Advertise on podcast: The MSP Zone

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 management, and other integrated services. It presents a framework for assessing vendor-related risk through questions such as: Where does risk begin when a supplier is compromised? Who is responsible when the MSP does not control the underlying system? When does operational efficiency create concentration risk? What information and support should vendors provide to MSP partners? How should contracts, liability, and evidence be managed across the service chain? Charles also outlines five tests MSPs can use to evaluate their technology stack: the control test, concentration test, substitutability test, contract test, and failure test. These tests help determine whether vendor relationships support resilience and clarify how an MSP would respond to a service failure. The episode also considers supplier access, industry consolidation, and the operational impact of relying on a limited number of platforms. It is intended for MSP owners, security leaders, and others responsible for managing customer risk and vendor relationships.

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 actually selling. You'll discover: Why revenue growth can mask rising delivery costs, service obligations, and risk How the client expectation gap turns every "small ask" into unpaid work Why security and compliance are not just tool markups, but ongoing services How AI creates a rare opportunity to reset pricing and redefine scope Why per-user pricing is only a starting point, not a real risk model Charles also explains why mature MSPs need to move toward risk-based pricing, how to quantify complexity and accountability, and why annual price reassessment is no longer optional. He makes the case that if a service creates liability, expertise, or ongoing support, it should be in your service catalog and priced accordingly. This is essential listening for MSP owners, operators, and leaders who want growth that actually improves the bottom line - not just the revenue chart. If you've ever wondered why a "great" client is quietly eroding profitability, this episode gives you the framework to find out.

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 product problem How MSPs can translate technical exposure into business risk What a partial CISO operating model looks like in practice Why cyber insurance, compliance, and legal obligations all depend on the same leadership layer How to set boundaries, define authority, and protect both the MSP and the customer in writing Charles also explains the guardrails that matter: contract language, risk allocation, and the distinction between recommending corrective action and accepting a customer’s risk. Using examples such as cyber insurance questionnaires, MFA gaps, backups, encryption, and EDR, he shows how MSPs can frame security issues in terms business owners understand. MSPs that remain focused only on tickets and tools risk becoming less relevant while the client’s underlying exposure goes unresolved. Those that develop a credible security leadership capability become more valuable to every client they serve.

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 examines whether “AI safety” has become a catch-all term for everything from ordinary business risk to speculative extinction scenarios, and why that distinction matters for businesses making decisions today. You’ll discover: Why public calls for government oversight may be less about safety than competitive advantage The cyber hygiene basics that already reduce AI risk, including identity, access, encryption, logging, retention, and human approval Why MSPs and SMBs do not need to start from zero to govern AI safely How regulation can become a barrier that only the biggest players can clear What the Manhattan Project and the space race reveal about the relationship between innovation, national security, and regulation Charles also gets practical, outlining what MSPs should do now: inventory every AI tool, review every connector and permission, require human approval for consequential actions, and test how quickly AI access can be revoked when something goes wrong. This episode is essential listening for MSPs, security leaders, and business owners who are being told to fear AI while also being pressured to adopt it quickly. If you want a clearer, more practical way to evaluate AI risk without the hype, this conversation provides the framework.

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 companies may move faster than many established providers expect. The conversation also explores the expanding role of the MSP. Customers are no longer looking only for technical support or software licenses. They need guidance on automation, business process improvement, cyber hygiene, and resilience. That creates significant opportunity, but only for MSPs willing to rethink their platforms, operating models, and advisory capabilities. This episode offers a practical look at what is changing, why it is happening now, and how MSP leaders can navigate the disruption without losing sight of the opportunity.

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 also raises hard questions about governance, pricing, risk, and how far into a customer’s business processes an MSP should go. Key Themes Charles breaks down the biggest themes shaping the market right now: why peer groups outside your echo chamber matter, how AI is creating both opportunity and hidden costs, why compliance is moving past simple control checklists into real advisory work, and why operational maturity is pushing MSPs to abandon vendors who stop investing. He also explains why event fatigue is real, what MSPs actually want from conferences, and why genuine MSP-to-MSP connection matters more than noise. You’ll Discover Why AI is no longer experimental for MSPs How consulting and business process advice can become a new revenue engine The hidden financial danger of unmanaged AI usage Why compliance and cybersecurity are becoming broader advisory services How best-of-breed tool choices are driving vendor churn Why the MSP profession is finally being forced to "prove it" Who Should Listen If you serve SMB clients, run an MSP, or want to understand where the managed services market is heading next, this episode gives you the clearest view yet of the shift already underway. Essential listening if you want to stay relevant as the MSP model evolves beyond pure IT.

