MSP 1337

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

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.

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.

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.

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.

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 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.

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

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.

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.

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.

With IT Nation Connect Global only a week away, we wanted to share some of the workshops and the value frameworks play in helping shift the conversations about cybersecurity from speed and feeds to Risk. Josh Hohbein of CentrixIT to get his perspectives and why he is so passionate about helping other MSPs and their clients better understand how frameworks help and the importance of the GTIA Cybersecurity Trustmark.

First ever monlogue with CJ... I recap some of the things I found to be of interest over the past few weeks with Pax8 EMEA and ChannelCon EMEA... Tell some stories and then looking forward to MSP Global. This one is short and sweet and I hope you find some entertainement in it.

Incident Response Planning and tabletop exercises have been discussed on the show several times. However, how do you get culture adoption and buy-in from all staff? I sit down with Amanda Lachapelle of Auvik to talk about IR Games, how to do them, and the importance of doing them, not just internally but also with your clients.

A Discussion around the global proliferation of cybersecurity and technology events, noting regional differences, the heavy concentration of events in October, and the increasing overlap in topics and audiences. Chris and Henry Timm of Phantom Technology Solutions also reviewed the agendas and standout features of key events they plan to attend—PAX8 Beyond, Channel EMEA, and MSP Global—highlighting session themes, notable speakers, and unique elements shaping the month’s cybersecurity dialogue.

Pax8 Beyond EMEA 2025 is less than a week away, and I wanted to take a minute to talk about the cyber sessions. What Matt Lee, of Pax8, is doing (today's guest), specifically his AI and CTF session. We might drift a bit in our conversation and go down a deep rabbit hole when setting up a home lab on the cheap. Enjoy!

Using a framework to assess a client is a great way to baseline security and compliance. We explore the challenges, hurdles, and best outcomes when you look at who is responsible for different pieces. Some safeguards can only be implemented or addressed by the MSP. Other safeguards require the participation of both MSP and the client. Lastly, some safeguards require the client to lead. Jim Harryman of Kinetic Technology Group shares their approach to get the desired outcome.

At Channelcon25, I was able to capture a few of our members in some in-person interviews on different topics. Dustin Bolander of Beltex Insurance had some really interesting insights that I wanted to share before we get to cybersecurity month.

Identity is who we are, and it is constantly being subjected to many different threats. I sat down with Kristen Costagliola CTO at Syncro, to talk about the challenges and some of the solutions to help MSPs and their clients make good decisions about protecting their identity.