I love apps and services and websites that let something of the personality of the creators show through. I'm drawn to software vendors like Panic for instance, partly just because of the great name, and Bare Bones Software who's brilliant text editor "doesn't suck".
You see that in their marketing and know straight away you can work with these people, or their wares. Unless of course their personality doesn't happen to appeal. Maybe the strapline "It doesn't suck" could put off an extremely square sys-admin or two, but the attrition rate is probably pretty low, and the number of people who will warm to them precisely because of their personality is likely to be higher.
Personality is arguably even more important with a small company (like ours, for example). We've all seen those websites from sole-traders trying to make it sound like they're bloody Microsoft! "We at Edward Smith Web Corp pride ourself - oops, selves on our Commerce Grade hosting packages from just $299 per month..." Yeah, right.
Be honest! "Hi, I'm Eddy. I'm not big, but I am clever. Call me about your hosting and IT support, any time."
I try to make sure we let our own personality show through in our web services. For example, with Todobedobedo - our shared to-do lists application - we implore you to get your friends and colleagues to "share the misery" of that great pile of crap you have to wade through! It's not very blue chip, but in reality we're not aiming to get rolled into the next release of Lotus Notes.
404: personality not found
This strategy can be dangerous when your personality blows of course. I know Microsoft are easy to poke fun at... so let's do that right now! I challenge anyone - including Bill Gates - to suggest they'd rather have tea with Steve Balmer than Steve Jobs. When you have a company run by such a blustering, humourless, un-personable er, person then trying to make your consumers feel comfortable with you is always going to be a hard sell. Yet they insist on trying to make out that Windows 7 was 'invented' by some trendy young woman in a cab.
The thing that brought this subject to mind was Joe's idea for the 404: not found page on our new website. It's nicely functional (it includes a couple of useful links and a contact form) but it's also honest about the situation. Someone screwed up, probably us. Where's the goddam page?! So it shows the company boss (that would be me) looking confused and apologetic, and rightly so!
Another example of personality I really like is that of my friend Jeremy Keith who, when asked his name on his company website replies "Inigo Montoya. You killed my father. Prepare to die." It tells you a lot more about the man than any straightforward answer ever could.
Don't be afraid. The Internet's a big place, so let your personality - and your honesty - shine. There are plenty of people out there who will love you for it.