WordPress supportAuthor note: I just got an alert on my calendar that tomorrow is Halloween, so it’ll be Halloween when this is published. Happy Halloween.

Author note #2: Part of this is a rant.

For those of you who don’t know, I started WP Site Care a few years ago. It’s become a great business for my family and our employees, but it’s been anything but rainbows and butterflies.


Nearly every single day I see a new WordPress support and maintenance company come out of nowhere, ready to take on clients and make a place for themselves on the web.

I applaud that.

I wouldn’t be here if I hadn’t started doing the same thing as a freelancer five years ago. Not to say that I’ve made it,” or that I even consider myself a success, but as far as companies in this space are concerned, I can probably say that ours is as established and well-known as any of the others.

Now it’s time for some real talk.

I’ve seen articles showing up talking about Starting a WordPress Management Business in a Day, or Great WordPress Businesses for Building a Predictable Income, and either the author’s are just incredibly naive, or downright ignorant. Or maybe they’re just a gun for hire that needed to meet the weekly article quota and ended up spitting out nonsense.

They paint a picture of a low overhead, easy to start business for any Solorpreneur,” and that’s simply not the case.

WordPress Support and Maintenance Isn’t a Kid’s Game


I’m sure that anyone who has worked with companies like Maintainn, WP Valet, WP Curve, or WP Maintainer can attest to the hustle required to run this type of business (I know there are a slew of other companies that I haven’t listed here, but I want to save your wrists from excessive scrolling).

You don’t just wake up one morning, claim a free account from ManageWP and start taking on clients. I’m convinced that living this grind day in and day out is something that only truly sick individuals can embrace. You have to have a special place in your heart for solving the most complex issues, and an addictive personality that won’t let you quit until that last ticket’s closed. You’d also better love helping people, because people need help. And I assure you, that once you say you’re ready to help, people won’t stop asking until they’re satisfied with the solution.

If that’s not enough, you’d better have some thick skin. Even if all of your customers are happy, which is the equivalent of discovering the holy grail, you’re still going to have some dweeb on the internet talking about you in a derogatory way because they just do support over there.”Sidenote: The ego trips on the internet are prevalent but shouldn’t be acknowledged. Haters gonna hate and all that.

You will have your integrity questioned for no reason at all. People will issue chargebacks against payments because they think they deserve a free trial, even though you spent six hours fixing their site. You’re probably going to be in your office before your kids wake up, and crawling back into bad long after they’ve gone to sleep. You’ll have clients who believe they’re smarter than you, and in some cases they might be. If you’re quick to anger in your personal dealings now, don’t even think about dipping your toes into the waters of WordPress support. You’re going to be miserable.

Bottom line: This line of work isn’t for the faint of heart. Proceed with caution and know that 16 hour days are going to become the norm for a while, and your inbox will never be the same. This isn’t a fucking autopilot lifestyle business. It becomes your life.

What You Really Need to Run a Site Management Company


If you were able to stomach the test above, and you’re still reading this and thinking that site management is something you’d like to do, then 1) we should probably be best friends, and 2) here are some items that are going to be must haves if you want this type of business to work.

