Episodes

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.

In the current threat landscape, one can easily become overwhelmed. I sat down with Noam Morginstin, founder of Exigence, to talk about realistic ways MSPs can begin building their Incident Response Plan and how to tackle successful Tabletop Exercises and prepare for resilience.

If you are an MSP, there is probably at least one tool in both the physical space and the digital space that you were just awestruck when you finally got your hands on it. I sit down with Charles Love of ShowTech Solutions to talk about some tools from the wayback days and how the tools today are in some ways truly transformational in how they save us time, make us more accurate, and help us take better care of our clientsIf you are a Managed Service Provider (MSP), you likely have experienced a...

How do you get your clients to take cybersecurity seriously? I sat down with Ann Westerheim of Ekaru to discuss strategies for helping MSP clients improve their cybersecurity posture.

Getting to compliance... Do you end up with more to do because you have the GTIA Cybersecurity Trustmark Assured? I sit down with Chase Griffin with ShowTech Solutions to talk about their experience and what has transpired since achieving Assured status and how that changed their outlook on improving their compliance to a standard and setting them up to be resilient.

When a client is hit with ransomware, it can be paralyzing. After the tabletop exercises carried out at #ChannelCon25, Jason Comstock of Clarity Technology Solutions explored ransomware and the path to recovery. Stay tuned to the end for Jason's after-action report.

With more than 100 attendees for a full day of networking and learning. The TD preday and another 30+ next door for MSP-Ignite peer group facilitated discussions, it was a learning and growing experience for all. I sat down with Roddy B. of ShureWeb to get his take and perspective. We went off script a few times, and I'll be sure to bring some more insights in future episodes. Insights to be had for sure all the way around.

Charles Love of ShowTech Solutions and I sit down to discuss Channelcon25. Why you should attend and a preview of some of the sessions. From MSP-Ignite and their peer group style conversations to Tech Degenerates and many other communities coming together for a Monday Pre-day and then rolling into the daily agenda, centered, of course, on sessions that pertain to Cybersecurity and perhaps a path to developing the skills to help you on your GTIA Cybersecurity Trustmark journey.