The digital stage lit up as I welcomed Jamison West to Sunny Silver Linings. There are entrepreneurs, and then there are “entrepreneurs of entrepreneurs” – a rare breed, and Jamison embodies it. His journey isn’t just a testament to building businesses; it’s a living blueprint for scaling impact and, crucially, mastering the delicate art of letting go.
Our conversations always spark something new and today was no exception. Jamison, with his impressive resume spanning two decades in the IT services world, including software companies like TimeZest, and his work with ConnectStrat (now MSP+), revealed the profound lesson etched into his entrepreneurial soul: being replaceable is the goal.
For any founder, especially with their first “baby” business, this concept hits differently. I remember my own journey; the intense love and dedication poured into every brick of that first venture. It’s an instinct to be deeply entwined with every operational detail. But as Jamison candidly shared, his early company was “the cult of Jamison.” He couldn’t scale himself. The realization hit him like a lightning bolt: true growth, true impact, comes from building through process and great people.
I immediately recalled my coach, Dan Sullivan’s profound concept of “who not how.” It’s about leveraging the unique strengths of others to multiply your own impact. Jamison’s philosophy perfectly aligns with this. If you can build value with more people, your reach expands exponentially – a 10x, even a 100x leap.
The “Five Ps”: A Framework for Scalable Success
I wanted to double-click on this for our listeners, especially the founders of the MSP channel who often feel tethered to their businesses. Jamison dove into his “Five Ps,” a powerful framework for systematizing any company, a pathway to greater work-life harmony and enterprise value:
- People: Always, always start with the right people. Surround yourself with individuals who are more skilled and knowledgeable in their roles than you could ever be. This isn’t a weakness; it’s a superpower.
- Process: Ditch tribal knowledge. Create repeatable, teachable processes. This is the foundation for effective delegation and consistent quality, freeing entrepreneurs from constant operational firefighting.
- Priorities: Master the art of setting clear goals. Break them down into manageable rocks and weekly priorities. This ensures the important doesn’t get swallowed by the urgent.
- Performance: “Measure everything,” Jamison emphasized. KPIs and metrics, when visible and understood by all, empower teams to self-manage. It transforms subjective management into objective alignment.
- Perspective: The owner’s crucial role. Step back, see the forest for the trees. Regularly realign your vision and strategy, ensuring the daily grind remains connected to the long-term destination.
These “Five Ps” – People, Process, Priorities, Performance, Perspective – are not just words; they’re actionable pillars for creating a truly scalable, valuable business.
Overcoming the Delegation Dilemma: Finding Your “Number Two”
But applying this, I know, brings up the biggest fear for many founders: delegation. The terror of entrusting their “baby” – their brand, their financials, their hard-earned reputation – to someone else. Especially for MSPs hovering around the $5 million mark, built with years of sweat and capital, the fear of failure in delegation is very real.
“What do you look for in that number two?” I asked, pushing on this vital point. Jamison’s insight was a refreshing splash of cold water on a common industry mistake. He looks for someone who understands the business of running the business. This means having a strong financial acumen and a broad business background rather than a purely technical one. He’s seen too many technical leaders promoted into operational roles only to flounder because their mindset isn’t geared towards holistic business management. His surprising example? The CFO often steps in as interim CEO in larger enterprises – a testament to the power of financial and business acumen.
He’s currently coaching MSP owners through this very transition, and consistently, their successful “number twos” are not primarily technical; they’re financially astute individuals who grasp the broader operational landscape.
Crucially, Jamison stressed that this isn’t a quick fix. Building the trust required to “let go of the vine” is a journey. It requires defining clear guardrails, setting precise expectations, providing autonomy, and then critically trusting but verifying. As the number two demonstrates proven value, their “territory” can expand, creating a virtuous cycle of growth and delegation.
Jamison also highlighted a critical aspect of this partnership: aligning incentives. He believes that a strong number two, who is truly leading and growing the business, should have a “bite of whatever this outcome may result in,” whether through profit sharing or phantom equity. This alignment ensures that the number two is “betting on themselves,” just as the owner is betting on the business, fostering a powerful mutual commitment and driving the highest level of performance.
Common Pitfalls and the Power of Highest and Best Use (HABU)
So, what are the common pitfalls for MSPs struggling with this powerful strategy? Jamison pointed to two major areas:
First, owners getting in their own way. That deep emotional connection to the “baby business” can actually hamper success. It’s understandable from the owners’ perspective but often ends up in owners settling for sub-optimum results. Jamison admitted he only truly grasped this after selling his own MSP, realizing his emotional ties had been a drag. The key mindset shift? Like a child should be given the will and freedom to grow independently once he becomes an adult, the same principle applies to any business. You have to let go!
Second, for the “number twos” themselves, the challenge is relinquishing their core, comfortable roles. A technical leader promoted to a strategic position might naturally gravitate back to technical work when faced with a pile of tasks. Jamison emphasizes the concept of Highest and Best Use (HABU): elevating into leadership means focusing on deep, strategic work – not urgent, low-value tasks that can be automated or delegated. He even considers using time trackers to help leaders identify how much time they’re truly spending on high-value, low-interruption activities versus reactive, low-value work. “You can’t elevate a business if you’re in the weeds,” he declared.
The Path to Freedom: Mindset, Execution, and Impact
The path to freedom and scaled impact, as Jamison outlines, begins with a mindset shift: embrace HABU and view your business as an asset. Once that internal shift happens, the next steps are clear: rigorously apply the Five Ps. Get the right people in the right seats, build robust processes (and then get out of their way), prioritize effectively, measure performance relentlessly, and consistently step back to maintain perspective. This leads to an operationally mature organization where the owner isn’t tied up to daily operations.
Jamison shared inspiring examples from his clients: some now enjoy three or four-day weekends, focusing only on a sales leadership role that aligns with their unique abilities. Others have freed up half their time to pursue new passions, like real estate investing. This is the “passion freedom” and “purpose freedom” that comes from aligning your unique strengths to the highest-level contribution. Your energy skyrockets, your impact multiplies, and others are empowered to grow the asset alongside you.
I couldn’t help but reflect on our common friends from our Evolve peer group, MSPs, who made the strategic pivot to private equity. Their immediate focus? A CFO, someone with that crucial financial and business acumen as their number two. They learned what Jamison has always preached: it’s not always the best technical lead who makes the best operational head. This is the social proof – the tangible evidence – that Jamison’s blueprint for time freedom, asset building, and enterprise value creation isn’t just theory; it’s a proven path to joy and fulfillment in entrepreneurship.
The Future of the MSP Industry: Exciting and Transformative
As the conversation drew to a close, Jamison expressed his excitement for the MSP industry’s ongoing evolution, from managed services to cloud, security, and now the transformative wave of automation and AI. This renewed focus on “Highest and Best Use” – whether human or technological – makes it an exhilarating time to be an MSP, a time ripe for strategic thinking and impactful change.
Thank you, Jamison, for sharing your profound wisdom and illuminating the path for so many entrepreneurs. Your impact on this channel is immeasurable.
