Lately, I’ve been thinking a lot about the problems that are attempting to be solved online right now. This is Web 2.0 and there’s a newfound enthusiasm for sites providing services which means that everyone is trying to provide a service online. The problems facing Web 2.0 entrepreneurs are different from those facing Web 1.0 entrepreneurs, when everything was new and people “surfed” the Web. I’ve been collecting these thoughts in my head and sharing them with people over lunch, dinner, and instant messaging for a while, so I figured I’d go ahead and share with the rest of the world as well. These posts will be prefixed with “Internet Problem” for easy reference.

I was talking today with Dan Gill, one of the founders of Huddler, about one of the biggest problems I see for Web 2.0 businesses: getting users. I call this the dating site dilemma because the problem can be summed up in the following scenario.

Suppose you want to create a new dating site. The main draw to any dating site is, logically, people to date. I will join a dating site because I want to date someone and you are providing that pool of potential dates. But how do you get the first person to join?

The problem of getting users is more complicated now than before. People have routines; those routines now include Internet usage. Each person spends a certain amount of time online and that time is divided into a certain set of activities. Some of that time is surely used checking and responding to email, then maybe some social networking followed by visiting various news sites and blogs. As a new site, your problem is getting a piece of that pie. It’s unlikely that the person will create more Internet time simply to fit your site into his or her habits. You actually need to take time away from one or more of the user’s Internet haunts.

I hear a lot of people say things like, “it’s like MySpace but better because it has x, y, and z.” Well that’s great, but how are you going to convince MySpace users to jump to your product? All of that person’s contacts are on MySpace and your x, y, and z features don’t make up for that. What is the value proposition that gets those users, the ones you’re clearly targeting, to jump onto your site?

I don’t have the solution to this problem, I just know that the problem exists. Everyone wants a slice of the Internet pie, but it is a finite resource. In the world of Web 1.0, no one had Internet habits so the fight was to become one. In Web 2.0, the fight is to alter habits, which I believe is a more difficult task. It was easy to set my mom up with an AOL e-mail account so she could keep in touch with friends; it was very difficult to get her to drop AOL for a more personal email address even though it would be easier for her, and everyone else, to remember. How can I find a date on your site if I’m the first one? That’s the dating site dilemma.