SMB Community Podcast

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 present potential financial benefits and strategic advantages for MSPs engaging with Microsoft's offerings.

The episode also touches upon the increased adoption of onboarding fees among MSPs. While some MSPs prefer to integrate initial setup costs into project-based work, a growing percentage now charge explicit onboarding fees. One discussed model involves charging a fee equivalent to one month's recurring service cost, with some offering waivers for multi-year agreements. Another creative approach noted is using the onboarding fee to fund sales commissions, providing sales representatives with negotiation leverage. This trend suggests a shift in how MSPs are structuring their client acquisition and initial service delivery processes.

Further discussions in the podcast address the broader labor shortage in the technology sector, which is reportedly more significant than concerns surrounding AI's impact on jobs. The shortage particularly affects highly educated IT professionals, including those with degrees and senior engineering expertise, with an estimated 50,000 jobs at risk. This situation presents opportunities for existing industry professionals to advance and for AI or new entrants to fill entry-level roles. Concurrently, there is a recognized need for enhanced business acumen and financial literacy among IT professionals to better understand client business needs and articulate the return on investment for technology solutions.

For MSPs and IT service providers, the updated Microsoft Partner Program offers tangible financial incentives and opportunities for service expansion, particularly with the introduction of the Copilot specialization. The increasing prevalence of onboarding fees warrants a review of client acquisition strategies, balancing revenue generation with potential client apprehension. The persistent labor shortage underscores the importance of continuous training and upskilling, with a particular emphasis on developing business and financial literacy alongside technical expertise. Finally, the discussion on mergers highlights the critical importance of cultural alignment and clear, written agreements regarding governance and exit strategies, as poorly managed mergers can significantly diminish business value.

Is it worth it to become a certified Microsoft Partner?   

Labor shortage link: https://www.linkedin.com/news/story/record-labor-shortage-may-pose-larger-threat-than-ai-8379017/

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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 revenue.

Discussion highlighted that many MSPs lack a formalized marketing plan and treat the absence of active marketing as a matter of pride, despite clear evidence that consistent marketing activities are essential for growth and resilience. According to James Kernan, "marketing is the oxygen of your business," and its absence correlates directly with reduced new business opportunities. Strategies such as recurring in-person or online engagement with clients, regular assessment of marketing practices, and leveraging written marketing plans were identified as actionable recommendations for sustaining pipeline health.

A secondary focus examined operational risk and opportunity related to "shadow AI"—unauthorized or unmanaged use of AI tools by clients’ staff. Amy Babinchak detailed three core risks: accidental exposure of confidential data, violation of contracts or regulatory requirements, and a lack of auditable records for actions taken by shadow AI tools. The discussion identified practical risk mitigation steps, including staff education, policy development, and implementation of monitoring tools, all of which represent billable opportunities for MSPs while reducing downstream liability in the event of a breach.

For technology service providers and decision-makers, the episode underscores the operational imperative of formal, consistent marketing—even during slow periods—as well as the need for vigilant governance over emerging technology risk vectors such as shadow AI. By proactively engaging clients through both marketing and risk education, MSPs can better protect their businesses while expanding stable, recurring revenue streams rooted in demonstrable expertise and accountable service delivery.

Title:   How do I get more business when it’s slow?

M&A Topic: Why is an elevator pitch for my business important?

Article: Why is finding new clients harder? Double the number of MSPs in Kasaya reported said so. https://www.kaseya.com/blog/msp-growth-challenges-2026/

QBR Talk: Talk to your clients about Shadow AI https://www.thirdtier.net/2026/06/25/speak-to-your-client-about-shadow-ai/

Tales from the field: A fictional tale about the Trunk Slammer from Hell. 

https://www.reddit.com/r/msp/comments/1u82vnh/i_got_obsoleted_by_ai_so_i_wrote_you_all_a_bofh/

UPCOMING CHANNEL EVENTS

Mastermind LIVE in Omaha NEJuly 30-31st

Register: 

https://kernanconsulting-mastermind.mykajabi.com/mastermind-event

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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 customer retention and service transferability are not contractually secured.

