Most MSPs invest in security tools — firewalls, endpoint protection, SIEM — but few have a reliable way to know whether those tools are actually configured correctly. Misconfigurations in the very products designed to protect your clients are one of the leading attack vectors in cybersecurity today. Adam Bennett has spent 25+ years on the front lines and built a company to solve exactly this problem.

Adam Bennett is the Co-Founder & CEO of SureStack and CEO of Crosshair Cyber. In this conversation, we explore why security stack misconfigurations create silent compounding risk, how cyber insurance gives many SMBs a false sense of protection, and why the MSP that takes ownership of security posture earns the trust — and contracts — of serious clients.

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🎙 What We Cover in This Episode

• Why the tools meant to protect you may be your biggest vulnerability
• Real-world incidents caused by two unchecked configuration boxes
• The growing role of regulation and compliance in driving security adoption
• How SureStack automates continuous security stack validation using AI
• Why MSPs should enforce minimum security stacks for every client
• Using security posture assessments as a pre-sales differentiator
• Adam's journey from government cybersecurity to building a product company
• Cyber insurance gaps: what happens when the application doesn't match reality

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👤 Guest Links

Guest LinkedIn: https://www.linkedin.com/in/adam-bennett-0290881bb/ Company Website: https://surestack.ai

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📝 Credits

Host: Josh Peterson Producer: Bering McKinley Episode: #92 — Your Security Stack Is Lying to You | From the Trenches (Adam Bennett)