Zach Abramowitz is Legally Disrupted
- Episódios
- 62
- Publicação
- quinzenal
- Último episódio
- 5 nov 2026
Sobre o podcast
This is a podcast for the people who want to understand and shape the future of the law.
Hey there, I'm Zach Abramowitz and I am Legally Disrupted! 15 years ago, my legal career was disrupted by tech.
Today, I'm advising the some of the most influential legal service providers in the world on their AI strategy and investing in some of the promising #legalAI startups. Every week, I talk to the builders, founders, operators, and decision-makers driving change in a legal ecosystem being reshaped by AI. We don't just revel in the gloriousness of AI -- we do that too! But, we also break down complex ideas and separate signal from noise. Our content focuses on what’s real, what matters, and what everyone else is missing. So what are you waiting for? Let's get disrupted!
Episódios 62
In Memory of My Dad, Chaim Abramowitz, Of Blessed Memory
Zach takes a break from the regular podcast to say a few words about his late father Chaim Abramowitz. Chaim was a talented athlete, coach, businessman and was an active member of the Houston and Jerusalem …
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Zach takes a break from the regular podcast to say a few words about his late father Chaim Abramowitz. Chaim was a talented athlete, coach, businessman and was an active member of the Houston and Jerusalem community. But, first and foremost, he was a family man.
E61 - How To Get a Job at Harvey, Katie Burke, COO, Harvey
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 …
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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 HarveySubscribe to Zach’s newsletter: https://www.legallydisrupted.com/
Follow Zach on LinkedIn: linkedin.com/in/zachabramowitz
Follow Zach on X: https://x.com/ZachAbramowitz?s=20Follow Katie: https://www.linkedin.com/in/katie-burke-965767a/
Engage Killer Whale Strategies: https://www.killerwhalestrategies.com
Capítulos (19)
E60 - Alex Su, President, Latitude Legal
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 …
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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?Subscribe to Zach’s newsletter: https://www.legallydisrupted.com/
Follow Zach on X: https://x.com/ZachAbramowitz?lang=en
Follow Alex: https://www.linkedin.com/in/alexander-su
Engage Killer Whale Strategies: https://www.killerwhalestrategies.comCapítulos
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E59 - Legora and Legal AI are Moving into Litigation: Greg Mostyn, CEO Wexler.ai
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 …
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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 SaulSubscribe to Zach’s newsletter https://www.legallydisrupted.com/
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
Capítulos
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E58 - Zach and Richard’s Excellent Legal AI Adventure: Will Legal AI Cause Legal to Actually Change?
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 …
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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?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
Capítulos
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E57 - We are a Judgement-First Law Firm, Brian Belt, Founding Partner, Acevedo Belt
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 …
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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?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
Capítulos
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E56 - AI-Pilled, Not AI-First: Arlo Devlin-Brown, Founding Principal, TDB Law
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 …
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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 https://www.killerwhalestrategies.comCapítulos
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E55 - Lawyers Leaving Trad Law for AI-First Firms? Norm Law Partner Batya Nadler
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 …
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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
Capítulos
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E54 - Who Will Win AI for In-House Counsel? Ross McNairn, CEO Wordsmith.ai
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 …
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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
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 https://www.legallydisrupted.com/ Engage Killer Whale Strategies https://www.killerwhalestrategies.com
• 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 legalCapítulos
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E53 - The AI First Firm Valued at Close to $1 Billion, Manifest OS CEO Dan Mishin
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 …
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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
E52 - Is Legal AI a Trillion-Dollar Opportunity? Legora CEO, Max Junestrand
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 …
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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
E51 - Can Open Source Compete with Harvey and Legora? Mike OSS Founder William Chen
What happens when a former lawyer looks at the biggest names in legal AI and decides he can build a competing product in two weeks? In this episode, Zach speaks with Will Chen, founder of Mike, an open-source …
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What happens when a former lawyer looks at the biggest names in legal AI and decides he can build a competing product in two weeks? In this episode, Zach speaks with Will Chen, founder of Mike, an open-source legal AI platform that has quickly gained attention for challenging conventional wisdom in legal tech. They discuss why some lawyers are frustrated with existing legal AI products, the rise of vibe coding, and how AI is making software development more accessible than ever. The conversation also explores open-source legal AI, the growing movement toward law firms building their own tools, and why some believe the future of legal technology may be far more decentralized than today's market leaders expect.In this episode:
- Why Will believes many legal AI products are little more than thin wrappers around frontier models
- How vibe coding is enabling lawyers to build software without traditional engineering backgrounds
- The case for open-source legal AI and local-first deployment in law firms
- Why more firms are exploring building their own AI tools instead of buying them
- How AI could lower the barriers to starting a law firm or legal tech company
Capítulos
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E50 - Inside Harvey with Winston Weinberg, Founder & CEO of Harvey
How did Harvey become the defining company in legal AI and where does the industry go from here? In this episode, Zach speaks with Winston Weinberg, founder and CEO of Harvey, about the company’s rapid rise at …
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How did Harvey become the defining company in legal AI and where does the industry go from here? In this episode, Zach speaks with Winston Weinberg, founder and CEO of Harvey, about the company’s rapid rise at the center of the legal AI boom. They discuss how law firms are actually adopting AI, why legal workflows are uniquely suited for large language models, and what it takes to build products trusted by the world’s top legal organizations. The conversation also explores the evolving relationship between lawyers and AI, the challenges of scaling legal technology, and why the next generation of legal professionals may work very differently than the last.In this episode:
How Harvey became one of the most influential companies in legal AI
What law firms are actually looking for when adopting AI tools
Why legal work is especially well-suited for large language models
The biggest challenges in building trusted AI products for lawyers
How AI could fundamentally reshape the future of legal practice and legal careers
Capítulos
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E49 - Harvey and Legora vs AI First Firms, Logan Brown, Soxton
What happens when you rebuild a law firm from scratch in the age of AI? In this episode, Zach speaks with Logan Brown, founder of Soxton, an AI-first law firm serving startups as an on-demand, AI-powered …
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What happens when you rebuild a law firm from scratch in the age of AI? In this episode, Zach speaks with Logan Brown, founder of Soxton, an AI-first law firm serving startups as an on-demand, AI-powered general counsel. They discuss how Soxton is rethinking legal services from the ground up, why fixed pricing and automation are expanding access to legal help, and where traditional law firms still have the edge. The conversation also dives into the explosion of new startups, the rise of AI-driven litigation, and whether Big Law is facing a slow but inevitable transformation.
In this episode:
How AI-first law firms are redesigning legal services and pricing models
Why startups are delaying hiring in-house counsel with AI-powered alternatives
Where traditional law firms still win—and where they’re most vulnerable
Why AI could drive both more startups and more litigation
How legal careers and firm structures may fundamentally change in the next decade
E48 - What Top VCs Actually Think About Legal AI with Keith Rabois, Khosla Ventures
Money is pouring into legal AI, but how do top-tier investors actually evaluate the space? In this episode, Zach speaks with Keith Rabois, Managing Director at Khosla Ventures and one of the most successful …
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Money is pouring into legal AI, but how do top-tier investors actually evaluate the space? In this episode, Zach speaks with Keith Rabois, Managing Director at Khosla Ventures and one of the most successful investors of the past two decades, about how he thinks about legal tech in the age of AI. They discuss why elite founders are suddenly flocking to legal, the risks facing application-layer startups, and what separates real opportunities from hype. The conversation also explores why Rabois invested in Spellbook, why he’s skeptical of some of the biggest names in legal AI, and how changing incentives across law firms and in-house teams are reshaping the market.
In this episode:
Why top VCs are following talent, not verticals, into legal AI
The biggest risk facing legal AI startups: speed of replication and weak moats
Why in-house legal teams may be a better market than Big Law
What makes Spellbook compelling, and why contracts are the real opportunity
How AI is challenging traditional software economics and long-term value
E47 - Zach and Richard’s Excellent Legal AI Adventure: Harvey and Legora vs Claude?
Is the legal AI race still a two-horse battle, or has a new contender changed everything? In this episode, Zach speaks with Richard Tromans, founder of Artificial Lawyer, about the rapid rise of Claude and what …
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Is the legal AI race still a two-horse battle, or has a new contender changed everything? In this episode, Zach speaks with Richard Tromans, founder of Artificial Lawyer, about the rapid rise of Claude and what it means for the broader legal tech ecosystem. They unpack how frontier model providers are reshaping the market, why law firms are experimenting with multiple AI tools at once, and whether general-purpose AI could start replacing legal-specific platforms. The conversation also explores shifting buying behavior in law firms and in-house teams, the real “moats” in legal AI, and why recent hallucination controversies may say more about legal workflows than the technology itself.
In this episode:
Why Claude is suddenly at the center of the legal AI conversation
How general-purpose AI tools could disrupt legal tech spending
The real competitive moat in legal AI: brand, trust, and distribution
Why law firms are adopting multiple AI models instead of picking one
What AI hallucination cases reveal about legal workflows - not just the tech
E46 - AI for Judges? AAA CEO Bridget McCormack and Learned Hand CEO Shlomo Klapper
Recording at LegalWeek in New York, Zach sits down with Shlomo Klapper (founder of Learned Hand) and Bridget McCormack, former Chief Justice of the Michigan Supreme Court and now CEO of the American Arbitration …
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Recording at LegalWeek in New York, Zach sits down with Shlomo Klapper (founder of Learned Hand) and Bridget McCormack, former Chief Justice of the Michigan Supreme Court and now CEO of the American Arbitration Association, to challenge one of the biggest double standards in legal AI: “AI for me, but not for thee.” Lawyers are now widely using AI, but the moment it touches judges or arbitrators, support drops off.
That hesitation comes as courts are under real strain, with judges handling thousands of cases a year and only minutes to decide each one, and no realistic way to keep up. Shlomo describes Learned Hand’s “AI law clerk,” built to support judicial research, analysis, and drafting, while Bridget brings the perspective of someone who has both made decisions on the bench and now leads a major dispute resolution institution. The conversation moves beyond AI as an assistant and into a harder shift: AI as part of decision-making itself, and whether the system can continue to function without it.
Learn More: Bridget - http://www.aaaicdrfoundation.org/director/bridget-m-mccormack Shlomo - https://www.learned-hand.ai/ Zach - https://www.legallydisrupted.com/ Follow Along: Bridget - https://www.linkedin.com/in/bridget-mary-mccormack-26700b30 Shlomo - https://www.linkedin.com/in/sklapper Zach - linkedin.com/in/zachabramowitzE45 - How to Get a Job at Legora, Harvey and Other Legal AI Startups, Kyle Poe, VP of Legal Innovation at Legora
What does it actually look like to go from practicing law to building the future of legal AI? In this episode, Zach speaks with Kyle Poe, former Big Law partner and now a leader at Legora, about his …
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What does it actually look like to go from practicing law to building the future of legal AI? In this episode, Zach speaks with Kyle Poe, former Big Law partner and now a leader at Legora, about his unconventional path from litigation to legal tech. Kyle shares how early frustrations with outdated legal workflows pushed him to build internal tools, why generative AI changed everything, and what it really takes to break into the legal AI space today. They also dive into how billing models are evolving, the emergence of the “legal engineer,” and why relationships and adaptability may matter more than ever in an AI-driven legal industry.
In this episode:
How Kyle transitioned from Big Law to a leading role in legal AI
Why generative AI is a true inflection point for legal practice
The emergence of the “legal engineer” and new career paths for lawyers
What lawyers get wrong about breaking into legal tech—and how to do it right
How AI is shifting legal careers toward relationships, adaptability, and high-agency work
E44 - Building a Law Firm and a Product: LawPro.ai Co-Founder and Zirkin Schmerling Partner, Josh Schmerling
Zach Abramowitz sits down with Josh Schmerling, partner at Zirkin & Schmerling and co-founder of LawPro.ai, to explore how building technology inside a law firm is reshaping personal injury practice. Josh …
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Zach Abramowitz sits down with Josh Schmerling, partner at Zirkin & Schmerling and co-founder of LawPro.ai, to explore how building technology inside a law firm is reshaping personal injury practice. Josh shares how an internal tool for processing medical records evolved into a broader litigation platform, and what it means to commercialize a product while still running a high-volume plaintiff’s firm. The conversation dives into product-market fit, adoption dynamics, and how tech, combined with private equity, could fundamentally change the competitive landscape of PI law. In this episode:How an internal tool became a market-facing legal tech product
The advantages (and tensions) of building software inside a law firm
What drives real product-market fit in legal tech
Adoption trends across personal injury firms
The role of private equity in reshaping the PI ecosystem
Learn More: Josh - https://www.lawpro.ai/team/josh-schmerling Zach - https://www.legallydisrupted.com/ Follow Along: Josh - https://www.linkedin.com/in/josh-schmerling-287489ab Zach - linkedin.com/in/zachabramowitzE43 - AI and the Future of In-House Legal, Sandstone Co-Founder Jarryd Strydom
What are in-house lawyers actually doing with AI right now? In this episode, Zach speaks with Jarryd Strydom, co-founder of Sandstone, about what he learned from a cross-country road trip meeting with corporate …
