As you can read here, I have been trying many different businesses. Did I like them all? No, not really. So how can you pick a business you are going to like without trying that all like I did. I’ll try to sketch my experiences, so maybe you can decide faster and more accurate on what you are going to like.

My companies can be seperated into the following ‘categories’:

• small services
• big services
• small product
• big product
• small online ‘product-services’

That is quite obvious, but I would like to actually make another division here, as I experienced that they make a large difference:

• small software services; programming for money on small projects (< $50.000)
• big software services; programming for money on big projects (> $50.000)
• small hosting services; running a small hosting company with < 1000 small clients
• big hosting services; running a large hosting company with > 100.000 small clients
• small product; selling a ‘cheap’ software product (license < $150 per server)
• big product; selling an expensive software product (license > $50.000 per server)
• small online product-services; selling online software for a monthly fee or living off monthly ad-income (< $5000 per month)

Ofcourse, there are many more nuances to make, but this is already quite enough to pick what you like. Because all companies I was in were started from the scratch, I had a lot of different positions in those companies at different times:

• programmer
• administrator
• project manager
• consultant
• ceo
• cto

The companies and included positions are very different from each other. I will try to explain this using the following factors:

• clients
• colleagues
• company focus
• growth potential
• my take on it

Small software services

You’ll be selling small to medium sized, custom programmed or customized software to your clients. Projecs will be things like building a website with hotel-reservation service and payment back-end for a 3 hotel-in-the-city company.

Clients are small to mid level companies; these clients like very close contact, are often informal and want to know how every $0.1 of their project was spent. If they are happy they will never leave you, but they get upset (very) really fast on a personal level if they feel your service is off. Your cliens need face to face contact and if that is not possible at all (like, you are in the hospital), they want telephone. They don’t want that newish stuff like e-mail, IM, project management systems online or video conferencing.

You are looking at people that have shorter attention span, probably like job-hopping. Basically the more risk-taking individuals. This is simple to explain: when you grow and get bigger clients, the projects will get (much) larger, but you don’t want that, as you started this company to maintain a lower profile than the behemoth software integrators of this world (see the next company type). So you cannot take that kind of assignment, making your company in a continued state of start-up feel, as real big clients won’t pick you or stay with you as they like you and want to spend their very big software projects also. The biggest mistake you can make here (and we did ofcourse…) is to take that big project anyway, blowing up your current strategy, starving your smaller project client base and killing your employees/colleagues. Watch for this sign in your company: if not perfectly executed, the company might die from this if management is not strong enough.

This kind of company can grow huge, but as said before, it almost never does as you should consistently not take those biggies or decide to have a management growth path to become a large software vendor.

I like this kind of company if they are able to keep it up. As a programmer you get to do many very different assignments; you learn a lot and get to meet many different people. Being a CTO in such a company is very stimulating at first, but might get to be a bit boring after some years, as you are rolling out yet another Ruby-on-rails/php/java/whatever e-commerce site. Project management in this kind of company I found difficult, but I am not a project manager I found out. The contact with the clients this kind of company gets is tiring if you don’t give them more than they paid for. They will keep pushing for the max return on their investment (every one does, but the smaller clients make it very personal, very quickly).

If you like small, informal, many, many different projects through-out a year, you’ll like this kind of thing. Does not really matter in which role. One of the great things about this kind of company I really like is the fact that the software usually actually is being used by the client after it is done. This is unlike some other companies. Read on.

Read Part II