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SMB Community Podcast

SMB Community Podcast

De : Dave Sobel
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Podcasts, articles, and reference materials for Managed Service Providers. Produced by MSP RadioMSP Radio Direction Economie Management et direction Politique et gouvernement
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  • Should MSP Agreements Stop Ex-Employees From Taking Clients?

    Should MSP Agreements Stop Ex-Employees From Taking Clients?
    Oct 29 2026
    Employee departures and the risk of client solicitation by ex-staff emerged as the episode’s principal issue. Multiple instances were described where former employees attempted to take clients with them, resulting in legal disputes and operational stress for MSPs. To mitigate this risk, contractual safeguards such as non-disclosure and non-solicitation clauses in employment agreements were identified as standard practices. The discussion emphasized the limitations of these measures, especially in right-to-work states like California and Michigan, where prohibiting employees from earning a living is not permitted, but protecting trade secrets and customer relationships remains crucial.Further supporting commentary outlined approaches to both prevention and response. Hiring staff aligned with core business values was highlighted as a first line of defense, acknowledging that even well-selected employees may at times violate trust. Emphasis was also placed on maintaining strong client relationships, as clients themselves may resist overtures from ex-employees and alert the business to solicitation attempts. The balance between proactive oversight and acceptance of limited risk was positioned as a key operational consideration, with practical actions centered on the clarity of employment agreements and ongoing relationship management.Additional segments addressed opportunities for increasing monthly recurring revenue (MRR) and the growing prominence of AI and related security and governance issues. Strategies for broadening MRR included packaging not only core IT support but also ancillary services such as printer management, mobile device support, and surveillance system maintenance. The conversation also covered the rising importance of including AI usage clauses in NDAs, particularly for M&A transactions where confidential business data might be shared with AI platforms. Concerns were raised about the exposure of proprietary information if uploaded to external AI providers and the need for specific contractual language to address this risk.For MSPs, the key takeaways center on operational risk containment, the necessity for disciplined employment and client contracts, and governance practices attuned to both human resource management and technology adoption. Service providers are urged to strengthen their policies and agreements to protect confidential information and client relationships, remain vigilant regarding the transfer or misuse of business data—especially in digital and AI-driven environments—and consider the broader implications of their vendor and partnership decisions during organizational transitions or M&A activity.Protecting Your MSP from Ex-Employees and Growing MRRShow Rundown & Banter: Protecting clients and employees from poaching, growing MRR, AI security concerns, and AI in M&A.Question of the Week: Have Ex-Employees Ever Stolen Clients or Staff?Use non-solicitation agreements, employee contracts, and signed handbook acknowledgments to protect your business.Topic: Growing MRR Beyond Core ServicesExplore VOICE, CYBER, MDM, and BACKUP. Reinvent Telecom is one voice partner to consider.Something New: Mac Introduces TouchscreenApple explores touchscreen functionality. Is it useful, or is it a feature other platforms have had for years?Topic: AI Security and ConsciousnessDiscuss concerns around Claude, AI consciousness, and Anthropic’s conversations with religious leaders.https://youtu.be/TBLHdXABwAg?si=upyYBVLm7Set5YXeTopic: AI Clauses in M&A NDAsA seller’s NDA prohibits uploading confidential financial documents to free AI chatbots that may train on user inputs.Tales from the Field: Selling Your MSP to an Inexperienced VC GroupWhat can go wrong when selling to investors without MSP experience?Wrap & Upcoming EventsMastermind LIVE Tampa, December 3–4, 2026.https://kernanconsulting-mastermind.mykajabi.com/mastermind-event About the SMB Community Podcast: Weekly business advice for small MSP owners from Amy Babinchak and James Kernan of the Small Biz Thoughts community — MSP sales, MSP pricing and agreements, hiring and leading an MSP team, MSP operations, selling your MSP, and AI for small MSPs. Produced by MSP Radio. More for MSP owners at smallbizthoughts.com.SMB Community Podcast is supported by our partners:OvekaSupporting the IT services community through insights, analysis, and transparency. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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    24 min
  • Should Your MSP Take the Fall If AI Leads to Malware? | MSP agreements