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 team built Workspace Audit, a continuous scanning tool designed to solve the biggest flaw in point-in-time security audits: they go stale fast. You'll discover: Why Google Workspace adoption is far stronger than most MSPs assume, especially in education and among startups The real market numbers behind Google vs. Microsoft across schools, SMBs, and enterprise Why Google Workspace support can be simpler than Microsoft 365, with fewer moving parts and less tool sprawl How MSPs can monetize Google through support agreements, migrations, security audits, backups, and third-party apps Why Chrome browser management, Chromebooks, and identity controls matter more than many MSPs realize Charles and Dan also tackle the practical questions MSPs ask most: Do you need an RMM? Can you keep your single pane of glass? What tools actually carry over from a Microsoft-centric stack? The answer is yes, often more than you think. Dan explains how MSPs can layer Google into an existing service model without starting from scratch, and why the real risk is not complexity. It is dismissing qualified Google prospects before you understand the ecosystem. This conversation is especially valuable if you support SMBs, schools, or vertical markets like legal, dental, finance, or education and want to expand your serviceable market without adding unnecessary overhead. If you've ever passed on a prospect because they used Google Workspace, this episode shows why that decision may be costing you more than you know. Dan Taylor is the founder of Apps EDU, a Google Workspace-focused MSP serving schools and businesses around the world. His team also built Workspace Audit, a multi-tenant security and optimization platform for Google environments. If you want a clearer view of how to support, secure, and profit from the Google ecosystem, this episode is essential listening.

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 leaders and MSPs alike, this episode offers a practical way to think about provider expectations, client maturity, and why replacing the MSP will not fix the problem if the diagnosis is wrong.

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 comprehensive policies, tailored contracts, and proactive documentation help mature MSPs reduce litigation risk and build client confidence. Andy Runyan from UKON offers a behind-the-scenes look at how insurance, compliance, and technology must align, especially as AI and shadow IT accelerate risk. He points out that MSPs using AI internally may be ahead of the curve, but they must ensure their contracts and policies evolve to cover new vulnerabilities. You’ll discover: Why size doesn’t determine maturity, and how operational discipline and legal rigor matter more. How to structure contracts that clearly define responsibilities and limit MSP liability. The truth about cyber insurance claim denials versus paid claims, and how to optimize coverage. The emerging role of AI and shadow IT, and how MSPs can proactively manage these risks. Practical steps to integrate legal, insurance, and certification pillars for true MSP maturity. Why does this matter? Because in today’s landscape, a misstep can cost thousands, or even put you out of business. MSPs who master risk management and invest in operational excellence build resilience, command higher valuations, and avoid costly disputes. Whether you’re an MSP owner, a cybersecurity professional, or an insurance strategist, this episode equips you with practical ideas to elevate your practice. Get ahead of the curve, embrace maturity, protect your enterprise, and unlock new growth opportunities. Guest Credibility: Rob Scott is a seasoned legal expert in MSP contract law, leading Monjur’s legal and risk advisory practice. Andy Runyan is Head of UKON, specializing in MSP insurance solutions and operational risk management, and is known for guiding MSPs toward comprehensive cyber risk strategies. Don’t miss this essential conversation. Your MSP’s future depends on it. Tune in now.

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, outdated pricing models, and the operational maturity gaps that prevent MSPs from turning demand into sustainable profit. The takeaway is simple: the MSPs that thrive over the next decade will not necessarily be the largest. They will be the ones that understand their true cost to serve, price for risk, simplify their operations, and convert expertise into margin.

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 effective cybersecurity strategies that balance security and opportunity.You’ll discover:- The real reason behind the CMMC Phase 2 suspension and what the Department of War’s ATS framework aims to accomplish- Why the core issue with CMMC was never the controls — but the flaws in its testing and assessment methodology- How MSPs can turn this uncertainty into a competitive advantage by focusing on operational maturity, continuous assurance, and scalable security practices- Practical steps for organizations to maintain compliance, strengthen cybersecurity hygiene, and prepare for a future framework rooted in efficiency and effectivenessStaying locked into outdated certification methods risks leaving your organization vulnerable — but understanding the shift reveals a massive opportunity for innovation and resilience. The government’s reevaluation isn’t a retreat; it’s an invitation to rethink how we validate cybersecurity success.Whether you’re an MSP, a defense contractor, or a cybersecurity leader, this episode equips you with the clarity and guidance to navigate these changes with confidence. Continue your security journey, invest in operational excellence, and stay ahead of the evolving compliance landscape, the future is being rewritten, and this episode shows you exactly how to lead it.Guest credibility: Charles Weaver is the founder of MSP Alliance, a pioneer in advocating for scalable, effective cybersecurity solutions for MSPs and critical infrastructure sectors, with decades of experience shaping industry standards and policies.Perfect for: MSPs, defense industry professionals, cybersecurity executives, and policy influencers committed to smarter, less bureaucratic security measures. Don’t miss this insights-packed discussion on what’s next for cybersecurity compliance and how your organization can thrive in the new era.Stay tuned for actionable strategies that will help you turn regulatory uncertainty into your biggest advantage. Hit play now and be part of the transformation.

