#17 – From the Trenches - Calculated MSP Growth & Risk (Ron Oppermann)

In this episode of From the Trenches on the BMK Vision Podcast, Josh Peterson sits down with Ron Oppermann for a grounded conversation about the kind of growth most MSP owners say they want—but often unintentionally sabotage: growth that’s intentional, financially disciplined, and operationally survivable.

This is not a discussion about “working harder,” buying another tool, or chasing the next marketing hack. Ron’s story moves from industrial engineering to MSP ownership, and it carries a clear throughline: scaling is not a motivation problem—it’s a systems and risk-management problem. He shares the real tradeoffs behind hiring, partnering, merging, building sales motion, and funding growth without starving payroll or burning out the owner. It ties directly to the operating-discipline mindset behind Vision: people, process, and performance aligned under one execution cadence.

If you’re an MSP owner trying to move from “solo survival” to “managed growth”—without blowing up service delivery—this episode will feel uncomfortably familiar in the best way.

How do you grow an MSP without breaking operations?

Short answer: you stop treating growth like a revenue goal and start treating it like a risk-and-capacity decision.

Most MSPs don’t fail because they can’t sell. They fail because selling exposes what was already fragile: unclear roles, inconsistent execution, underpriced service, and an owner who is still the final escalation point for everything. Ron frames growth as something you earn through structure—by building capacity intentionally, funding it responsibly, and removing yourself from the “hero operator” position long before you feel ready.

In this episode, Ron’s lens is simple: plan the work, then work the plan—and make sure your cash flow can survive the plan.

• Calculated risk beats reactive hustle (especially in hiring)
• Cash discipline protects payroll, culture, and execution
• Systems create scale; heroics create churn

The MSP problem this episode solves

Many MSPs get trapped in a painful middle zone: they’re busy, they’re “profitable enough,” and the owner is exhausted—yet the business still feels one bad month away from chaos.

This episode addresses three common MSP challenges:

• Growing revenue faster than service capacity, creating operational debt
• Hiring too late (or too cheaply), then paying for it in rework and stress
• Funding growth inconsistently, which turns payroll into a monthly anxiety event

Ron’s experience highlights a truth most owners resist: the bottleneck is not effort—it’s structure. If you don’t build structure on purpose, growth will build pressure on accident.

Calculated risk vs. reckless growth

Reckless growth looks like:

• Signing deals because “sales fixes everything,” then hoping ops keeps up
• Hiring only after service delivery is already failing
• Pricing that wins the deal but can’t sustain payroll and standards
• Owner involvement in every decision because “no one can do it like I can”

Calculated growth looks like:

• Building capacity before you need it (and measuring it honestly)
• Funding payroll with discipline, not optimism
• Creating roles that scale—not roles that depend on one person’s memory
• Designing a sales motion your ops team can absorb cleanly

The point is not to avoid risk. The point is to choose risk intentionally—and accept that growth is always a trade: you can buy speed with chaos, or buy stability with discipline.

From “in the trenches” to “owner mode”

Ron’s background in industrial engineering shows up as a leadership advantage: he thinks in workflows, constraints, and throughput. In MSP terms, that translates into a bias toward operational design—what work exists, who owns it, and how you make it repeatable.

• Early-stage MSPs run on versatility; scaled MSPs run on role clarity
• Your first hire is not a “helper”—it’s a commitment to payroll discipline
• Delegation is not a personality trait; it’s a business requirement

The hardest shift is psychological: stepping out of the work feels like losing control. In reality, staying trapped in the work is what prevents control. Owner mode is not doing less—it’s doing different: building the machine instead of being the machine.

The cash-flow rule most MSP owners learn too late

Hiring changes the game because payroll creates responsibility. And responsibility changes how you manage money. Ron explains a pattern many owners stumble into: revenue comes in, bills go out, payroll comes due, and suddenly the “successful” MSP owner is living in a constant state of financial vigilance.

The fix is not complicated, but it requires maturity: separate profit and payroll protection from day-to-day spending decisions. When an MSP funds growth without cash discipline, it turns every operational decision into a stress decision—especially when sales cycles stretch or onboarding gets delayed.