Further details outlined by Amy indicate that reluctance to implement contracts stems from concerns about client reactions, particularly in longstanding relationships. She observed that auto-renewal clauses and periodic, non-intrusive contract updates can streamline compliance and reduce friction. A personal account highlighted that, out of numerous customers, only one refused to sign an agreement, and this isolated case did not lead to client loss but necessitated risk pricing adjustments. James Kernan advised that contract clarity—covering terms, automated payments, and built-in annual price adjustments—should be positioned as a value to both parties, reinforcing operational stability and predictability.

Adjacent topics addressed contemporary service risks such as the proliferation of shadow AI applications and exposure to business email compromise. Amy reported discovering over 150 unmonitored AI-powered apps at client sites, emphasizing these as vectors for data exfiltration and compliance gaps. The Guards Cybersecurity Statistics report was cited, identifying business email compromise and social engineering as persistent attack methods, while underscoring that modern threat actors often bypass traditional privilege escalation in favor of capturing identity credentials and tokens. The operational focus for MSPs was advised to shift toward email, AI governance, and identity protection rather than legacy device vulnerabilities.

For MSPs and IT service providers, the main takeaways involve reassessment of contractual practices and a heightened approach to governance and risk management. Documented client agreements are necessary not only for valuation at exit but also for protection against operational disruptions and liability. Simultaneously, providers are urged to implement discovery and control mechanisms for AI use and to refresh security postures in line with current attack methods. The importance of establishing relationships with specialized advisors, attorneys, and alternative financing partners was also articulated, illustrating the multi-layered risk landscape that management teams must navigate for business resilience.

Show title: “How to Start a MSP”

1. How to Start a MSP- Resources: www.itspu.com

2.    New article from Third Tier: Taming Shadow IT before it tames you https://www.thirdtier.net/2026/06/21/taming-shadow-ai-before-it-tames-you/

3.    Guardz released a new cyber security statistics report: https://guardz.com/blog/security-awareness-statistics-msps-cant-ignore/

4.    Thoughts about whether an MSA is needed? Send them through the website: www.smbcommunitypodcast.com

5.    Anthropic Partner Program - https://www.anthropic.com/news/services-track-partner-hub

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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 research on the prospect and a clear pricing structure—can facilitate business wins, especially in competitive settings where prospects expect streamlined proposals.

A key theme that emerged was the importance of preparation ahead of initial client meetings. The discussion clarified that researching client backgrounds, conducting preliminary discoveries, and leveraging prior experience with similarly sized environments enable MSPs to present informed, realistic pricing. The conversation addressed that exceptions remain: in complex environments or when the client lacks clear infrastructure visibility, an assessment may still be necessary prior to quoting. However, these situations are reportedly less common, as clients often provide substantial upfront context during pre-meeting calls.

Secondary topics included practical guidance for financing large product orders, navigating out-of-state project requirements, and managing margin compression. The discussion explored options for financing substantial hardware purchases, highlighting leasing through distributors or manufacturers, encouraging clients to handle their own financing where possible, and considering purchase order (PO) financing to reduce resource strain. For out-of-state projects, building a professional network through peer groups or leveraging distributor partner networks was recommended. Regarding margin management, participants suggested standardizing service stacks, packaging recurring solutions, and reviewing contracts to ensure annual rate adjustments. The use of value-added services, such as cybersecurity and compliance, was recommended to offset margin thinning.

The discussion outlined several implications for MSPs and IT leaders. Responsive, transparent pricing aligns with current buyer expectations but requires robust preparation and established pricing models to maintain accountability and ensure fair risk allocation. For hardware procurement, shifting financial responsibility to clients or utilizing external financing tools can preserve operating capital and mitigate margin erosion. Resilient operational models—incorporating peer collaboration, flexible service packaging, and annual price reviews—enable firms to adapt to ongoing industry pressures including rising costs and tightening margins. MSPs are advised to prioritize accountability in client communications, vendor negotiations, and conflict resolution policies to reduce operational risk and protect organizational wellbeing.

Title:       Should you give a proposal at the first meeting?

MSP Question of the week:   Should you give Managed Services pricing to your prospect on the first meeting?

Topics/Events

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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 speakers emphasized transparent conversations with employees about the company’s billing structure, the sources of revenue, and the tradeoffs required to increase compensation. Performance-based incentives, such as commissions or bonuses tied to measurable business milestones (e.g., revenue targets, net new business), were noted as effective mechanisms for aligning individual rewards with organizational profitability. The discussion also noted risks when negotiation dynamics become adversarial, underscoring the importance of maintaining professionalism in both management and staff behaviors.

