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AI agents can do a lot more than answer questions—but how much access should they actually have?

Dan Tomaszewski and Amanda Makowsky of ThreatLocker discuss the risks of giving AI too much control, real-world examples of what can go wrong, and how MSPs can put the right guardrails in place while still taking advantage of AI and automation.

How much time are you spending on work that could be happening without you?Dan and Curtis Armstrong of Benji Pays talk automation, finances, profitability, and why MSP owners need to get their heads out of the books and back into growing the business.Because the goal isn’t just to save a few hours—it’s to put those hours somewhere that actually matters.

If you stepped away from your MSP for two weeks, would opportunities keep moving—or would everything grind to a halt?

Dan Tomaszewski and Pete Busam of Equilibrium Consulting dig into what happens when the owner becomes the bottleneck, how to transfer your vision to your team, and why building abusiness that doesn’t depend entirely on you is critical for growth.

Cyber insurance isn’t just about having coverage. It’s about being able to prove you’re doing what you said you were doing.

Dan sits down with Jared Casner of Blacksmith InfoSec to talk about the liability MSPs may be taking on without realizing it—from filling out insurance applications for clients to claiming security controls are in place without the evidence to back them up.

They also dig into risk management, compliance, and how MSPs can build a stronger security program for themselves and their clients.

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.