#31 - From the Trenches - The CIO Mindset - MSPs, Luck & Learning (Bob Coppedge)

Most MSP owners quietly overestimate how much control they have. They believe the right tools, the right hire, or the right sales script will “solve” growth. In reality, the MSP business behaves less like chess—where perfect logic produces predictable outcomes—and more like poker, where probability, incomplete information, and timing are always in the room. In this episode of From the Trenches on the BMK Vision Podcast, Bob Coppedge (Simplex-IT) and Josh Peterson explore what changes when you accept that truth—and why that acceptance is the foundation of disciplined execution. If you’re building for durability, this conversation pairs naturally with Vision and the kind of operating rigor it enforces inside a growing MSP.

This is not a discussion about chasing hype—AI, marketing, or “the next thing.” It’s about how leaders build organizations that can absorb continual change without breaking. Bob frames the last decade of technology disruption (big data, security, and now AI) as a shift from “technology” problems to “information” problems—where the question is no longer what the hardware can do, but what leaders decide to do with the data, the risk, and the opportunity. That lens matters because commoditization is not a market condition—it’s a leadership failure. The MSPs who keep winning are not the ones stacking more services onto a brochure; they’re the ones building a position the market can actually recognize and trust.

If you’re an MSP owner who feels like you’re doing “all the right things” yet can’t explain why outcomes stay inconsistent, this episode will resonate. It offers a cleaner mental model: treat every major business decision as a bet, design your process around repeatable probabilities, and stop confusing occasional wins with proof you’re doing it right. That mindset also reshapes how you approach marketing: not as noise, but as a durable asset that helps prospects self-select you—especially as search behavior shifts toward AI-driven answers instead of keyword-driven clicks.

Is MSP success more like poker than chess?

Short answer: yes—and pretending otherwise is expensive.

Chess is comforting because it implies determinism: if you think hard enough, you can calculate your way to certainty. MSP ownership doesn’t work like that. Markets shift. Clients change leadership. A major vendor updates licensing. A security event rewrites a customer’s priorities overnight. Your competitors make irrational moves. You can make a well-designed strategic decision and still lose the hand.

Bob’s point isn’t fatalism. It’s discipline. If business is a probabilistic game, then your job is to build a repeatable decision process that increases your odds across hundreds of hands—pricing, packaging, hiring, client selection, and delivery. That’s what separates a mature MSP from a lucky one: not confidence, but a willingness to audit results, refine process, and keep playing without rewriting history every time the river card hits.

The MSP problem this episode solves

Many MSPs are “successful” on paper but fragile in practice because they confuse activity with control. They keep shipping effort—tickets, projects, tool rollouts—without a leadership framework that ties execution to outcomes.

This episode solves a more foundational problem: how leaders think. Bob and Josh get to the uncomfortable reality that many MSP owners are excellent technologists who never had to become strong business operators to survive—because early MSP market conditions made the value proposition easy (“we’re cheaper than internal IT”). That era is fading. Today, you are usually replacing another MSP, which means your differentiation can’t be “we do the same thing, but for less.”

The modern MSP must build a posture that clients can feel: a clear operating cadence, a clear strategic lens, and a clear message about what changes in the business when you are involved. That isn’t marketing fluff. It’s executive leadership made visible.

AI, disruption, and the danger of “get off my lawn” thinking

Every few years, IT changes the rules. Bob frames the last waves as big data, security, and now AI—and emphasizes that these are fundamentally information problems, not hardware problems.

The leadership risk isn’t that AI exists. The risk is the familiar pattern: an industry of technologists becoming emotionally invested in yesterday’s certainty. When MSP leaders dismiss AI outright, they aren’t “being careful.” They are signaling that they no longer know how to learn—exactly when their clients need them to be the most adaptive.

This is also where marketing and operations converge. As search shifts toward AI-generated answers, leaders who create clear educational content (that can be indexed, interpreted, and cited) are building distribution that doesn’t rely on constant ad spend or endless outbound pressure. That’s not a tactic. It’s a strategic asset.

