Technically Legal - A Legal Technology and Innovation Podcast

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 inte...

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...

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 Rocke...

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...

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...

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 reimagin...

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. Ke...

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...

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 tril...

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...

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 t...

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...

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 servic...

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 overco...

One of the most listened to episodes in 2025 featured a conversation with Andrea Muttoni, President of Story Protocol . The discussion explores how blockchain technology is being used as a foundational infrastructure for intellectual property (IP), aiming to simplify and modernize the process of registration, licensing, and monetization for creators and IP owners. Muttoni details his journey from...

Avaneesh Marwaha, the CEO of  Litera , visits the show to discuss his journey from IP lawyer to becoming a legal tech CEO and investor. He discusses the motivations behind his career pivot, including his desire to be a decision-maker and his passion for the business side of law. The conversation delves into the evolution of Litera, from its origins as a document-focused migration software company...

In one of the most popular episodes of the year, Legalbenchmarks.ai  Founder  Anna Guo discusses her organization's research that tests whether artificial intelligence custom-made for legal tasks better than general AI tools. Anna is a former BigLaw lawyer who left the practice to become an entrepreneur and now focuses her energies on quantifying the utility of AI in the legal industry. Anna's ini...

In the most listened to episode of 2025, author of " Systemology " and business systems expert, David Jenyns , discusses the importance of systemizing business processes, even in the nuanced field of law. Jenyns debunks the myth that legal work is too bespoke to be systemized, explaining how just like any other business, documenting legal workflows unlocks scalability and creativity. He shares his...

Meredith Kildow, President of Consilio discusses her career path from finance to leading global operations and delivery for one of the largest companies in the legal and eDiscovery space. Meredith shares insights into building a revenue organization from the ground up and the shift to her current role overseeing operations and delivery for a highly acquisitive company. The conversation focuses on...

This episode features a conversation with Cecilia Ziniti , Co-Founder and CEO of GC.AI . Cecilia traces her career from early the early days of the internet to founding an AI-driven legal platform for in-house counsel. Cecilia shares her journey, starting as a paralegal at Yahoo in the early 2000s, working on nascent legal issues related to the internet. She discusses her time at Morrison & Foerst...

In this episode, Sabastian Niles , President and Chief Legal Officer at Salesforce , takes a deep dive into the intersection of corporate strategy, in-house legal careers, and the transformative power of Agentic AI. Sabastian shares his unique career path from a near two-decade tenure at a prestigious law firm before joining Salesforce. This conversation is essential for anyone interested in the e...

Is artificial intelligence custom-made for legal tasks better than general AI tools like Google Gemini and ChatGPT? That is the topic of this episode featuring Legalbenchmarks.ai Founder Anna Guo . Anna is a former BigLaw lawyer who left the practice to become an entrepreneur and now focuses her energies on quantifying the utility of AI in the legal industry. Anna's initial anecdotal research for...

Justin Wales , Head of Legal for the Americas at Crypto.com, and author of The Crypto Legal Handbook visits the show to provide his unique perspective on pivoting from a career in Constitutional Law, including work on high-profile appellate cases like the Obergefell gay marriage decision, to becoming a trailblazer in crypto law and blockchain technology.  He shares his serendipitous journey stemmi...

Avaneesh Marwaha, the CEO of Litera , visits the show to discuss his journey from IP lawyer to becoming a legal tech CEO and investor. He discusses the motivations behind his career pivot, including his desire to be a decision-maker and his passion for the business side of law. The conversation delves into the evolution of Litera, from its origins as a document-focused migration software company t...