Zach Abramowitz is Legally Disrupted

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 Take4:22 Why Katie Burke Left HubSpot for Harvey8:48 Betting on Winston and Gabe in Their 20s11:39 The “Harvey Is Going to Zero” Tweet Cycle12:54 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 SLAs22:37 Why Top Engineers Suddenly Want to Work in Legal25:40 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 Interview36:18 Where Harvey Is Hiring Right Now38:00 The HubSpot Playbook at Harvey39:50 Should You Even Make a Three-Year Plan?41:18 Dharmesh Shaw Called It in 202342:30 You Don’t Need to Write Code to Use AI45:08 Where to Find Open Roles at Harvey
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Follow Zach on LinkedIn: linkedin.com/in/zachabramowitzFollow Zach on X: https://x.com/ZachAbramowitz?s=20
Follow Katie: https://www.linkedin.com/in/katie-burke-965767a/
Engage Killer Whale Strategies: https://www.killerwhalestrategies.com

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 Take3:22 Harvey vs. Legora vs. Claude5:58 Can Claude Gobble Up Harvey?8:00 Why Haven't Junior Associates Been Replaced?10:30 In-House Is Outpacing Law Firms on AI12:49 Why Hasn't AI Killed the Billable Hour?17:49 Why Hourly Rates Could Go Up20:04 Is Anyone Less Busy Because of AI?22:39 Where AI-Native Law Firms Could Win24:28 If NDAs Are Never Litigated, Why Sign Them?28:06 AI Made My Content More Human31:11 How We Actually Use AI for Writing38:28 How Many Lawyers Do You Need With AI?40:22 When AI Gets Better, Trust Matters More44:50 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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Follow Zach on X: https://x.com/ZachAbramowitz?lang=enFollow Alex: https://www.linkedin.com/in/alexander-suEngage Killer Whale Strategies: https://www.killerwhalestrategies.com

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 Take07:33 - Already Seeing the Benefits of Joining Legora08:26 - Wexler Is Just to the Right of eDiscovery10:44 - The Atomic Unit of Analysis Is Facts13:12 - Building a “Case Brain”15:02 - Scalpel vs. Swiss Army Knife17:21 - AI for Litigators21:08 - Are We in an AI Bubble?24:24 - Product Advice from an Old-School Judge26:53 - Why Security and Accuracy Are More Important than Speed28:59 - The Main User of Wexler Is the Wexler Agent30:55 - Can You Run AI Live in a Deposition?33:57 - Can Lawyers Build This Themselves?38:46 - Story behind Legora’s Acquisition43:50 - Getting in the Room Is the Hard Part46:01 - Will AI Kill Relativity?46:58 - Inspired by Kim Wexler from Better Call Saul
 
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Follow Zach on X https://x.com/ZachAbramowitz?lang=en
Follow Gregory https://uk.linkedin.com/in/gregory-mostyn-9b3a89b8
Engage Killer Whale Strategies https://www.killerwhalestrategies.com

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 Take00:42  Could Harvey be Valued at $16B?01:50   Legal AI Fatigue03:20  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 Impact21:36   Valuations Signal Technology is Essential In Legal Service Delivery23:02   Jevons Paradox and the Volume of Modern Contracts30:08   AI Still Needs Daycare36:48   “New Mod” and “AI First” Firms are Pressuring Big Law44:18   Is the Market Wrong on TR/Lexis49:48   Are Chief AI Officers CINOs Differently Packaged?
 
Subscribe to Zach’s newsletter https://www.legallydisrupted.com/
Follow Zach on X https://x.com/ZachAbramowitz?lang=en
Engage Killer Whale Strategies https://www.killerwhalestrategies.com
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 Take4:25      The Big Law Veteran Who Loves AI6:21      "Harvey Writes Better Than I Do"7:39      Why "ROI" Is the Wrong Metric11:13     Clients Notice the Difference13:47     You Can Finally Train Junior Associates16:07     New Way to Train Associates21:17     Scaling Up and Scaling Down24:24     Why Harvey Is Better for Small Firms28:46     Legal AI is a Bargain!34:46     Process Mapping & the Best Use Cases36:59     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?
 
