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
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
98
July 7, 2026
#98 - Anna Richards
Mary sits down with Anna Richards, Head of Community at Brightflag, to catch up on what's actually happening on the ground in legal ops right now. They dig into the shifting skill sets legal ops leaders need, how to think about building a tech stack from scratch, and why the job keeps getting harder even as expectations keep climbing. This episode is presented by Workday. Join Mary’s Substack Community Follow Mary on LinkedIn Rate and review on Apple Podcasts ~~~ Thank you to our sponsors for
97
June 23, 2026
#97 - The Senior Talent Problem Nobody Wants to Talk About
In today's episode, Mary sits down with James O'Dowd, CEO and founder of Patrick Morgan, to explore what legal can learn from the PE and AI disruption already reshaping accounting and consulting. James breaks down why governance is the real unlock private equity brings, how compensation models are shifting away from legacy profit-sharing, and why cultural buy-in ultimately determines whether any of it sticks. On AI, James unpacks the concept of "talent debt" and closes with a bold prediction: a
96
June 9, 2026
#96 - Curating AI Tools for a Global Law Firm
In today's episode, Mary sits down with Ilona Logvinova, Chief AI Officer at HSF Kramer, to talk about what it actually takes to turn a global law firm into an AI native organization. They cover why the Chief AI Officer title means something different from innovation, what it takes to build a forward deployed legal engineering function, and why the real edge isn't buying technology - it's the people and incentives behind it. This episode is presented by Workday ~~~ Thank you to our sponsors fo