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Email security is only part of the equation.Live from ChannelCon 2026, Dan sits down with Zach Schwartz, CRO of Trustifi, to talk about the security gaps MSPs may be overlooking across Microsoft 365. From account takeovers and social engineering to threats moving through Teams, SharePoint, and OneDrive, they break down why visibility beyond the inbox matters—and how MSPs can protect clients without adding even more tools to an already crowded stack.

MSPs have evolved before—from break/fix to managed services, from on-prem to the cloud. Now, another shift is here.

Dan Tomaszewski sits down with longtime MSP industry veteran Len DiCostanzo to talk about why AI isn’t about reinventing your MSP—it’s about expanding what you already do. They dig into consulting, business outcomes, new recurring revenue opportunities, and why understanding your clients’ businesses may be more important than ever.

Who decided every successful MSP needs to keep getting bigger?

In this episode, Dan Tomaszewski and Jason Kemsley of Uptime rethink what MSP growth can look like. They get into the realities of hiring, the fear around outsourcing, the opportunities AI is creating, and why sometimes the smartest way to scale is deciding what your team shouldn’t be doing.

Because the goal isn’t necessarily to build the biggest MSP. It’s to build the right one for you.

You spend years building your MSP. But are you building one someone will actually want to buy?

Josh Liberman joins Dan after selling Net Sciences to talk about the five years of preparation behind his exit, the decisions that increased the value of the business, and the lessons he wishes more MSP owners understood long before they put up the “for sale” sign.

What if your next client conversation started with the three biggest risks they’re facing instead of, “How’s everything going?”

Dan and Brian Doyle of vCIOToolbox explore how AI is changing the vCIO conversation—from faster assessments and smarter QBRs to finding the mundane work clients are ready to automate. And as AI adoption grows, so does a much bigger opportunity for MSPs: helping clients implement, secure, and govern it.

We may be living through the MSP industry’s next dot-com moment.

Eric Torres of Pax8 joins Dan to talk about the massive opportunity AI is creating for MSPs, the shift toward Managed Intelligence, and why building the right guardrails matters as adoption accelerates. They also dig into how Pax8 is using AI internally to eliminate repetitive work and why MSPs shouldn’t worry about being “behind.”

Whatever stage you’re at, the opportunity is still in front of you.

Forget the complicated platforms, elaborate builds, and AI buzzwords for a minute.

Tony Francisco joins Dan Tomaszewski to talk about how MSPs can start putting AI to work today—without overcomplicating it. From analyzing competitors and uncovering business gaps to identifying new opportunities for clients, Tony shares practical ways MSPs can use AI to work smarter and deliver more value.

Sometimes the smartest AI strategy is surprisingly simple. Dazzle them with the basics.

AI is creating opportunities that go far beyond automation and efficiency. Live from ChannelCon 2026, Dan sits down with Nancy Hammervik, Chief Channel Officer at GTIA, to discuss GTIA’s work with the United Nations’ AI for Good initiative, what it could mean for the channel, and why MSPs have a role to play in what comes next. They also explore GTIA’s new local chapters and why human connection may matter more than ever in an AI-driven world.

Copilot doesn't necessarily create your clients' security problems—it may just make them much easier to find.

Dan and Derik Belair of Augmentt explore what happens when AI meets years of overshared files, excessive permissions, global admins, and messy Microsoft 365 environments. Plus, they discuss how MSPs can turn Copilot readiness into a valuable security and advisory conversation with clients.

Your MSP stack shouldn't run on autopilot.

Dan sits down with John Douglass of Pileus Technologies at ChannelCon 2026 to talk about regularly evaluating your security stack, identifying gaps, proving the value of new tools, and keeping clients informed when things change. Because sometimes the biggest risk isn't choosing the wrong tool—it’s never questioning the one you already have.