#24 – From the Trenches - Starting an MSP - Sales, Tools, Automation (Chris Hart)

In this episode of From the Trenches on the BMK Vision Podcast, Josh Peterson sits down with Chris Hart for a grounded look at what it actually takes to start (or restart) an MSP in today’s market—without romanticizing the grind or hiding behind “word of mouth” as a growth strategy.

This is not a conversation about building the perfect tool stack before you have customers. It’s about building momentum: choosing a clear revenue target, running a repeatable outreach funnel, learning to sell with structure, and designing the business so it can become dependable—financially and operationally—long before it becomes “big.”

If you’re an MSP owner stepping out of W-2 stability into ownership risk, or trying to rebuild with more discipline than your first attempt, this episode will resonate. (And if you’re trying to grow into a more intentional operating model, explore Vision for a framework that connects execution, financial clarity, and leadership cadence.)

How do you start an MSP in a crowded market?

Short answer: you don’t “enter the market” with better tools—you enter with a clearer growth system.

Chris is direct about the reality: the market may feel flooded, but demand still exists because many providers overpromise “proactive” service and then fail to execute consistently. That gap creates opportunity—but only for MSPs willing to operate with standards instead of heroics.

• Start with a defined first-year target (revenue and number of clients)
• Build a repeatable outreach and follow-up cadence (not random networking)
• Make “doing what you said you’d do” a system, not a personality trait

The MSP problem this episode solves

Many MSP owners aren’t failing—they’re drifting. They can deliver support, keep clients happy, and survive on referrals… but they don’t have a growth engine, and they don’t have a leadership operating model that scales past the founder.

This episode addresses three common early-stage (and “restart”) MSP challenges:

• Relying on word-of-mouth while expecting the business to scale anyway
• Trying to build the perfect internal system before earning the right to
• Confusing activity with progress—especially around sales and follow-up

Chris’s approach is refreshingly pragmatic: start lean, sell with intention, and earn the right to complexity.

From “word of mouth” to a real sales engine

One of the most useful tensions in this episode is the difference between getting business and building a business.

Chris outlines a funnel most MSPs avoid because it feels uncomfortable: cold email at scale, a multi-step sequence, targeted follow-up, then a direct call asking for an appointment. It’s not glamorous. It’s measurable. And it creates a pipeline that doesn’t depend on luck.

• Target specific verticals and roles (owners, office managers, decision makers)
• Run a sequence, not a single email (“one-and-done” is not outreach)
• Use content as a trigger (timely issues that make the prospect say, “that’s us”)
• Follow up with a call and a clear objective: schedule the discovery meeting

Tool selection without the “stack trap”

Early-stage MSPs tend to make one of two mistakes: they overbuy tools to feel “ready,” or they underinvest and pay for it later in chaos. Chris navigates the middle by optimizing for two constraints: cash and focus.

The key is not which tool he chooses—it’s why: avoid long contracts, avoid big minimums, reduce tool sprawl, and buy time back so the founder can keep selling.

• Choose tools that consolidate early needs (RMM + ticketing + invoicing basics)
• Avoid multi-year commitments until revenue stability exists
• Optimize for “get clients and deliver consistently,” not “build a perfect architecture”

Proactive service is not a claim—it’s a cadence

Chris calls out a problem most MSP owners already know is true: “proactive” is often used as marketing language, while the actual business runs on reactive fire drills. That gap is where trust erodes—and where churn begins.

The antidote is simple, but not easy: define what proactive means in operational terms, then create process and automation so it still happens when you’re busy.

• Monthly and quarterly check-ins that are scheduled and systematized
• Automation that surfaces exceptions instead of generating noise
• Operational discipline that doesn’t collapse under ticket volume

Automation as an MSP growth lever

The episode also touches a bigger strategic horizon: automation isn’t just internal efficiency—it’s a client-facing opportunity. As business tools embed AI and workflow capabilities, clients won’t automatically become competent at using them. They will still need translation, setup, governance, and ongoing optimization.

The MSP that wins here won’t sell “AI.” They’ll sell outcomes: streamlined processes, fewer handoffs, and cleaner operations. And they’ll package it in a way that doesn’t turn the MSP into a random project shop.

• Use automation to make the MSP’s service delivery more consistent
• Offer process optimization selectively, as a defined service—not an endless favor
• Charge for value creation, not experimentation disguised as consulting

Episode highlights

• How an 18-year-old “server rescue” became the spark for an MSP career
• Why starting over at 38 can be an advantage—not a liability
• A measurable outreach funnel: cold email → mailer → call → appointment
• Discovery meetings and proposals that address specific business pain (not generic bundles)
• Tool strategy for new MSPs: keep costs down, avoid contracts, stay focused
• The difference between claiming “proactive” and building a cadence that proves it
• Automation as the next growth frontier for MSPs and their clients

About the guest: Chris Hart

Chris Hart is a Chief Technology Officer and Fractional CTO who works at the intersection of IT strategy and business execution. His focus is helping organizations turn technology into a repeatable operating advantage—through clearer decision-making, stronger infrastructure fundamentals, and business operations optimization.

With over two decades of hands-on experience across IT infrastructure and leadership, Chris brings a builder’s perspective to modern managed services: start with the realities of service delivery, create consistent standards, automate what should not rely on memory, and build a sales engine that can support the long-term vision.

View Chris on LinkedIn →

Frequently asked questions

Is it still possible to start an MSP in 2025?
Yes—if you enter with a defined niche, a repeatable sales process, and execution standards that prove you’re actually proactive.

How do MSPs grow beyond word of mouth?
By building a measurable outreach engine (targeting, sequencing, follow-up, and discovery) instead of hoping referrals will scale the business.

What should a new MSP prioritize first: tools or clients?
Clients. Choose a lean toolset that supports delivery, but avoid “stack building” as a substitute for selling.

Should a new MSP take projects or only recurring agreements?
Projects can make sense early if they’re part of a long-term path to recurring revenue—otherwise they create unstable cash flow and operational whiplash.

What does “proactive” actually mean in an MSP?
It means a scheduled cadence, documented standards, and automation that ensures critical work gets done even when tickets spike.

Related resources from Bering McKinley

• How to build an MSP marketing strategy that actually drives growth and consistency
• From pitch to payoff: how to build a business plan MSP investors can’t ignore
• ConnectWise project management for MSPs: building a scalable process from quote to completion

Want to continue the conversation?

If you’re an MSP owner starting over (or scaling up) and want help building clarity, discipline, and execution—explore the Vision operating system or apply to be a guest on the podcast.

👉 Apply to be on the BMK Vision Podcast
👉 Learn more about Vision