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You Can’t Out-Hustle a Broken Operating Model

by David Wilkeson | Nov 11, 2026 | MSP Strategy

I sat down with Alexej Pikovsky on Play It Smart to talk about the problems I see over and over in MSPs that have grown past the point where the owner can carry everything. The episode is live now.

We started with sales, because that’s where a lot of owners make an expensive mistake. They hire a salesperson and expect that person to fix a problem the owner hasn’t solved yet. Good sales organizations are systems. If you don’t have a process, a target client profile and a way to measure activity, the new hire is just experimenting while you are paying them. Referrals carry most MSPs early on, but they get harder to count on as you grow, and that’s usually when the pressure to hire shows up.

From there we got into the numbers. Your P&L and your true net profit are often two different things, and the gap is where most owners get surprised. I walked through why I hold MSPs to a 62% LLGM target, how to think about the tradeoff between labor and tools, and why bundling Microsoft licensing makes sense as long as your contracts protect you when terms change.

We finished on account management, structured client meetings, and what AI and consolidation mean for smaller MSPs over the next few years. If you run an MSP under $3M, that last section is worth your time.

Want help building the systems we talked about? Let’s talk.

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