Another story of someone who became free from 9 to 5…

Bonnie’s Bookstore is in the “casual game” genre, a genre that is receiving a lot of attention these days due to the successes of games like Bejeweled and Snood. In Bonnie’s Bookstore, you are presented with tiles of letters and you eliminate tiles by spelling words with them. It offers a quick break and can be quite addicting. I introduced the game to my wife just 45 minutes ago, and she’s still at it.

There’s also some sort of storyline to the game, but to be honest, I don’t know what it is because I skipped all that and went straight to the action. And sometimes, it accepts words I don’t think are words, like “NAE”, and other times, it doesn’t accept words I think it should, like “YOYO”. I guess it just depends on the dictionary the game uses. Nonetheless, I find the actual gameplay to be fun, entertaining and a good alternative to Minesweeper when you want a different sort of diversion.

Ian, please give us a little background on your business.

UserScape builds help desk software for small to medium size businesses and business divisions. The average customer so far tends to be a business with 1 to 5000 employees.

We were formally incorporated in March 2005, though in practice we started developing HelpSpot about a year ago now.

UserScape is located in the beautiful Hudson Valley, about 2 hours north of New York City.

Do you work from home?

Yes, I’ve set up dedicated office space in the house. I’m currently looking into office space, however, that will probably wait until the spring.

What kind of traditional 9 to 5 job(s) have you had in the past, if any?

I’ve had a bit of a wandering career. I started out as an accounting major. After school I went to work for Office Depot, where I was an assistant store manager. The money was good, but overall, the job was less than rewarding, so a few years in, I decided it was time for a change.

I left Office Depot and went to work for a startup in the educational technology field. There, I learned how to formally program, though I was always a bit of a computer geek. As a product manager, I was responsible for all customer support. This is really where the idea of HelpSpot started and many of the features I wish I had in my tools back then are the core of HelpSpot today. During this time, I also began consulting on the side, developing websites as well as several corporate intranets.

My last 9 to 5 was working for Marist College running the eLearning technology and programs. Among my responsibilities was the management of the support system for over 5000 people who used the eLearning system daily.

What led you to start your own business?

I’ve always been interested in starting my own business. I considered the possibility of starting a consulting oriented business many times, but I never really liked the economics there. Then, about 2 years ago, I started to focus on software. The economics make a lot more sense in software and so I started researching everything about starting a software company and the more I learned, the more I loved the idea of it.

How hard/easy was the transition from a 9 to 5 job to running your own business? Did you have other means of support while you were getting your business off the ground (part-time job, spouse, etc.)?

The transition wasn’t too bad from a financial perspective. I had a good job and my wife has an even better one so we were able to save up enough money to start the business, as well as have funds for over a year after the product launched. I consider this last part to be essential in starting a software business, because you really need to be able to give the business time to grow.

My wife is also a major part of the business, doing most of the writing for the website, emails, testing and development. I’m blessed with a semi-geeky wife which is a huge help!

Are there things you miss about a 9 to 5 job?

Not really. I do miss some of the people but that’s about it.

What are the hardest things about making your own living? What are the best things? Which do you prefer now?

I truly believe that a big part of your success is determined before you ever really start. To me, the 2 biggest things are choosing the right product/market and being financially prepared to see the product through. If you don’t do those 2 things right then you’re probably doomed before you even start.

The best thing is certainly the ability to set your own course. There’s a great degree of freedom that you feel, though it does take some getting used to since most of us are programmed to follow someone else’s orders when it comes to our jobs.

I definitely love owning my own business and don’t see myself returning to being an employee anytime soon.

Do you have any advice for someone who is trying make their own living and get away from a traditional 9 to 5 job?

Make sure you’re financially prepared. Be sure to pick a market you have some domain knowledge in and, even more important, you need to do your research. Here are a few tips that have served me well so far:

1. Pick a fragmented market. No dominant player and many small players. This proves a few things. First, that there are companies out there willing to pay for this type of software. Second, that there’s room for another player.
2. Don’t invent something “new”. New types of products require a lot of marketing because nobody out there is looking for your type of product. You’ll need to do a lot of explanation, etc. This is too much risk for a small company. You need to be in a market where you know people are looking for a solution and are willing to pay.
3. Design!! Pay somebody to do your design. Almost half the customers I’ve spoken with who have purchased HelpSpot have listed its design as an important factor in their decision to purchase. It doesn’t have to be perfect, but it needs to be professional. Most geeks (myself included) are limited to colored boxes. Don’t be cheap!

Thanks, Ian, for your time and best of luck to you and UserScape!

One of the things he wants to do is help others do what he did. That is, start a successful company. Paul is part of a group that is running a Summer Founders Program. If you’re accepted, you get to move to Cambridge for the summer and get a stipend for starting and running your own company. It beats the heck out of summer job. I wish there was something like this when I was a student!

Along the same vein, Steve Pavlina’s weblog contains a wealth of articles on finding your passion, your goals and your purpose in life. His weblog is about personal growth in general, but a subset of his articles focuses on finding out what you really want out of life, something that most traditional 9 to 5 jobs are at odds with. Steve completed a bachelor’s degree in something like 18 months, decided a 9 to 5 wasn’t for him, so he founded a successful PC game development company (Dexterity Software) and is now embarking on a new career in public speaking. Steve also has a bunch of great articles on his Dexterity website intended for independent game developers, but anyone looking to shed a 9 to 5 job would benefit from them.

“If it’s a slow afternoon and you want to lounge around outside the hub drinking coffee or even beer, no one will ever come over and ask you if that is an appropriate way to spend company time. Ever.”

“I often describe myself as a chronically lazy person, but to be honest, I don’t mind working. I simply hate working under an oppressive structure. As a coder, I would find myself slacking off just because the environment gave me no motivation to work hard. And at the same time, I hated the obligation to look busy from nine to five, regardless of how much actual work [there] was to do. And I hated working in a cubicle ten meters from my supervisor’s office.”

“Issues of pay aside, I can easily say that couriering is the best job i have ever had (and I have more than a few eclectic jobs on my resume). … And, even considering the fact that my pay as a courier is between half and two thirds what it was as a coder, it is a rare day that I seriously consider going back.”

Update: Upon further research, starting from his kuro5hin profile, it seems this coder turned courier has self-published a novel and wrote a guide to looking busy at work, sure signs of someone looking for alternatives to a 9 to 5.