According to CRN, The 20 MSP has acquired three more managed service providers—Red Level Group in Michigan, iStreet Solutions in Roseville, California, and InData Consulting in Santa Clarita, California. These latest deals bring their total to 44 acquisitions in just three years, with CEO Tim Conkle declaring they’ve been moving “too slow” and can now handle 25-40 acquisitions annually. The Red Level Group acquisition was particularly significant as it’s their largest ever at over $10 million in revenue, well above their typical $1-6 million sweet spot. The company also plans to expand their member MSP community from 175 to 600 while considering international expansion into Canada as their next natural step.
That’s Some Serious Ambition
Look, going from 44 acquisitions in three years to potentially 40 in a single year is a massive acceleration. Conkle’s basically saying they’re going to more than double their current pace. And when you’re talking about integrating entire companies with their own cultures, tech stacks, and teams, that’s where things get really tricky.
Here’s the thing about MSP acquisitions—they’re notoriously difficult to integrate successfully. You’re not just buying revenue, you’re buying people, processes, and client relationships that can walk out the door if the transition isn’t handled perfectly. The fact that they’re stretching beyond their $1-6 million comfort zone with that $10+ million Red Level deal suggests they’re feeling confident. But confidence and capability aren’t always the same thing.
The Community Play
What’s really interesting is their dual model—they’re both an MSP themselves and a platform for about 175 other MSPs. Conkle’s argument that “MSPs are better together” makes sense on paper. His math about creating $100 million in value from 50 smaller MSPs is compelling. But I’ve seen this movie before.
Community-based acquisition models have a mixed track record. The challenge is maintaining that community feel and value proposition as you scale from 175 to 600 members. Can you really provide the same level of collaboration and support when you’re that large? And what happens to the original members when the focus shifts to rapid expansion?
International Ambitions
Canada seems like the logical next step, but anyone who’s done cross-border expansion knows it’s never as simple as it looks. Conkle mentions “some entity stuff” and Canadian rules and laws, but that’s probably underselling the complexity. Different tax structures, employment laws, data privacy regulations—it’s a whole different ballgame.
The fact that they already have Canadian members helps, but rolling up those members into the main entity is a completely different challenge than just having them use your platform. Still, if they can crack the code on cross-border MSP consolidation, they could have a real competitive advantage.
The Reality Check
Let’s be real—this kind of hyper-growth ambition often comes with hidden costs. Employee burnout, integration failures, cultural clashes, client attrition during transitions. We’ve seen this story play out in other tech consolidation plays, and it rarely goes as smoothly as the CEO predicts.
But you know what? If they can actually pull this off while maintaining quality and their community ethos, they could fundamentally change how the MSP industry operates. The question is whether they’re building something sustainable or just assembling a house of cards that looks impressive until the first strong wind hits.
