#74 – Don’t Be That Guy: Your Business Is Awesome (Gary Boyle & Ryan Alter)

In this episode of Don’t Be That Guy on the BMK Vision Podcast, Josh Peterson is joined by Gary Boyle and Ryan Alter for an unusually important kind of conversation: not what MSPs are doing wrong, but what they’re doing right—and what it means when you finally admit your business model has real strength. The through-line is simple: the MSP industry is one of the rare SMB categories where you can build recurring stability, durable client relationships, and genuine enterprise value—if you learn to operate like a leader instead of a hero. That’s why the discussion keeps circling back to systems, financial visibility, and the owner’s transition from “best technician” to “chief steward.” If you want a framework for that transition, start with Vision—and if you want the pricing math that determines whether you’re building profit or just building workload, revisit agreement gross profit discipline and the way your contracts quietly shape behavior via SLA-driven pricing structure.

The deeper point isn’t “be proud of yourself.” It’s that pride, properly used, becomes strategy. Many MSP owners accidentally treat retention as proof they’re healthy, then avoid the hard conversations that keep the business investable: annual price increases, segmentation, tightening minimums, and defining what growth means (or admitting you don’t want growth). This episode frames the real risk as an identity crisis—wanting the comfort of stability while borrowing the guilt of “I should be bigger.” In that middle zone, owners get exploited: by shiny marketing promises, by chaotic client demands, and by a service model that erodes margin while everyone tells themselves it’s fine because “clients aren’t leaving.” The most mature MSPs don’t escape that trap by working harder. They escape it by choosing a lane, pricing to sustain that lane, and building a company that can run without their nervous system as the operating system.

If you’re an MSP owner who knows you’ve built something meaningful—but you’re not sure whether it’s scalable, sellable, or sustainable without you—this episode will feel less like encouragement and more like a correction: you’re not crazy for wanting more margin, more time, and more control. You’re simply overdue to run the business you already earned the right to run.

Why your MSP is awesome—and what that implies

Most MSP owners have been trained to treat their business like a fragile machine: one bad client, one bad tech hire, one bad incident, and the whole thing collapses. The reality is more nuanced. The MSP model is unusually resilient because it combines recurring revenue with operational stickiness—clients don’t churn easily when you’re embedded in their day-to-day continuity.

The problem is that resilience can feel like “normal,” which makes owners under-appreciate what they’ve built. When you stop treating your business like it’s always one step from disaster, you start making different decisions: you invest in process, you invest in leadership capacity, and you price like a firm that intends to be around in five years—not like a shop trying to survive the next five weeks.

The MSP problem this episode actually solves

This episode isn’t solving a technical problem. It’s solving an owner mindset problem: the gap between “I’m busy and clients like us” and “I’m building an asset that won’t eat my life.” That gap is where most MSP pain lives.

It shows up as over-retention (keeping clients you can’t afford), under-pricing (not keeping up with cost inflation or market value), and over-dependence (the company runs on the owner’s memory, not the company’s standards). If you’ve ever looked up and realized you’re working too many hours in a business that was supposed to buy you freedom, you’re not failing—you’re simply operating without an explicit model for stewardship.

Comfort vs. ambition: pick your lane on purpose

One of the most practical insights in this conversation is that “stuck” isn’t always bad. A plateau can be a deliberate destination—if you name it. The damage happens when you pretend to want growth while your decisions are optimized for comfort.

A comfort-led MSP often optimizes for:

• Predictability
• High retention (sometimes at any cost)
• Owner-led escalation
• A “good enough” service model

An ambition-led MSP optimizes for:

• Margin protection and pricing discipline
• Client segmentation and minimum standards
• Leadership capacity (not just technical capacity)
• Advisory value that justifies premium pricing

The episode’s point is not that one is morally better. It’s that indecision is expensive. When your identity is split, you become the easiest target for bad offers, bad clients, and bad internal expectations.

What stewardship looks like in MSP leadership

Stewardship shows up in practical, everyday decisions:

• Building processes so knowledge leaves your head and enters the business
• Raising prices consistently so retention doesn’t become margin decay
• Creating client standards (and enforcing them) instead of accepting every situation
• Protecting the team from “loudest-client-wins” operations

Stewardship doesn’t mean “go soft.” It means you stop confusing loyalty with self-sacrifice. It means you treat the business as a system you’re responsible to manage wisely—because your team, your clients, and your future optionality all sit downstream of that discipline.

A practical pricing and profitability checklist

If you want to keep the “awesome” parts of the MSP model while avoiding the classic traps, this episode points to a few non-negotiables:

• Make annual price increases a default mechanism, not a yearly negotiation
• Segment clients (good / better / best) and decide which tier you’re building for
• Know your effective hourly reality—even if you bill per user, per device, or “all you can eat”
• Stop funding low-margin contracts with high-stress labor
• Set a minimum client threshold and create a path (or exit plan) for clients below it

None of this requires a rebrand or a new tool stack. It requires clarity. The MSPs that win long-term don’t just “do IT well.” They run a firm that knows what it sells, who it’s for, and what must be true financially for the model to remain sustainable.

Episode highlights

• Why MSPs are one of the rare SMB models with real enterprise value
• The hidden downside of “90%+ retention” when you avoid price discipline
• Working on the business: how process transfers power off the owner
• Why under-pricing forces lower service quality and higher team burnout
• Good / better / best segmentation as a practical path to healthier margins
• Why “comfort” is fine—until you pretend you want growth

About the guest: Gary Boyle & Ryan Alter

Gary Boyle is an MSP operator and entrepreneur with deep experience building service businesses with repeatable process and strong financial discipline. In this conversation, he brings a pragmatic owner’s lens to pricing, margin, and the reality that “recurring revenue” only works when it’s anchored to profitable delivery. Connect with Gary on LinkedIn: https://www.linkedin.com/in/garyboyle/.

Ryan Alter is a former MSP owner with a sharp point of view on profitability, service design, and how billing models shape behavior. He’s especially candid about the difference between revenue and real operational health—and why many MSPs drift into “all hat, no cattle” dynamics when they stop measuring the fundamentals. Connect with Ryan on LinkedIn: https://www.linkedin.com/in/ryan-alter-896a5b11/.

Frequently asked questions

Why do MSPs struggle to raise prices even when clients stay?
Because owners confuse retention with permission, and they fear “re-selling” a relationship that should already be grounded in value. The longer a client is with you, the more disciplined you must be about protecting margin.

Is “getting stuck” at $1.5M–$2M in revenue always a problem?
No—unless you’re stuck by accident. A deliberate plateau can be a great outcome. The danger is living in the middle: wanting the identity of growth without the decisions required to earn it.

How do I know if my recurring revenue model is actually healthy?
Measure profitability at the agreement level and translate it back into time and labor reality. If the business needs heroics, after-hours pressure, or constant firefighting to stay afloat, the model is signaling under-pricing or weak standards.

What’s the simplest first step to move from owner-dependent to system-driven?
Start extracting what’s in your head into repeatable process: how decisions get made, how work gets done, how pricing gets updated, and how clients are reviewed. When the business can execute without you, it becomes both more livable and more valuable.

Related resources from Bering McKinley

• Why you’re not paying enough attention to agreement gross profits
• How MSPs can improve QBRs and client retention through account management

Want to continue the conversation?

If you’re an MSP owner who’s proud of what you’ve built—but you want to make it more profitable, more disciplined, and less dependent on you personally—apply to be a guest on the podcast or explore the Vision operating system.

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