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What are in-house lawyers actually doing with AI right now? In this episode, Zach speaks with Jarryd Strydom, co-founder of Sandstone, about what he learned from a cross-country road trip meeting with corporate legal teams across the United States. They discuss how legal departments are experimenting with AI tools, the growing “build vs. buy” debate as lawyers explore vibe-coding their own workflows, and why legacy legal tech infrastructure may struggle in an AI-native world. In this episode:- What in-house lawyers across the U.S. are actually doing with AI today
- The rise of “vibe coding” and the new build vs. buy debate for legal teams
- Why traditional CLM systems often fail to capture real business context
- How AI could finally unlock institutional legal knowledge inside companies
- Why legal teams are being pushed to adopt AI as other departments move faster
- How AI might reshape the structure of in-house legal teams
- What junior lawyers should be thinking about in an AI-driven legal market
Learn More: Jarryd - https://www.event.law.com/corpcounsel-gcc-east/speaker/2017419/jarryd-strydom Zach - https://www.legallydisrupted.com/ Follow Along: Jarryd - https://www.linkedin.com/in/jarrydstrydom Zach - linkedin.com/in/zachabramowitzE42 - Is Legal AI in Trouble or Just Getting Started? Cosmonauts Founder, Timo Karakashev
Just in time for Legal Week, Zach sits down Cosmonauts founder and legal tech insider Timo Karakashev for a wide-ranging conversation about where the legal AI market really stands. Timo shares what he’s seeing …
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Just in time for Legal Week, Zach sits down Cosmonauts founder and legal tech insider Timo Karakashev for a wide-ranging conversation about where the legal AI market really stands. Timo shares what he’s seeing on the ground: growing demand for “premium” legal AI tools, dissatisfaction with generic enterprise AI solutions, and a market that’s still in the very early innings of adoption. In this episode:
- Why legal AI tools like Harvey and Legora feel “premium” compared to generic AI
- The growing dissatisfaction with enterprise AI tools like Copilot
- Why demand for intelligence in legal work far exceeds human supply
- How legal AI adoption differs across regions, including Australia
- The debate over whether AI will disrupt or strengthen the SaaS model
- Why IP law has historically lagged in tech adoption and why that’s changing
- How legal tech conferences are evolving to focus more on practitioners and operators
- Why innovation at the top of the market could eventually improve access to justice
Learn More: Timo - https://www.crunchbase.com/person/timo-karakashev Zach - https://www.legallydisrupted.com/ Follow Along: Timo - https://uk.linkedin.com/in/timo-from-cosmonauts Zach - linkedin.com/in/zachabramowitzE41 - The Future of AI is People: Legal Quants Founders Jamie Tso & Raymond Sun
What if AI doesn’t just replace software, but shifts the value of a tech company from the product to the people? That’s the real shift hiding in plain sight. As the models get better and cheaper, the product …
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What if AI doesn’t just replace software, but shifts the value of a tech company from the product to the people? That’s the real shift hiding in plain sight. As the models get better and cheaper, the product layer starts to collapse. And when that happens, the leverage doesn’t sit with whoever licensed the right platform. It sits with the lawyers who understand what’s happening underneath, the ones building their own workflows, configuring the models directly, and rethinking how legal work is produced in the first place. This isn’t about another AI tool. It’s about agency. It’s about moving from billing time to designing systems. And the gap forming right now between lawyers who experiment and lawyers who hesitate is going to matter a lot more than the next headline valuation.
In this episode:- We’re probably focused on the wrong layer
- As the models improve, the product matters less
- Leverage is shifting toward lawyers willing to build
- This isn’t about adopting AI - it’s about agency
- The gap forming right now is going to compound
References: Legal Quants - https://www.legalquants.com/ Learn More: Zach - https://www.legallydisrupted.com/ Follow Along: Jamie - https://hk.linkedin.com/in/jttso Raymond - https://au.linkedin.com/in/raymond-sun-64576a122 Zach - linkedin.com/in/zachabramowitzE40 - Lawyer Value in an AI World: Litigator, Coder & AI Evangelist Damien Riehl
What does it mean to be a valuable lawyer in the age of AI? In this episode, Zach sits down with litigator, technologist, and AI evangelist Damien Riehl to explore how legal expertise evolves, not disappears …
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What does it mean to be a valuable lawyer in the age of AI? In this episode, Zach sits down with litigator, technologist, and AI evangelist Damien Riehl to explore how legal expertise evolves, not disappears, in a world of generative models and automation. From his unique path as both a practicing attorney and self-taught coder to his widely discussed “All the Music” project, Damien argues that the future belongs to lawyers who understand systems, leverage technology, and rethink what clients actually pay for. This is a conversation about professional reinvention, leverage, and why AI may amplify - rather than replace - the best lawyers.
