Technically Legal - A Legal Technology and Innovation Podcast - Podcasts

40:18

Best of TL: Legal's Moment to Move Beyond AI...

Technically Legal - A Legal Technology and Innovation... ·

2026/10/01

We welcome back Sabastian Niles, President and Chief Legal Officer at Salesforce, to discuss his recent "Open Letter to Law Firms." As the legal industry hits a critical inflection point, Sabastian argues that the era of "AI theater" and small-scale pilots is over. The conversation dives deep into the Innovator's Dilemma facing law firms, the shift toward agentic AI, and how firms must reimagine their business models to remain competitive. Sabastian highlights that legal professionals are uniquely

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41:57

On AI Evals, TAR vs. LLMs and What Will be Different...

Technically Legal - A Legal Technology and Innovation... ·

2026/09/17

In advance of this year's RelFest in Chicago, Aron Ahmadia, Vice President of Applied Science at Relativity, joins the podcast to discuss AI evaluation, AI benchmarking and the transition from traditional Technology Assisted Review (TAR) to generative AI in legal document review and eDiscovery. The conversation covers the daily operations of a global AI team, the concept of "evaluation as a product," and the methodology behind testing large language models (LLMs) for legal tasks. Aron also discusses

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32:53

Moving Beyond the Billable Hour: Pricing Legal Work...

Technically Legal - A Legal Technology and Innovation... ·

2026/09/03

Emily Logan Stedman, commercial litigator at Husch Blackwell, discusses moving beyond the billable hour not just to modernize legal billing but to also prioritize lawyer well-being. The conversation explores the practical steps required to transition traditional litigation models toward Alternative Fee Arrangements (AFAs). Emily details her methodical approach to utilizing secure legal AI tools to analyze historical time entries, allowing her to offer phased flat fees, strategic counsel

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34:07

AI Regulation: Where it is and Where it Might (or...

Technically Legal - A Legal Technology and Innovation... ·

2026/08/20

In this episode, Justin Wales, Chief Legal Officer for Crypto.com makes a second visit to the podcast. This time around, he discusses his new book, The AI Legal Handbook, the emerging regulatory landscape, liability frameworks, and practical applications of artificial intelligence. Justin outlines how attorneys and regulators should approach modern AI models, the mechanics behind AI, and the effect of generative AI on legal education. The discussion covers key regulatory principles, the balance

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31:50

From Managing Partner to Intel CLO: Career Lessons...

Technically Legal - A Legal Technology and Innovation... ·

2026/08/06

In this episode April Miller Boise, with stints as Chief Legal Officer at Intel and managing partner at Thompson Hine, shares insights from her career. The conversation explores the shifting dynamics between corporate legal departments and outside counsel and the necessity of embracing legal technology. April also provides advice for junior lawyers on developing long-term expertise and trusted relationships in an AI-driven environment. Things we Talk About in this Episode Career progression: From

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50:20

When Machines Have the Answers, Build Better Humans...

Technically Legal - A Legal Technology and Innovation... ·

2026/07/23

In this episode, theoretical neuroscientist Vivienne Ming discusses her new book, Robot Proof - When Machines Have All the Answers, Build Better People. The conversation examines the intersection of artificial intelligence and knowledge work, exploring how professionals can adapt to an increasingly automated economy. The discussion contrasts the limitations of basic AI task automation with the advantages of human-AI collaboration—the "cyborg" model—for solving complex, ill-posed problems. Ming

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30:07

Inside Microsoft Legal: A Look at AI Use Built for...

Technically Legal - A Legal Technology and Innovation... ·

2026/07/09

This episode features a discussion between host Chad Main and Rebecca Anderson, Head of Legal EMEA, Associate General Counsel at Microsoft, regarding the integration of artificial intelligence in corporate legal departments. The conversation covers Rebecca's career progression from a law firm associate to an international in-house counsel role. The core of the discussion examines Microsoft's internal AI deployment strategies, including the shift from personal productivity to intent engineering

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29:59

Cost, Speed and Quality - One Law Firm's Quest to...

Technically Legal - A Legal Technology and Innovation... ·

2026/06/25

In this episode of Technically Legal, veteran patent lawyer Laurence Brown and Partner at the UK-based intellectual property firm EIP discusses the evolving concept of the "AI-native" law firm and how EIP is actively navigating this transition through their hybrid intelligence service, Visser AI. Laurence shares insights from his 25-year career, discussing how EIP uniquely integrates litigators and patent attorneys to provide comprehensive IP services. The core of the conversation centers on

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31:59

Affordable & Accessible: The Democratization of Legal...

Technically Legal - A Legal Technology and Innovation... ·

2026/06/11

Tyler Foreman, the Vice President of AI at Rocket Lawyer, joins the show to discuss the intersection of artificial intelligence and the legal industry. Foreman shares his untraditional legal tech career path, spanning engineering at Intel, drone data analytics, and ultimately making the move to legal via contract lifecycle management (CLM) at DocuSign, before diving into his current work at Rocket Lawyer helping to provide legal resources for small-to-medium businesses and individuals. The

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51:29

Building Software for Less: The Death of Expensive...

