the[STACK]

Oct 19, 2026

AI Can Give Advice Too. So Why Does Your Client Need You?

For years, MSPs have worked to become their clients' trusted technology advisors. But what happens when AI can provide advice, analyze information, and help businesses make decisions too? In this episode of the[STACK], Dan Tomaszewski sits down with Brian Doyle, co-founder of vCIOToolbox, to explore how the role of the MSP is evolving and why simply managing technology is no longer enough. They discuss the art of external leadership, moving beyond traditional QBRs, building stronger relationships with business decision-makers, and using AI conversations to uncover new opportunities. Brian also

Oct 19, 2026

Your Client's Email Problem Is Your Problem

Your client's emails aren't reaching the inbox. Marketing blames IT. IT blames the sender. But who's actually fixing the problem? In this episode of the[STACK], recorded live at ChannelCon, Dan Tomaszewski and Mike Anderson of EasyDMARC discuss why MSPs can no longer afford to overlook email deliverability. Learn how better visibility, smarter DNS management, and a proactive approach can protect clients while creating new opportunities for MSP growth.

Oct 15, 2026

Your Microsoft 365 Is Showing Its Cracks

83% of MSPs are still managing Microsoft 365 reactively. And that's just the beginning Dan is joined by Derik Belair of Augmentt to break down the findings of the MSP Microsoft 365 Reality Report. They dig into overlooked security gaps, inconsistent tenant configurations, costly manual work, and why so many MSPs aren't confident their clients meet their own security standards. Plus, what happens when clients want Copilot before their environments are actually ready for it?

Oct 12, 2026

Your Next MSP Client Isn't Googling You

What if your next client isn't Googling for an MSP anymore? Eric Hanson of Inland Productivity Solutions joins Dan Tomaszewski to discuss how the shift from SEO to AEO is changing the way MSPs get discovered. From growing inbound leads to putting AI and automation to work internally, Eric shares what's actually working for his business and why MSPs can't afford to sit on the sidelines.

Oct 5, 2026

Give AI a Job, Not the Keys

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.

Oct 5, 2026

You Didn’t Start an MSP to Chase Invoices

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.

Sep 28, 2026

If You Disappeared for Two Weeks, Would Your MSP Still Grow?

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.

Sep 28, 2026

You Checked the Box. Can You Prove It?

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.

Sep 21, 2026

Your Inbox Isn’t the Only Way In

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.

Sep 17, 2026

Your MSP Doesn’t Need to Reinvent Itself

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.

Sep 14, 2026

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

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.

Sep 14, 2026

The Most Valuable Thing He Built Was the Exit Ramp

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.

Sep 8, 2026

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

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.

Sep 8, 2026

MSPs, This Is Your Dot-Com Moment

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.

Aug 31, 2026

Dazzle Them With the Basics: Start Here, Then Scale

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.

Aug 27, 2026

AI Is Going Global. The Channel Is Going Local.

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.

Aug 24, 2026

Your Client’s Data Was Already Exposed. Copilot Just Found It.

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.

Aug 20, 2026

Your MSP Stack Has an Expiration Date

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.

Aug 17, 2026

Before You Sell AI to Clients, Use It Yourself.

AI is moving beyond the hype and directly into the way MSPs work. Dan Tomaszewski sits down with Dee Zepf of Syncro to explore how AI is changing everyday MSP operations—from ticket summarization and intelligent dispatch to MCP, voice-driven workflows, and custom automation. They also dig into one of the biggest mistakes MSPs make when adopting AI, why starting small matters, and how to gain efficiency without losing the human connection clients still expect. Plus, as clients begin adopting AI themselves, what role should their MSP play in helping them do it securely? If you're wondering what