In this episode:
- Why AI changes how lawyers deliver value, but not why they matter
- The advantage of lawyers who can code (or at least think like engineers)
- Damien’s “All the Music” project and what it reveals about IP systems
- The difference between automation and augmentation in legal work
- How litigators should think about AI tools today
- Why understanding technology is becoming table stakes for legal credibility
- What the next generation of high-value lawyers will look like
E39 - AI vs Legacy SaaS in Legal: Min-Kyu Jung, CEO Ivo
Zach sits down with Min-Kyu Jung, founder of Ivo, to unpack one of the most honest AI startup stories in legal tech. This episode explores what it really takes to pivot in an AI revolution, why CLM may be in …
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Zach sits down with Min-Kyu Jung, founder of Ivo, to unpack one of the most honest AI startup stories in legal tech. This episode explores what it really takes to pivot in an AI revolution, why CLM may be in trouble, and how in-house legal teams are rethinking ROI in the age of AI.
In this episode:- Why Ivo scrapped its original product to go all-in on LLMs
- The “innovator’s dilemma” facing legacy CLM vendors
- Why in-house legal and law firms are fundamentally different AI markets
- How AI playbooks and redlining actually create ROI
- The shift from “adoption” to measurable business impact
- Why speed often matters more than accuracy in AI UX
- How contract intelligence is becoming CLM 2.0
E38 - How Will SaaSpocalypse Affect AI For Legal: Spellbook CEO Scott Stevenson
Zach checks in with second-time guest, Spellbook CEO, Scott Stevenson for a wide ranging conversation on some of the hottest topics of the day: Why positioning AI for Legal as a two horse race is deeply flawed …
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Zach checks in with second-time guest, Spellbook CEO, Scott Stevenson for a wide ranging conversation on some of the hottest topics of the day:
Why positioning AI for Legal as a two horse race is deeply flawed
The benefits of selling direct to lawyers as opposed to Chief Innovation Officers
In-house legal buyers versus law firms
BigLaw versus small and medium size law firms
- How AI Startups will need to contend with the SaaSpocalypse
E37 - Zach and Richard’s Excellent Legal AI Adventure: Claude and the Legaltech Apocalypse
Zach reunites with Richard Tromans of Artificial Lawyer for another wide-ranging Legal AI Adventure, breaking down what it really means now that major AI players like Anthropic are officially entering the legal …
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Zach reunites with Richard Tromans of Artificial Lawyer for another wide-ranging Legal AI Adventure, breaking down what it really means now that major AI players like Anthropic are officially entering the legal market. From the impact on commoditized legal AI tools to the rise of vibe coding, agentic workflows, and the looming decline of legacy legal tech implementations, Zach and Richard explore where legal AI is heading, and where lawyers should (and shouldn’t) be placing their bets as the industry moves toward an AI 2.0 era.In this episode:
Will LLMs Kill LegalAI or Legacy SaaS
Vibe coding vs enterprise software
- Generic AI versus Legal Applications
- Implementations are a grift
- The limits of automation
- What will AI 2.0 mean for lawyers?
E36 - Too Much FOMO: Why I'm Back on the Legal AI Startup Investor Train with Sandstone CEO Nick Fleisher
Zach announces that, for the first time since ChatGPT launched, he's investing in a legal AI startup. In this episode, he's joined by Nick Fleisher, CEO of Sandstone, to unpack why in-house legal teams, not law …
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Zach announces that, for the first time since ChatGPT launched, he's investing in a legal AI startup. In this episode, he's joined by Nick Fleisher, CEO of Sandstone, to unpack why in-house legal teams, not law firms, may be the biggest winners of the AI era. Drawing on Nick's background at McKinsey where he advised law firms on AI, the conversation explores why legacy tools are failing lawyers and how AI can solve a problem that plagues in-house teams: working seamlessly with their business without slowing them down and being a bottleneck.
