SMB Community Podcast

About SMB Community Podcast

Running a small MSP means being the CEO, the sales team, the HR department, and the escalation tech — usually in the same afternoon. The SMB Community Podcast is where MSP owners get straight answers on the business side of running an MSP. Every week, Amy Babinchak, and James Kernan — MSP owners and advisors from the Small Biz Thoughts community — take on the questions small MSP owners actually ask: How should I price? When do I hire? Should I give a proposal at the first meeting? What is my MSP worth? No vendor pitches and no theory — practical advice from people who have run, grown, and sold IT businesses. What this MSP podcast covers: • MSP sales and client growth — the MSP sales process, proposals, price objections, referrals, local marketing, and choosing a CRM • MSP pricing and agreements — MSP pricing models, single plan vs. tiers, price increases, managed service contracts, margins, and cash flow • Leading an MSP team — MSP hiring, tech compensation and commissions, accountability, culture, and EOS for small MSPs • MSP operations — processes, KPIs, documentation, your MSP stack, and the Microsoft Partner Program • Selling your MSP — MSP valuation, exit planning, private equity, and building a business that runs without you • AI for small MSPs — selling AI services, AI governance for clients, shadow IT, and what AI does to per-seat pricing Questions we answer: • How should a small MSP price its services — one plan or several? • When can an MSP owner afford the next hire, and how should you pay techs? • How do you raise prices without losing clients? • What makes an MSP worth more when it's time to sell? • How can a small MSP make money from AI? Whether you're starting an MSP, running a two-person shop, or building toward an exit, this is the show for the MSP owner-operator. The SMB Community Podcast is part of Small Biz Thoughts and produced by MSP Radio. More resources for MSP owners at smallbizthoughts.com.

Publisher

Dave Sobel, Amy Babinchak, Small Biz Thoughts, James Kernan

Category

business · business

Language

en

Explicit

No

First episode

18 Jul 2012

Latest episode

22 Oct 2026

Latest episodes

556 episodes in the feed.

1. 

   22 Oct 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 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 Font Microsoft’s project preserving Michelangelo’s work inspired a new font for Word. https://www.microsoft.com/en-us/download/details.aspx?id=108856 (https://www.microsoft.com/en-us/download/details.aspx?id=108856) Question 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 Incident Attackers exploited application credentials and excessive permissions, affecting a targeted group of MSPs. https://app.notion.com/p/Connectwise-Backup-Incident-3f98e07a4534804c9181e7c8c603dde3?pvs=21 (https://app.notion.com/p/Connectwise-Backup-Incident-3f98e07a4534804c9181e7c8c603dde3?pvs=21) MapQuest’s Comeback MapQuest adds surveillance-camera alerts to its maps. https://app.notion.com/p/MapQuest-surveillance-notices-3e88e07a453480f38df1d2fb15eeb486?pvs=21 (https://app.notion.com/p/MapQuest-surveillance-notices-3e88e07a453480f38df1d2fb15eeb486?pvs=21) Anthropic’s Public Benefit Corporation A new structure aims to direct company equity toward a public-benefit mission. https://app.notion.com/p/Anthropic-public-benefit-LLC-3fe8e07a453480f0834fd414d8e470f9?pvs=21 (https://app.notion.com/p/Anthropic-public-benefit-LLC-3fe8e07a453480f0834fd414d8e470f9?pvs=21) Pax8’s AI Revenue Opportunity MSPs can manage AI agents, control usage, and set their own pricing. https://app.notion.com/p/PAX-8-AI-money-making-opportunity-3fe8e07a45348022b281d63cd11355df?pvs=21 (https://app.notion.com/p/PAX-8-AI-money-making-opportunity-3fe8e07a45348022b281d63cd11355df?pvs=21) Tales 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. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com (https://pcm.adswizz.com) for information about our collection and use of personal data for advertising.

2. 

   15 Oct 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 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? 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. Question of the Week: What if My Clients Resist Change? Can I sell my own MSP? Yes, but should you? No — get professional help. 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. Topic: Cybersecurity Awareness Month Highlight the importance of cybersecurity awareness and staying proactive about protecting your business and clients. 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?” 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 (https://pcm.adswizz.com) for information about our collection and use of personal data for advertising.

3. 

   8 Oct 2026

   Can Employers Require Employees to Use AI Tools Like Copilot in the Workplace?

   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 imposing requirements. Supporting discussion points include the importance of intentional staff development and recognizing parallels to previous technology shifts, like the migration to cloud services. Resistance to learning new tools can result in employee attrition, reinforcing the need for ongoing education and active change management. Companies are advised to educate and incentivize employees, creating an environment where continuous upskilling is the norm. Secondary topics include recent Microsoft incentive program adjustments. Panelists note reductions in partner margins for lower-tier licenses, while incentives remain for Business Premium and enterprise plans. New AI-related incentives, such as Copilot bonuses, now require a minimum of 50 users, which may prevent smaller MSPs from participating. The conversation also explores the spread of AI-generated language into everyday business communication and shares practical security incidents observed in the field. MSPs and IT leaders are advised to manage AI adoption through robust training, transparent communication, and regular review of changing vendor incentive structures. Shifts in vendor programs and rapid technological change require proactive workforce planning, risk mitigation, and careful attention to evolving operational and compliance demands. Should I force my employees to start using AI? Show Rundown & Banter: Amy is back from ChannelCon. Question of the Week: Should I force employees to use AI? Discuss technology laggards, employee adoption, and whether forced AI use is really the right approach. In the Economy: 29,000 jobs and 2.2% growth — what does the economy mean for MSPs? Microsoft Incentive Changes: Microsoft is reducing incentives on many cloud programs while rewarding usage growth and partner skills. What does this mean for MSP margins? Are AI Chatbots Changing the Way We Speak? “LLMisms” like “It’s worth noting,” “Here’s the thing,” and “This is the key takeaway” are showing up more in workplace communication. https://www.wsj.com/tech/ai/claude-chatgpt-ai-speak-chatbot-cb804933 (https://www.wsj.com/tech/ai/claude-chatgpt-ai-speak-chatbot-cb804933) Tales from the Field: Another Tale of Espionage — a former employee continued accessing company systems and transferring client data to a new employer. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com (https://pcm.adswizz.com) for information about our collection and use of personal data for advertising.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

788,404

Score snapshot 15 Sept 2025

Podcast Authority Score: 60 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

87

Social presence

0

YouTube

86

Engagement

0

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Does not typically book guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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