The Model You Didn’t Choose: How Vendor Frameworks Buried an Unpriced Continuity Risk in Your StackSwitched OffHere’s a pairing that almost nobody put side by side. Start with Anthropic. The company... By: Dave Sobel/June 16, 2026/Artificial Intelligence, Business Strategy, Community Sentiment, Product & Company Updates, Regulation
Atera’s AI Shift: Gil Pekelman on Accountability and Risk in Autonomous IT for MSPsThe episode highlights a structural shift from automation that suggests actions to automation that executes actions... By: Dave Sobel/June 15, 2026/Artificial Intelligence, Business Strategy, Community Sentiment, Guest Interviews
The AI Cost Squeeze Rolls Downhill — And MSPs Who Out-Buy Instead of Out-Position Will LoseManufactured UrgencyTwo things were moving across the channel this week, and at first they look like... By: Dave Sobel/June 12, 2026/Artificial Intelligence, Business Strategy, Product & Company Updates, Regulation
MSPs Face a Structural Choice: Author AI Methodology or Deliver Someone Else’sChannel AI ShiftThe channel stack moved — at the distribution layer, at the platform layer, and... By: Dave Sobel/June 10, 2026/Artificial Intelligence, Business Strategy, Product & Company Updates
ConnectWise Scraps Asio as AI Billing Chaos, Agent Sprawl, and a $1B Roll-Up Signal the Same Governance Crisis for MSPsConnectWise RebuildsStart with ConnectWise. The company announced that it is dismantling Asio — the platform it... By: Dave Sobel/June 9, 2026/Artificial Intelligence, Business Strategy, Product & Company Updates
Michael Privat: Data Weakness, Not AI Tools, Derails Enterprise AI InvestmentsA central structural mechanism highlighted in this episode is the exposure and amplification of technical and... By: Dave Sobel/June 8, 2026/Artificial Intelligence, Business Strategy, Guest Interviews, Regulation
AI Is Being Franchised — Vendors Build Platforms, MSPs Inherit the AccountabilityMSP AI PlayStart with Anthropic. The company has been building one of the more structured enterprise... By: Dave Sobel/June 5, 2026/Artificial Intelligence, Business Strategy, Community Sentiment, Product & Company Updates, Regulation, Security
Jay McBain on How Microsoft’s AI Billing Passes Risk and Liability to MSPsThe episode examines a structural shift in the MSP business model driven by the introduction of... By: Dave Sobel/June 4, 2026/Artificial Intelligence, Business Strategy, Live Shows
From Multitenant Automation to Token Meters, MSP Stack Resets Around AI as Operational WorkloadMSP Stack ResetsAt the MSP tooling layer, we’re seeing the push toward platform-grade control and multi-customer... By: Dave Sobel/June 2, 2026/Artificial Intelligence, Business Strategy, Product & Company Updates
Forced Arbitration in Tech Contracts: Brendan Ballou on Vendor Accountability RisksForced arbitration clauses have become embedded as a dominant mechanism in technology vendor contracts, shifting legal... By: Dave Sobel/June 1, 2026/Business Strategy, Guest Interviews, Regulation
From Shadow AI to Rogue Agents: Business Has a Governance CrisisShadow AI SurgeThe next operational problem is becoming visible across software teams, enterprise users, vendors, and... By: Dave Sobel/May 29, 2026/Artificial Intelligence, Business Strategy, Product & Company Updates, Security
Vendors Structure MSP Demand; MSPs Absorb the Operational CostPartner Programs FormalizedThe signal is that vendor-to-MSP growth is becoming less informal and more systematized. Vendors... By: Dave Sobel/May 27, 2026/Artificial Intelligence, Business Strategy, Community Sentiment, Product & Company Updates
MSPs Are Getting Breached, and Clients Are Already Planning to LeaveBreach, Then SwitchThe observable shift starts with four facts showing up at the same time: MSPs... By: Dave Sobel/May 20, 2026/Artificial Intelligence, Business Strategy, Community Sentiment, Product & Company Updates, Regulation, Security
Small Business AI Is No Longer Experimental — It’s Embedded and UngovernedWorkflow TakeoverAI is showing up in small business operations in a way that is more concrete... By: Dave Sobel/May 19, 2026/Artificial Intelligence, Business Strategy, Security
Chad Gaydos on AI Moving Procurement from Record-Keeping to Automated Decision ExecutionThe episode highlights a structural transition from software systems that record tasks to platforms that actively... By: Dave Sobel/May 18, 2026/Artificial Intelligence, Business Strategy, Guest Interviews
AI Enters MSP-Managed Systems, Bringing Governance Gaps and Unpriced LiabilityManaged AI RiskThe signal is that AI is moving out of isolated experiments and into the... By: Dave Sobel/May 15, 2026/Artificial Intelligence, Business Strategy, Product & Company Updates, Security
Unmanaged AI Participants Are Creating Records, Liability, and Audit Gaps MSPs Don’t Own YetAgents UncheckedWIRED has a new, ugly data point on what happens when “anyone can ship software... By: Dave Sobel/May 12, 2026/Artificial Intelligence, Business Strategy, Regulation, Security
The Bottleneck Has Shifted: AI Demand Is Real, Governance Isn’t Ready, and MSPs Are in the MiddleAI Infrastructure SurgeWe’re seeing a specific pattern across the largest tech platforms: AI is no longer... By: Dave Sobel/May 11, 2026/Artificial Intelligence, Business Strategy
AI Consumption Billing Creates Accountability Gap in MSP ContractsAI Bill DueStart with Microsoft. In late April, BleepingComputer reported that admins can now remove the... By: Dave Sobel/May 8, 2026/Artificial Intelligence, Business Strategy, Community Sentiment, Product & Company Updates, Regulation
From AMD PCs to Stripe Wallets, Agentic AI Demands Operating-Model Redesign, Not Feature RolloutAgents Take OverWe’re seeing four very specific signals across endpoints, cloud platforms, payments, and infrastructure provisioning... By: Dave Sobel/May 5, 2026/Artificial Intelligence, Business Strategy, Community Sentiment, Security