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164 Episodes

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Your Inbox Isn’t the Only Way In

2026-09-2108:23

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.

Your MSP Doesn’t Need to Reinvent Itself

2026-09-1714:24

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.

What If Your MSP Doesn’t Need to Get Bigger?

2026-09-1418:27

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.

The Most Valuable Thing He Built Was the Exit Ramp

2026-09-1415:30

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.

Stop Asking Clients, “How’s Everything Going?"

2026-09-0814:38

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.

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