  1. Become the best communicator on planet earth - I struggled with this for the longest time. I’d avoid awkward or uncomfortable conversations because I was afraid that people would be angry with me. Give people more credit than I did and be honest with them. If you make a mistake or screw something up, own it and be an adult. If you’re going to miss a deadline, let your customer know a day or two beforehand so they can start working on plan B. The worst thing you can possibly do is try and hide. You’ll feel guilty and the work still doesn’t get done. Always err on the side of too much communication.
  2. Organize your conversations - One of the best ways to become a great communicator is to be able to keep tabs on the hundreds of virtual conversations that can be going on at any given time. We use Help Scout and it’s been a life saver. With as many tools as there are out there, there’s no reason to have sloppy or unkempt communication. At any given moment you should be able to find the status of any customer request or project.
  3. Commit long term - In any type of business where you’re billing customers every month, it’s essential that you build enough trust with your initial and potential customers to let them know you’re in it for the long haul. We’ve self-funded everything at WP Site Care because the last thing we’re looking for is an exit strategy. Bootstrapping is our way of showing our customers that we’re in this to serve them for years and years.
  4. The customer is always right, until it hurts chemistry - Staying humble is crucial in a support role. Out of control tempers rarely solve anything, but laying down isn’t always the right answer either. Nothing is more important for the chemistry of my team than them knowing I have their back 100%. We’ve had experiences in the past where customers have gotten out of hand and resorted to name-calling or making threats. In times like those, be prepared to end your relationship with your customer immediately. Never let anything jeopardize your team chemistry, including a bully customer.
  5. The little things matter - When you’re first starting out, attention to detail like small client gifts, or answering that late night email will make all the difference. Give your original clients no choice but to become raging fans. If you’re smart, and I know you are, try and build trust within a community. When I started Revive My Blog, which was essentially a service where I dug into existing websites and overhauled them completely for $250 or $300 (yes, you read that right), I found a big group of customers and friends in an online fitness community. Then when the question of who should I have fix my blog” came up, the answer was always a resounding use Ryan!” I’m still very fortunate to have some of those same clients 4 years later.
  6. Learn by doing - Education is vitally important, and people should learn as much as they can as often as they can. There’s no substitution for going through a painful learning process on your own. In the early days I didn’t have any other developers to reach out to, and it was deliver or die, so I was constantly up against it. And you know what? I didn’t die. There are still instances that come up nearly every day where I’m able to use random bits of knowledge that I learned years ago by working through the problem on my own. For a lot of the issues there’s still no support documentation. You either know it because you’ve dealt with it before, or you don’t know it at all.
  7. Move fast and forgive quickly - You aren’t going to have time to worry about the he said she said” that’s going on around you. I learned early on from a good friend of mine that cutthroat competition just isn’t worth it, and he was right. I made a really stupid mistake early on with WP Site Care that made me look foolish. I easily could have been called out for it but I wasn’t. I’ve made many more mistakes since, but I’ll never forget how quickly I was forgiven on that occasion, and my mistake was forgotten.
  8. Be an advocate for your customers - There are going to be many occasions where you become the point of contact for all things WordPress. If your client is getting the run around from a hosting company, don’t be ok with the status quo. Go to bat for them and show your clients that you want what’s best for them. That’ll go a long way toward building trust, and in a business where you become your client’s first point of contact for pretty much every technical item they encounter, trust is everything.
  9. Be yourself. You have a lot to offer - Our site design and copy are constantly ripped off. We’ve invested a lot of time and money into making it right, so I understand why. I mean, it’s really awesome, but at the same time I think the biters are selling themselves short. A more simple design with more copy about themselves as individuals, and what they specifically can bring to the table would be a lot more effective than a Site Care knockoff. There are likely things you can do that set you completely apart from the competition. Find those things and be confident in them. There’s no reason to sell yourself as something you’re not. Be Rolex, not Bolex.

Now You’re Ready

Did you notice how I didn’t mention anything about the inner workings of my business? I didn’t talk about anything technical, or legal, financial, or logistical. I may write about more of that later, but for the most part you can figure that stuff out. The stuff I wrote about here, most people are going to shy away from because it isn’t fun to hear. But the fact remains, if this is something you’re seriously considering as a business, you should know what to expect from the beginning.

The good news is, there is so much good that will come from this type of business. You’ll make life long friends, learn skills you never could have anywhere else, create partnerships with other awesome companies, probably get to travel a bit, and assuming you keep grinding and remember these essentials, you’ll create a more comfortable life for you, your employees, and your family.

The reality is that as challenging as all of this is, there’s nothing I’d rather be doing right now. I love the work I get to do every day for WP Site Care, and that’s probably why I can stomach most of these challenges. There are days where it isn’t easy at all, but it’s incredibly rewarding to take a deep breath every once in a while and realize that you’ve been something solid that’s helping people every day.

Now you’re ready to conquer the world. Go forth and create the best competitor WP Site Care has ever seen. You’ll be happy that you did.

Have you ever thought of support & maintenance as an easy business to run or get started? If so, what gave that impression? Is it part of your business? I love real conversations, so please don’t hesitate to share all your thoughts and musings in the comments below.

October 31, 2014