In this episode of the From the Trenches series, Josh Peterson sits down with Tim Taylor — a 40-year IT veteran, early MSP pioneer, author, and founder of Tim Taylor Consulting.

Tim shares what the industry looked like before the term “MSP” even existed, including mainframe programming, Novell networks, pagers, handwritten timesheets, and selling hardware before managed services became the standard.

Through decades of experience, Tim explains why hourly work used to be highly profitable, how he transitioned into managed services, what broke profitability for so many MSPs, and why mindset, pricing confidence, and focus are the biggest drivers of growth today.

This is a rare, candid conversation full of history, perspective, and practical wisdom for any MSP trying to grow past the early stages and operate with intention.

👉 Learn about the BMK Vision Operating System: https://beringmckinley.com/vision

• Early career in mainframes and PC installation

• Building Novell networks in the 80s and 90s

• Starting a break-fix IT business with only $500

• The first managed services contract

• Why hourly billing was profitable and predictable

• The shift from hardware margin to service margin

• The rise of MSP tools and “shiny object syndrome”

• Copier dealers entering MSP and disrupting the market

• Why so many MSPs stay under $1M

• Pricing confidence and overcoming limiting beliefs

• The owner’s real job: selling and building relationships

• Three KPIs every MSP should track

• Growth mindset vs. technician mindset

• Why constant PSA/RMM switching destroys profitability

This conversation offers an unfiltered look at the early days of the IT services industry and the lessons that still apply today. Tim’s perspective on pricing, sales, mindset, utilization, focus, and leadership gives MSP owners a roadmap for building a healthy, sustainable, and profitable business.

Founder, Tim Taylor Consulting

Tim Taylor is a 40-year IT veteran and pioneer of the early MSP movement. He built his MSP from scratch in the late 1990s, scaling it with break-fix, hourly work, and eventually managed services. Today he runs Tim Taylor Consulting, helping small MSPs (typically under five employees) stabilize, price confidently, and grow with structure and clarity.

🌐 Website: https://www.timtaylorconsulting.com

📬 Email: ttaylor@timtaylorconsulting.com

CEO, Bering McKinley

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast. A leading consultant to MSPs worldwide, Josh helps owners scale by improving operations, service delivery, financial structure, leadership, and strategic planning through the BMK Vision Operating System.

🌐 Learn more: https://beringmckinley.com/vision

🌐 Bering McKinley: https://beringmckinley.com

In this episode of the From the Trenches series, Josh Peterson sits down with Michael Milhouse, President and Co-Founder of Bridgepoint Technologies, for a candid look at what it really takes to build, stabilize, and scale a $3–$5M MSP.

Michael shares his journey from old-school COBOL programming in the 1980s to leading a 32-person organization with multiple service lines—including managed services, custom application development, and a SaaS offering. He breaks down how Bridgepoint transitioned from break/fix to 90% managed services, why the Customer Success Manager (CSM) role became central to client retention and revenue growth, and how implementing EOS® aligned three equal partners around accountability, structure, and measurable execution.

This episode delivers practical, hard-earned lessons for MSP owners who want to move beyond the owner-operator phase and build a scalable, predictable, and healthy business.

👉 Learn about the BMK Vision Operating System: https://beringmckinley.com/vision

• Breaking into IT in the 1980s and early programming work

• Consulting career in Chicago’s financial sector

• Founding multiple IT consulting firms before launching Bridgepoint

• Co-founder dynamics and aligning three equal partners

• Scaling to 32 employees across MSP, SaaS, and app dev

• Moving from break/fix to managed services

• The evolution and value of the CSM role

• Running Strategic Business Reviews (SBRs) that clients actually engage with

• Understanding revenue mix across recurring, project, and hourly

• Chart of accounts complexity when managing multiple business lines

• The “3–5M Valley of Death” and why it stalls MSP growth

• The mindset shift from technician to leader

• Why EOS requires a facilitator and not self-implementation

• Level 10 meetings, scorecards, rocks, and partner accountability

• Communicating vision and strategic direction across the organization

This is a real, practical conversation about the struggles and breakthroughs MSP owners experience on the path to operational maturity. Michael’s transparency around CSM strategy, EOS implementation, service delivery, financial organization, and leadership growth makes this a must-listen for owners ready to scale beyond $1M–$2M and build a truly mature service organization.

President & Co-Founder, Bridgepoint Technologies

Michael Milhouse is the President and Co-Founder of Bridgepoint Technologies, an Illinois-based MSP and technology solutions company offering managed services, custom application development, and a SaaS platform (ToodleBox). With more than 30 years in IT—beginning with COBOL programming and mainframe systems in the 1980s—Michael has built and scaled multiple consulting and technology organizations. Today, he leads a team of 32 professionals focused on delivering modern IT solutions and long-term client partnerships across the Midwest.

