In a post last month, I pointed out that some of the most popular Web 2.0 companies still haven’t figured out Customer Service 1.0.

Even though they’re related, customer service is one thing and your money is another.

Yesterday, ‘people-powered‘ search engine Mahalo announced that it was taking a new approach:Mahalo is giving users the ability to claim and build Mahalo pages in exchange for the right to earn 50% of the revenue those pages generate. Payment will be in the form of Mahalo Dollars, which pay out 75 cents on the American dollar.

Shortly after posting the news, TechCrunch published another post: something was seriously wrong with the Mahalo website. After signing up, TechCrunch’s Jason Kincaid noticed that the username he was apparently logged in under was constantly changing. In total, he reported that “Over the course of the next twenty minutes, I was logged in as at least 8 different users“. He could apparently post questions as these other users and worse, was able to view which pages they were currently managing.

Which begged the question: if he claimed a page, would it be added to his account or someone else’s? Needless to say, the launch of Mahalo’s new model looks to be a disaster because of this serious issue.

The incident made me ask myself a question: would I trust a ‘Web 2.0‘ company like Mahalo with my money? It’s an important question, especially as Web 2.0 companies ramp up how much of it they’re trying to make and the ways they’re trying to make it.

In the case of Mahalo, the company wants me to do its work for it in exchange for a split of revenue. Yet the nasty-looking bug which slipped through its QA process leaves a lot of doubt. Could I trust a company that let something like this happen to accurately administer a revenue sharing program? How do I know that Mahalo won’t fall victim to another bug that affects page revenue tracking or credits someone else’s account? By essentially taking its relationship with users to the level of affiliate revenue sharing, the standard Mahalo reasonably has to meet to win trust is much, much higher. After all, you wouldn’t sign up for an affiliate program if you didn’t think the operator was capable of tracking your earnings accurately, would you?

Mahalo isn’t alone in having to step up its game.

Let’s take Facebook, which is currently testing an internal payment platform of its own. An associate of mine has been trying for over a month to get a fake Facebook fan page for a high-profile client removed. And it was recently discovered that photos deleted from Facebook are still available after 30 days. What do these things have to do with Facebook’s payment platform? Well, would you trust your money with a company that doesn’t respond to a serious complaint from a high-profile figure? And would you feel comfortable handing your credit card number over to a company that apparently can’t ensure the removal of a photo when a user requests its deletion?

You could also look at Twitter, which has had its fair share of security problems, some that one would think could have been prevented quite easily with the escaping of user-provided data. With Twitter contemplating paid services at some point, such basic security issues are of concern for obvious reasons.

Personally, I think the issue lies with the ‘Web 2.0‘ philosophy. So many startups have become used to a ‘release early, release often‘ approach to software development that works fine when you’re dealing with a consumer-oriented, user-generated website but doesn’t work so well when you’re dealing with functionality that handles (other people’s) money. And most of these startups, by virtue of the fact that they attempt to offer their core services free, haven’t built up a culture of customer service. After all, they haven’t really had customers whose concerns they can take to heart; thus far it’s been ‘take it or leave it’. If one user is lost, 5 more come along.

These things just don’t cut it when it comes to money. While fits and starts are always expected, I suspect the issue of how capable Web 2.0 startups are when it comes to their friendships with your money is going to be a real problem as more of these companies try to befriend our wallets.

Photo credit: yomanimus via Flickr.