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From Technical Founder To Business Leader

Many MSP businesses have a similar origin story. As the Founder, you are a technically skilled individual with entrepreneurial tendencies. The corporate IT route was never all-that appealing to you, as it lacks the creativity and ability to innovate that you crave. You may have or develop an interest in business, but financial success is rarely the motivating factor. Freedom is often the driving force, and you are willing to bear an incredible amount of pressure and pain to achieve it. I know this story all too well because I too have lived a similar tale (on multiple occasions). 

While this is undoubtedly a noble journey, it’s one that often comes with pitfalls. The same circumstances that led to your company’s creation can also be what undermines its success entirely. While cruel, this is just the nature of the business that we’re in. While these pitfalls look different for some, they ultimately come down to the same fateful decision to be made. That’s the decision to take off the technical hat that got you here and step back from the day-to-day to actually run the business. 

While these moments are never easy to navigate, the self-awareness to know that you are experiencing them can mean all the difference. To help kickstart this process of reflection, I called on MSP Strategic Coach and Former MSP Owner, Brian Hoppe, who has lived this very situation and now helps MSPs break through it themselves. 

When To Step Back From The Day-To-Day

Together, Brian and I brainstormed what these moments look like and when they might be a sign that you need to step back from the day-to-day: 

Your Business Growth Has Stalled 

Motivational speaker Tony Robbins often says “If you aren’t growing, you are dying.” While this may seem a bit dramatic (as gurus often do) it’s not without merit. While MSPs often tout high retention, involuntary churn can quietly eat away at revenue. The problem comes when you reach a tipping point. As Hoppe explains,”If you’re under $2 million, or even under $1 million, you’re probably used to growing just from referrals and your relational network. You don’t even have to try that hard to grow. But then at some point, it stops. Either A: that referral pipeline dries up, or B: it’s not going to allow you to grow fast enough to reach your goals in the timeframe you want.”

“At that point, as the owner, you have to step back and say, ‘Alright, my focus is now on building an engine for client acquisition,’ rather than just relying on word-of-mouth.” While this sounds great in theory, the execution is often difficult. Brian went on to suggest that “This is where a lot of MSP owners struggle. They’re used to just maintaining the business, but now they need to shift their focus to strategic growth—whether that’s marketing, outbound sales, partnerships, or something else.”

Your Clients Demand To Talk To You

In a service-based business, boundaries are difficult. This is because there is a trust and comfort that lies in humans (not brands) and this equity is often non-transferrable. This is especially true in the scenario of owner-led sales where the Founder is first to make contact with the customer and if a proper handoff is not made, can suddenly become the de facto point of contact. Brian Hoppe warns, “You train your clients by what you allow. If you give them your cell phone and take their calls directly, you’ve trained them to expect that. If you train them to call the help desk, submit a ticket, or use chat, they’ll do that instead.”

“I’ve seen MSP owners completely change their phone number—just shut it down and forward everything to the help desk. That’s how bad it can get if you don’t set boundaries from the start.” In fact, my MSP experienced this same problem and forwarding the phone number was the only way to stop it. The customers would of course ask to speak to the Founders as soon as they reached someone, but we were eventually able to prep them on what to say. We also made sure that our Technicians were jumping in to help them right away, retraining the customer to understand that our Help Desk can in fact solve their problems on their own. 

You’re Consumed By Low-Value Tasks

Being productive and being busy can often feel the same, but lead to very different outcomes. This is a pitfall that many Founders succumb to, as they get stuck in the quicksand of technical and administrative tasks. Hoppe offered some keen advice on how to manage these situations; “You’ve got to take the time to think through what is your highest and best use for the company. The trap is doing things you don’t like and aren’t good at because you feel like you ‘have to’ as the owner. But there are people out there who love doing the things you hate.”

“I usually suggest a time audit. Write down everything you do in 15-minute increments for a couple of weeks. Categorize it—things you love doing and are great at, things you’re okay at, things you hate doing. Then, work diligently to offload everything in the bottom categories. The goal is to eventually only be doing things that are in your ‘zone of genius’—the things that you’re uniquely good at and love doing. That’s when you truly step into your role as a business leader, not just an operator.” This concept of the ‘zone of genius,’ popularized by Gay Hendricks in his book The Big Leap, is the perfect mental model for how to manage these situations. 