In this episode:
Why Zach decided to invest in a legal AI startup now
What in-house legal teams actually need from AI
Why CLM tools struggle with adoption and ROI
How AI changes legal’s relationship with the business
Measuring success beyond “time to contract”
Why vertical legal software beats generic AI tools
What makes Sandstone different from Harvey, Legora, and CLMs
References:
Learn More:
Zach - legallydisrupted.com
Nick - sandstone.comFollow Along:
Zach - linkedin.com/in/zachabramowitz
Nick - https://www.linkedin.com/in/nicholas-fleisherE35 - Are Legal AI Assistants Moving In-House? GC AI Founder Cecilia Ziniti
Zach speaks with Cecilia Ziniti, founder and CEO of GC AI, about why in-house legal teams are often ahead of law firms when it comes to adopting AI - and what that signals for the future of the profession …
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Zach speaks with Cecilia Ziniti, founder and CEO of GC AI, about why in-house legal teams are often ahead of law firms when it comes to adopting AI - and what that signals for the future of the profession. Drawing on her experience as a former general counsel and AI leader, Cecilia explains why legal AI must be purpose-built for real workflows, how trust and precision shape adoption, and why lawyers who learn to work with AI will gain a lasting edge.
In this episode:
Why in-house legal teams are leading AI adoption
The limits of generic AI tools for legal work
What lawyers actually need from AI systems
Trust, accuracy, and citations in legal AI
How AI is reshaping legal workflows and roles
What it means to be an “AI-native” lawyer
Learn More:
Zach - legallydisrupted.com
Cecilia - https://gc.ai/company/aboutFollow Along:
Zach - linkedin.com/in/zachabramowitz
Cecilia - https://www.linkedin.com/in/ceciliazinitiE34 - How Will AI Work with Document Management? NetDocuments CPO Dan Hauck
Zach sits down with NetDocuments Chief Product Officer Dan Hauck to unpack how AI is truly being used inside law firms and in-house legal teams today - from large-scale document profiling to agentic assistants …
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Zach sits down with NetDocuments Chief Product Officer Dan Hauck to unpack how AI is truly being used inside law firms and in-house legal teams today - from large-scale document profiling to agentic assistants that search, summarize, and edit directly within the DMS. Recorded live at ND Inspire conference, Dan explains why lightweight models are unlocking new automation, how in-house teams are often leading on adoption, and why the real ROI of legal AI goes beyond efficiency to include better onboarding, less isolation, and more confident decision-making for lawyers at every level.
In This EpisodeThe biggest changes Dan has witnessed after 8 years of the Inspire conference
How firms are using AI at scale — not just on pilot use cases
Why automated document profiling is now possible across millions of docs
Understanding small models vs. large models in legal workflows
How AI pipelines classify, extract, and enrich metadata instantly
New use cases emerging inside the DMS (repapering, diligence, discovery, onboarding)
Why in-house teams are often ahead of firms in AI adoption
How agentic AI assistants reduce loneliness and cognitive overload
The ROI debate: real numbers vs. intangible benefits
What lawyers gain: better focus, faster context loading, and stronger client service
Why this moment feels like a once-in-a-generation shift in legal technology
Learn More:
Zach - legallydisrupted.com
Dan - https://www.netdocuments.com/company/our-people/dan-hauck/Follow Along:
Zach - linkedin.com/in/zachabramowitz
Dan - https://www.linkedin.com/in/danhauckE33 - Building the AI-First Law Firm: Jen Berrent on Covenant and the Next Era of Legal Services
Zach talks with Jen Berrent, former WeWork executive and founder of Covenant, an AI-first law firm reimagining how deals get done. They dive deep into what it means to build a law firm from the ground up around …
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Zach talks with Jen Berrent, former WeWork executive and founder of Covenant, an AI-first law firm reimagining how deals get done. They dive deep into what it means to build a law firm from the ground up around artificial intelligence — not as a tool, but as the foundation. Jen shares her perspective on why too much work still runs through Big Law, how AI is transforming the middle tier of legal work, and what it takes to balance human expertise with machine efficiency.
In this episode:
What an “AI-first” law firm actually looks like
How Covenant is redesigning legal workflows from scratch
The problem with Big Law’s “too much work, too few alternatives” model
Why reading comprehension is AI’s legal superpower
Building client trust in the age of automation
How AI can accelerate deals — without sacrificing rigor
The difference between a “relationship ramp” and a “SaaS snowball”
The challenges (and advantages) of raising funding in legal AI
Lessons from Robin AI’s struggles — and why clarity of business model matters
Why this is a once-in-a-generation moment for lawyers who want to innovate
Learn More:
Zach – legallydisrupted.com
Jen – https://covenant.co/aboutFollow Along:
Zach – linkedin.com/in/zachabramowitz
Jen – https://www.linkedin.com/in/jenniferberrent
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