Adjacent topics included the increasing relevance of AI proficiency for workforce retention and the emerging terminology in the sector, such as “Managed Intelligence Provider” (MIP). It was observed that employees lacking AI skills face elevated layoff risks, a factor attributed to shifting operational priorities and the need for continuous learning. While new acronyms like MIP may gain industry attention, participants agreed that most services related to intelligence and data management could be incorporated within the MSP framework, suggesting minimal structural change for service providers.

For MSPs and IT leaders, the session underscores the necessity of clear compensation policies, ongoing staff development—especially in AI—and cautious positioning during merger or acquisition discussions. Risk mitigation includes frank financial communication with staff, investments in workforce upskilling, and careful negotiation to avoid undervaluation during business transitions. Performance incentives and clear cultural alignment are practical steps to balance employee satisfaction with organizational sustainability.

1. MSP Question of the week: My employee wants more money- what should I do?

2. A single decision that triples some workers layoff risk – Tech workers who regularly use artificial intelligence tools are far less likely to be laid off compared to colleagues who use AI less frequently, Bloomberg reports, citing new Gallup research. It puts infrequent users' layoff risk at 18%, tripling the 6% layoff risk for frequent users. Earlier this year, researchers tracked how often 23,000 employed and displaced workers used AI

3. The RISE of the Managed Intelligence Provider

4. M&A: How do I find the right buyer? Amy’s Book: https://amzn.to/4dSYOcR

5. Tales from the Field: Merger conversation – make sure it’s a culture fit and be fair with the price (no lowballing)

Mastermind Event – July 30-31st, 2026

Register here: https://portal.kernanconsulting.com/mastermind-event

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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 into daily operations. Immediate disruptions included the cessation of SEO and analytics engines, RMM automation, and bespoke backup solutions that relied on the now-restricted AI platforms.

Further clarification showed these suspensions are tied to concerns about potential backdoor access, disputed by Anthropic but acted upon due to US Government findings. Additional context revealed Amazon—the largest investor in Anthropic and a direct competitor—alerted federal authorities to the supposed vulnerability. Stock prices of competitive AI offerings in China reportedly rose by 48% following the announcement, indicating market reactivity to perceived US regulatory risks. The episode underscored that AI model dependencies—whether managed internally by MSPs or by third-party vendors—can introduce sudden continuity hazards if access or legal standing is rapidly altered.

Adjacent discussions evaluated operational models for MSP service offerings. Contrasting perspectives highlighted the tradeoff between providing a single comprehensive managed services plan, designed for streamlined staff training and high-touch customer experience, versus offering a tiered set of plans (“good, better, best”) that, according to shared data, can result in about 70% higher revenue through client segmentation and option-based sales. The choice was framed as fundamentally cultural, influencing both workforce structure and scalability, with differing risk and complexity profiles for technical delivery and sales management.

Key implications for MSPs and IT leaders include the need for explicit risk assessments around reliance on AI platforms and third-party tools. Business continuity planning should contemplate not only technical redundancy but also legal and regulatory exposures to abrupt vendor or governmental action. When building service portfolios, organizations should align plan standardization or diversification with internal capacity, capability for sales-driven growth, and staff training. Establishing clear governance for evaluating the ongoing viability and risk exposure of both internally developed and vendor-supplied technology is critical for operational resilience in an environment of rapid regulatory change.

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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 promoting ownership and alignment but that this benefit is more likely realized when an organization reaches a scale where individual ad hoc communications become inefficient.

Supporting these observations, it was emphasized that EOS, as detailed in resources such as Gino Wickman’s book and related summaries, is designed with flexibility to span small, medium, and large teams. Examples were offered indicating that even companies with four employees have derived benefits through formalizing updates and consolidating communication, provided their baseline culture supports collective knowledge sharing. However, one position outlined that simply reading EOS materials may be sufficient for the smallest organizations to improve focus without fully implementing the structure, especially when daily meetings or formal processes are not otherwise necessary.

