On the Road with MSPs
Last week on the road, I spent time with MSPs in Chicago and Toronto. The conversations made one thing clear: the MSP market is changing quickly, but not in a panic-driven way. The change is practical. It is showing up in how MSPs think about AI, compliance, operational maturity, and what it means to be a trusted advisor. What stood out was not a new tool or a flashy product pitch. It was a shift in how MSPs are turning these ideas into services clients can understand, buy, and trust.
Summarize with AI
Open this article in your favorite AI assistant for a quick summary.
Show Notes
MSPs are crossing a threshold, and the winners will be the ones who move beyond tool sales and technical support into AI advisory, compliance, and business process consulting.
Charles Weaver returns from a week on the road with blunt, firsthand takeaways from MSPWorld Connect in Chicago and the MSPAlliance Inspire Peer Group in Toronto.
What he heard from real MSPs was bigger than event buzz. The conversation has shifted from “which AI tool should I resell?” to “how do I monetize AI inside my practice?” That opens a new lane for mature MSPs, especially those with vertical expertise, but it also raises hard questions about governance, pricing, risk, and how far into a customer’s business processes an MSP should go.
Key Themes
Charles breaks down the biggest themes shaping the market right now: why peer groups outside your echo chamber matter, how AI is creating both opportunity and hidden costs, why compliance is moving past simple control checklists into real advisory work, and why operational maturity is pushing MSPs to abandon vendors who stop investing.
He also explains why event fatigue is real, what MSPs actually want from conferences, and why genuine MSP-to-MSP connection matters more than noise.
You’ll Discover
- Why AI is no longer experimental for MSPs
- How consulting and business process advice can become a new revenue engine
- The hidden financial danger of unmanaged AI usage
- Why compliance and cybersecurity are becoming broader advisory services
- How best-of-breed tool choices are driving vendor churn
- Why the MSP profession is finally being forced to "prove it"
Who Should Listen
If you serve SMB clients, run an MSP, or want to understand where the managed services market is heading next, this episode gives you the clearest view yet of the shift already underway. Essential listening if you want to stay relevant as the MSP model evolves beyond pure IT.