#52 – From the Trenches: Firefighting, MSP Longevity & the Changing Client Mindset (Todd Holloway)

Most MSP owners assume longevity is a byproduct of having the “right stack.” The reality is harsher and simpler: longevity is the reward for calm execution under pressure—the kind of leadership that prevents small operational misses from becoming margin leaks, client churn, or culture decay. In this episode of From the Trenches, Todd Holloway (a veteran MSP owner and former firefighter) brings a rare perspective on how durable service businesses are built: not through heroics, but through repeatable standards, earned trust, and decision-making that holds up when the day goes sideways. If you’re trying to operationalize that kind of clarity, the Vision operating system exists for exactly this purpose—turning “good intentions” into a business that can scale without breaking. The subtext of the conversation also intersects directly with financial truth-telling (especially Agreement Gross Profit discipline) and the people-side of retention (where trust is built long before a client ever considers switching).

This is not a conversation about “winning more deals” through clever messaging. It’s a conversation about what happens when the market shifts and buyers get tired. Todd describes what many MSPs are seeing right now: price fatigue, more competitive noise, and prospects who “already know what an MSP is” and are mostly shopping from perceived cost instead of outcomes. That creates a dangerous temptation—race downward, simplify promises, or chase the wrong accounts just to keep top-line moving. Todd’s counterweight is instructive: a boutique MSP can stay broad and still win by staying close to the customer, running Technology Business Reviews that actually mean something, and maintaining operational discipline that protects the client experience and the P&L at the same time.

If you’ve felt the tension between being busy and being in control, this episode will land. The discussion moves from sales realities (why outsourced appointment setting often fails and why in-house SDR functions can outperform) to service realities (time-entry hygiene, technician flow, and why culture is the only enforcement mechanism that scales). The core takeaway isn’t a tactic—it’s a leadership posture: build a business that stays steady when the world gets noisy, and you’ll outperform the MSPs that depend on constant adrenaline to survive.

How does firefighting translate into better MSP leadership?

Short answer: It trains leaders to make calm, accountable decisions when the stakes are high—and that’s exactly what mature MSP operations require.

In MSP land, the “fire” isn’t literal—but it’s constant: client urgency, technician interruptions, tool sprawl, and financial ambiguity that slowly compounds into stress. Todd’s background reinforces a leadership model many MSPs lack: when pressure rises, you don’t speed up your emotions—you slow down your thinking. That shows up as clear ownership, predictable responses, better prioritization, and a culture that doesn’t depend on heroics. The result is a service business that can keep clients for decades because it behaves consistently when it matters.

The MSP problem this episode solves

Many MSPs are not struggling because they lack knowledge. They’re struggling because they lack operational truth.

When time entry is inconsistent, tickets are messy, and client communication is reactive, the business starts running on stories instead of data. You can’t trust profitability reporting. You can’t coach technicians with clarity. You can’t build accurate pricing models. And you definitely can’t scale calmly. Todd’s perspective is a reminder that “discipline” isn’t a personality trait—it’s a system: expectations that are inspected at the same rate they’re demanded, reinforced by culture, and connected to client outcomes.

Price fatigue is real—so what do you do about it?

Short answer: You stop trying to win on price and start winning on relationship clarity, operational credibility, and differentiated service posture.

Todd describes a 2025 reality many MSP owners are seeing: prospects entering conversations with “price” already as the primary filter. That doesn’t mean the MSP should drop standards or race to the bottom. It means the MSP must learn to articulate value in terms the buyer can recognize: responsiveness that’s consistent, leadership access that’s real, and Technology Business Reviews that reduce uncertainty—not just pitch add-ons. When buyers can’t tell MSPs apart from websites, your differentiator becomes what you can prove through process, communication, and trust.

Why in-house SDR often beats outsourced appointment setting

Short answer: Because the caller becomes part of your culture and learns your standards—outsourced callers can’t represent what they don’t actually understand.

The nuance matters: the goal isn’t “more appointments.” The goal is qualified appointments that deserve owner time. Todd’s logic is simple and correct: in-house SDR functions improve list quality, improve qualification, and improve internal coordination because the SDR is sitting inside the business, learning what good looks like, and adapting messaging to the MSP’s real positioning. Outsourcing can put you in front of people; it rarely builds the kind of credibility that closes the right clients.

A practical MSP longevity checklist

• Run TBRs that are real: treat them as relationship infrastructure, not a sales ritual.
• Protect the owner’s time: qualify appointments so you spend time only where you can win profitably.
• Inspect time entry during the day: don’t “discover” missing hours at payroll or invoicing.
• Sell outcomes, not effort: reduce buyer confusion by anchoring to measurable business value.
• Build a calm culture: eliminate hero dependence so clients trust your consistency, not your adrenaline.

Episode highlights

• 00:00:45 – From firefighting to IT: how the MSP journey started “by mistake.”
• 06:04 – The physical reality of firefighting—and what it teaches about pressure and leadership.
• 12:55 – Pricing early managed services, missing time, and learning profitability the hard way.
• 16:00 – Price fatigue, buyer expectations, and why the market feels different in 2025.
• 18:01 – Re-thinking service tiers: lower-entry offers, blocks of time, and value tradeoffs.
• 30:20 – Why outsourced appointment setting struggles—and the case for in-house SDR.
• 49:20 – Time-entry discipline, technician mindset, and culture that scales.
• 56:35 – Enjoyment, purpose, and what “done” looks like after 30+ years in the business.

About the guest: Todd Holloway

Todd Holloway is a veteran MSP owner and former firefighter with more than three decades of experience in technology and emergency services. Based in Metro Atlanta, Todd leads a boutique MSP focused on long-term client relationships, disciplined operations, and practical execution. His background in high-pressure decision-making informs his approach to leadership, service delivery, and customer trust.

👉 Connect with Todd on LinkedIn
👉 Visit Custech

Frequently asked questions

Why are MSP buyers more price-sensitive right now?
Because many buyers feel uncertain about what they’re actually receiving for the monthly fee, and market saturation makes MSPs look interchangeable. Clear communication and credible process reduce that uncertainty.

What makes a Technology Business Review (TBR) actually effective?
A TBR works when it’s treated as executive communication: what changed, what risks exist, what decisions need to be made, and what outcomes the business is buying—rather than a tool demo or an upsell script.

Is in-house SDR worth the effort for a smaller MSP?
Often, yes—if you define the role around qualification and brand representation, not just volume. The goal is fewer wasted owner hours and more conversations with your true ICP.

How do I improve time-entry discipline without becoming a tyrant?
Inspect time entry throughout the day, reinforce expectations consistently, and connect time capture to business clarity (profitability, staffing, and client experience). Culture scales what enforcement cannot.

Related resources from Bering McKinley

• Why you’re not paying enough attention to Agreement Gross Profits
• Keys to measuring profitability in ConnectWise PSA
• Solving common profitability challenges with MSP financial services
• People-first account management & smart prospecting

Want to continue the conversation?

If you’re an MSP owner building toward a steadier, more disciplined operating model—where client trust compounds and profitability becomes predictable—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