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

In this From the Trenches episode, Todd Holloway joins Josh Peterson for a wide-ranging conversation that blends decades of real-world firefighting experience with more than 30 years of building and operating an MSP. Todd shares how his career began accidentally—balancing firehouse shifts with building computers in the early 1990s—and how that side work evolved into a long-standing boutique MSP focused on deep client relationships, operational discipline, and longevity. Throughout the discussion, Josh and Todd explore how leadership, trust, and calm decision-making under pressure translate directly from emergency response into effective MSP operations. The episode reinforces themes central to the Vision operating system and the realities MSP owners face as they scale.

The conversation also dives into modern MSP challenges, including pricing fatigue, PE activity, sales execution, and shifting client expectations in 2025. Todd explains why long-term client retention depends less on tools and more on communication, accountability, and Technology Business Reviews that actually matter. Josh and Todd unpack why MSP sales is still one of the hardest roles to get right, why bringing SDR functions in-house often outperforms outsourcing, and how cultural alignment drives better results across service delivery and financial performance. For MSP owners thinking about sustainability, profitability, and leadership maturity, this episode offers candid perspective grounded in experience and aligned with how BMK Vision approaches execution.

For MSP leaders looking to strengthen execution and long-term performance, explore related resources from Bering McKinley: how to build profitable service agreements, creating a people-first MSP culture, and improving MSP financial operations through better data.

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Episode Highlights

• 00:00:45 – From firefighting to IT: how an MSP career started by accident.
• 06:00:00 – Lessons from the firehouse that shape MSP leadership and decision-making.
• 12:50:00 – Early MSP pricing, time tracking challenges, and learning profitability the hard way.
• 16:30:00 – Client price fatigue, PE activity, and how buyer expectations are changing.
• 18:00:00 – Re-thinking service tiers, lower-entry offerings, and value-based relationships.
• 30:00:00 – Why bringing SDRs in-house beats outsourced appointment setting.
• 49:20:00 – Time entry discipline, technician mindset, and sustainable service culture.

About the Guest

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 →

About the Host

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast. Through the From the Trenches series, Josh speaks candidly with MSP owners and operators about growth, execution, and the realities of building sustainable service businesses.

🔗 Connect with Josh on LinkedIn →