    Should Your MSP Take the Fall If AI Leads to Malware? | MSP agreements
    Oct 22 2026
    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 to elevate Exchange permissions and control additional ConnectWise-related OAuth apps. It is emphasized that deactivating an unused app is insufficient, as historic use of SkyKick over the past decade could still leave MSPs exposed. A recommended response is a comprehensive review of OAuth permissions, referencing guidance from Guardz, which outlines multiple mitigation steps for MSPs to follow, regardless of current product usage.Other topics addressed include evolving responsibilities when artificial intelligence (AI) tools direct users to malicious destinations. MSPs were advised to maintain protective controls and thorough documentation, as operational accountability typically resides with the MSP, especially when security layers like EDR effectively prevent incidents. Additional coverage centers on Anthropic’s creation of a public benefit corporation, MapQuest’s feature updates including surveillance detection, and Pax8’s announcement of AI agent solutions that MSPs may resell to clients.The practical implications for MSPs and IT decision-makers center on maintaining vigilance over third-party integrations and long-lived permissions, enforcing clear lines of communication with clients and vendors, and proactively documenting risk mitigation efforts. Vendor management and operational transparency, especially regarding software vendor issues or AI-related incidents, are underscored as essential practices for reducing harm and preserving client trust.Whose Responsibility Is It When AI Sends a User to a Malware Site?Show Rundown & Banter: AI security, the ConnectWise incident, MapQuest, Anthropic, and Pax8.Something Fun: Michelangelus FontMicrosoft’s project preserving Michelangelo’s work inspired a new font for Word.https://www.microsoft.com/en-us/download/details.aspx?id=108856Question of the Week: Who’s Responsible When AI Directs Users to Malware?A user followed ChatGPT’s instructions to a fake verification site. EDR caught the threat. Where does the MSP’s responsibility begin and end?ConnectWise Backup IncidentAttackers exploited application credentials and excessive permissions, affecting a targeted group of MSPs.https://app.notion.com/p/Connectwise-Backup-Incident-3f98e07a4534804c9181e7c8c603dde3?pvs=21MapQuest’s ComebackMapQuest adds surveillance-camera alerts to its maps.https://app.notion.com/p/MapQuest-surveillance-notices-3e88e07a453480f38df1d2fb15eeb486?pvs=21Anthropic’s Public Benefit CorporationA new structure aims to direct company equity toward a public-benefit mission.https://app.notion.com/p/Anthropic-public-benefit-LLC-3fe8e07a453480f0834fd414d8e470f9?pvs=21Pax8’s AI Revenue OpportunityMSPs can manage AI agents, control usage, and set their own pricing.https://app.notion.com/p/PAX-8-AI-money-making-opportunity-3fe8e07a45348022b281d63cd11355df?pvs=21Tales from the Field: The Ungrateful Client?An MSP worked nights and weekends to recover from a software update failure, only to be fired by the client. About the SMB Community Podcast: Weekly business advice for small MSP owners from Amy Babinchak and James Kernan of the Small Biz Thoughts community — MSP sales, MSP pricing and agreements, hiring and leading an MSP team, MSP operations, selling your MSP, and AI for small MSPs. Produced by MSP Radio. More for MSP owners at smallbizthoughts.com.SMB Community Podcast is supported by our partners:OvekaSupporting the IT services community through insights, analysis, and transparency. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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    25 min
  • Should MSP Owners Sell Their MSP Themselves or Use a Pro?

    Should MSP Owners Sell Their MSP Themselves or Use a Pro?
    Oct 15 2026

    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 accuracy, and legal safeguards were either secured or compromised depending on professional involvement.

    Supporting details include a specific example involving a failed contract provision: a business sale transacted without an M&A attorney resulted in an omitted clawback clause. Subsequently, more than half of the recurring revenue was lost after the sale, and the seller remained liable for the note without protection. Remediation only became possible after legal intervention, which reduced the seller’s exposure, though such outcomes are considered rare. Both speakers recommend establishing an advisory team comprised of an experienced M&A advisor or broker, a specialized tax expert, and a dedicated M&A attorney, underscoring that operational familiarity with contracts is insufficient for high-stakes divestments.

    Secondary topics addressed include risk management in cyber insurance procurement and leveraging Cybersecurity Awareness Month for internal team development and customer marketing initiatives. Amy Babinchak distinguishes between basic, low-cost cyber insurance add-ons and comprehensive policies, noting the latter’s higher cost is justified by enhanced coverage, embedded compliance services, and access to consultative support. The segment also briefly references the importance of leadership mindset, noting that focusing on team strengths as a management approach can drive better organizational outcomes.

    For MSPs and IT leaders, the episode’s discussions reinforce the operational risks of do-it-yourself approaches in high-value transactions and regulated domains like cyber insurance. Key takeaways include prioritizing qualified external counsel for significant business events, maintaining adequate and tailored insurance coverage, and adopting intentional leadership and governance strategies. These measures serve to reduce organizational risk, safeguard asset value, and enhance decision quality in complex or regulated IT services environments.

    Can I Sell My Own MSP?
    1. Show Rundown & Banter: Why selling your MSP alone can be risky, the importance of cybersecurity insurance, Cybersecurity Awareness Month, leadership mindset, and more stories from the field.
    2. Question of the Week: What if My Clients Resist Change?
      • Can I sell my own MSP? Yes, but should you? No — get professional help.
    3. Topic: Cybersecurity Insurance
      • Understand different insurance options and scenarios. James recommends working with an insurance professional to find the right coverage for you and your business.
    4. Topic: Cybersecurity Awareness Month
      • Highlight the importance of cybersecurity awareness and staying proactive about protecting your business and clients.
    5. Topic: Leadership Mindset
      • Instead of asking, “What’s wrong, and how do I fix it?” ask, “What’s right, and how do I grow it?”
    6. Tales from the Field: The Importance of Using Attorneys
      • Be careful with DIY contracts, agreements, and business deals. AI is not a substitute for legal advice. The NORCAL deal involved a seemingly favorable LOI, but handling the agreement himself led to a key detail being missed. Good agreements matter.

    About the SMB Community Podcast: Weekly business advice for small MSP owners from Amy Babinchak and James Kernan of the Small Biz Thoughts community — MSP sales, MSP pricing and agreements, hiring and leading an MSP team, MSP operations, selling your MSP, and AI for small MSPs. Produced by MSP Radio. More for MSP owners at smallbizthoughts.com.


    Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
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    23 min
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