Inside Microsoft Legal: A Look at AI Use Built for Scale (Rebecca Anderson - Head of Legal EMEA Microsoft)

July 09, 2026 4:04am 30 min

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 departme...

Cost, Speed and Quality - One Law Firm's Quest to Deliver All Three (Laurence Brown, Partner EIP and Head of Visser AI)

June 25, 2026 4:41am 29 min

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 nav...

Affordable & Accessible: The Democratization of Legal Tech (Tyler Foreman VP of AI - Rocket Lawyer)

June 11, 2026 4:20am 31 min

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 en...

Building Software for Less: The Death of Expensive SaaS in the AI Era? (Nathan Wenzel - LegalOperatorAI)

May 28, 2026 4:11am 51 min

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 e...

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

May 14, 2026 4:10am 34 min

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 lawye...

The AI Pilot is Over: Legal's Moment to Move Beyond Experiments and Avoid the Innovator's Dilemma (Sabastian Niles, President & CLO Salesforce)

April 30, 2026 4:56am 40 min

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...

Ayana Dow on Updating Crypto Regulation and Preserving the Freedom to Build (Senior Counsel, Defi Education Fund)

April 16, 2026 3:52am 36 min

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 f...

Descrybe's Quest to Democratize Legal Research (Kara Peterson & Richard DiBona)

April 02, 2026 4:04am 38 min

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 dyna...

The Uberization of UPL? How AI Is Outpacing the Unauthorized Practice of Law (Ken Crutchfield, Bill Henderson, Jim Doppke)

March 19, 2026 4:45am 45 min

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 d...

From Water Pistols to Tanks: Why Data Science is the Gold Standard to Counter Class Action Fraud (Donald Beshada, CEO, Covalynt)

March 05, 2026 3:17am 56 min

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 a...

Stacking Legal Skills: How Stints at Big Law, Biz Dev and and Legal Ops Paved the Way to the C-Suite for Akshay Verma (COO, SpotDraft)

February 19, 2026 4:53am 37 min

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 l...

The Legal Ops Force Multiplier: How Nextdoor GC Sophia Contreras Schwartz Built a Lean Legal Team From Scratch

February 05, 2026 5:00am 30 min

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...

Tokenization of Real World Assets: From Art to Real Estate to Private Equity (Lucas Moskowitz, General Counsel, Robinhood)

January 22, 2026 4:11am 27 min

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 ...

Bridging Law Firm Silos: How Law Firms Can Maximize AI-Driven Cross-Selling (James Barclay, CEO Passle)

January 08, 2026 5:35am 27 min

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 inte...

Best of 2025: Building a Modern IP Infrastructure and Protecting Creators in the AI Age (Andrea Muttoni - President Story Foundation)

December 30, 2025 4:01am 40 min

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 ...

Best of 2025 - From IP Lawyer to Investor to CEO to Legal Ecosystem Builder (Avaneesh Marwaha, Litera CEO)

December 24, 2025 9:26am 40 min

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 dec...

Best of 2025 - Benchmarking Legal AI: Measuring the Delta Between Man and Machine (Anna Guo Legalbenchmarks.ai)

December 18, 2025 12:00pm 27 min

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 too...

Best of 2025: The Future of Real Estate is Here (and It's on Blockchain) -Daniel Rollingher (GC Fabrica)

December 16, 2025 5:01am 37 min

Best of 2025: Building and Documenting Better Legal Workflows: Insights from Systemology Author David Jenyns

December 11, 2025 10:00am 43 min

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...

Future-Proofing Legal Ops: AI Literacy, Innovation and Augmentation (Meredith Kildow, President Consilio)

December 04, 2025 5:34am 30 min

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 bu...