The episode additionally examined risk management and operational best practices surrounding MSP business growth and eventual sale. The dialogue discouraged running a business constantly as if preparing for immediate sale, citing the need for risk-taking during growth phases. Factors such as maintaining diverse client portfolios, implementing clear master service agreements (MSAs), reducing owner dependency, and minimizing client concentration risk were underscored as practices that support both ongoing scalability and future valuation. A case was discussed in which valuation was negatively impacted by an overreliance on non-contracted, concentrated clients and a lack of W2 employees, illustrating the risk implications of operational decisions.

For MSPs and IT service leaders, the discussion underscored the importance of regularly reviewing operational frameworks and business hygiene regardless of size. The tradeoffs between structure and agility require clear-eyed evaluation, particularly in managing risk, scaling sustainably, and ensuring future options for valuation or exit. While formal systems like EOS can strengthen accountability and communication, overengineering processes in very small teams may reduce efficiency. Careful attention to client diversification and contractual commitments is essential for risk reduction and maximizing enterprise value.

Title:    Is EOS good for a small MSP?

What are we talking about today:

Amy and James Events:

SMB Online Conference- June 25th panel. Free registration for SMB Online Community members. Register at www.smbonlinecommunityconference.com

Mastermind Event – July 30-31st, 2026 in Omaha, NE. Register at 

https://kernanconsulting.com/mastermind-event/

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Discussion centered on the evolving role of Artificial Intelligence (AI) in the MSP technology stack, emphasizing the necessity for MSPs to deploy tools that can comprehensively manage AI, particularly concerning security and shadow IT. Multiple participants highlighted the lack of current solutions that aggregate and control AI activity via a single interface, with an explicit focus on the requirement to educate clients about AI privacy, security, and usage costs. The practical challenge of MSPs asserting thought leadership in AI was underscored, as was the complication of usage-based AI billing models leading to unexpected customer expenses.

Supporting details were drawn from the recently released Kaseya State of the MSP report, which showed that customer acquisition remains the sector’s main challenge, with 71% of surveyed MSPs identifying it as their top concern. The report further found that only a minority of MSPs are executing effective sales and marketing strategies to educate clients. Additionally, 48% of respondents reported AI and automation as top client needs, yet a significant drop was observed in customers spending more than $25,000 a year with MSPs, falling from 75% to 41%. This reduction is attributed to clients undertaking technology initiatives independently, diminishing the perceived value of MSP services.

Adjacent discussions addressed common issues around automation and AI adoption. Several practitioners noted a prevailing trend of automating legacy processes rather than leveraging AI for forward-looking transformation. It was emphasized that most AI implementations among peer groups are focused on operational efficiencies for past tasks, such as help desk and marketing automation, with few examples of innovative new service offerings. The dialogue also covered practical, risk-related aspects of managing client relationships, particularly when enforcing security measures such as multi-factor authentication in the face of client resistance.

Implications for MSPs and IT leaders include the need to strengthen governance around AI adoption and service stack adjustments, actively communicate the value of AI security and management services, and anticipate client concerns about cost control and privacy. The observed decrease in customer spending points to operational and strategic risks around client engagement and service value. MSPs are advised to ensure that automation efforts align with future requirements, not just past service models, and to enhance accountability in both vendor and client-facing operations.

Title:    Should I Adjust My Stack for AI? 

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A central development addressed is the projected effect of AI on the per-seat pricing model that underpins many MSP service offerings. According to the discussion, AI could reduce white-collar jobs by 30-50%, leading to fewer user seats for MSPs to support and bill for. This scenario presents significant revenue risk for MSPs reliant on per-user contracts. The discussion also references Microsoft’s introduction of Agent365, a product designed to license AI agents within enterprise environments, indicating a move by vendors to adapt licensing models while protecting enterprise relationships.

Participants noted that if customer organizations reduce headcount, MSPs will face declining license and seat-based revenue. Discussion suggested alternative business models, such as switching to per-device pricing or developing new service streams, with an emphasis on advisory services and security. The timeframe for these changes was cited as two to three years, which was described as an operationally compressed window for MSPs. Additionally, security, data management, compliance, and governance were highlighted as ongoing service areas with continued relevance as the MSP landscape evolves.

