EPISODE · Jul 15, 2025 · 19 MIN
73. How Free AI Tools Become Expensive Mistakes (with Michael Moore, VP & Head of Legal at Glean)
from The Security Podcast of Silicon Valley · host YSecurity.io
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 🔒 Sponsored by YSecurity Closing a big deal and getting hit with a vendor questionnaire, SOC 2 request, or pen test requirement? That's exactly what we handle. YSecurity embeds a team of security engineers with backgrounds from Apple, Uber, Microsoft, Robinhood, and Brex directly into your company. No full-time hire, no bloated retainer. You set a monthly cap and we handle everything. Book a free strategy call and we'll tell you exactly where you stand. 👉 Book your free call: 30 Min Meeting | YSecurity.io | Cal.com 👉 Learn more: YSecurity | On-Demand Cybersecurity Team for Startups — SOC 2 in 5 Months
What this episode covers
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 🔒 Sponsored by YSecurity Closing a big deal and getting hit with a vendor questionnaire, SOC 2 request, or pen test requirement? That's exactly what we handle. YSecurity embeds a team of security engineers with backgrounds from Apple, Uber, Microsoft, Robinhood, and Brex directly into your company. No full-time hire, no bloated retainer. You set a monthly cap and we handle everything. Book a free strategy call and we'll tell you exactly where you stand. 👉 Book your free call: 30 Min Meeting | YSecurity.io | Cal.com 👉 Learn more: YSecurity | On-Demand Cybersecurity Team for Startups — SOC 2 in 5 Months
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73. How Free AI Tools Become Expensive Mistakes (with Michael Moore, VP & Head of Legal at Glean)
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