The MSP Zone

Oct 20, 2026

The ConnectWise Cloud Backup Incident Raises a Bigger MSP Risk Question

Using the ConnectWise Cloud Backup shutdown as a case study, Charles Weaver examines a recurring issue for MSPs: they may be held accountable for risks in systems they do not directly control. He considers what this means for MSPs, vendors, and customers as security requirements and oversight continue to increase. The discussion focuses on how MSPs should respond when a supplier’s access is misused, why customers expect answers from the MSP, and how responsibility should be addressed when operational control is shared. The episode is relevant to MSPs that manage backup, EDR, password managemen

Oct 5, 2026

MSPs Don’t Have a Sales Problem - They Have a Profitability Problem

Most MSPs do not have a sales problem - they have a profitability problem. Charles Weaver lays out why growing top-line revenue can quietly destroy margin, and what to do before your business scales itself into a cliff. He breaks down the hidden cost of accepting more responsibility without charging for it, why modern clients now expect security, compliance, reporting, executive advice, and AI guidance, and how those demands reshape the real economics of managed services. If your pricing model still revolves around seats and devices, this conversation will challenge you to rethink what you're

Sep 29, 2026

Why MSPs Are the Best Answer to the CISO Gap

MSPs are no longer just managing technology. They are well positioned to close the CISO gap for small and mid-sized businesses. The underlying problem is not a lack of tools, but a lack of security leadership. MSPs already have the trust, visibility, and operational context needed to help clients turn technical findings into business decisions. In this episode, Charles explains why many organizations remain exposed, why adding more products will not solve the problem, and how MSPs can define a practical security leadership role. You’ll learn: Why the CISO gap is a leadership problem, not a pro

Sep 22, 2026

If AI Is So Dangerous, Why Are CEOs Still Selling It?

AI leaders are warning about catastrophic risks while racing to sell, license, and monetize the very systems they say could be dangerous. What is really going on: genuine alarm, strategic posturing, or an attempt to shape regulation before competitors do? Charles Weaver examines that contradiction and argues that the immediate challenge is not slowing innovation. It is putting proven controls into practice. He traces recent warnings from OpenAI and Anthropic executives and asks the question most people avoid: if these products are truly unsafe, why are they still being shipped? He also examine

Sep 14, 2026

Why AI and Debt Are Reshaping the MSP Market

The MSP market is entering one of its most disruptive periods in years. Private equity debt is coming due, AI is changing the economics of service delivery, and a new class of technology companies is challenging assumptions about how MSP platforms are built and funded. In this episode of MSP Zone, Charles Weaver speaks with Michael George about the forces creating what George calls a “perfect storm” in the managed services market. They examine the debt wall facing private equity-backed vendors, the difference between AI as a feature and AI as an operating advantage, and why venture-backed comp

Sep 1, 2026

On the Road with MSPs

MSPs are crossing a threshold, and the winners will be the ones who move beyond tool sales and technical support into AI advisory, compliance, and business process consulting. Charles Weaver returns from a week on the road with blunt, firsthand takeaways from MSPWorld Connect in Chicago and the MSPAlliance Inspire Peer Group in Toronto. What he heard from real MSPs was bigger than event buzz. The conversation has shifted from “which AI tool should I resell?” to “how do I monetize AI inside my practice?” That opens a new lane for mature MSPs, especially those with vertical expertise, but it als

Aug 23, 2026

Why MSPs Keep Missing Google Workspace Revenue

Most MSPs are overlooking a bigger Google Workspace opportunity than they realize. Charles Weaver and Dan Taylor of Apps EDU break down why Google is not a niche side platform, but a real managed services market hiding in plain sight for schools, nonprofits, startups, professional services firms, and globally distributed businesses. Dan built Apps EDU after moving from enterprise consulting and Microsoft-heavy environments into the Google world. He shares what that shift taught him about support, security, migrations, and the business model behind Google Workspace. He also explains why his tea

Aug 18, 2026

Why You Fired Your MSP for the Wrong Reasons

Before you fire your MSP, make sure you are solving the right problem. In this episode of MSP Zone, Charles Weaver examines why businesses often replace their managed service provider only to face the same frustrations months later. The issue is not always poor service. Sometimes the real gap is executive-level technology leadership, including CIO and CISO guidance around risk, security, compliance, budgeting, and long-term planning. Charles breaks down the difference between reactive IT support, true proactive managed services, and mature MSPs offering vCIO or vCISO capabilities. For business

Aug 4, 2026

How MSP Maturity Has Moved Beyond Revenue

Unlock the secrets to MSP success in 2026 with insights from industry veterans Rob Scott and Andy Runyan. Discover why maturity, beyond size or revenue, is your ultimate competitive edge in an evolving cyber threat landscape. This episode examines how MSPs are transforming into risk management powerhouses by using legal, operational, and insurance strategies to protect themselves and their clients. Rob Scott from Monjur explains why legal protections and smart contract design are fundamental to risk mitigation. He explores common misconceptions around cyber insurance denials and highlights how

Jul 28, 2026

Why MSPs are Losing Money Despite Record Sales

Most MSPs do not have a sales problem. They have a profitability problem. In this episode of MSP Zone, we look at why so many managed service providers are generating record revenue while keeping less of it. Growth has been the dominant conversation in the MSP profession for years: more monthly recurring revenue, more clients, more endpoints, more vendors, and more services. But growth does not automatically create a healthier business. Charles Weaver breaks down the hidden margin pressures facing MSPs today, including tool sprawl, rising cybersecurity obligations, unfunded AI advisory work, o

