#10 – From the Trenches - MSP Exit & EOS Lessons (Jeff Wynn)

In this From the Trenches episode, Jeff Wynn, founder and former owner of New River Computing, joins Josh Peterson to share his two-decade journey of building, leading, and successfully exiting his MSP. From starting as a side hustle with his best friend to implementing EOS (Entrepreneurial Operating System) and preparing for an emotional, well-structured exit, Jeff reflects on the practical, financial, and human lessons that define sustainable entrepreneurship.

He talks candidly about financial missteps, leadership growth, peer group influence, and the importance of designing your business—and your life—around a clear end goal. This episode offers MSP owners a transparent roadmap for building real business value and leading with intention, not burnout.

This insightful conversation explores:

• Jeff’s early years turning “walking around money” into a scalable business
• How peer networks and financial literacy fueled his company’s turning point
• Transitioning from reactive leadership to structured EOS implementation
• The emotional and strategic realities of preparing for a business exit
• How transparency with employees during an acquisition builds trust and continuity
• Why connecting business outcomes to life goals creates purpose and alignment

To learn more about EOS, leadership, and financial clarity, explore our related articles: EOS for MSPs: How to Create Focus and Accountability, Solving Common Profitability Challenges, and Why MSPs Need to Master Financial Literacy.

For more leadership stories and conversations, visit the BMK Vision Podcast main page →

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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.

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.

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