TLDR Preview: Most MSP owners start off wearing many hats in their business when it’s starting up. Many do not have a plan for how their role will change as the business grows. They are buried in day-to-day tasks, and eventually they burn out and/or the business stalls. The first step to avoiding (or escaping) this trap is some honest self-reflection.

In a previous blog (The Road Less Traveled ), we asked a pointed question: Are you building a business or are you the business? If many MSP owners were to answer that question honestly, they would have to admit that they are the business. If they were to get hit by the proverbial bus tomorrow, their business would either immediately cease operations or be sold off in a fire sale to someone who would try to salvage the clients and perhaps a technician or two.

When a bootstrapped business starts up, it’s the most natural thing in the world for the owner to take on many roles. The young person starting a landscaping business not only finds accounts and sends invoices, they also cut the grass. With MSPs, this dynamic usually takes place without the founder even giving it a second thought. The owner is usually the salesperson, the engineer, the finance person, the project manager, the procurement person, the account manager, the dispatcher, the one who determines the technology stack, and the list truly goes on and on. 

There’s nothing wrong with a business starting this way.

The problem comes when no thought is given to how the company, and specifically the owner’s role, should change as the business matures. In order to really succeed, business strategy needs to be introduced, and that rarely happens when the owner is so consumed by the day-to-day tasks of operating the business that they have no time or mental energy to work on decreasing the business’ dependence on them. This can lead to what we call the hamster wheel: the owner pushing ever harder to get ahead, but experiencing frustration because pushing the business equates to pushing themselves until the business has essentially taken over their lives. They are completely maxed out in terms of time, stress, and health. So the business stalls, and it does so in a place where the owner is a prime candidate for burnout.

Shawn Recalls The Hat Man

A while back, a local plumbing company did a TV commercial campaign called “Bill’s Hats.” The business was named after Bill, and the concept was that he wore many hats, each representing a service that he could provide.

The character on TV had a tall stack of hats on his head, each with the service it represented emblazoned on the front. It was memorable, but I thought, What happens when Bill goes on vacation? I chuckled, thinking, Bill shouldn’t be wearing the hats—he should be showing off his team wearing all those hats!

The unfortunate reality is that the ad agency probably got it right. Too many business owners see that “crown of many hats” as a badge of honor, instead of what it really is: an albatross around their neck. An anchor keeping them from growing a self-sufficient business.

They hesitate to pass those hats on to others who can do the work. This keeps them working IN the business instead of working ON the business. And it keeps them on the phone all day at Disney World like I once was, repeatedly holding up a finger to indicate to my family that they’d have my attention shortly. Many MSP owners can relate. Bit by bit, the truly important things in life are passing them by.

The Book Review Guy

“Whether you think you can, or you think you can’t—you’re right!” 

— Henry Ford

Now, we’re sure after talk of a wasted vacation, you are thinking, I’m won’t let that happen to me! But we see it happen repeatedly. So why do so many entrepreneurs fall into the trap of trying to wear all these hats? The most basic reason is that deep down inside, they worry that no one else can do the job as well as they can. That putting too much trust in others might lead to failure.

As we contemplated writing The Pumpkin Plan for MSPs, we decided to look over some of the feedback on the original Mike Michalowicz book The Pumpkin Plan. We thought it would be a good idea to see what people liked and what they didn’t. We perused the Amazon reviews. We don’t know about you, but when we check reviews, we always start with the bad ones first—they’re more fun!

There were the usual negative reviews that lacked imagination.

“I don’t like Mike’s writing style.”

“He swears too much.”

“The information is too basic.”

Hey, we get it. You can’t please all the people all the time. But one review in particular stood out.

This reviewer wrote that the information provided was of no use, because like with so many other business books, the writer had no real-world experience running a business, that he was just another consultant trying to sell books. We wondered whether this reviewer had even read the book. Mike is a serial entrepreneur whose first business was a proto-MSP. 

Book Review Guy wrote: “Nobody can run my business like I can.” He claimed that it was not a transferable skill, and the only way to make money was to work harder and put in more hours.

“Giving up your family life and your friends and being a workaholic is the cost of being in business,” because employees just don’t care like he does.

Wow! This one left us shaking our heads. We wish we could have responded to his review or been able to reach out to him. We can assure you, this poor guy has no quality of life. Chances are his family feels like they are less important than his work. He will most likely drop dead at his desk…or in a server room, where at least the body will stay cold.

It doesn’t have to be that way.

Sorry, Book Review Guy. We beg to differ. And your beliefs are not going to make your business better; they are only going to make you and the people around you stressed out and unhappy. Without a significant paradigm shift, Book Review Guy will never build a business. He will remain self-employed the rest of his life, and not in a good way. The way he views his business will prevent it from ever scaling. It will have little value to anyone besides him, since he is resolved that the business will always revolve around him.

If the owner is the only one who can ever run the business, why would anyone else ever purchase that business?

But we’ve all had thoughts similar to that Amazon armchair quarterback. If his sentiments were unique, we wouldn’t be talking about them. He felt trapped, but he wasn’t looking for a way out. Instead, he pounded his chest and proclaimed how tough he was since he was able to live life running around with a bear trap on his leg. That might make someone tough, but it doesn’t make them wise.

Defining A “Real Entrepreneur”

“Entrepreneurs don’t do most of the work. Entrepreneurs identify the problems, discover the opportunities, and then build processes to allow other people and other things to do the work.”

— Mike Michalowicz in The Pumpkin Plan

When our MSPs were in their early stages, we weren’t real entrepreneurs. At least by Mike’s astute definition. We were Book Review Guy, minus the attitude. The Hat Man minus a few of the hats. For a long time, we didn’t build processes, and we didn’t allow other people and other things to do the work. We ran on that hamster wheel until it started smoking and eventually burst into flames.

Well, we’ve got great news. We found our way off the hamster wheel…and you can too.

The First Step: An Honest Look In The Mirror

We’ll detail everything that goes into getting off the hamster wheel in future blogs. But in order for any of it to matter, you need to assess honestly if you are content with your business and your role in it. No one changes unless they recognize the need for it. How do you know if change needs to happen? There is something about your business that is hampering your life. You can’t “turn off” at night. You’re not making enough money to live the life you want. Your spouse needs to work when they’d rather be home with the kids. Your relationships are suffering. Vacation planning is stressful instead of fun. 

You need to recognize that the pain of not changing will be greater than the pain of changing. Many owners never pursue another way, because they’ve never stood still long enough to recognize the toll the business is taking on them (and on those they care about). Then there’s the ones who do realize it and take the Book Review Guy approach, throwing up their hands and saying “It is what it is. I’ll always be a slave to the grind.”

In a future blog, we’ll discuss taking a ruthless inventory of your customer base. But the first ruthless inventory you must take is of yourself and your role in the business.

The path to becoming a “real entrepreneur” is not easy, nor is it without its challenges. It requires a fundamental shift in mindset and a willingness to let go of the control that many MSP owners have grown accustomed to. But the rewards – both personal and professional – are immeasurable. By embracing strategic planning, delegation, and process development, MSP owners can create businesses that not only survive without them tomorrow but also provide the freedom and quality of life they originally sought as entrepreneurs today.

Adapted from Chapter 2 of The Pumpkin Plan for Managed Service Providers by Dave Cava and Shawn P. Walsh. Read a chapter for free here: