Pearls On, Gloves Off
Pearls on Gloves Off isn’t your typical legal podcast—and that’s exactly the point. This is where legal innovation gets real. We dive into what’s broken, what’s changing, and what it will take to reinvent how legal services are delivered from technology to talent to new business models. You’ll hear unfiltered conversations with the visionaries, challengers, and quiet disruptors who are shaping what’s next. If you’re tired of how things have always been done and ready to explore how they should be, you’re in the right place. Welcome to the conversation.
Recent Episodes
104
Sept. 29, 2026
#104 - Flight Simulators for Lawyers: The Rise of the Legal Engineer and How the Profession Learns
Mary sits down with Stanford Law's Adam Sterling and Irene Liu to unpack the school's new Legal Engineering Academy. They dig into what a legal engineer actually is, why the legal apprenticeship model has been broken for years, how AI-powered 'flight simulators' could compress a decade of experience into months, why AI may be pushing demand for young lawyers up rather than down, and what the legal talent ecosystem could look like ten years from now. This episode is presented by Workday. Join M
103
Sept. 15, 2026
#103 - The Lawyer Personality Unpacked: What the Data Says After 32 Years of Research
Mary sits down with Dr. Larry Richard, psychologist, former lawyer, and the foremost researcher on lawyer personality, for a return visit that goes even deeper than their first conversation. They dig into the seven personality traits that make lawyers uniquely wired for the law and uniquely challenged by everything else, why nine out of ten lawyers are thin-skinned, why empathy has dropped 50% in the last twelve years, what that means for legal leadership in an AI-driven world, and what the scie
102
Sept. 1, 2026
#102 - Inside Crosby: The AI Law Firm Rethinking How Legal Work Gets Done
Mary sits down with Ryan Daniels, Co-Founder and CEO of Crosby, for a rare look inside one of legal tech's most talked-about AI native law firms. They dig into why Ryan built a law firm instead of a legal tech company, how fixed fee pricing completely changes the unit economics of legal services, why Crosby lawyers are evaluated on speed not hours, how they're building a data moat from every contract they touch, and what it actually looks like when a law firm is designed from day one to hand wor
101
Aug. 18, 2026
#101 - Ford's Warning Shot: Adapt or Get Left Behind
Mary sits down with Darth Vaughn, Associate General Counsel and Managing Director of Policy and Legal Ops at Ford Motor Company, for a candid conversation about what it actually looks like when one of the world's largest legal departments stops waiting and starts building. They dig into why the billable hour model is structurally broken, what Ford actually expects from its outside counsel, why AI native firms still have a trust problem, and what the legal department of the future really needs to
100
Aug. 4, 2026
#100 - The Future of Legal Is Already Here - A Conversation with CLO Eric Greenberg
Mary sits down with Eric Greenberg, EVP, Chief Legal Officer, and Corporate Secretary at Cox Media Group, for a milestone 100th episode conversation about what it actually takes to lead a legal department through transformation. They dig into why AI governance is really an anthropology problem, why buying software is the beginning not the end, the future of big law and outside counsel relationships, and why the most important leadership skill right now is making it okay to be wrong. This episode
99
July 21, 2026
#99 - Who Is Sandstone? Inside Legal Tech's Most Talked-About Company
Mary sits down with Nick Fleisher, Co-Founder and CEO of Sandstone, to pull back the curtain on legal tech's fastest-rising company. They dig into why great software still matters in the age of AI, how Sandstone is solving the permissions and context problem that's plagued in-house legal for years, why law firms will never out-build tech companies, and how an AI-native team is redefining what it means to build lean. This episode is presented by Workday. Join Mary’s Substack Community Follow Ma