? His answer to the second one is the part I'd replay. And yes, the company is named after Kim Wexler.

In this episode:

00:00 - Zach’s Hot Disruptive Legal Take 07:33 - Already Seeing the Benefits of Joining Legora 08:26 - Wexler Is Just to the Right of eDiscovery 10:44 - The Atomic Unit of Analysis Is Facts 13:12 - Building a “Case Brain” 15:02 - Scalpel vs. Swiss Army Knife 17:21 - AI for Litigators 21:08 - Are We in an AI Bubble? 24:24 - Product Advice from an Old-School Judge 26:53 - Why Security and Accuracy Are More Important than Speed 28:59 - The Main User of Wexler Is the Wexler Agent 30:55 - Can You Run AI Live in a Deposition? 33:57 - Can Lawyers Build This Themselves? 38:46 - Story behind Legora’s Acquisition 43:50 - Getting in the Room Is the Hard Part 46:01 - Will AI Kill Relativity? 46:58 - Inspired by Kim Wexler from Better Call Saul

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Richard Tromans of Artificial Lawyer is back with Zach and on the attack as they square up over whether massive Legal AI funding, truly signals systemic transformation. They then discuss whether these massive sums of money are hitting a tipping point and what could happen if the levee breaks. Maybe the legal industry is simply running in place.

In this Episode:

00:00 Zach’s Hot Disruptive Legal Take 00:42 Could Harvey be Valued at $16B? 01:50 Legal AI Fatigue 03:20 Harvey, Legora and The Big Short? 08:46 Legal AI a Luxury Handbag Market? 10:31 AI Wizards and Muggles in Big Law 13:35 The Seeds of Systemic AI Impact 21:36 Valuations Signal Technology is Essential In Legal Service Delivery 23:02 Jevons Paradox and the Volume of Modern Contracts 30:08 AI Still Needs Daycare 36:48 “New Mod” and “AI First” Firms are Pressuring Big Law 44:18 Is the Market Wrong on TR/Lexis 49:48 Are Chief AI Officers CINOs Differently Packaged?

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Learn more about Richard - tromansconsulting.com, artificiallawyer.com

Follow Richard - linkedin.com/in/artificiallawyer, https://x.com/ArtificialLawya

A 35-Year Big Law Veteran Is Doing the Best Work of His Career With AI But He Doesn’t Call His Firm AI-First. Brian Belt explains why Acevedo Belt is “judgment-first,” why he thinks legal AI is a bargain, and how AI is changing everything from junior-lawyer training to the kinds of matters a small firm can take on.

In this episode:

0:00 Zach's Hot Disruptive Legal Take 4:25 The Big Law Veteran Who Loves AI 6:21 "Harvey Writes Better Than I Do" 7:39 Why "ROI" Is the Wrong Metric 11:13 Clients Notice the Difference 13:47 You Can Finally Train Junior Associates 16:07 New Way to Train Associates 21:17 Scaling Up and Scaling Down 24:24 Why Harvey Is Better for Small Firms 28:46 Legal AI is a Bargain! 34:46 Process Mapping & the Best Use Cases 36:59 Why Not Just Use the Base Models? 37:54 Do Your Old Big Law Colleagues Get It? 40:32 What Is a "Judgment-First" Law Firm? 43:21 Do the Best Lawyers Run on No Sleep?

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Follow Brian on LinkedIn: https://www.linkedin.com/in/brianbelt

Engage Killer Whale Strategies: https://www.killerwhalestrategies.com

What happens when a veteran litigator starts treating AI less like a chatbot and more like an operating system for his cases? In this episode, Zach speaks with Arlo Devlin-Brown, founder of TDB Law, about how AI is changing the way he actually practices law. They discuss why AI may be particularly powerful for litigators, how Arlo has built an AI-powered system that continuously tracks his cases, and why the technology is more useful for exploring arguments and strategy than simply generating finished work. The conversation also explores the future of junior lawyers, why big law’s leverage model may be under pressure, and why Arlo rejects the idea that firms should sell themselves as “AI-native” rather than simply being excellent lawyers who use AI well.

In this episode:

Why AI may be more transformative for litigation than transactional law

How Arlo uses AI as an operating system and shared memory for his cases

Why AI can make junior lawyers more valuable, not obsolete

How AI could fundamentally reshape the Big Law leverage model

Why “AI-native” law firms may be missing the point

What happens when a veteran Big Law attorney leaves a traditional partnership to help build a law firm from scratch? In this episode, Zach speaks with Batya Nadler, Partner at Norm Law, about her decision to join one of the legal industry's most ambitious AI-native firms. They discuss how Norm combines experienced lawyers with legal engineers and AI agents, why repeatable legal workflows are the ideal starting point for automation, and how AI is changing, not replacing, the role of senior attorneys. The conversation also explores why client relationships remain the foundation of legal practice, what skills lawyers need to thrive in an AI-first world, and why Batya believes the future belongs to firms built around AI from day one.

In this episode:

• Why Batya left Big Law to help build an AI-native law firm from the ground up
• How legal engineers and AI agents are transforming repeatable legal workflows
• Why senior lawyers remain essential, even as AI automates more legal work
• How Norm is rethinking the traditional law firm model around AI-native infrastructure
• What lawyers can do today to become AI-fluent and prepare for the future of legal practice

In this episode:

•⁠ ⁠Why AI is turning general counsel into technology leaders inside their organizations •⁠ ⁠Why enterprise legal teams need more than ChatGPT to transform their workflows •⁠ ⁠How legal departments can finally measure ROI and demonstrate business value •⁠ ⁠Why traditional CLM systems failed and what comes next •⁠ ⁠How legal engineering is becoming one of the most important new roles in corporate legal