Jul 21, 2026

Why the Suspension of CMMC Phase Two Might Be a Game-Changer for Small MSPs

Most MSPs are asking: Is the future of cybersecurity compliance fundamentally changing — or just on pause? This episode uncovers what the recent suspension of Cybersecurity Maturity Model Certification (CMMC) Phase 2 really means for defense contractors, MSPs, and the broader industry.Charles Weaver dives deep into the Department of War’s groundbreaking shift: suspending the traditional, burdensome verification process in favor of a more scalable, resilient, and innovation-friendly approach called ATS. He reveals how this pause isn’t a sign of weakness but a catalyst for smarter, more effectiv

Jul 12, 2026

Cisco, MSPs, and the Future of Proactive IT

Most MSPs are still caught in a reactive cycle, responding to problems instead of turning technology into measurable business outcomes. In this episode, Cisco channel leaders Jason Gallo and Brad Feldman explain why that model is changing, and how MSPs can position themselves for the next era of AI-driven cybersecurity, infrastructure, compliance, and outcome-based service delivery. How the channel is moving from siloed voice and data services toward holistic, business-focused solutions. Why AI, automation, and cybersecurity are creating new opportunities for MSPs willing to move quickly. Why

Jun 22, 2026

Your Clients Reflect Your MSP Practice

Your MSP mirror is not lying — it’s showing you where your future is hiding. Are your clients pulling you toward maturity, or dragging you into reactive chaos?If your MSP practice feels like it’s always running uphill, right now might be the moment you need to ask: What does my customer base say about me — really? Charles Weaver drops the truth bomb: your clients are a mirror of your true MSP maturity. The more reactive, the more you’re risking burnout, lost margins, and a future uncertain of growth or valuation. But here’s the bold truth — you don’t have to stay stuck in reactive firefighting

Jun 16, 2026

Can you 'GRC' your way to MSP Maturity?

What if the biggest barrier to your MSP’s growth isn’t your technology, but your mindset? Charles Weaver and Chris Viau expose the dangerous myths around compliance, GRC tools, and operational maturity that could be sabotaging your success, and share the bold truth: You don’t need complex tools to excel.Forget the tick-box chaos! Discover why MSPs operating like true partners, not just reactive fixers, are the ones turning compliance into a competitive edge. We break down how the real secret isn’t in apps or frameworks, but in mature processes, disciplined operations, and leadership. You’ll le

Jun 3, 2026

Why is my MSP Cyber Insurance so High?

Navigating the complexities of cyber insurance can be daunting for MSPs—rising premiums, intricate applications, and a gap between underwriter expectations and MSP capabilities. This episode offers a transformative approach to mastering your insurance strategy, ensuring you’re not just covered but optimally protected.We delve into the MSPAlliance Cyber Insurance program, revealing how MSPs can effectively manage costs, enhance credibility, and position themselves as secure, insurable entities. If you're frustrated with overpaying or facing unexpected challenges at renewal, this episode is your

May 20, 2026

How a Caribbean MSP Is Leading the Global Shift in Cybersecurity

Most MSPs are on the front lines of a major shift in cybersecurity and AI, with an increasingly important role to play as the industry evolves. In this episode, Guy Phoenix, Managing Director of Fresh Mango Technologies, shares a clear view of what it takes for MSPs to stay ahead in a rapidly changing landscape. He highlights how MSPs can better align their services with the growing security and AI needs of their clients—and why stepping into that role is critical to delivering long-term value and trust.From the Caribbean to the UK, Guy shares a bold, insider perspective on the global MSP land

May 6, 2026

Aligning MSP Service Catalogs with Service Agreements

Most MSPs are unknowingly risking their business with outdated contracts and misaligned service descriptions. What if you could transform chaos into clarity; turn your service catalog into a legal powerhouse that defends, scales, and sells your business effortlessly? In this episode of the MSP Zone, Charles and legal tech visionary Rob Scott expose the silent danger lurking in your service descriptions and contracts, and show you how a well-synced service catalog can be your ultimate shield and growth hack. Discover the real reason MSPs face disputes, margin erosion, and legal exposure—and lea

Apr 22, 2026

The Role of Penetration Testing in MSP Cybersecurity

Unlock the truth about penetration testing — it’s not just a box to check but a vital armor for MSPs fighting unseen threats every day. Are you truly protected, or are your assumptions leaving gaps in your security fortress? This episode dives deep into the misunderstood world of pen testing, revealing why it can make or break your reputation, trust, and legal standing.Meet Steve Smith and Shaun Peapell from Rootshell Security — experts who turn the sneaky tactics of hackers into your strongest line of defense. They break down the real purpose of pen testing and how it extends beyond a once-a-

Apr 9, 2026

MSP Profitability - Who Cares?

Profitability in MSPs is not the ultimate badge of success — yet it’s widely treated as the holy grail. Why? Because behind the obsession with margins and EBITDA, we’re ignoring the real foundation of resilient, scalable managed services: operational maturity.Charlie Weaver blows the lid off the myth that profit alone equals strength. He reveals how MSPs can be highly profitable and dangerously immature, exposing hidden risks like cyber hygiene failures, disorganized processes, and regulatory blind spots. These issues threaten your business far more than fleeting financial metrics.You’ll disco