#20 – From the Trenches - From Navy Comms to MSSP - Leap into Entrepreneurship (Will Robinson)

In this From the Trenches episode, Will Robinson shares his inspiring journey from a 30-year career in IT and cybersecurity—including Navy communications and government service—to launching his own MSP and MSSP. Will’s story blends discipline, courage, and a commitment to learning as he transitions from employee to entrepreneur, balancing technical mastery with a new sales mindset.

The discussion explores his approach to pricing, client acquisition, and tool selection, as well as innovative staffing through internships. Will’s experience offers a blueprint for MSP founders striving to combine operational excellence with community impact and sustainable profitability.

To learn more about MSP growth and entrepreneurship, check out our guides on starting an MSP business and essential first steps, pricing strategies to avoid undercharging your services, and why sales training is critical for MSP owners.

For more episodes and insights, visit the BMK Vision Podcast main page →

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Episode Highlights

• 00:02:00 – 30 years of IT and cybersecurity experience including Navy communications.
• 00:04:00 – Overcoming the fear of finding paying clients versus free consultations.
• 00:07:00 – Adopting the CEO-as-salesperson mindset as an introvert.
• 00:11:15 – Targeting small local businesses (4–20 computers) for managed IT and cybersecurity.
• 00:25:00 – Investing early in ConnectWise and CRM tools to streamline operations.
• 00:30:00 – Leveraging community college interns and Virginia’s VTOP program.
• 00:39:00 – Pricing model: salary × 4.5–5.2 multiplier ensures profit and sustainability.

Key Insights

• Experience as a Differentiator: Military and government IT experience builds instant credibility and deep cybersecurity trust.
• Sales and Client Acquisition Challenges: Learning to convert conversations into paying clients by setting clear value boundaries.
• CEO as Chief Salesperson: Personal involvement in sales builds relationships and accelerates growth, even for introverted founders.
• Niche Market Focus: Targeting small local businesses creates manageable growth and strong community relationships.
• Prudent Tool Investment: Investing early in the right tools prevents inefficiencies and tool churn common among startups.
• Workforce Innovation: Internship programs reduce cost, grow talent, and strengthen community ties.
• Structured Pricing for Profitability: Transparent pricing based on cost and utilization ensures long-term financial health.

About the Guest

Will Robinson is the founder of a Virginia-based MSP and MSSP dedicated to serving small businesses through cybersecurity and managed IT services. Drawing on 30 years of experience in military and government communications, Will focuses on service excellence, community growth, and mentorship.

🌐 Connect with Will on LinkedIn →

About the Host

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast. Through From the Trenches, Josh highlights stories of resilience and innovation from MSP owners redefining success through leadership and community impact.

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