Thanks for these posts, by the way--I find them patently inspiring. It's nice to know I'm not the only developer with a million ridiculous project ideas. Keep up the good work!
I built a product (back in 2008) that was aimed at the education sector for students and teachers to use to study in groups, but alas it never got much traction with large groups like I intended. But it was heavily popular with international users from (mainly) Europe.
I had pretty much 0 luck marketing to school districts or schools, just a few classrooms.
It seems the school district market is a hard nut to crack that I've been wondering how one can angle on..
Thanks a ton for the tips Matt!
Fact: you are one guy doing this on your own. And that's the only fact they need to know. Everything beyond that can fabricated to build confidence and brand perception. Don't get me wrong, I'm definitely not saying you should lie or be dishonest in any way, but their perception of you (and your business) is entirely what you make it out to be. If you say you're doing this as a side project and you're blatantly advertising it as such, you're selling yourself short. Side projects die, and nobody wants to pay for a service that will die in the foreseeable future. On the other hand, if you advertise this as a one-man bootstrapped profitable business that you pour your life and energy into, then you create a whole different perception. People will support that. People will be impressed, and they will talk - as long as you can deliver what is expected. And there's some free word-of-mouth marketing for you. They will also be more understanding if you make mistakes, as long as you accept the blame and correct those mistakes. People are naturally understanding - especially when they're dealing with other people, not a giant faceless bureaucratic machine.
So I say fuck that. Don't hide yourself. Be open. Share your numbers with the world. Tell the world who you are, and tell them you're serious about what you do. If you aren't confident about your product, others will see that - and they won't be confident either. Don't make it a side project, make it your baby. Nobody will love your product if you don't love it first.
On the other side, I think that some people, seeing he is making some money, would feel he's charging too much (or something else). It may not happen, but why take the risk ?