#33 - From The Trenches - Cyber Risk, Claims & Coverage (Bill Haber)

In this From the Trenches episode, Josh Peterson sits down with Bill Haber, Co-Founder and CEO of TEKRiSQ, to unpack the messy intersection of cyber risk, cyber insurance, and MSP-led security for small and midsize businesses. Drawing on decades in telecom, software, data platforms, and now cyber risk, Bill explains why SMBs are squarely in attackers’ sights, how independent risk assessments map to practical remediation, and what insurers actually look for when deciding whether a business is truly insurable. The conversation moves beyond fear-based selling to a pragmatic, business-first view of cyber, showing how owners can use structured assessments, right-sized controls, and the BMK Vision platform to make security an enabler of growth rather than just a cost of doing business.

Across real breach stories, debated statistics about post-incident business survival, and a candid look at underwriting shortcuts, Bill clarifies the differences between cyber events, incidents, and breaches—and why that language matters when legal, insurance, and incident-response teams get involved. He also highlights how AI-driven, avatar-led assessments let SMBs evaluate their risk privately and honestly, giving MSPs and brokers a cleaner starting point for remediation plans and coverage discussions. For MSP leaders and risk advisors who want to align assessment, remediation, and insurance into a single motion, this episode offers a practical playbook for being “cyber ready” before the ransom note appears on screen and pairs well with BMK’s broader guidance on MSP consulting services that help you lead, scale, and win.

For MSPs navigating small-business growth and innovation, explore these related articles: how MSPs can use ConnectWise reporting to measure what actually matters, client engagement strategy for MSPs: from onboarding to QBRs, and MSP consulting services that help you lead, scale, and win.

Return to the BMK Vision Podcast main page →

Listen on Your Favorite Platform

Episode Highlights

• 00:03:00 – Bill’s journey from telecom, software, and data platforms into cyber risk and insurance entrepreneurship.
• 00:10:30 – Using flood-insurance-style analogies to explain contextual, risk-based cyber underwriting.
• 00:14:30 – A $250,000 loss story tied directly to a refusal to implement multifactor authentication.
• 00:17:00 – Why a single cyber breach can be an existential event for SMBs, even when survival statistics are debated.
• 00:22:00 – How insurers struggle to balance speed, simplicity, and depth when underwriting cyber policies.
• 00:30:00 – Attackers “camping out” quietly inside networks, waiting for the perfect moment to strike.
• 00:47:00 – AI-driven, avatar-led cyber risk assessments that increase honesty and scale for SMBs and advisors.

About the Guest

Bill Haber is the Co-Founder and CEO of TEKRiSQ, a cybersecurity company focused on helping small and midsize businesses—and the risk professionals who serve them—assess, remediate, and insure cyber risk. With more than two decades of experience across telecom, enterprise software, big data, digital health, and network infrastructure, Bill brings a rare blend of technical, operational, and commercial insight to the exploding world of cyber insurance and risk transfer.

At TEKRiSQ, Bill and his team deliver automated risk assessments, compliance-ready reporting, and expert guidance that make cyber risk understandable in plain business language. Their avatar-led assessments and data-driven recommendations help SMBs strengthen controls, satisfy insurer and regulatory requirements, and build cyber resilience without being overwhelmed by jargon or fear-driven sales tactics. 🌐 Connect with Bill on LinkedIn → | Learn more about TEKRiSQ →

About the Host

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast. Through the From the Trenches series, Josh highlights MSP leaders who redefine growth through creativity, resilience, and genuine client connection.

📺 Subscribe on YouTube →