A model-year approach to continuous improvement

One of the most practical frameworks in the episode is Simplex-IT’s “model year” program: a structured, annual upgrade cadence that sets expectations with clients that IT will not stay still.

Most MSPs try to introduce change only when pain forces it—after a breach, after an outage, after a vendor surprise. That creates a reactive relationship where the MSP is always “selling the next thing” under duress. A model-year approach flips the posture: it normalizes progress, makes budgeting more predictable, and gives clients an explicit choice to remain on an older model—with clear tradeoffs.

Operationally, this is what maturity looks like: you stop treating change like a crisis and start treating it like a planned leadership function.

A practical vCIO differentiation checklist

If you want to move beyond commodity MSP competition, this episode points to a few non-negotiables:

• Adopt a probabilistic mindset: build processes that improve odds over time
• Stop selling “IT things” and connect decisions to business outcomes and risk posture
• Normalize change with clients through a cadence (model year, QBR/QBR-like rhythm, planned upgrades)
• Use educational content to let prospects self-qualify (and to train the market how to buy you)
• Lower the barrier to action: simple scripts, cut edits, and consistent publishing beat perfection

Episode highlights

• Why disruption favors new entrants—and punishes complacent incumbents
• “Poker, not chess”: how to lead when outcomes are probabilistic
• Why commoditization is a leadership problem, not a marketing problem
• Big data → security → AI: the shift from technology problems to information problems
• The “model year” framework for predictable client progress and planned upgrades
• They Ask, You Answer: building trust with a simple, repeatable video engine
• How to use AI + cut edits + lightweight editing to publish consistently without a studio

About the guest: Bob Coppedge

Bob Coppedge is the Founder & CEO of Simplex-IT, a managed and co-managed IT services provider serving Northeast Ohio. With a career in IT dating back to the late 1970s—including work as a developer, consultant, and former CIO—Bob brings an executive lens to the MSP model that prioritizes business outcomes over “blinking lights.”

Bob is also a long-time educator and communicator in the MSP space, known for simplifying complex topics and pushing leaders to resist commoditization through clear positioning, disciplined improvement, and consistent client education. His practical approach to content—built on answering real client questions—helps MSPs create trust at scale without relying on fear-based marketing.

Visit Simplex-IT
Connect with Bob on LinkedIn

Frequently asked questions

Is MSP growth mostly skill or mostly luck?
It’s both. Skill is the process you control; luck is the variance you don’t. Mature MSP leaders build repeatable systems that improve odds over many “hands,” instead of rewriting history based on one win or one loss.

Why do many MSP owners struggle with business leadership?
Because many entered the industry through technical competence, not operator training. As market conditions tighten and MSPs replace MSPs, business fundamentals and differentiation become non-optional.

How does AI change MSP marketing and search?
AI-driven search increasingly favors content that answers questions directly and clearly. Educational videos paired with transcripts and on-site scripts can become durable assets as buyers shift from keywords to answers.

What is a “model year” program for an MSP?
A planned, annual modernization cadence that sets expectations with clients that IT evolves every year. It makes upgrades predictable, reduces reactive selling, and strengthens budgeting and risk conversations.

How can an MSP start YouTube without overcomplicating it?
Start with real client questions. Use AI to draft a short script, record in simple segments, and rely on cut edits. Consistency beats production value—and you only need to publish a little more than your competition.

Why don’t most MSPs do content consistently even when they know they should?
Because action is emotionally harder than agreement. Content forces visibility, vulnerability, and repetition. Leaders who treat publishing as a discipline—not a mood—win the long game.

Related resources from Bering McKinley

• MSP consulting services that help you lead, scale, and win
• Strategies for sustainable growth for MSPs
• AI in MSP: how machine learning can predict IT issues before they happen

Want to continue the conversation?

If you’re an MSP owner building toward a more disciplined, differentiated business—one that can absorb change without losing control—we’d love to connect. 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