In this episode of GC Sidebar, Paragon Legal CEO Trista Engel sits down with Michael Stein, General Counsel at Gambling.com Group, for a candid conversation about the realities of legal tech adoption, the all-hands nature of being GC at a small company, and the career role that changed everything.
Michael shares a pragmatic view on how to cut through the hype around legal tech by weighing cost, ROI, and implementation against real business needs. He offers a behind-the-scenes look at what the GC title actually entails in a lean organization—where “other duties as assigned” can mean anything from complex negotiations to making sure the coffee is hot and the meeting runs smoothly.
From negotiating Britney Spears’ first Las Vegas residency contract to navigating the transition from Big Law to in-house, Michael reflects on the moments and mindsets that shaped his career, plus why he sees himself as a trusted, quiet voice of reason in the room.
Watch the trailer now. Full episode drops on August 27, 2025.
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