Episodes

Most MSPs don’t fail at cybersecurity because of missing tools; they stall because they miss the maturity inflection point where governance must replace tactics. In this episode, we break down what actually defines cybersecurity maturity, contrasting technical frameworks with governance-driven models that reflect real organizational behavior. Using the GTIA Cybersecurity Trustmark’s four-level maturity lens alongside Josh’s five-step cybersecurity maturity journey (built from cyber insurance an...

In this episode, we unpack one of the most misunderstood topics in the MSP industry: insurance. From Errors & Omissions to cyber insurance, we break down what these policies actually cover, and more importantly, what they don’t. The conversation challenges the assumption that buying insurance equals risk transfer and explores how liability really plays out across MSPs, clients, and third‑party vendors. We discuss why cyber insurance typically protects only the insured entity, how E&O applies to...

Clear communication is one of the most overlooked and most costly challenges in IT service providers. In this episode, Chris sits down with Amy Reczek, communication and presence expert, to unpack why misalignment happens between leadership, teams, and clients, and how understanding the “why” behind communication changes everything. From ineffective meetings and virtual body language to intent versus impact, this conversation dives into the human gaps that tools and systems can’t fix, and what I...

The critical importance of going beyond just getting technology to work, addressing the underlying security, scalability, and proper implementation, rather than just fixing symptoms. Eric Hansen, of Inland Productivity Solutions, emphasized the importance of starting troubleshooting at the very beginning, even when engineers claim they've already done everything. He discussed their hiring process, which prioritizes people skills and problem-solving abilities over technical expertise, using unsol...

A real-world phishing incident. Real financial impact. Real lessons for MSPs. In this episode, we unpack a phishing attack that led to unauthorized access to an Azure subscription and significant financial loss for an MSP client. The conversation goes beyond the incident itself to examine where policy gaps, weak controls, and unclear ownership increased liability, and what changed when the MSP committed to cybersecurity maturity. Joined by Chad Holstead, we walk through how pursuing the GTIA C...

Google Ads can disappear overnight, and for millions of businesses, it has. In this episode, John Horn of Stub Group breaks down the growing cybersecurity risks behind Google Ads account suspensions and why 39 million accounts were shut down in 2024. We explore Google’s automated, all‑or‑nothing enforcement model, how website vulnerabilities, phishing attacks, and account takeovers trigger suspensions, and why recovery is often harder than prevention. The conversation also dives into the impact...

Cybersecurity maturity isn’t earned in audits, it’s earned in the operational moments where governance either shows up… or it doesn’t. Today’s conversation with Mike Stewart of Anchor Networks goes deep on MSP maturity. How leadership tone, culture, and repeatable decision systems turn policies into actual behavior. We cover why security awareness must be frequent (not annual), why “the why” behind policies matters, and why AI is now a governance challenge as much as a technical one—especially ...

Managed Service Providers are being pushed to “get compliant fast.” In my discussion with Bruno Leqoc, we reframe the challenge. Compliance isn’t security, and lasting compliance depends on security maturity first. Highlighting how AI policy can extend existing governance frameworks, why Microsoft Secure Score is a practical readiness indicator, and why foundational controls (MFA, patching, device management/remote wipe) must come before certifications and GRC tooling. In this episode, we also e...

Exploring the fast-moving intersection of AI governance, ethics, and cybersecurity, examining how organizations are struggling to adopt AI responsibly while keeping pace with innovation. The conversation highlights a growing disconnect between enthusiasm for AI tools and the absence of clearly defined use cases, governance models, and security guardrails. As AI capabilities rapidly expand, Dr. Adeel Sheikh Mohammed emphasizes that organizations must move beyond checkbox compliance and adopt a s...

Phishing simulations are one of the most debated tools in cybersecurity awareness, but do they actually work? In today’s episode, we’re joined by David Shipley, former soldier turned cybersecurity researcher and founder of Beauceron Security, to unpack what the data really says about phishing simulations, human behavior, and why zero clicks has never been, and will never be, the goal.

Have you ever been stuck in an elevator? What happens when you push the call button? Physical safeguards managed by a 3rd party are often ignored or marked as N/A. What happens when processes and procedures don't get updated after a change? Listen in as Charles Love of ShowTech Solutions shares his experience of being trapped in an elevator and what we should all take away in lessons learned.

A much-needed discussion on the fast‑shifting world of data privacy in 2026 and what it means for MSPs on the front lines. From the tangled web of U.S. state privacy laws to the rising risks hidden in modern data flows (yes, even your car!), guest Andy Sambandam, Clarip CEO & Founder, lays out why every security breach is now a privacy breach, and why security and privacy are officially a forever marriage. We dig into transparency, consent, data mapping, retention policies, and the growing press...

In this episode, we cut through the AI hype with Alane Boyd to unpack what MSPs really need to know about today’s AI landscape. We cut right to the chase on data‑privacy pitfalls and free-tool misconceptions, and on the rise of AI agents that go far beyond simple automation. We explore practical, business-ready use cases, how to build safe and effective AI policies, and why better prompting (and better balance with our mental health) matters more than ever. If you’ve wondered how AI can help you...

Chris Johnson and cybersecurity expert Robert Siciliano dive into the human side of security, exploring why default trust and denial make people vulnerable to social engineering and cyber threats. They discuss the cultural framing of security, the importance of personalizing security practices, and why leadership must model proactive behaviors. The conversation introduces the concept of a “strategic human firewall,” emphasizing that proper protection comes from security appreciation, not just aw...

Resilience and Continuous Improvement for ITSPs as we go into 2026. I discuss what it means to be on a resilience journey with Charles Love of ShowTech Solutions. ShowTech Solutions has reached a milestone in its maturity journey, achieving Assured status, and continues to advance its maturity process. Experiences and lessons learned that will help any ITSP on their own journey.