Additional topics included increased local competition among MSPs, as evidenced by survey data reporting 100% of respondents encountering significant competition in 2024. Differentiation and targeted marketing were underscored as necessary responses to commoditization pressures. Emotional considerations related to M&A were also discussed, with particular focus on the personal and organizational impact of business sales. Security operations in MSP settings were identified as a rising operational burden, amplified by rapid changes and the challenge of upskilling staff hired for traditional IT roles.

Key implications for MSPs and IT service providers center on the need for rapid operational restructuring, with greater emphasis on knowledge-based services such as IT advisory, risk, security, and compliance. There is a recognized accountability for customer education on evolving threats and for managing new AI-related risks that impact both data sovereignty and contractual obligations. The discussion suggests that MSPs unable or unwilling to adapt to these shifts may seek exit strategies, while those staying will need to reassess both revenue models and the skills composition of their teams. Participation in industry peer groups was recommended to share best practices and address common operational challenges.

MSP Question of the week:    How will AI impact the per seat model? 

-  How will AI impact the per seat model? 

-  Captera did a survey on local competition: Captera did a survey of MSPs. 100% of surveyed MSPs say competition in their region is high.  This was a 2024 study—  in 2026, it has to be worse. MSPs that can't differentiate are suffering. https://www.capterra.com/resources/managed-service-provider-for-small-business/

- Emotions of selling your business – AMY’S NEW BOOK: https://sellmymsp.com/book

-  How AI Is Transforming Security Operations: https://www.thirdtier.net/2026/05/11/how-artificial-intelligence-helps-managed-service-providers-deliver-smarter-security/When I talk with MSPs today—whether in my mentored-peer groups or consulting gigs—the same pattern shows up. Security has become the heaviest part of the workload. SOC-like responsibilities are landing on teams that were originally built for backups and patching. That mismatch is where AI can make a measurable difference and a wake-up call for MSPs looking toward the future.

               - Not meeting with clients because you don’t know what to say? Speak To Your Clients About Email Threats: https://www.thirdtier.net/2026/05/19/speak-to-your-clients-about-email-threats/

            - Tales from the field: Why MSP’s are exiting the channel 

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The most consequential development discussed is the rapid proliferation of Shadow IT in client environments, with emphasis on the unchecked adoption of cloud SaaS applications and artificial intelligence (AI) tools by end users. Speakers noted that this has led to a substantial loss of MSP control over client IT environments, eroding trusted advisor status and prompting clients to question the ongoing necessity of working with their MSP. The pervasive use of AI and SaaS products without guidance or oversight introduces governance and security risks, particularly relating to sensitive business data being accessible to third-party vendors and potentially incorporated into external data sets.

The episode provided details on how Shadow IT emerges, highlighting the ease with which employees can adopt SaaS and AI tools through free trials, personal accounts, or non-business credit cards, often outside of IT’s direct visibility. According to Amy and El, clients are increasingly self-serving their technology needs, shifting traditional MSP-client dynamics. The conversation outlined specific governance issues, such as most AI tools ingesting client data into the cloud, with limited assurance as to how it will be used or protected unless higher tiers of service are paid for—an unlikely scenario for most SMBs using free versions.

Secondary discussion focused on broader industry fragmentation and the challenges it poses for knowledge-sharing, consensus-building, and vendor feedback. The speakers recalled a time when MSP best practices spread rapidly through tightly-knit peer groups or single platforms but observed current information channels are numerous and scattered, such as Discord, Reddit, LinkedIn, and Facebook. This dispersion hinders both MSPs and vendors from collaborating effectively and reduces the feedback loop necessary for responsive product development and operational improvement.

The key implications for MSPs and IT leaders include the pressing need to shift operational models from rigid, tool-centric offerings to relationship- and advisory-focused services. There is heightened risk if MSPs fail to address governance and security concerns, especially as end users continue adopting technology independently. Speakers recommend implementing proactive client education, detailed risk analysis on SaaS and AI integrations, and establishing clear communication strategies to reclaim the advisory role. MSPs are encouraged to align compensation models to advisory activities, as future client value is projected to depend more on strategic guidance than product-resale or ticket-resolution metrics.

Title: How are you managing Shadow IT?

Topics:

Upcoming events:

Zero Trust Workshop- 3 sessions starting May 28. 

Mastermind Event with James (and Amy is a guest speaker!) in Omaha, NE

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