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
March 17, 2026
#90 - Clients "Do Their Own Research." That's A Problem for Law Firms
This episode of Pearls On, Gloves Off is powered by Workday. Learn more at workday.com. In this episode, Mary sits down with Claire Hart, Chief Operating Officer, Chief Legal Officer, and Board Member at Groq, to talk about w...
March 3, 2026
#89 - AT&T's New In House Law Firm
In this episode of Pearls On, Gloves Off , Mary sits down with Bill Ryan, Senior Vice President and Chief Compliance Officer at AT&T, and Ava Guo, Assistant Vice President and Senior Legal Counsel, to talk about leading throu...
Feb. 17, 2026
#88 - Big Law: Record Profits… For Now
In this episode of Pearls On, Gloves Off , Mary sits down with Mike Abbott, Head of the Thomson Reuters Institute, to unpack the paradox: how can firms be thriving on paper while the ground shifts beneath them? Clients are ti...
Feb. 3, 2026
Updates & Hot Takes with Alex Su
Mary O’Carroll kicks off a new era of Pearls On, Gloves Off - independent, sponsor-curious, and still laser-focused on what’s actually changing in legal. Her first guest in this new chapter is the person many listeners will r...
Jan. 20, 2026
#86 - Mary Talks to her Digital Twin
Mary O’Carroll isn’t experimenting for fun, she’s trying to solve one of legal’s biggest scaling problems: the fact that the profession’s best judgment and hard-earned experience still lives in people’s heads, buried in lapto...
Jan. 6, 2026
#85 - Edward Jones CLO Is Moneyball-ing Legal Risk
Keir Gumbs, Chief Legal Officer at Edward Jones, isn’t here to maintain the status quo. He joined the largest U.S. financial services firm not to run legal as usual - but to lead a transformation. In this episode, Keir and Ma...