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)

Most MSP owners who struggle with sales performance aren't dealing with a bad salesperson - they're dealing with no system. In this roundtable, Josh Peterson and Gary Boyle respond to a real listener email from an MSP owner who has tolerated five years of inconsistent results from a salesperson he's afraid to hold accountable. The diagnosis: this isn't a sales problem. It's a leadership problem wearing a personnel costume.

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🎙 What We Cover in This Episode

• Why no quota means no sales role - not a flexible arrangement
• How the owner's vision must precede the salesperson's target
• The two-quota framework: activity quota and results quota
• What base pay is actually purchasing - and why most MSP owners have it backwards
• How to interview a salesperson to reveal whether they're metrics-driven before you hire them
• What to do when the horse is already out of the barn
• Why accountability is clarity, not punishment - and how to introduce structure without blowing up the relationship

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👤 Your Hosts

Josh Peterson - CEO, Bering McKinley

Gary Boyle - Partner for Strategy & Business Development, Bering McKinley

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🚀 Subscribe & Follow BMK Vision

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🔎 SEO Keywords

• MSP sales management
• MSP salesperson performance
• MSP sales system
• Managed service provider sales quota
• MSP accountability
• BMK Vision Podcast

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📝 Credits

Host: Josh Peterson

Co-Host: Gary Boyle

Producer: Bering McKinley

Episode: #91 - No Quota, No Sales Role: The MSP Sales System Reset

Most MSPs have invested heavily in perimeter security. But there is a financial risk hiding in plain sight: the unstructured data organizations create every day — spreadsheets, Word docs, old deal rooms, payroll files — that has never been inventoried, valued, or protected at the file level. That gap is what Return on Mitigation was built to close.

James Oliverio is the Founder & CEO of ideaBOX and a Senior Advisor at Actifile. With 30+ years spanning Wall Street CIO roles, MSP ownership, and a Harvard certification in cybersecurity risk management, James developed the ROM framework to help C-suites quantify data exposure in dollars and connect that number to the controls that actually reduce it.

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🎙 What We Cover in This Episode

- What Return on Mitigation (ROM) is and how the financial calculation works - Why traditional DLP tools detect risk but stop short of real remediation - How AI tools like ChatGPT are creating a new hidden liability for organizations - Why 44% of 2024 cyber insurance claims were denied — and how to protect clients from that trap - How to run a data risk assessment on your own MSP before offering it to clients - The FAIR Institute methodology and financial modeling for breach exposure - File-level encryption as the true remediation strategy — not just detection - How to position the ROM conversation at the C-suite level

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👤 Guest Links

Guest LinkedIn: https://www.linkedin.com/in/james-oliverio-7659ab/ Company Website: https://ideabox.com

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🔎 SEO Keywords

- MSP cybersecurity - Return on Mitigation - Data risk management - Cybersecurity insurance - Unstructured data security - DSPM - AI data exposure - MSP security strategy - Data breach liability - ideaBOX

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📝 Credits

Host: Josh Peterson Producer: Bering McKinley Episode: #90 — Data Risk Is the MSP's Invisible Liability