SMB Community Podcast: Business Advice for Small MSP Owners

Oct 22, 2026

Should Your MSP Take the Fall If AI Leads to Malware? | MSP agreements

A significant development highlighted is the recent compromise involving ConnectWise Backup, which originated from ConnectWise’s acquisition of SkyKick. The breach stemmed from the compromise of OAuth app credentials within Microsoft 365 tenants, enabling attackers to access and elevate permissions, primarily targeting MSP tenants. The full method of credential compromise has not been disclosed. However, the presence of lingering OAuth permissions is posited as an ongoing risk vector. Further details presented by Amy Babinchak specify that attackers targeted a few hundred MSP tenants, seeking

Oct 15, 2026

Should MSP Owners Sell Their MSP Themselves or Use a Pro?

The discussion centers on the tradeoffs and risks associated with self-managing the sale of a Managed Service Provider (MSP) business, highlighting a real case in which the absence of professional M&A, legal, and tax advisory led to contract errors, unfavorable terms, and substantial financial exposure. Both James Kernan and Amy Babinchak, drawing from direct advisory experience, argue that while selling an MSP independently is technically possible, the lack of specialist counsel introduces significant pitfalls. The synopsis emphasizes concrete instances where negotiation leverage, contract ac

Oct 8, 2026

MSP Culture: Can You Require Employees to Use Copilot?

The episode addresses the push for mandatory adoption of artificial intelligence (AI) tools among employees in MSP and IT service environments, citing cases where use of products like Microsoft Copilot is being enforced under threat of termination. Contributors emphasize that while AI proficiency is becoming a key factor for employability in the technology sector, mandating use through ultimatums is likely to provoke resistance and undermine change efforts. The consensus is that sustainable progress depends on providing structured training and fostering a collaborative culture rather than impo

Oct 1, 2026

MSP Processes: How AI Is Changing Patch Management

The episode scrutinized the operational impact of accelerated patch velocity, largely attributed to AI-driven vulnerability discovery. Microsoft’s patch release cadence has intensified, as evidenced by the increase from 200 patches in June to 900 patches in September. Despite this uptick, panelists noted that patch delivery is now consolidated—vulnerabilities are addressed through a single cumulative update per cycle rather than via hundreds of discrete patches. This structural change reduces exposure to widespread outages, but risk must still be evaluated based on deployment timing and organi

Sep 24, 2026

AI Services: Practical Ways for MSPs to Monetize AI

Public speaking for technical professionals and the development of practical business process automation using AI were identified as areas with tangible operational impacts for MSPs. Structured preparatory practices, such as rehearsals and simulated audiences, were described as beneficial for reducing employee apprehension and improving presentation quality, according to Amy Babinchak. Applying a process-oriented approach, including content development and reference to audience-specific expertise, can support staff development, help mitigate presentation anxiety, and promote more effective com

Sep 17, 2026

AI Has Changed MSP Lead Generation Forever: Now What?

Microsoft's Copilot platform has recorded a 33% growth, growing its user base from 20 million to 30 million seats in a three-month period, according to reported company data. Increased adoption is attributed in part to Microsoft's strategy of bundling Copilot licenses with existing products. Copilot lacks custom code-generation features, instead focusing on business process optimization and employee productivity. Microsoft's switch from OpenAI to Anthropic as the underlying model for Copilot reflects a shift toward features that align more closely with user workflow support. Supporting this de

Sep 10, 2026

Top 10 Moves to Make Before You Sell Your MSP

The episode centers on operational best practices and core risk factors for MSPs preparing to sell their businesses. The discussion highlights that a business must be able to function independently of its owner, with Amy emphasizing that the most important prerequisite for sale is organizational self-sufficiency. Buyers prioritize businesses that can maintain their operations, client relationships, and financial health following a change in ownership. The need for clean, auditable financials and contract organization is underscored as key requirements for reducing risk and promoting transactio

Sep 3, 2026

Lead Generation: How Local MSPs Can Outshine Big Nationals

A primary development addressed is the increasing scrutiny and demands from cyber insurance providers on MSPs and their clients. Amy highlighted a case where an insurer canceled a client policy after the MSP could not produce comprehensive reports and logs verifying device management for all endpoints, including BYOD and personal devices. This incident underscores rising expectations from insurers for documented security controls covering all systems interacting with sensitive data, and the risk of coverage denial when undisclosed devices or unmanaged endpoints are discovered following a breac

Aug 27, 2026

MSP CRM: What Is the Best CRM for Small MSPs?

Merger and acquisition activity within the MSP sector has accelerated, with data cited indicating a 73% year-over-year increase in transactions for 2026 compared to 2025. Jay McBain’s reported statistics also highlight strong international momentum, particularly in EMEA, and a marked 800% rise in acquisitions specifically targeting managed security service providers (MSSPs). While the consolidated figures suggest heightened activity in large, visible deals, several participants noted that the true frequency of smaller, unreported transactions likely exceeds official tallies, underlining persis

Aug 20, 2026

MSP Culture: Building a People-Led Learning Organization

Halo PSA has launched a customizable artificial intelligence capability and announced a price reduction for its product, separating its approach from other PSA vendors. According to Amy Babinchak, Halo’s model allows users to build their own AI agents for a range of business processes, including quarterly reporting and project management, without charging additional fees. The company indicates that future price reductions may occur as user adoption milestones are met. This development is especially notable in an environment where other providers are raising prices while limiting flexibility. H

Aug 13, 2026

AI Governance: Who Should Set AI Standards for MSPs?

