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

There’s a specific kind of courage required to leave a stable, competent career and walk into a market that doesn’t owe you a single client. In this From the Trenches episode of the BMK Vision Podcast, Josh Peterson sits down with Will Robinson—a 30-year IT and cybersecurity veteran whose background spans Navy communications, government service, and long-term technical leadership—now making the leap into MSP/MSSP entrepreneurship.

This isn’t a “how I picked my tools” conversation. It’s a founder conversation. Will is stepping into the uncomfortable middle zone where expertise is real, but the business still isn’t. That’s where most new MSPs get psychologically trapped: the work is obvious, the market is noisy, and the only immediate feedback loop comes from sales conversations that don’t convert. The episode names that reality plainly—and then walks through the disciplines that keep founders from bleeding out in the early innings: sales boundaries, focused targeting, simple financial math, and resourceful hiring.

If you’re an MSP owner (or future owner) who knows you can deliver outcomes, but you’re still learning how to get paid for them consistently—this episode will feel familiar in the best way. It reinforces a leadership truth most technicians learn late: the business doesn’t scale when you “know more.” It scales when you decide what you’ll sell, how you’ll price it, and how you’ll protect your time and attention long enough to earn momentum.

What actually changes when a technician becomes a founder?

The first shift isn’t technical. It’s psychological: you stop being rewarded for competence and start being rewarded for conviction. Founders discover quickly that “being right” doesn’t produce revenue. People will happily take free guidance, nod along, and disappear—especially in small business markets where owners are under pressure and hoping for a shortcut.

Will describes this early pain clearly: you can have a helpful conversation, share real solutions, and still never earn the right to invoice. That moment is where many MSP founders develop a defensive posture (“people don’t value IT”), when the actual lesson is simpler: you must learn how to sell boundaries before you can sell outcomes.

• Expertise earns attention; boundaries earn commitment
• “Free advice” is not generosity—it’s often a failure to qualify
• A founder’s job is not to solve problems in discovery; it’s to earn trust and define the next step

The MSP problem this episode solves

Most new MSPs don’t fail because they can’t deliver. They fail because they can’t survive the gap between capability and repeatable acquisition. That gap is where confidence gets eroded: you launch the entity, buy the first tools, build the website, and then realize that none of it creates demand. Demand is created through disciplined prospecting—repeated conversations with strangers—until the market can finally “see” you.

Josh frames the uncomfortable reality: many MSPs can reach roughly $1M in revenue primarily through a founder’s natural network and referrals over time. But that path is slow and fragile, and it breaks the moment the network is exhausted. The owners who shorten the timeline—and protect their future scalability—do one thing earlier than everyone else: they operationalize sales as a daily non-negotiable.

• Define your ideal client in plain language (industry, size, constraints)
• Talk to new people daily, not “someday this month”
• Stop confusing activity (tools, branding) with traction (appointments, deals)
• Build confidence through reps, not theory

A founder’s early-stage sales model that actually works

Will’s approach is refreshingly grounded: start local, serve small businesses (roughly 4–20 endpoints), and build a base where relationships and trust can compound. That market isn’t glamorous, but it’s underserved—and it allows a new MSP/MSSP to become indispensable without needing an enterprise-level brand on day one.

He also names a critical positioning nuance: security-first messaging often creates a better opening than “we do IT.” Many prospects already have “an IT guy.” Few feel confident about cybersecurity. That difference creates a wedge: you can lead with security credibility while still offering broader support where appropriate.

• Lead with the business risk you reduce, not the tools you deploy
• Use “you already have an IT provider” as an opening, not an objection
• Sell yourself first, company second, services last
• Let the prospect talk—your job is to ask better questions than their current provider

Pricing isn’t a “rate” problem—it’s a survival problem

New MSPs often price based on what feels fair, what competitors claim to charge, or what the prospect can tolerate. That produces an invisible failure mode: you can win clients and still build a business that cannot sustain payroll, tool costs, and growth.

Josh walks through a simple cost-based anchor that cuts through the noise: if a technician costs $80,000/year, that’s roughly $40/hour at 2,000 hours—before utilization, overhead, mistakes, and leadership time. A multiplier (roughly 4.5–5.2x) isn’t greed; it’s math. It’s the difference between being a professional service business and being a subsidized job you created for yourself.

• Price to cover utilization reality, not calendar fantasy
• Mark tools with intent (and stop pretending pass-through pricing is “fair”)
• Protect your delivery margins early—fixing underpricing later is far more expensive
• Use your P&L as a decision-making tool, not just a tax artifact

Resourceful hiring: how to build capacity without sinking the boat

Hiring too early is a classic founder mistake. Hiring too late is the quieter one—because the founder becomes the bottleneck and mistakes “busyness” for progress. Will’s path offers a practical middle ground: internship pipelines and state-supported workforce programs can create real leverage when cash is tight.

More importantly, this approach reinforces a leadership posture that scales: don’t default to “I can’t.” Default to “how can I?” If you can build even a small bench—technical help, delivery support, or appointment-setting—you buy back the only resource that matters in year one: founder focus.

• Internships can become a talent pipeline, not just cheap labor
• Workforce programs can subsidize early hiring when used intentionally
• Mentorship builds loyalty—and creates a culture worth scaling
• Delegation is not abdication; it’s strategic capacity-building

Episode highlights

• 00:02:00 – Will’s 30-year IT and cybersecurity foundation (including Navy communications) and why he’s making the leap now.
• 00:04:00 – The “free advice” trap: prospects taking solutions without paying—and the boundaries founders must learn.
• 00:07:00 – CEO-as-salesperson: why ownership requires selling, even for introverts.
• 00:11:15 – Target market strategy: building locally with small businesses (roughly 4–20 endpoints).
• 00:24:00 – Tool-stack commitment: why “clean slate” decisions matter and tool churn becomes expensive noise.
• 00:30:00 – Resourceful staffing: internships and workforce programs as capacity multipliers.
• 00:39:00 – Pricing anchor: cost-based math, utilization reality, and why multipliers protect profitability.

About the Guest

Will Robinson is a cybersecurity-focused MSP/MSSP founder and long-time IT professional with a background that includes Navy communications, government service, and decades of experience in secure systems and technical leadership. His work is shaped by a disciplined, service-first mindset—helping small businesses adopt practical security, improve operational resilience, and build the confidence to grow without becoming an easy target for modern cyber threats.

🌐 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, discipline, and long-term strategy.

🔗 Connect with Josh on LinkedIn →

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