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PODCAST

MSP 1337 - Cybersecurity Maturity Journey | Guidance and Best Practices for MSPs and MSSPs

Chris Johnson - Cybersecurity Maturity Enabler

Educational sound bytes to help MSPs and their clients navigate Cybersecurity. Cybersecurity maturity is a journey; don"t go it alone. Interviews and guidance from fellow MSPs and other Industry experts. Our goal is Secure Outcomes, and together we can make a difference.

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All Episodes

00:15:46

GTIA On Location Interview: A Phishing Expedition and...

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2026/03/18

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

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00:30:08

Suspended, Hacked, or Outbid - Cybersecurity and...

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2026/03/10

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 of AI

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00:31:47

Operational Maturity Meets Cybersecurity

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2026/03/03

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 as

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00:24:04

AI Governance and the MSP Maturity Model

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2026/02/24

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

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00:29:38

Governing AI in a High Risk World

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2026/02/17

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 shared,

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00:42:30

Do Phishing Simulations Really Work?

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2026/02/10

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.

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00:29:40

Physical Safeguards and Process and Procedures

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2026/02/03

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.

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00:34:17

Data Privacy and Security Trends in 2026

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2026/01/27

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

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00:36:26

Exploring AI Usage, Misconceptions, and of course...

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2026/01/20

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 your

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00:34:20

Human Behavior and Shifting from Security Awareness...

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2026/01/13

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

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00:33:32

ITSP Reslience in 2026

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2026/01/07

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.

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00:23:24

December Series 2025 Wrapup

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2025/12/30

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 future of CoPilot and other unique changes we can expect in 2026.

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00:33:08

Data, Security, and The Human Edge

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2025/12/23

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 is just a glimpse of the insights Ben Wilcox of ProArch shared this week.

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00:24:47

Look Ahead Part 3

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2025/12/16

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.

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00:35:16

Risk Management In 2026?

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2025/12/09

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 the Risk Register and its role as we enter 2026. He advocates that MSPs move beyond discussions of technical tools and engage in business and risk conversations with their clients.

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00:33:38

Cybersecurity Spend Decisions For 2026

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2025/12/02

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.

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00:29:16

Just Sell Me The Minimum

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2025/11/25

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 risks are exaggerated, with Dorota providing real-world examples from their experience at Accurate Networks.

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00:28:46

Cybersecurity and Simplicity

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2025/11/18

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 contracts. Practical insights on risk management, prioritizing critical systems, and building resilient, client-focused MSP services.

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00:38:45

DNS Records: Secure and Correct?

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2025/11/11

By the end, it is hard to believe that in 2025, less than 30% of all Web Domains have properly configured SPF, DMARC, and DKIM records. Yep, less than 30% of the top 10 million domains. I sit down with Al Iverson of Valimail to talk about DNS records and the importance of SPF, DMARC, and DKIM records. Might sound a bit boring...At the end of November, bulk mailing will stop working for your company if you don't have those records configured correctly.

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00:18:13

Biggest Challenge Facing MSPs

MSP 1337 - Cybersecurity Maturity Journey | Guidance... ·

2025/11/04

Once upon a time, I was an MSP. Looking at everything that MSPs have to keep track of, both internally and client-facing, can be overwhelming. I sat down with Dor Eisner of Guardz.com to talk about the biggest challenge facing MSPs.

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