#37 – From the Trenches Building a $3–$5M MSP, CSM Strategy and EOS Execution (Michael Milhouse)

In this From the Trenches episode, Michael Milhouse, President and Co-Founder of BridgePoint Technologies, joins Josh Peterson to unpack what it really takes to build and stabilize a $3–$5M MSP. Michael traces his path from a programming background and early consulting hustle to leading a mature service organization, explaining how clear role separation across sales, service delivery, and finance unlocks scale and reduces founder bottlenecks. Along the way, he and Josh connect these lessons to the broader need for structure, metrics, and intentional leadership—reinforcing how programs like the BMK Vision program help owners turn scattered effort into a disciplined operating system for growth.

Building on that foundation, Michael describes how introducing Customer Success Managers (CSMs) and evolving from traditional QBRs into Strategic Business Reviews (SBRs) transformed client engagement, revenue expansion, and long-term retention. He shares candid insight into navigating the “valley of death” between $3M and $5M in revenue, where many MSPs stall without stronger processes, cleaner service hygiene, and a willingness for founders to let go of day-to-day control. The conversation closes with a deep dive into implementing EOS (Entrepreneurial Operating System) with a professional facilitator—bringing discipline, accountability, and focus to the leadership team—and how MSPs can combine structured client engagement, like the practices outlined in BMK’s client engagement strategy for MSPs, with the kind of scale-focused support offered to MSPs in the $3–15M+ revenue range.

For MSPs working to break through growth ceilings, clarify leadership roles, and professionalize client management, explore these next-step resources on client engagement strategies from onboarding to QBRs and scaling MSPs in the $3–15M+ revenue band.

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Episode Highlights

• 00:01:00 – Michael’s pivot from programming into MSP entrepreneurship, inspired by conversations with his electrician father and a desire to build something scalable.
• 00:09:00 – Early-stage hustle stories, including staking out train lobbies to generate leads and growing a consulting business from a bedroom card table.
• 00:12:00 – Why clearly separating ownership of sales, service delivery, and finance is essential to avoid overlap, confusion, and stalled growth.
• 00:18:00 – How introducing Customer Success Managers as revenue-generating account managers reshaped client relationships and expansion opportunities.
• 00:25:00 – Reframing traditional QBRs into forward-looking Strategic Business Reviews that align IT initiatives with client business goals.
• 00:43:00 – Navigating the $3–$5M “valley of death” and the mindset shifts required for founders to move from doers to strategic leaders.
• 00:51:00 – Implementing EOS with a professional facilitator to create real accountability, execution discipline, and leadership alignment.

About the Guest

Michael Milhouse is the President and Co-Founder of BridgePoint Technologies, an MSP based in the Chicago suburbs that specializes in managed and co-managed IT services, cloud solutions, cybersecurity, and IT strategy for law firms, non-profits, and senior care organizations. Since 2004, he and his team have focused on building a high-touch, process-driven service model that helps clients stay secure, compliant, and operationally resilient.

🌐 Learn more about BridgePoint Technologies →

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 highlights MSP leaders who redefine growth through creativity, resilience, and genuine client connection.

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