The episode’s primary focus centers on the introduction of China-based Alibaba's new artificial intelligence (AI) model, which is positioned to rival existing US-developed models. This development has triggered concerns within the US federal government regarding the potential superiority of these foreign AI models and resulting security and data governance risks. The discussion further noted that recent import bans in the US have included consumer and business products containing AI elements, such as robotic vacuum cleaners, reflecting heightened regulatory scrutiny and caution toward foreign

Aug 6, 2026

Is Private Equity a Threat or Opportunity for Small MSPs?

Private equity (PE) acquisition trends in the Managed Service Provider (MSP) sector are targeting smaller firms at increasing rates, with offers now being extended to MSPs in the $1–3 million revenue range. PE activity, once limited to companies exceeding $5 million in annual revenue, is now resulting in more than half of current offers for these smaller businesses coming from large financial entities. This development creates both opportunities and risks for small and boutique MSPs, especially those with specialization or unique market positioning. Market data and discussion on the podcast hi

Jul 30, 2026

MSP Sales Process: How to Run a Pre-Sales Assessment

A key focus of the episode is on practical approaches to conducting pre-sales assessments for prospective managed service clients, particularly those with existing MSP relationships and under 100 employees. Hosts discussed that frontline assessment methods often prioritize observational “walk-arounds” and targeted questioning rather than the deployment of specialized tools, except in cases where complexity or asset uncertainty warrants additional rigor. The conversation emphasized that visible signs of technological investment (or lack thereof) and management engagement provide valuable risk i

Jul 23, 2026

Is It Worth It for Your MSP to Become a Microsoft Partner?

A significant development discussed in the SMB Community Podcast episode highlights the evolving Microsoft Partner Program. Microsoft has updated its partner program at the start of its fiscal year, introducing new opportunities and incentives. Notable changes include the loosening of Agent365 licensing, allowing its addition to Business Premium licenses and other tiers, and offering a 25% discount on Windows 365 licenses for both new and existing customers. Additionally, Copilot for Business is now available with a 15% discount for the upcoming year through the partner program. These updates

Jul 16, 2026

When Business Slows Down: Lead Generation for Small MSPs

The episode addressed the heightened challenges MSPs and IT service providers face in client acquisition, with specific reference to a recent Kaseya report indicating that twice as many MSPs describe obtaining new clients as more difficult compared to the previous year. This shift is attributed, in part, to changes in marketing efficacy and the increased reliance on referrals rather than structured marketing strategies. These findings emphasize the need for a consistent, proactive marketing approach—moving beyond informal networks—to counteract periods of slow business and ensure stable revenu

Jul 9, 2026

MSP Contracts: What Missing Agreements Cost You at Sale

The episode prioritizes the operational and exit-planning risks associated with MSPs lacking formal contracts. According to Amy , approximately half of MSP business owners operate without managed service agreements (MSAs), a decision that frequently results in reduced business valuation during sale negotiations. Both James and Amy emphasized that the absence of documented agreements is commonly flagged by buyers as a significant risk, often resulting in a devaluation of the acquired customer relationships. This exposes small and mid-sized providers to continuity risks, particularly where custo

Jul 2, 2026

Should You Give an MSP Proposal at the First Meeting?

The conversation focused on the practice of providing managed service pricing to customers during an initial meeting. One concept discussed was that MSPs are encountering prospects who increasingly expect immediate, transparent pricing, with many decision-makers opting to make choices after a single round of vendor meetings. The discussion explored how this shift contrasts with traditional industry advice that recommends withholding pricing until after an in-depth assessment and value-building process. Several points were raised, including the observation that coming prepared—with thorough res

Jun 25, 2026

When Employees Want More Money: Tech Compensation for MSP Owners

The episode’s principal focus is on managing employee compensation requests within MSP operations, specifically addressing scenarios in which employees request significant raises. The discussion highlights the need for MSP leaders to weigh current market rates and organizational financial constraints in response to such requests. Both collaborative problem-solving—engaging employees in discussions regarding revenue generation—and performance-based compensation structures were identified as practical strategies for balancing employee retention with business viability. Supporting this, the speak

Jun 18, 2026

Should Your MSP Offer a Single Plan or Multiple Options?

A significant regulatory development affecting MSPs was discussed: the US Government ordered the suspension of access to the Fable 5 and Mythos 5 AI models by any foreign national, including those inside and outside the United States, citing national security authorities. As reported in the Anthropic company statement, this directive forced abrupt discontinuation of these AI tools for all customers, regardless of business impact. The decision resulted in the sudden loss of access to custom-built AI applications and business process automation tools that MSPs and their clients had integrated in

Jun 11, 2026

Is EOS the Right Fit for Small MSPs?

A central discussion in the podcast focused on the applicability of the Entrepreneurial Operating System (EOS) for small Managed Service Providers (MSPs). Divergent perspectives were presented regarding whether the EOS framework is suitable for MSPs with very few staff. The conversation highlighted that while EOS provides accountability, transparency, and structured communication, some very small organizations (e.g., four employees or fewer) may find the framework’s meeting cadence and process requirements disproportionate to their operational needs. It was noted that EOS promises value in pro