Rule-breakers: the podcast about disruption in digital publishing.
Every month, Rule-breakers host, Sean McGrath dives into the fascinating world of digital publishing, exploring how technology is reshaping a very important part of modern life: the way we create and access laws, standards, and guidance.
If you’re curious about the forces affecting change in this space, you’re in the right place.
Ep #15: From digital books to digital agents: Edd Wilder-James on the Evolution of Structured Information
Edd Wilder-James joins us in this episode for a wide-ranging conversation that begins in the early XML and SGML communities and stretches all the way to today’s AI-driven world. Along the way, we revisit the rise of pivotal standards such as DocBook, HTML and DITA. Edd and Sean discuss the unique culture of the structured document markup conferences that brought together technologists, publishers, academics, and information architects from radically different disciplines ranging from hi-tech engineering to the liberal arts.
Edd reflects on the optimism and intellectual energy of that era, including debates around standards, schemas, hypermedia, and the Semantic Web, while also acknowledging some of the orthodoxy and “tech tribalism” that shaped those communities. The discussion explores how ideas from SGML, HyTime, RDF, and structured publishing continue to resurface in modern systems, often under different names.
The conversation also looks at the Big Data (Hadoop) era in the formative years of cloud computing, the evolution of open-source ecosystems at Google and Microsoft including his current work at GitHub around Copilot and large-scale agentic AI systems.
Throughout the episode, Edd offers a thoughtful perspective on recurring patterns in computing: the tension between elegant models and practical systems, the repeated reinvention of timeless old ideas, and the enduring importance of context when interpreting information.
27 Apr 2026
Ep #14: Information Architecture and Structured Documents in an AI world
In this episode, Sean McGrath sits down with Alex Smith, Global Product Lead for Knowledge, Search, and AI at iManage, to unpack what’s really happening at the intersection of AI and the world of legal practice.
With a career spanning nearly two decades at LexisNexis, leading innovation at Reed Smith, and now shaping AI-driven knowledge systems at iManage, Alex brings a rare, perspective on how legal information actually works, and why many people misunderstand it.
Sean and Alex explore the evolution of digital information from CD-ROM publishing to today’s AI-powered knowledge management systems, the enduring importance of structured data, and why “IA before AI” – Information Architecture before Artificial Intelligence - might be the most important consideration for anyone building legal knowledge management systems with modern AI tools. Along the way, they tackle hallucinations, trust in citations, knowledge graphs, and the gap between what today’s AI can realistically generate and what legal professionals can safely rely on being accurate.
This is a deep dive into the infrastructure behind legal knowledge—and why the future of AI in the world of law depends less on better and better AI LLMs models, and more on the quality of the information we feed to these models.
23 Mar 2026
Ep #13: Identity, security and privacy - with digital identity pioneer, Eve Maler
In this episode of Rule Breakers, Sean McGrath sits down with Eve Maler, a pioneer in digital identity and a long standing member of the XML community who was influential in shaping XML itself, based on her expertise in its predecessor SGML.
Eve has accumulated decades of experience shaping the digital identity landscape, from her role in developing the XML-based SAML (Security Assertion Markup Language) to today’s User Managed Access (UMA) OAuth extensions.
Eve shares insights into why authorization—not identity—is now the frontier of innovation, and how emerging models empower users to define and manage access to their own data online.
This episode is both a historical journey and glimpse into the frontier of digital identity where traditional person/role-centric authentication/authorisation meets fast moving world of autonomous Agentic AI.
16 Feb 2026
Ep #12: From SGML (1986) to LLMs (2026): Jon Udell on The Tools That Make Digital Knowledge Work
In this episode of Rule Breakers, we’re joined by author and software developer Jon Udell, a longtime explorer of the tools that shape how we write, publish, and work with knowledge. From the early days of SGML and semi-structured content to the modern web and today’s AI-powered knowledge management workflows, Jon shares a sweeping perspective over the last forty years of knowledge management innovations.
5 Jan 2026
Ep #11: XML, HCI, and a retrospective on markup and the Web with Steven Pemberton
Steven Pemberton, a web pioneer, discusses the origins of the web, the tension between ease of use and implementation, and his work on Invisible XML, offering insights into web standards and design in an interview.
1 Dec 2025
Ep #10: Markup Goes Beyond Tags: Rick Jelliffe on Language Markup, Structure & Semantics in XML
Rick Jelliffe explores the evolution of markup languages, focusing on the pivotal role of XML in enabling multilingualism and the innovative Schematron validation language in this interview.
3 Nov 2025
Ep #9: The Web Before Google: Liam Quin on HoTMetaL, XML, and the First Web Standards
Liam Quin recounts his early work on HoTMetaL, XML, and web standards, revealing the evolution of structured content and the excitement surrounding the Web's emergence in an interview with Sean Jackson.
6 Oct 2025
Ep #8: The evolution of structured data formats — from XML to AI with Anthony Coates
Sean McGrath interviews Anthony Coates about the evolution of structured data formats, exploring XML's breakout success and the role of FPML in encouraging XML tool vendors to support W3C XML Schema.
1 Sept 2025
Ep#7 The quiet innovator: the building blocks of structured documents with James Clark
Host Sean interviews James Clark, a pioneer in structured documents, about his foundational work shaping the modern web and simplifying complex coding languages.
4 Aug 2025
Ep#6: Tim Bray: How did the internet learn to 'read' and organize information?
Tim Bray recounts his pivotal work on the Oxford English Dictionary and co-creating XML, which still influences web technologies, in a conversation with Sean, highlighting the enduring role of structured data.
7 Jul 2025
EP#5: Thomas Bruce: the Renaissance man behind the Cello browser and Legal Information Institute
Sean interviews Thomas Bruce, who shares his journey from master electrician to developing the Cello browser and co-founding the Legal Information Institute, revealing connections between his diverse passions.
2 Jun 2025
Ep#4: Designing for knowledge complexity: DITA, AI, and next-generation delivery with Eliot Kimber
Content engineering pioneer Eliot Kimber discusses managing complexity in content systems, exploring structured content's value and preparing for an AI-powered future in this interview.
5 May 2025
Ep#3 Before AI, there was DocBook: Simon St.Laurent on the tech foundations that still matter
Simon St.Laurent offers an insider's perspective on the evolution of structured content and markup technologies at O'Reilly and throughout his career, emphasizing how tools like DocBook, Framemaker, and SGML laid the groundwork for today's componentized publishing models. In this podcast, Simon discusses the enduring value of structured data formats and how early practices are proving essential in the age of AI.
14 Apr 2025
Ep #2: Metal Type to the Web: Peter Flynn & the Birth of HTML
In this episode of Rule-breakers, Sean talks to Peter Flynn, an expert in markup languages and typesetting. With a background in traditional printing and computer typesetting, Peter transitioned into academia at UCC, where he became involved in early web development. He met Tim Berners-Lee while serving on a European Community committee, witnessing the demonstration of the nascent World Wide Web. Inspired, Peter downloaded the source code and launched Ireland's first website, subsequently contributing to discussions on HTML standardization.
7 Apr 2025
Ep #1: 25 years of Law and Tech: AI, Documents, and the Next Generation
In this episode, Sean and John talk about 25 years of technological change, focusing on AI's impact on legislation and regulation. They highlight the shift to natural language interfaces and the need for responsible AI adoption, emphasizing data quality and human oversight. While excited about AI's potential, they caution against its unbridled use and the dangers of treating it as a human persona.
Who has been a guest on Rule-Breakers
Names identified in recent episode analyses. Showing up to five guests.
Steven Pemberton
Rick Jelliffe
Liam Quin
Anthony Coates
James Clark
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