🌐 Website: https://www.mybridgepoint.com

📍 Based in Lombard, Illinois

CEO, Bering McKinley

Josh Peterson is the CEO of Bering McKinley and host of the BMK Vision Podcast. A leading authority on MSP business operations, Josh has spent decades helping Managed Service Providers build scalable, profitable organizations. His work focuses on service maturity, financial structure, leadership development, and the BMK Vision Operating System — a framework designed to help MSP owners grow with clarity and intention.

🌐 Learn more about BMK Vision: https://beringmckinley.com/vision

🌐 Bering McKinley: https://beringmckinley.com

Independent assessor Dan Collins breaks down how SMBs should think about compliance (PCI, SOC, HIPAA), where MSPs fit, and why the vCISO lane is the biggest growth play. You’ll leave with a clear map of assessor vs. MSP roles, policy realities, insurance pressure, and sales metrics that drive enterprise value.

✅ Enjoyed this episode? Like, subscribe, and share your biggest takeaway below. https://beringmckinley.com/bering-mckinley-podcast-blog

In this episode of the BMK Vision Podcast, Josh Peterson sits down with Dan Collins of 360 Advanced, an independent security assessor serving the mid-market. Collins explains how assessors validate environments against standards like PCI, SOC, HIPAA, and StateRAMP/FedRAMP requirements—while MSPs remain the hands-on implementers and remediators. The conversation tackles real-world friction in healthcare and dental, why “teeth” in enforcement (and insurers) change buyer behavior, and how incident response should flow when things go sideways. It also spotlights a major opportunity: the Office of the CISO (vCISO) as a high-margin, MRR-friendly service motion MSPs can add without “hands on keyboard.” 👉 Clear roles: assessor vs. MSP vs. insurer vs. IR teams—who does what and when 👉 Healthcare/dental reality: weak HIPAA enforcement, low risk awareness, and what flips the switch 👉 Government pressure: StateRAMP/FedRAMP/CMMC are cascading down to state/local and vendors 👉 Insurance is the throttle: underwriting, questionnaires, and event-driven requirements 👉 Growth play for MSPs: vCISO policy/oversight, planning, and security governance as MRR 👉 Sales metrics that matter: balancing EBITDA + growth (Rule-of-40 style) for higher multiples Collins closes with practical sales org structure, demand-gen tooling, and target spend bands to hit sustainable growth. Visit https://beringmckinley.com for more MSP resources.

🔗 Resources & Links • Dan Collins at 360 Advanced: https://360advanced.com • Bering McKinley MSP Consulting: https://beringmckinley.com

⏱️ Chapters • 00:00 – Dan’s path from systems dev to independent assessor • 02:11 – “We’re not an MSP”: what independent assessors actually do • 03:44 – Why assessors don’t remediate (and where MSPs plug in) • 04:35 – Ideal client size & sophistication (50–3,000 seats) • 06:17 – Healthcare & dental: low security urgency and HIPAA’s “no teeth” • 10:12 – StateRAMP/FedRAMP/CMMC trickle-down and MSP opportunity • 19:41 – Insurers as de-facto enforcers: underwriting & questionnaires • 22:50 – When breach happens: call tree, stop bleeding, collaborate • 26:28 – The Office of the CISO (vCISO) explained—no hands on keyboard • 28:39 – Building a profitable vCISO practice (MRR margins) • 41:10 – Sales evolution: org design, demand gen, and playbooks • 47:21 – Sales/marketing spend bands & targeting sustainable growth • 50:24 – Diminishing returns past ~20% growth; prioritize EBITDA • 51:26 – Where to find Dan

🔍 Primary Keywords vCISO services, security assessment, StateRAMP, FedRAMP, CMMC, MSP growth

🔍 Secondary Keywords HIPAA compliance, PCI DSS, SOC 2 audit, cyber insurance underwriting, incident response

🏷️ Tags bmk vision podcast, bering mckinley, josh peterson, dan collins, 360 advanced, vciso, compliance, pci dss, soc 2, hipaa, stateramp, fedramp, cmmc, cyber insurance, msp growth, sales metrics

#️⃣ Hashtags #bmkvisionpodcast #beringmckinley #msp #msplife #cybersecurity #vciso #compliance #hipaa #pcidss #soc2 #stateramp #fedramp #cmmc #cyberinsurance #incidentresponse #mspsales #mspmarketing #itservices #infosec #riskmanagement