Technically Legal - A Legal Technology and Innovation... ·

2026/05/28

We catch up with legal tech entrepreneur Nathan Wenzel to discuss his journey from founding and exiting SimpleLegal to launching his newest venture, LegalOperator.ai (formerly Lexiomatic). Nathan shares insights on the evolution of private equity (PE) structures, the shifting economics of the enterprise software market, and how artificial intelligence is disrupting traditional software development and corporate legal operations. Key Takeaways The Reality of Private Equity: Nathan breaks down the

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34:54

The Rise of the Legal Quants (Jamie Tso & Raymond Sun)

Technically Legal - A Legal Technology and Innovation... ·

2026/05/14

Jamie Tso and Ray Sun, the founders of LegalQuants, discuss a fundamental shift in the legal profession: the transition from legal engineering to "legal quant" work. The conversation explores how technically fluent lawyers are using vibe coding, frontier AI models, and first-principles thinking to move beyond mere efficiency and toward the complete redesign of legal services. Jamie and Ray share their backgrounds in Big Law and their journeys into building custom legal tech tools. They delve into

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40:18

The AI Pilot is Over: Legal's Moment to Move Beyond...

Technically Legal - A Legal Technology and Innovation... ·

2026/04/30

We welcome back Sabastian Niles, President and Chief Legal Officer at Salesforce, to discuss his recent "Open Letter to Law Firms." As the legal industry hits a critical inflection point, Sabastian argues that the era of "AI theater" and small-scale pilots is over. The conversation dives deep into the Innovator's Dilemma facing law firms, the shift toward agentic AI, and how firms must reimagine their business models to remain competitive. Sabastian highlights that legal professionals are uniquely

en

36:26

Ayana Dow on Updating Crypto Regulation and...

Technically Legal - A Legal Technology and Innovation... ·

2026/04/16

Ayana Dow, Senior Counsel at the DeFi Education Fund (DEF) shares her unique career trajectory from Big Law and Capitol Hill to the forefront of decentralized finance policy. The discussion centers on the critical need for regulatory clarity in crypto, the distinction between decentralized protocols and centralized entities, and the ongoing efforts to educate lawmakers on blockchain technology. Key takeaways include an analysis of how current market structure bills might shift oversight to the CFTC

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38:41

Descrybe's Quest to Democratize Legal Research (Kara...

Technically Legal - A Legal Technology and Innovation... ·

2026/04/02

Kara Peterson and Richard DiBona, the husband-and-wife co-founding team behind Descrybe, discuss the legal research platform they built designed to "democratize access to the law." The discussion explores the unique dynamics of married cofounders and how they are leveraging Generative AI to disrupt a landscape long dominated by high-cost legacy providers. Richard, a software engineer, and Kara, a marketing expert, share their journey from a personal legal issue to building a platform that processes

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45:05

The Uberization of UPL? How AI Is Outpacing the...

Technically Legal - A Legal Technology and Innovation... ·

2026/03/19

The legal industry is not confronting a single disruption but a redistribution of work, capital, and regulation across a system under stress. The boundaries of Unauthorized Practice of Law (UPL) in the near term may be defined more by what regulators must allow than what they restrict. These are just a couple of conclusions from author and legal business strategist Ken Crutchfield in a recent trilogy of articles he penned about the pressure artificial intelligence is placing on legal service

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56:02

From Water Pistols to Tanks: Why Data Science is the...

Technically Legal - A Legal Technology and Innovation... ·

2026/03/05

Donald Beshada, former litigator turned legal tech entrepreneur and CEO of Covalynt shares his journey from big-law to the forefront of using data science in litigation. Specifically, to address systemic fraud in class action settlements. The conversation explores the evolution of claims administration—from the traditional "People Magazine" notice era to the current digital landscape dominated by targeted advertising and sophisticated fraud bots. Donald explains how his company uses data science and

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37:37

Stacking Legal Skills: How Stints at Big Law, Biz Dev...

Technically Legal - A Legal Technology and Innovation... ·

2026/02/19

Akshay Verma, COO of SpotDraft explores his non-linear journey through the legal industry. From his early days as a big-law paralegal to lawyer to a business development role to leading legal operations at tech leaders like Facebook and Coinbase, Akshay shares his unique perspective on why the most successful legal departments prioritize process over technology. The conversation dives deep into the realities of Contract Lifecycle Management (CLM), the evolution of the "agentic" legal tool, and why

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30:59

The Legal Ops Force Multiplier: How Nextdoor GC...

Technically Legal - A Legal Technology and Innovation... ·

2026/02/05

Sophia Contreras Schwartz, General Counsel at Nextdoor, discusses her unique journey of building a legal department from the ground up. Sophia discusses how her background as a musician and fitness instructor informs her collaborative leadership style and why Nextdoor identifies as "Middle Tech"—a category of companies often overlooked by one-size-fits-all regulations. The conversation explores the strategic value of hiring Legal Operations early, the specific tech stack that keeps a lean team of

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27:24

Tokenization of Real World Assets: From Art to Real...

Technically Legal - A Legal Technology and Innovation... ·

2026/01/22

Lucas Moskowitz, General Counsel at Robinhood returns to the show to talk tokenization of Real World Assets and the current state of crypto legislation. Lucas updates us on Robinhood's evolving demographics, noting that while the platform remains a hub for first-time investors, the customer base is maturing alongside the platform's product offerings, such as retirement matching and advisory services. Moskowitz also highlights the company's commitment to financial literacy. The core of the

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27:29

Bridging Law Firm Silos: How Law Firms Can Maximize...

Technically Legal - A Legal Technology and Innovation... ·

2026/01/08

In this episode, James Barclay, CEO of Passle, discusses how legal technology is evolving to solve a big challenge in the legal industry: cross-selling. James shares the journey of Passle—from its roots in the early internet gold rush to becoming a leading thought leadership platform for the Am Law 200. The conversation covers Passle's new AI-driven tool, CrossPitch, which helps attorneys overcome the "trust and awareness" barriers that prevent internal collaboration and revenue. James explains that

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Technically Legal - A Legal Technology and Innovation Podcast

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