Web Development Business

Starting your own web development business

Matt McCandless Consulting, Opinion, Programming, Technology Snapshot 2 Comments

So you think you have finally arrived! You have “mastered” a handful of technologies that allow you to create a website solution from a full stack standpoint. You have experience setting up a database, experience in some language or a couple options, and you know your way around CSS well enough to make a shiny looking product.

So then the thought occurs to you, “I’ll open up my own business….I can make websites for companies who need some sort of solution for their business, church or organization!”

Whoa!!! Slow down partner! There are many different ways that you can approach a web development career focus.

In this article we will discuss going at it from a self-employed 1099 perspective. We’ll aim to look at some of the gotchas and pitfalls of being a professional web developer while being self-employed. There are often things that people forget about when getting started their own business. This will hopefully remind folks of things that must be considered when starting a business.

Author’s Note: this blog post is not an explanation of my experience working at Keyhole Software (of which I am an employee), but of previous/separate experience in IT.
Editor’s Note: At Keyhole, you get the variety of consulting and working on different project types, but none of the negatives of working solo listed below (as you’re surrounded by a strong team with defined projects based upon your interests). Check out our culture to see if it’s a fit.

You don’t know it all

This one may be the most obvious drawback to independent consulting. Once you begin working on a solution, it’s likely that someone will ask you to do something that you have no-to-very-little experience in. You may be a Java developer, but your client has something that exists in Perl or .Net. Be ready for curve balls that come your way.

Have a time limit you are willing to expend on learning new things before telling the customer that you cannot do what they are asking. Have an alternative if possible.

Server administration

Word to the wise here! You better have the know-how to handle server administration or get a quality server provider who can handle most of the setup for you. You will have things like SSL certificates, database installs, application server installs, email setup, domain setup, etc. This list can go on for days.

Be mindful that there are many, many options in the world web hosting. The cloud has many different flavors and plans out there. Know what your need is or the best guess of what it will be. Plan accordingly!

The Cloud isn’t always dreamy

Real world scenario: I asked the server administration of the host I am using to setup a particular function that I could not get the available script to run properly on. I was given a “thumbs up,” we’ll get it running for you. About two hours go by and I receive a call from the customer. We can’t log in, is the server down? What is going on?

Luckily, the application has about a four user user-base and they had a manual way to continue work without it. After logging into the server I found in the bash history, “yum remove mysqldb”.

For all those that understand what just happened, I was absolutely floored! What idiot would do that? Luckily it was backed up and they re-installed MySQL DB and restored everything. Don’t expect the server admin on the other end to “get the big picture.” Be ready for things to go wrong and to not know why.

Don’t quit your day job

Seriously, though, don’t do it. If you want to start out on your own, get a portfolio together and get enough work going to a place where you’re comfortable to call it quits on your day job. Be sure you are able to drum up enough work to pay the bills and live off of.

One month of good income isn’t enough to base this off of. A yearlong worth of results is the best measure of how you are doing. If your goal is to simply supplement, then you are a little less serious here, but it still matters. Be sure to keep your day job. This means, know where the majority of your effort needs to go. Take the most care to keep the job that keeps food on your table.

There are different ways to drum up business. There are websites setup like Freelancer.com, that will give you a platform for finding work. You can take to the social media world using Facebook, Twitter, etc. You can even go old fashioned by printing business cards and flyers and post them around places where you think your skillset will be sought.


This is a huge item to take into consideration. Be ready to spend some money, but do not take out a loan. If you do, you have just changed your boss to the bank instead of the customer. You no longer have the ability to be flexible with your timeframe because you now owe the bank.

Have a budget prepared in advance and be willing to lose it all. If you lose it all, be willing to shut it down. Obviously you did something wrong and need to rethink what you are doing. Avoid debt when starting a business. Make the customer your boss and sole focus.

Personal Cost

This is one of the biggest problems. Believe me! There will be many late nights and weekends spent in front of the computer. You will get called, texts, and emails all the time about all different kinds of things. You may miss sporting events, concerts, and the like. The kids will ask, “when can daddy play” or comment “daddy is always working.” Ouch, these can hurt.

Be sure to balance your time as well as you can. Set limits up of when to say enough for today and spend time with the family or friends.


There are many different ways you can approach web development: Self-employed as a consultant as we’ve talked about, or even an employee of a consulting company like Keyhole (where you get to focus on the development and miss out on some of the negatives described above). Or you could even just be a full-time employee of an enterprise organization.

All in all, there are many different things that can grab you by the ankles and keep you from reaching the peak of starting your own successful business. Be ready for them and don’t let them get you down.

If you really want to start your own business, by all means try it. I am not discouraging anyone from doing so, but be ready for failure and/or mediocrity. Sometimes things will work out well for you and your company will explode with opportunities. That is for another time and another blog, maybe?

— Matt McCandless, asktheteam@keyholesoftware.com

About the Author
Matt McCandless

Matt McCandless

Matt McCandless is a developer based in Wichita, KS. He is married to his wife Melissa of 15 years and has 4 kids. Currently developing in BackboneJS, Matt has experience in Java, JavaScript, PL/SQL, Perl and other various languages. He spends a lot of his spare time with the kids and spending time outside, occasionally running a 5k here and there to keep himself in shape.

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Comments 2

  1. Ryan LaRue

    Hey Matt, I enjoyed this post! I will second the bit about server admin. I underestimated the time, effort and cost in that area! This is especially true when dealing with software that handles any kind of larger files (images and videos, for example).

    Another bit that was a new experience for me (and involved a learning curve) was just the aspect of starting a new business. For someone that has never done it, it’s a bit of a black box… where does one even start, what kind of business do I need, what state should I create my business in, how much will it cost me, and on and on. Eventually, you find your way through the darkness, but help in this area is harder to come by than one might think (or maybe that was just me…).

    Lastly, I whole-heartedly agree with the ‘keep your dayjob’ idea – it’s the path I took, as well. On the other hand, I also have a great admiration for people that have the guts to go full bore and focus all their time and effort on their dream. If someone has some reserve money to tide him/her (and the family) over for a while, maybe that’s the way to go. Not for me…. I would never, but for someone else, absolutely. 🙂 Thanks!

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