Episodes: 106
Frequency: Every two weeks
Rating: 4.7/5.0
Estimated listeners: 100 - 1,000
Listener location: USA
YouTube: 48 subscribers
Publicly listed emails
john.weeke@ironcladhq.com
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Mary O'Carroll - Legal operations and legal innovation executive known for her leadership in legal operations at Google and her work advancing legal technology and modern legal departments.
Ryan Daniels - Ai-native Law Firms, Fixed-fee Pricing, Legal Services Economics, Lawyer Performance, Contract Data, And Agent-enabled Legal Work.
Darth Vaughn - Modernizing Corporate Legal Departments, Outside Counsel Expectations, Billable-hour Alternatives, Ai-native Firms, Trust, And The Future Of Legal Operations.
Eric Greenberg - Leading Legal Department Transformation, AI Governance, Legal Technology Adoption, Outside Counsel Relationships, And Leadership.
Nick Fleisher - Legal Technology, Ai-native Teams, Software Development, Permissions And Context In In-house Legal Work, And Lean Company Building.
Anna Richards - Legal Operations Leadership, Evolving Skill Requirements, Legal Technology Stacks, And Rising Expectations For Legal Operations Teams.
#105 - Disrupt Yourself First: How Redgrave Is Rebuilding the Law Firm Model
October 13, 2026
Mary sits down with Erica Zolner, Britney Colton, and Ray Mangum of Redgrave LLP, an information law firm that runs nothing like a traditional firm. They dig into what happens when lawyers and technologists work side by side, how AI turned 600,000 contract PDFs into a risk picture in five days, why disrupting yourself beats waiting to be disrupted, why clients still hold on to the billable hour, and how real-time feedback shapes how the firm rewards its people. This episode is presented by PL...
#104 - Flight Simulators for Lawyers: The Rise of the Legal Engineer and How the Profession Learns
September 29, 2026
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 ...
#103 - The Lawyer Personality Unpacked: What the Data Says After 32 Years of Research
September 15, 2026
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 s...
Technically Legal - A Legal Technology and Innovation Podcast · Medium booking difficulty · 100 - 1,000 listeners
Pearls On, Gloves Off: The Legal Innovation Podcast is hosted by Mary O'Carroll. Its publicly listed email is john.weeke@ironcladhq.com. For guest bookings, the host or producer is usually the best person to reach. Podseeker helps you find direct host and producer contacts and pitch from your own inbox.
The publicly listed email for Pearls On, Gloves Off: The Legal Innovation Podcast: john.weeke@ironcladhq.com.
Podseeker estimates Pearls On, Gloves Off: The Legal Innovation Podcast reaches 100 to 1,000 listeners per episode. Only the publisher has exact numbers.
Pearls On, Gloves Off: The Legal Innovation Podcast typically books industry leaders. Typical guest background: General Counsels, Chief Legal Officers, senior legal operations executives, founders and CEOs of significant legal technology companies, and leaders with direct experience transforming legal services. Common among recent guests: Leading a major corporate legal department; Driving legal operations or technology transformation; Founding or scaling a legal technology or AI-focused company. Recent guests include Ryan Daniels, Darth Vaughn, and Eric Greenberg.
High. It mostly books established leaders in its field.
Recent episodes cover Legal Innovation, Legal Technology, Legal Operations, Artificial Intelligence, and Legal Services. Pitch an idea tied to one of these topics and mention a recent episode.
Publicly listed emails
john.weeke@ironcladhq.com
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