============================================================ TITLE: #10 – From the Trenches - MSP Exit & EOS Lessons (Jeff Wynn) TYPE: blog VERSION: 1 VERSION_ID: 4dcb5751-61e1-4fed-8845-ec14fc0af578 GENERATED_AT: 2026-01-30T23:20:34.081Z SUMMARY: Jeff Wynn shares how EOS, peer learning, and financial clarity helped him build, lead, and successfully exit his MSP after 20 years of ownership. AUTHOR: Josh Peterson DATE PUBLISHED: July 29, 2025 DATE MODIFIED: December 24, 2025 READING TIME: 8 min WORD COUNT: 1430 KEYWORDS: MSP Exit & EOS Lessons (Jeff Wynn), Episode highlights, Frequently asked questions SOURCE URL: https://beringmckinley.com/blog/bering-mckinley-podcast-blog/10-from-the-trenches-msp-exit-eos-lessons-jeff-wynn ============================================================ KEY TAKEAWAYS: * Listen on Your Favorite Platform * The exit isn’t the event—it’s the operating model * The MSP problem this episode solves * From technician momentum to strategic leadership * Target customer profile is a profitability decision In this From the Trenches episode of the BMK Vision Podcast, Josh Peterson sits down with Jeff Wynn—founder and former owner of New River Computing—for an executive-level conversation about the part of MSP ownership most leaders postpone until the last minute: designing an exit that serves the owner, the team, and the client base. Jeff’s story is not “how to sell your MSP fast.” It’s a clearer, harder, more useful idea: every MSP owner exits—so the only real question is whether the exit is intentional, planned, and value-creating…or accidental, rushed, and value-destroying. This is not a vendor conversation or a tactics showcase. It’s a leadership discussion about stewardship—treating a business as something you are responsible to build well, not merely something you “run” until you’re tired. Jeff walks through the long arc: starting with “walking around money,” learning the financial language of the business, narrowing the client profile, adopting EOS, and ultimately spending years shaping the organization into something worth buying. The deeper lesson is uncomfortable but liberating: profitability and clean operations aren’t accounting outcomes—they’re leadership behaviors. If you’re an MSP owner who’s still carrying the burden of ownership in your body—stress, anxiety, constant mental load—this episode is a practical reframing. The goal is not to “sell someday.” The goal is to build a company that can stand on its own: a company you’d be proud to work for, a company your team can grow inside, and a company that creates options—whether that option is a sale, a lifestyle business, or a legacy. For MSP owners who want that kind of clarity and execution discipline, explore the Vision operating system. ## Listen on Your Favorite Platform * * * * * * * * * * * ## The exit isn’t the event—it’s the operating model Most MSP owners treat an exit like a future transaction: “Someday I’ll sell.” Jeff frames it differently: the exit is the consequence of years of decisions—about financial discipline, client fit, leadership maturity, and operational clarity. If you’re building for optionality, you don’t wait until a buyer appears to become “ready.” You build readiness into the business: * Financial visibility that supports decisions (not just bookkeeping) * A leadership structure that doesn’t require daily owner heroics * A service model that produces durable margin and trust * A team environment you’d be proud to recruit into ## The MSP problem this episode solves Many MSPs grow into revenue before they grow into leadership. They wake up one day with real payroll, real responsibility, and real stress—but without the financial and operational infrastructure to scale cleanly or exit intentionally. This episode addresses three common MSP traps: * Building a “walking around money” business that accidentally becomes a life sentence * Operating without financial literacy—unable to read the true story the P&L and balance sheet are telling * Staying owner-dependent (sales, strategy, escalations), which destroys value and amplifies burnout ## From technician momentum to strategic leadership Jeff’s arc is familiar: early success comes from technical competence and hustle. The turning point comes when the owner learns the business language—finance, positioning, process, and decision discipline. His practical shift was not complicated, but it was decisive: * Start learning from peers who have already made the mistakes you’re about to make * Upgrade financial understanding so you can predict outcomes—not just react to them * Adopt an operating cadence (EOS, or another