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 maturity, trust, and execution matter more than company size in the evolving Cisco partner ecosystem. The role of foundational infrastructure in strengthening cybersecurity, resilience, and national security readiness. How MSPs can shift from technical delivery to outcome-focused service models built on transparency and accountability. Practical steps MSPs can take now to accelerate their evolution before the market moves past them. Whether you are an emerging MSP or an established provider, this conversation offers a clear view of where the channel is headed and what it will take to stay relevant. The future belongs to MSPs that can move with speed, earn trust, and deliver outcomes clients can see and measure. Jason Gallo and Brad Feldman bring deep Cisco channel experience to a timely discussion about technology, trust, growth, and the future of managed services. If you are ready to move beyond reactive support and build a more strategic MSP business, this episode is a practical and compelling place to start.

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. You can elevate your entire practice by setting clear boundaries, raising your minimum standards, and demanding the respect you deserve.In this episode, Charles cuts through the noise and reveals a shocking reality: the lowest-rated client is dictating your entire practice’s health. He breaks down the mirror effect—how customer behavior reflects your MSP’s true maturity, and what it really takes to turn that reflection in your favor. You’ll discover:How those ‘fire department’ clients are draining your team and your profitsThe secret to establishing a minimum service standard you won’t compromise onWhy you must clear your client portfolio of low-maturity risk — before it’s too latePractical steps to enforce your service floor and radically improve margins, security, and valuationThe critical impact of pushing your customers upward — one rung at a timeThe stakes are high: a reactive, risky customer base will cripple your growth, inflate your operational costs, and sabotage your MSP’s worth — especially if you ever want to sell or scale. But by actively shaping your customer portfolio, you position yourself as a true leader, not just a fireman. You’ll future-proof your practice, lower your risk, and boost your valuation — empowering you to serve better, earn more, and retire sooner.This episode isn’t for the faint of heart — it’s your call to action. Are you ready to look in the mirror and finally see the MSP you really want to build? The clock is ticking. It’s time to enforce standards, elevate your clients, and craft a modern, mature MSP practice that commands respect and delivers exceptional value.Your mirror is waiting. Will you look? Or keep running in circles?Perfect for MSP owners, leaders, and ambitious technologists ready to stop fighting fires and start building a revolution.

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 learn:-Why GRC tools won’t make you compliant or mature, but honest operational processes will.-How MSPs often fool themselves into thinking green checkboxes mean real security.-The overlooked role of internal processes versus tool stacks in audit success.-Why jumping into frameworks like CMMC without a plan can sabotage your reputation, and when to actually certify.-Actionable steps for MSPs to lead their customers toward true compliance, profit, and peace of mind.This isn’t just about avoiding fines or passing audits, it’s about transforming your entire practice. If you’re tired of complexity and ready for clarity, this episode is your wake-up call to operate smarter, not harder.Chris Viau, MSP compliance expert and leader of MSP certifications, reveals the insider truths that will elevate your game. This is for the MSPs daring to be more than just support, to become trusted, mature partners with operational integrity at their core.Don’t settle for the illusion of compliance. Tune in and learn how to build an MSP that’s resilient, profitable, and truly compliant.

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 essential guide.Discover how the insurance industry evaluates MSP risk and why many MSPs are unknowingly overexposed. We provide honest insights into the evolving landscape, influenced by global events and a shifting cybersecurity environment. Learn how to safeguard your business through strategic risk management, robust contracts, and informed insurance choices.Key takeaways include: • Leveraging the MSPAlliance program to avoid traditional broker pitfalls and adopt standards-based approaches. • Evaluating existing policies and claims to save money and identify coverage gaps before renewal. • Right-sizing your limits, negotiating premiums, and avoiding the dangers of dual policies and outdated contracts. • Partnering with the MSPAlliance to secure better coverage, reduce costs, and achieve accurate risk assessments, regardless of your size or location. • Understanding the impact of legal cases, social engineering, and operational changes on your insurance needs.This episode is about redefining your MSP’s cybersecurity posture, legal standing, and market reputation. If you’re committed to reducing risk, gaining control, and making insurance work for you, this episode is your blueprint. Perfect for MSPs ready to eliminate confusion and overpayment.The future of MSP risk management starts with education, standards, and decisive action. Are you ready to elevate your strategy? Tune in now to begin your journey.