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

Chris Johnson - Cybersecurity Maturity Enabler
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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.

  1. 2 DAYS AGO

    Do Phishing Simulations Really Work?

    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.

    43 min

  2. 3 FEB

    Physical Safeguards and Process and Procedures

    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.

    30 min

  3. 27 JAN

    Data Privacy and Security Trends in 2026

    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 pressure on businesses to actually practice what their privacy policies preach. If you want to stay ahead of compliance, client expectations, and real‑world data risks, this episode gives you the clarity and direction you need.

    34 min

  4. 20 JAN

    Exploring AI Usage, Misconceptions, and of course Security Concerns

    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 team without putting your data at risk, this episode delivers the clarity you’ve been looking for. If you are looking to connect with Alane Boyd, her website is biggestgoal.ai

    36 min

  5. 13 JAN

    Human Behavior and Shifting from Security Awareness to Appreciation

    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 awareness. From AI-driven fraud and voice cloning to practical steps like password managers and two-factor authentication, this episode highlights how mindset shifts and personal responsibility are key to resilience in today’s threat landscape.

    34 min

  6. 7 JAN

    ITSP Reslience in 2026

    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.

    34 min

  7. 30/12/2025

    December Series 2025 Wrapup

    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.

    23 min

  8. 23/12/2025

    Data, Security, and The Human Edge

    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.

    33 min
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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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