• Protect payroll first, then invest in growth intentionally
• Use process—not hope—to manage cash timing
• Growth funding is a strategy decision, not a mood

Partnerships, mergers, and buying back time

One of the most instructive parts of Ron’s story is how long he and his partner operated “side-by-side” before formally merging. It’s a common MSP pattern: collaboration happens organically, trust builds slowly, and the business grows—but the structure never catches up.

Ron’s reflection is candid: merging sooner would have accelerated their trajectory because it would have reduced duplicated effort, clarified ownership, and created a cleaner operating model. For MSP owners, the leadership lesson is broader: time is the only resource you can’t recover, and many owners pay for “independence” with years of unnecessary friction.

Episode highlights

• 00:00:00 — Ron’s origin story: industrial engineering mindset → MSP ownership “by doing,” not by credential
• 00:03:26 — The first pivot: a small “fix a computer” request becomes the seed of a real IT business
• 00:04:26 — The evolution path most MSPs live: break/fix → networking → managed services
• 00:06:29 — Early entrepreneurship and the “billable hours” lesson: efficiency is leverage, not just hustle
• 00:12:53 — The first hire moment: when being the technician, dispatcher, and owner becomes the constraint
• 00:14:33 — Getting proactive: why “reactionary support” caps growth (and how toolsets changed the game)
• 00:15:36 — A foundational operator insight: your first engineer often becomes your culture (and your future leaders)
• 00:19:12 — Payroll stress and discipline: why protecting payroll forces smarter cash behavior
• 00:20:13 — Lifestyle business vs. scale business: home-based operations, perception, and building credibility early
• 00:22:18 — Contrarian move during COVID: why they invested in office space when others were exiting
• 00:23:17 — Growth engine mechanics: lead gen + execution cadence + showing up in the room consistently
• 00:24:32 — The “be present to win” principle: relationships and peer groups as a compounding advantage
• 00:25:38 — Repositioning and language: when “MSP” becomes a loaded term and you must sell outcomes
• 00:27:56 — Pipeline reality: the difference between “not enough at-bats” and “bad closing motion”
• 00:28:53 — Sales cycle extremes: why one deal closes in weeks while another takes years—and what that teaches you
• 00:30:41 — The growth trap: selling what ops can’t absorb (and why owner micromanagement blocks scale)
• 00:31:17 — The leadership cleanse: upgrading operations leadership to stop steering the ship alone
• 00:32:27 — Prepaying as strategy: using cash flow to fund reinvestment (not owner withdrawals)
• 00:34:22 — The “psychic income” of scale: realizing you’re building livelihoods, not just revenue
• 00:40:25 — The one do-over: merging sooner to buy back time and accelerate clarity
• 00:43:30 — The takeaway for MSP owners: take risk—but make it calculated, planned, and executed

About the guest: Ron Oppermann

Ron Oppermann is an MSP operator and growth-minded leader who brings a rare blend of engineering discipline and real-world MSP scar tissue. His perspective centers on building a business that scales without collapsing under the weight of its own success—through calculated risk, financial discipline, and an owner’s willingness to evolve.

Connect with Ron Oppermann on LinkedIn →

Frequently asked questions

What does “calculated growth” mean for an MSP?
It means aligning sales, hiring, and delivery capacity so growth doesn’t create operational debt that eventually destroys margins and culture.

When should an MSP hire its first technician?
When the owner can no longer protect standards and response times while also selling and running the business—and when cash discipline can reliably support payroll.

Why do MSPs feel stressed even when revenue is increasing?
Because revenue growth without role clarity and cash discipline increases complexity faster than the business can absorb it—turning every week into firefighting.

How can MSP owners fund growth without risking payroll?
By separating payroll protection and reinvestment decisions from day-to-day spending, then investing in hiring and sales based on a plan—not optimism.

What’s the biggest risk in MSP scaling?
Believing that effort will compensate for missing systems. Scale amplifies what’s already true—good or bad.

How do I move from “operator” to “owner” in my MSP?
By building repeatable processes, clarifying roles, and creating accountability cadences that allow the business to run without your constant involvement.

Related resources from Bering McKinley

• MSP consulting services that help you lead, scale, and win
• Managed service provider consulting: your partner for MSP excellence

Want to continue the conversation?

If you’re an MSP owner building toward sustainable growth—and want help creating 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