PROPYLON
Rule-Breakers
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.
Where to listen?
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Episodes
Ep #15: From digital books to digital agents: Edd Wilder-James on the Evolution of Structured Information 02.06.2026 59:20
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,...
Ep #14: Information Architecture and Structured Documents in an AI world 27.04.2026 58:55
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 le...
Ep #13: Identity, security and privacy - with digital identity pioneer, Eve Maler 23.03.2026 56:59
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 La...
Ep #12: From SGML (1986) to LLMs (2026): Jon Udell on The Tools That Make Digital Knowledge Work 16.02.2026 1:00:29
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 inn...
Ep #11: XML, HCI, and a retrospective on markup and the Web with Steven Pemberton 05.01.2026 1:00:02
In this episode, we speak with Steven Pemberton, a pioneer of the early web, the first user in Europe to connect to the open internet, and a long-time contributor to standards at the W3C including CSS and XHTML. He also worked on the ABC programming language that heavily influenced Python. Steven traces the origins of the web from Tim Berners-Lee’s original vision of a connected information system...
Ep #10: Markup Goes Beyond Tags: Rick Jelliffe on Language Markup, Structure & Semantics in XML 01.12.2025 1:17:25
Dive into an in-depth conversation with Rick Jelliffe, one of the most influential figures in the world of markup languages and structured data. Rick's contributions to markup and markup standards span from SGML in the 1980s, XML in the Nineties, up to the present day. He brought his extensive expertise in character encoding to the work on the XML standard. This was a pivotal feature of XML, ensu...
Ep #9: The Web Before Google: Liam Quin on HoTMetaL, XML, and the First Web Standards 03.11.2025 1:11:38
The latest episode of Rule-Breakers features Liam Quin a pioneering figure in the world of electronic publishing and generalized markup. In this conversation, we learn about Liam’s journey from a childhood fascination with typesetting that started with the fonts used in his copy of The Lord of the Rings, to a lifelong passion for digital documents that included working at the W3C on the XML standa...
Ep #8: The evolution of structured data formats — from XML to AI with Anthony Coates 06.10.2025 47:00
Join Rule-breakers host, Sean McGrath and our latest guest, Anthony Coates, for a deep dive into the history and necessity of structured content. Drawing on his experience at Reuters and his work on major financial standards such as FPML, Tony recounts the various factors that allowed XML to break out and become successful, how FPML played a role in encouraging XML tool vendors to fully support W3...
Ep#7: The quiet innovator: the building blocks of structured documents with James Clark 01.09.2025 56:33
Ever wonder how websites and apps are built to look organized and work the way they do? In the latest episode of Rule-breakers, Sean talks to James Clark, a true pioneer who helped create the hidden rules and structure that make the modern web possible. James talks about his incredible journey from the early days of computers and typesetting to becoming a central figure in shaping foundational te...
Ep#6: Tim Bray: How did the internet learn to 'read' and organize information? 04.08.2025 59:22
Sean talks to Tim Bray, a true pioneer in the world of digital documents and computing. Tim talks about his early work, including the groundbreaking Oxford English Dictionary (OED) project at the University of Waterloo. Tim went on to co-create the foundational XML standard that powers so much of the web today. Exploring the surprising prevalence of XML in places like WhatsApp, Tim offers his pers...
EP#5: Thomas Bruce: the Renaissance man behind the Cello browser and Legal Information Institute 07.07.2025 31:32
In this episode of Rule-breakers, Sean talks to Thomas Bruce about his remarkable career. From his days as a master electrician for the Yale Rep to touring with music legends, Thomas developed the Cello web browser, one of the internet's first graphical web browsers for Windows. He also co-founded the Legal Information Institute (LII) at Cornell in the early nineties when only fragments of legal i...
Ep#4: Designing for knowledge complexity: DITA, AI, and next-generation delivery with Eliot Kimber 02.06.2025 54:40
In this episode, content engineering pioneer Eliot Kimber shares key lessons from his career on managing complexity in content systems. Author of DITA for Practitioners Volume 1: Architecture and Technology, Eliot explores the value of structured content, the challenges of legacy systems, and preparing for an AI-powered future. This conversation offers a look at what it takes to build intelligent...
Ep#3 Before AI, there was DocBook: Simon St.Laurent on the tech foundations that still matter 05.05.2025 59:58
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 i...
Ep #2: Metal Type to the Web: Peter Flynn & the Birth of HTML 14.04.2025 59:11
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....
Ep #1: 25 years of Law and Tech: AI, Documents, and the Next Generation 07.04.2025 44:29
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.
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