MSP 1337 | Cybersecurity Education & Security Guidance

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” behin...

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 begi...

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 poli...

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 en...

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...

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 S...

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 defi...

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 simu...

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 ...

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 w...

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, bu...

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 ...

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 proce...

Predictions and challenges in the technology and cybersecurity space for 2026, with a focus on Microsoft ecosystem changes, licensing, security, and the impact of AI and Copilot. I had a chance to catch up with Shay Cohen of Optimize365.io this week, and I think you will find his insights on the fut...

In 2026, AI will increasingly integrate into business processes, emphasizing strong data quality and security as prerequisites for success. AI agents, distinct from chatbots, will operate with machine identities to automate tasks while supporting, rather than replacing, human decision-making. This i...

Looking ahead to 2026 trends and challenges in the MSP (Managed Service Provider) space, focusing on AI, automation, security, risk management, and social engineering. In a conversation with Josh Hohbein of Centrex IT, we discussed the key challenges and opportunities as we enter 2026.

Predictions for the Managed Service Provider (MSP) cybersecurity landscape in 2026, with a focus on risk management, the continued importance of basic cyber hygiene, open-source adoption, and the strategic use of risk registers. Did I say Risk Register? Dom Kirby brings it home: the importance of th...

I sat down with Chris Loehr to discuss the varying approaches businesses are taking toward cybersecurity spending as they plan for 2026, highlighting the influence of private equity and the unpredictability in budget increases or reductions even within the same industry.

From what keeps us up at night, to just meeting the minimums and nothing more to be compliant. Dorota Ulkowska of Accurate Networks and I discuss the recurring challenge of clients, tiny businesses, resisting recommended cybersecurity practices due to cost, perceived inconvenience, or a belief that ...

Sitting down with Bobby Glen James of Boteka about the importance of simplicity in IT security for MSPs. Bobby shares lessons from decades in the industry, advocating for Lean IT practices, streamlined technology stacks, and a service-first approach that avoids hardware upselling and long-term contr...