#9 – From the Trenches: Why Most MSPs Stay Stuck – And How to Break Through (Alex Farling)

In this episode of From the Trenches on the BMK Vision Podcast, Josh Peterson sits down with Alex Farling for a leadership conversation that strips away one of the MSP industry’s most dangerous myths: that experience alone eventually turns into clarity. Alex’s story is not a clean ascent—it is a long arc of accidental ownership, repeated reinvention, financial pressure, and ultimately self-awareness. From buying a failing break/fix shop with $8,000 and no employees, to surviving the 2008 financial collapse, to selling his MSP during COVID, Alex embodies the reality many owners quietly live: most progress is earned through endurance, not certainty. The lessons align directly with what we build inside Vision—an operating system that replaces heroics with structure and replaces hope with execution.

This is not a conversation about tools, tactics, or growth hacks. It is a leadership autopsy. Why do MSPs get trapped by decade-long pricing mistakes? Why does “being busy” masquerade as progress? Why do so many owners insist on holding roles they are poorly suited for? Alex reframes MSP leadership as an honesty exercise. He argues that most businesses stall not because the market is unfair, but because owners avoid confronting three truths: sales is a practiced discipline, profit is a prerequisite—not a reward, and the bottleneck is almost always the owner. Without those realizations, MSPs default into survival mode—working harder each year to stand still.

The emotional center of the episode is Alex’s willingness to name what changed everything for him: admitting he was a strong sales leader and a weak CEO. That single insight unlocked more enterprise value than 17 years of effort ever did. The takeaway for MSP owners is uncomfortable but freeing—your title does not define your value. Your willingness to design the right operating model does. Whether that means redefining your role, building leadership capacity, or preparing for an eventual exit, the path forward requires deliberate choice, not inertia.

What “failing forward” actually looks like in an MSP

Failure is often romanticized in entrepreneurship. Alex removes the romance. Failing forward is not a single lesson—it is a long sequence of consequences. Pricing mistakes that linger for a decade. Side ventures that collapse under economic pressure. Leadership hires that never stabilize. Each failure compounds unless it is confronted directly.

The practical distinction Alex makes is this: failure becomes progress only when it is paired with reflection and correction. MSPs don’t fail because they make mistakes. They fail because they repeat the same ones while convincing themselves they are “too busy” to fix the underlying issue.

The MSP problem this episode solves

Many MSP owners believe they are stuck because of the market, pricing pressure, or lack of leads. Alex argues the problem is internal. Owners want growth, but behave like operators protecting comfort. They say sales is hard, yet refuse to practice it. They say profit matters, yet underprice to avoid uncomfortable conversations.

• Owners rely on referrals instead of building a sales muscle
• Pricing decisions are made once—and paid for forever
• Execution fatigue sets in from half-implemented systems
• Leadership roles are defined by ego, not aptitude

Sales is not talent—it is repetition

One of the clearest insights in the conversation is Alex’s reframing of sales. Most MSP owners think they are “bad at sales,” when in reality they simply don’t practice it. Closing referrals is not sales mastery—it is familiarity.

Alex compares sales to any physical discipline: if you only take ten swings a year, you will never improve. Five deliberate outreach actions per day compound faster than any marketing campaign. Sales does not require personality—it requires repetition, coaching, and consistency.

The hidden ceiling: identity and ego

The most consequential moment in the episode is Alex’s admission that he was a poor CEO. For years, identity held him hostage. Ownership created the illusion that he had to be the CEO—even when it drained energy and limited the company’s growth.

When Alex stepped out of that role, enterprise value accelerated dramatically. The lesson for MSP owners is stark: the business does not exist to validate your title. It exists to create value. Your job is to put yourself where you contribute most—and design leadership around that truth.

What a healthy relationship with profit looks like

Alex highlights a quiet constraint in the MSP industry: discomfort with profit. Discounting feels easier than justifying value. Thin margins feel noble—until they prevent hiring, transformation, or succession planning.

A low-profit MSP is not virtuous—it is fragile. Profit funds leadership capacity, change management, and optionality. Without it, MSPs are forced into reactive survival and eventual burnout.

• Discounting avoids conflict but creates long-term drag
• Low margins block transformation and delegation
• Profit enables stewardship instead of heroics
• Healthy margins turn effort into durability

A practical leadership self-check

If this episode resonated, use this checklist to assess where the constraint actually lives.

• Role clarity: Are you operating in the role you are best at—or the one your ego chose?
• Sales discipline: Do you practice sales daily, or only when growth feels urgent?
• Pricing posture: Can your margins fund leadership, change, and recovery?
• Execution maturity: Do initiatives reach completion—or fade into background noise?
• Optionality: If you stepped away for 30 days, would the business stabilize or panic?

Episode highlights

• 00:01:00 – Accidental entrepreneurship and buying a failing computer shop
• 00:09:25 – Surviving the 2008 financial collapse as an MSP
• 00:11:35 – How early pricing mistakes haunt MSPs for years
• 00:18:30 – Lifecycle budgeting as a survival mechanism
• 00:27:30 – Sales as a muscle—not a personality trait
• 00:38:00 – Letting go of the CEO identity
• 00:55:40 – Why clarity accelerates enterprise value

About the guest: Alex Farling

Alex Farling is a veteran MSP founder and co-founder of Empath MSP. He built and sold Delaware Micro after more than 16 years of ownership, then co-founded Lifecycle Insights, which was later acquired. Alex now helps MSPs escape commoditization by improving positioning, pricing discipline, and sales execution.

🔗 Connect with Alex on LinkedIn →

Frequently asked questions

Why do MSPs struggle despite years of experience?
Because experience without reflection reinforces bad habits instead of correcting them.

Is sales really the biggest constraint?
Often, yes. Most MSPs rely on familiarity-based deals instead of building a repeatable sales engine.

What role does profit play in MSP sustainability?
Profit funds leadership, transformation, and recovery. Without it, every setback becomes existential.

Should every MSP owner be the CEO?
No. Value accelerates when owners operate in their true strengths and design leadership accordingly.

Want to continue the conversation?

If you recognize pieces of yourself in Alex’s story, the next step is not more effort—it is clarity. Decide what role you should play, what model you are building, and whether your operating system supports it.

👉 Apply to be on the BMK Vision Podcast
👉 Learn more about Vision