You’re Too Busy For Strategic Planning

While I was studying for my Scrum certification, the instructor would often say that “The work expands to fit the time.” This quote has stuck with me to this day, as it always seems to prove true. As Founders, there is an endless amount of work to fill your day with, but that doesn’t mean that what you are doing is important or necessary. As Brian Hoppe puts it,”You have time for exactly what you prioritize. If you’re too busy for strategic planning, it’s because you haven’t made it a priority. No one else is going to do it for you.”

“A lot of MSP owners love the tech, so they find themselves taking on a server migration because ‘everyone is so busy.’ But if you’re stuck doing the work, you’re not running the business. That’s where owners get into trouble.” He went on to explain that there is a viable solution and framework to solve this problem. “A business operating system is a game changer. It forces you to step back and think. At a minimum, you should be revisiting your strategic plan once a year. Where do you want to be in three years? What’s your big, long-term target? Without that structure, you just get caught in the day-to-day firefighting.”

Your Business Can’t Run Without You 

The closer you are to the day-to-day, the harder it is for your business to run without you. If you are constantly the one turning the wheel, then you likely have no idea what will happen when you stop. Brian suggests that you do exactly that; “If you want to figure out what’s broken, go away for three weeks and see what happens. If you can’t step away and have everything run smoothly, then you don’t have a business—you have a glorified job.”

“As the owner, your goal should be to make yourself as irrelevant to the day-to-day operations as possible. The more irrelevant you are, the more valuable your business becomes.” He went on to reflect; “My goal as an owner was always to become irrelevant to the day-to-day. When you do that, not only does the business run better, but it also becomes more valuable if you ever want to exit. If you build a business that doesn’t rely on you, you get more time, your team is empowered, and the company is worth more. There’s literally no downside to making yourself unnecessary.”

Your Team Is More Capable Than You 

There are few ‘good problems to have’ on this list, but this is certainly one of them. The last thing you want as an MSP Founder is to hold onto the crown of the “Smartest Technician” at your company. While this may make you feel superior, suppressing talent is not a way to grow a resource-based business. Brian Hoppe explains, “A lot of MSP owners take pride in being the best tech in their company. But that shouldn’t be the goal. The goal should be to find people who are smarter than you—especially technically. Get them on your team and then get out of their way. That’s when you’re actually building a business.”

As he recalled from his own experience, “I got to a point where I literally couldn’t do the tech work anymore. I had lost the skills because I hadn’t been in it for so long. That happens, and it’s okay. When you accept that your team is better than you in their respective roles, that’s when you unlock real scalability. It’s not about you—it’s about building a team that can operate at a high level without your constant involvement.”

You Dread The Work You Used To Love 

It’s important to mention that sometimes the Founder’s job is simply to take the company from nothing to something. While many eventually transition to CEO as the company matures, it’s important to remember that it’s your company, you can do whatever the h*ll you want. That starts with recognizing what parts of the business give you energy, and what parts take it away. Brian offered this reminder as well; “If you get to the point where you don’t even enjoy running the business anymore, that doesn’t mean you have to leave entirely. There’s still something of value you can do for the company—you just have to figure out what that is.”

“A lot of MSP owners think, ‘Well, I’m the owner, so I have to be the CEO.’ But maybe not. There might come a time when you realize you’re not the best person for that job anymore. You might be a great CEO up to $3 million in revenue, but beyond that, you may need someone else to take it further. If you don’t want to grow in that way, go find the right person to do it.” He also expressed that; “At the end of the day, the business should be structured in a way that works for you. Whether that means stepping into a different role, bringing in leadership, or even just stepping back—it’s about designing a business that fits your life, not forcing yourself into a role you no longer enjoy.”

Conclusion

Being a Founder is one of the most difficult jobs to have. While having complete autonomy over your work offers unlimited growth potential, it also comes with unlimited ways to crash and burn in the process. Most Founders accept this fate early on and have agreed that the risk is well worth the reward. It’s important to remember that when your idea becomes a company, it’s no longer just you against the world. You have employees, your employees have families, careers and so on. Those people need a leader and in most cases, they expect that leader to be you. Will you answer the call? That is the MSP Founder’s dilemma.