73. How Free AI Tools Become Expensive Mistakes (with Michael Moore, VP & Head of Legal at Glean)

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Previously titled “How Free AI Tools Become Expensive Mistakes (with Michael Moore, VP & Head of Legal at Glean)” — renamed by the publisher on Aug 11, 2026

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Recorded15 Jul 2025

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Free AI tools promise speed—but they can quietly kill enterprise deals. In this episode, Michael Moore, VP and Head of Legal at Glean, unpacks the legal, privacy, and trust pitfalls that most AI startups overlook. He explains how to design AI products that survive legal scrutiny, earn buyer trust, and actually close. Michael: www.linkedin.com/in/michaeltimmoore Glean: www.glean.com  Jon: www.linkedin.com/in/jon-mclachlan   Sasha: www.linkedin.com/in/aliaksandr-sinkevich YSecurity: www.ysecurity.io

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