I just attended my first Unstick.me Live put on by Alex Hillman. Basically Alex webcasts himself while a bunch of people watch, ask questions and help answer others' questions. I thought it was really cool, really helpful and a great way to get to know others. But why am I bringing this up?
Well, right near the end of the session Alex was asking Allan Branch a few questions about Allan's business, when it came up that Allan answers all support emails for their (LessEverything's apps). He made the very good point that being involved in support keeps him close to what his user's are experiencing. Alex then mentioned that he thought it was cool that when he emailed 37signals about one of their apps he actually received a reply from DHH. Allan mentioned that that was another reason he kept up on support, to build brand.
Now, I agree that it would be really cool, from my perspective, if I received an email from either DHH or Allan in response to a support request for either of their apps. And to some degree it would build their brand in my mind, but, and I raised this in the session, it's only effective because I know who DHH and Allan are.
The company I work for just started using Basecamp for project management. My colleagues are not technical users in any respect. They're going to be using it because they find it useful and that's it. If anyone at work (besides me) sent an email and received a reply from David or Jason or Ryan or anyone for that matter the effect would be nil. To them those names mean nothing, they're just someone who's helping them out.
Now that's not to say that 37signals' or Allan's approach is worthless or misguided but I would think that as your business begins to grow and you get more users those users will be further and further removed from what your company is about and will be more focused on simply what your products can do for them. Your early adopters will most likely be people who are interested in more than just the product - they'll be interested in you and they will think it's awesome to receive a message from you. But eventually the majority of users either won't care or, if they do, it'll be more like "cool, the CEO took care of my problem" not, "holy shit, I can't believe I got an email from Bill Gates himself about Vista always crashing."
What this means is that it stops being so much about personal brand and more about company brand. And company branch can be built without the CEO having to answer every support request. Regular users will be happy to get good help from anyone in your company.
In the Unstick.me Live session Alex wanted to know where the line was when you'd stop doing support and just work on the app. Allan said he'd rather go the other way - more support, less app. That's commendable for Allan but I know, for myself at least, I'd want support to shrink so I can work on the app.
And so I think the answer to Alex's question is this: you can stop personally answering support requests when your user base reaches the point that the majority of people don't know or care who you are, they just want to use your app because it works for them. At that point you can hire someone to take the easy support off your hands and focus on the harder questions. Don't pull out of support altogether but don't be point either. And if you leave yourself open to outside contact I think you'll find that the users who do contact you will be those who recognize your personal brand and will appreciate hearing back from you.