When you are a professional politician, sometimes being TOO careful can hurt you.
Barack Obama and Hillary Clinton both created websites, but only one of them established themselves in cyberspace as a real player. One of them saw the Internet as a fund raiser and a campaign statement source, the other saw it as a tool. One had vision. The other was afraid of its vast power, and wanted some amount of control. Unfortunately, people know censorship and paranoia on the web when they see it, and they often react negatively.
I signed up for both sites at the time when Obama first established his own site. Over at the Hillary site, they recruited bloggers to 'submit comments' for the chance to be posted up 'first'. Meanwhile, Obama tossed the keys to the servers to the public and let them establish individual blogs, free linking to other users, set up their own groups, and basically implemented the entire gamut of tools available to a normal site. He went into the game unafraid and did not restrict content, or screen postings.
This was a brilliant move on Obama's part. He took a chance, and it worked. This is partly the reason he was able to raise so much money for his campaign in such a short time.
By doing this, Barack Obama became the first Presidential candidate in history to utilize the full potential of the Internet. Within days, hundreds of thousands of people set up blogs on his site, exchanging views, opinions, concerns, and linking to each other locally. It is now a juggernaut of major proportions, bringing people together in virtually every community in America, both in cyberspace and in reality.
Meanwhile, you have Hillary Clinton. She learned a hard lesson, and became so five minutes ago - at least in cyberspace.
(EDIT: June 14, 2016. Hillary Clinton has taken the lesson she learned in 2007 to heart. Her website is a lot better this time around.)