Subscribe to Zach’s newsletter: https://www.legallydisrupted.com/
Follow Zach on X: https://x.com/ZachAbramowitz?lang=en
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
 
Subscribe to Zach’s newsletter
https://www.legallydisrupted.com/
 
Follow Zach on X
https://x.com/ZachAbramowitz?lang=en
 
Follow Along on LinkedIn:
Arlo - https://www.linkedin.com/in/arlodb
Zach - www.linkedin.com/in/zachabramowitz
 
Engage Killer Whale Strategies
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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
 
Subscribe to Zach’s newsletter
https://www.legallydisrupted.com/
 
Follow Zach on X Zach 
https://x.com/ZachAbramowitz?lang=en
 
Follow Batya
https://www.linkedin.com/in/batya-nadler-1ba85410
 
 
Engage Killer Whale Strategies
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Why are some general counsel suddenly becoming the most influential executives in the C-suite? In this episode, Zach speaks with Ross McNairn, founder and CEO of Wordsmith, about why AI is fundamentally changing the role of in-house legal teams. They discuss how legal departments are evolving from cost centers into strategic operators, why generic AI chatbots aren't enough for enterprise legal work, and how the next generation of legal technology will help GCs measure ROI, manage legal operations, and reduce reliance on outside counsel. The conversation also explores why traditional CLM systems have fallen short, the emergence of legal engineering, and what the future of corporate legal teams looks like in an AI-native world.
 
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
 
Follow Along:
Ross - https://x.com/rossmcnairn?lang=en, https://www.linkedin.com/in/rossmcnairn
Zach - https://x.com/ZachAbramowitz?lang=en, www.linkedin.com/in/zachabramowitz
 
Subscribe to Zach’s newsletter
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Engage Killer Whale Strategies
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Why would top venture capital firms invest $60 million into an immigration law startup at a $750 million valuation? In this episode, Zach speaks with Dan Mishin, founder and CEO of Manifest, about his vision for transforming one of the most complex and underserved areas of legal practice. They discuss why immigration law became the company's first focus, how AI is helping lawyers process cases faster and more accurately, and why Manifest is building far more than a traditional law firm. The conversation explores the challenges facing both lawyers and clients in the immigration system, the opportunity to create AI-native legal infrastructure, and what happens when software, operations, and legal expertise are combined into a single platform.
 
In this episode:
Why investors valued Manifest at $750 million after its first major funding round
How AI is transforming immigration law through speed, accuracy, and automation
Why Manifest is building legal infrastructure, not just another law firm
The hidden operational problems holding back many legal practices
How AI-native platforms could help lawyers serve more clients at lower cost
 
Learn More:
https://www.legallydisrupted.com/
 
Follow Along:
Dan - https://x.com/mishindan1, https://www.linkedin.com/in/danielmishin
Zach - https://x.com/ZachAbramowitz?lang=en, www.linkedin.com/in/zachabramowitz
 
Subscribe to Zach’s newsletter https://www.legallydisrupted.com/
 
 
Engage Killer Whale Strategies
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As AI capabilities accelerate, how should law firms and legal departments prepare for a future where agents can perform increasingly complex legal work? In this episode, Zach speaks with Max Junestrand, CEO and co-founder of Legora, about the rapid evolution of legal AI and what it means for the future of legal services. They discuss the recent wave of law firms building their own AI initiatives, why legal teams are adopting AI faster than many realize, and how firms can rethink their business models in an agent-driven world. The conversation also explores the role of legal-specific AI products, the growing importance of transformation partners, and why Max believes legal AI represents a trillion-dollar opportunity.
 
In this episode:
Why law firms are investing heavily in AI
How legal teams can prepare for a future where AI agents perform increasingly complex work
Why legal-specific AI products still matter in a world of Claude, GPT, and other frontier models
How AI is changing the economics of legal services and creating new opportunities for firms
Why Max believes legal AI could become a trillion-dollar market opportunity
Subscribe to Zach’s newsletter
https://www.legallydisrupted.com/
 
Follow Zach on X
https://x.com/ZachAbramowitz?lang=en
 
Follow Max on X
https://x.com/MaxJunestrand
 
Engage Killer Whale Strategies
https://www.killerwhalestrategies.com