The digital stage lit up as I welcomed Chris Day to the latest episode of Sunny Silver Linings. There are entrepreneurs, and then there are “entrepreneurs of entrepreneurs” – a rare breed, and Chris truly embodies it. His journey isn’t just a testament to building successful businesses; it’s a living blueprint for navigating industry shifts, solving systemic problems, and achieving what few MSP leaders have.
Our conversations always spark something new, and today was no exception. It was so great to finally meet Chris in person at PAX8, after previously connecting in Vancouver during a mastermind. But visiting his office truly gave me a deeper understanding. One word resonated when I reflected on his journey: “entrepreneur of the entrepreneurs.”
Chris candidly shared how his journey, while unique in its scale, began similarly to many in IT services. After an impactful three years as a sales engineer at F5, traveling the world and discussing complex tech with Fortune 500 companies, he saw a glaring gap: small businesses weren’t getting access to the same high-end tech advantages. This insight, coupled with a fortunate exit from F5’s IPO, sparked his entrepreneurial fire. He was an early adopter of the recurring revenue mindset, charging $100 a month for VPN links and managing them, long before “managed services” became the industry standard.
He then navigated the immense pivot from break-fix to managed services, and later the critical shift to cloud. His experience spans the entire spectrum, from a one-person shop to a 500-person MSP, including significant M&A activities and transformations. As he aptly put it, “It’s never easy, is it? We all have that in common.”
Solving the Unspoken Problem: The Birth of IT Glue
One of the most remarkable aspects of Chris’s journey, and something I deeply relate to as an MSP entrepreneur, is his solving of the industry’s pervasive documentation problem. As an MSP owner in New York City, I vividly recall the constant struggle with documentation and achieving operational maturity.
Chris recognized this inefficiency early on. His MSP was literally spending $200,000 to $300,000 a year on their own internal documentation app. That’s how critical they believed it was! The true “aha!” moment, however, came from his peers in HTG and Service Leadership groups. They saw what he had built internally and repeatedly asked, “Can I use this? Can you sell me this?”
This organic demand sparked his transition from MSP owner to software visionary. In 2013, he handed the CEO reins of his MSP to Joel Abramson, realizing he had stumbled upon a software category that was virtually absent. It was a blend of foresight and “luck, or maybe preparation and a little bit of luck,” as he put it, that led to the creation of IT Glue. His conviction was simple: if everyone had this tool, it would elevate the entire industry.
The Relentless Pursuit: Perseverance as the Entrepreneur’s North Star
When I asked Chris about the greatest lesson he’d share with other entrepreneurs, his answer resonated deeply: “relentless perseverance.” He wisely noted that taking a big swing “never quite goes the way you expect” and it “always takes a lot longer”: much like a home renovation that costs twice as much and takes twice as long.
Perseverance, as I often reflect, is like protein for growth. You can’t go around adversity; you have to go through it. As a quote on my desk reminds me, “The moment you are ready to quit is usually the moment right before a miracle happens.” It’s about keeping calm and carrying on, even when the path is uncertain.
Beyond the Plumber Role: The Strategic Advisor
Chris, a true thought leader, shared profound insights on the dangerous opportunities and strengths within our industry, especially with the rise of AI. He expressed a healthy “adverse reaction to the word growth” if it solely means adding new customers. For him, the real gold lies in becoming the “trusted advisor.”
He highlighted the uncomfortable truth: if you ask a typical MSP customer about their experience, the answer is often, “It’s fine. It’s not bad. Whatever.” We’ve been relegated to a necessary “plumber role,” maintaining and implementing. However, the true opportunity, and the very threat to losing business, lies in stepping into the strategic advisor role: being in the boardroom, helping customers look around the next corner, and planning for what’s coming, like AI.
Chris believes this pivot can happen quickly if MSPs reframe their engagement, bring the right people to the table, and ask the right questions. The five-person MSP, where the CEO directly engages with client CEOs, often does this best due to the personalized, high-level strategic conversations. This isn’t just a challenge for small MSPs; it’s an “all MSP problem.”
The AI Summit: From Anxiety to Opportunity
The buzz around AI often comes with anxiety, a fear of being left behind. As Chris wisely points out, the real valuable use cases will take time. What’s more immediate and impactful is how MSPs can become the “AI shepherds for SMBs.”
Even for us in tech, getting our arms around AI is challenging. SMBs, however, are already asking for help, seeing new tools, and wanting to automate everything. This creates a massive opportunity for MSPs to guide them. As we discussed in a mastermind session, even simple “expert-type prompts” for ChatGPT can be incredibly powerful. Imagine charging $5,000 a month for such knowledge and guidance – the market isn’t there yet, but the need certainly is.
As I reflected on my recent Mount Everest climb, I realized the journey to the AI summit is similar. There are groups a few steps ahead, but everyone is still figuring it out. This realization can be fuel for our anxiety: no one truly “knows” everything. We’re all making things up, trying to make them real, and then making them repeatable.
Chris echoed this: no matter what an MSP brings to the boardroom regarding AI, the SMB will perceive them as being two or three steps ahead. Given the massive inefficiencies within SMBs in handling manual processes, data analysis, and customer interactions, MSPs are uniquely positioned to help them navigate these opportunities.
Beyond Growth: Net Profit, Compliance, and Enterprise Value
Chris brought up crucial points beyond just growth. He highlighted two main issues: net profit not being high enough and the immense opportunity in compliance (GRC). ScalePad’s GRC product is their fastest growing for a reason: industries are getting regulated, customers want to feel safe, and MSPs can leverage this to almost double their MRR by offering vCSO/compliance as a service. This is a boardroom-level conversation that elevates the MSP from a “plumber” to a strategic partner.
He also challenged the industry average of 15% year-over-year growth, noting that it’s often due to a failure in expansion. We haven’t fully leveraged advanced security stacks, AI services, or other offerings to grow existing accounts. It’s about “good old running a business” and focusing on financial metrics.
As I always emphasize, especially at Pax8 where we discuss digital labor and global talent access, enterprise value is what truly matters. It’s not about being the biggest revenue MSP, but the most profitable, the most strategically valuable. Building IP and focusing on EBITDA can lead to significant enterprise value.
Impact: The Growth Loop and the Next Step Altitude
Chris passionately articulated that the future of the industry hinges on customer success, something the traditional “VCIO” role has largely failed to deliver consistently. It’s about reliably getting in front of customers with the right cadence, message, and questions, making it part of the service, not just a “best effort.”
His one word to sum it all up is “impact.” Focus on making a measurable impact for a customer. If you’re successful, that creates a growth loop for you: make impact, build trust, get to make another impact. This “growth loop” is missing in our space and, while technology can help, it’s more about the “aha moment” of realizing this is a significant issue that needs solving. When SMBs grow, MSPs grow, and the entire industry flourishes.
So, if you’re an MSP listening, focus on VCIO, on thought leadership, on helping your customers identify dangers, opportunities, and strengths. Your success will be a byproduct of their success. As Chris powerfully articulated, don’t take the next step as a plumber. Go from ticket to trusted advisor, from break-fix to boardroom, and then, perhaps, to billionaire.
Connect with Chris & Build Your Future
Chris Day shares his insightful, often opinionated ideas weekly on LinkedIn. You can find him there and connect with him!
