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

Josh Peterson sits down with Will Robinson—a 30-year IT veteran and former federal technologist—who’s launching an MSSP focused on small businesses. They cover CEO-led selling, real-world pricing math, tool stack choices (including ConnectWise), and smart early hiring via internships and state programs. In this candid conversation, Josh Peterson welcomes Will Robinson to unpack what it really takes to start and grow an MSSP from zero. Will shares his path from the U.S. Navy (telecom and encryption) to federal IT and why he’s betting on entrepreneurship to bring cybersecurity-first managed services to underserved small businesses (4–20 endpoints). The duo dive into CEO as chief salesperson, networking that actually converts, and the biggest early trap—giving away solutions for free during sales calls.

Josh walks through a simple pricing framework (effective hourly rate, utilization, and a 4.5× labor mu

ltiple) and how to translate tool costs into profitable monthly agreements. They discuss building a practical stack—why Will chose ConnectWise (https://www.connectwise.com) for RMM/PSA and a lightweight CRM—and the danger of shiny-object tool churn. Will also shares a smart hiring play: community-college internships and Virginia’s VTOP wage-matching program to affordably build capability before revenue catches up.

You’ll hear how to position MSSP + MSP services without conflict, when to co-manage alongside an incumbent provider, and why consistent daily prospecting beats monthly targets. If you’re launching or rebooting a security-led MSP, this episode is your blueprint: sell yourself first, package outcomes, price with conviction, and execute daily. Learn more about Will’s company at https://thirdiviewcorp.com. For battle-tested MSP playbooks (sales, service, financials) and the Vision system to tie goals to execution, visit https://beringmckinley.com 

[MSP startup] [MSSP] [cybersecurity for small business] [MSP pricing] [ConnectWise onboarding] [managed services sales] [effective hourly rate] [tool stack for MSP] [MSP internships] [co-managed IT] [how to start an MSSP] [CEO as salesperson in MSPs] [pricing managed services agreements] [Virginia VTOP internship program] [community college tech interns] [avoid tool churn in MSPs] [co-managing with incumbent MSP] [building a security-first service stack] [MSP sales daily habits] [small business cybersecurity roadmap]

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