CZ and Friends
What if the best thing a lawyer could do is figure out how to make themselves obsolete? Jimmy Toy, Chief Legal Officer at Articore Group (the company behind Redbubble and TeePublic), has been using AI and machine learning in legal work for over 10 years. In this episode of CZ and Friends, Jimmy joins host Cecilia Ziniti to share why the future of legal is not about working faster with AI, but about working differently. Jimmy and Cecilia cover: * Why the best lawyers five years from now will use AI to stop doing legal work entirely, shifting from authoring outputs to reviewing them and architecting systems * How the billable hour trained lawyers to fear efficiency, and what in-house counsel can do to shed that mindset * What it looks like to manage 40+ IP cases across global jurisdictions, including a landmark Australian trademark case against the Hells Angels that created new platform liability law * How Articore built an AI-powered knowledge base from decades of court filings, deposition transcripts, and briefs so any team member can surface consistent legal positions in seconds * Why Jimmy tells his team to embrace being replaced, and how he built an AI champion role inside his legal function * The three values that guide his legal team: light touch, no surprises, and make every dollar count * What it means to be a turnaround GC, and how legal can have a direct impact on OpEx even when it cannot drive revenue Jimmy also shares his take on copyright, platform liability, user-generated content at scale, and why the 20% that AI cannot replicate is where lawyers need to live. Follow Jimmy: @Jimmy Toy [https://www.linkedin.com/in/james-toy-attorney/] on LinkedIn Chapters: 00:00 Preview 00:12 Welcome and intro: Jimmy Toy, CLO at Articore Group 00:25 Redbubble, TeePublic, and 70 million user-generated images 00:48 Jimmy's 10+ years using AI before modern LLMs 01:16 The future of legal: from authoring to architecting 02:10 Why lawyers resist AI more than other professions 04:21 The billable hour and the psychology of legal work 06:10 In-house vs. firm: shedding the hours-based mindset 07:38 What legal looks like in five years 09:27 Articore's platforms and how the marketplace works 12:42 IP risk, DMCA, and managing copyright at scale 14:51 40+ IP cases across global jurisdictions 16:37 The Hells Angels case and creating Australian platform law 18:54 Deciding to appeal: balancing cost, risk, and principle 21:57 AI and litigation knowledge bases 25:05 The "VP of Existing Obligations" problem and how AI solves it 27:44 Decentralizing institutional knowledge with AI 28:44 What surprised Jimmy most about his tenure 30:44 Has the board noticed legal as a product? 31:07 Being a turnaround GC: cost, OpEx, and impact 33:31 The three team values: light touch, no surprises, make every dollar count 34:17 Lightning round: advice, books, and favorite thing about being a lawyer Follow us on all social platforms to get each new episode when it drops. @Cecilia Ziniti [https://www.linkedin.com/in/ceciliaziniti/] on LinkedIn @CeciliaZin [https://x.com/CeciliaZin/status/1788847013280493832] on Twitter/X @GC AI [https://www.linkedin.com/company/gc-ai/posts/?feedView=all] on LinkedIn @gcai [https://x.com/gcai_co] on X gc.ai [https://www.getgc.ai/] website
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