discipline) to reduce chaos and build clarity That’s the deeper leadership move: turning experience into repeatability. ## Target customer profile is a profitability decision One of the most valuable moments in the conversation is Jeff describing the discomfort—and then the freedom—of saying, “I don’t think we’re a good fit.” That decision is not “sales.” It’s leadership. A focused MSP competes on fit, not on willingness: * Define the client size range you can serve exceptionally well * Clarify your service standard (security-conscious, outcomes-focused, aligned expectations) * Stop trying to turn every prospect into a client—build a business that wins by selectivity When you choose your client profile, you are choosing your margin, your delivery model, and your future exit options. ## Transparency during an exit is a leadership test Exit planning creates a brutal tension: the business may value transparency, but the transaction demands confidentiality—until it doesn’t. Jeff describes the emotional weight of carrying that secret, and then the relief of being able to tell the team truthfully and directly. For MSP owners, this is the quiet standard worth adopting: * Assume your team will feel anxiety—don’t dismiss it * Frame the exit as a stewardship decision: people, clients, and continuity matter * Choose buyers and terms that preserve trust, not just valuation ## Episode highlights * 00:00:00 – Reconnecting with long-time peers and lessons from the MSP community. * 00:06:24 – The turning point from “walking around money” to strategic financial growth. * 00:08:01 – Linking business outcomes to lifestyle goals through financial modeling. * 00:14:25 – How financial literacy transformed decision-making and leadership. * 00:17:17 – Why consultative, owner-led sales drive loyalty and profitability. * 00:42:05 – Managing transparency during an exit—balancing trust and confidentiality. * 00:54:37 – Post-sale involvement: staying connected without ownership burnout. ## Frequently asked questions How early should an MSP owner start planning for an exit?As early as possible. A strong exit is rarely a last-minute event—it’s the result of years of improving profitability, reducing owner-dependence, and building clean operational and financial systems. Does EOS help an MSP prepare for an acquisition?It can. EOS (or any strong operating cadence) helps create focus, accountability, and repeatability—exactly what buyers want when they assess risk and sustainability. What increases MSP valuation the most?Clean financials, consistent profitability, reliable service delivery, and leadership depth that doesn’t rely on the owner. Strong client fit and low churn matter because they reduce buyer risk. Should MSP owners hire a salesperson to replace owner-led sales?Not automatically. Many MSPs succeed with consultative, owner-led sales—but the goal is to build a machine that can sell and deliver without requiring the owner for every step. How do you decide which clients to say “no” to?Use a target customer profile: size range, expectations, security posture, and values alignment. Saying “no” is often the difference between growth that adds stress and growth that adds value. ## Related resources from Bering McKinley * EOS for MSPs: How to Create Focus and Accountability * Solving Common Profitability Challenges * Why MSPs Need to Master Financial Literacy For more leadership stories and conversations, visit the BMK Vision Podcast main page → ## About the Guest Jeff Wynn is the founder and former owner of New River Computing, a successful Virginia-based MSP. After nearly 20 years building and leading the company, Jeff completed a strategic exit and now mentors other entrepreneurs through operational frameworks like EOS and peer learning. His experience blends deep technical expertise with practical leadership wisdom, helping MSP owners align business value with personal vision. 🌐 Connect with Jeff on LinkedIn → ## 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 sits down with MSP owners and leaders to discuss real-world experiences, growth strategies, and the personal journeys behind successful IT service companies. 🔗 Connect with Josh on LinkedIn → 📺 Subscribe on YouTube → ------------------------------------------------------------ ABOUT THIS CONTENT ------------------------------------------------------------ Source: https://beringmckinley.com/blog/bering-mckinley-podcast-blog/10-from-the-trenches-msp-exit-eos-lessons-jeff-wynn Author: Josh Peterson Published: July 29, 2025 This content is provided for informational purposes. Please visit the original source for the most up-to-date information.