I met Ian Landsman through our blogs at the beginning of the year. We were both embarking on the microISV ownership path. He and his company, UserScape, have been far more successful than me. Here’s his story…

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!