I recently heard from a singer in his 20s who asked for some insights on getting discovered or signed... That's the g'zillion dollar question with no simple answer.
For what it's worth, here's may take on it. - jb
Thanks for writing. I'm glad you somehow found and like the work of We Five.
I'm afraid I don't have any great insights on how to be discovered. We now live in the era of downloads and American Idol-- and it didn't exist when I got started. We were discovered because my partner Michael's brother was in the Kingston Trio and he was a great mentor who eventually led us to a record deal.
Regarding record deals, record labels don't sign and develop acts the way they used to do. They package material by artists that have a following, or serve as an outlet for entertainment management companies that link talent to an audience.
The only thing I can suggest (and it applies to everything, not just music), is to:
1) get good at what you want to do -- that means study (with people better than you), don't limit the kind of music you listen to or sing, and practice everything. Figure out what the successful people are doing regardless of your personal taste and learn to do it; then use your talent to make it your own.
2) find places that use what you want to do and get involved. For a singer, that could be a school, church, theater group or someplace like Disneyland, a band, etc. (though being in a band with friends will often limit your exposure to a lowest common denominator that may limit who sees you. Assuming everyone is good, your singing and performing needs fit what's going on--and yet still somehow stand out).
3) Try out for a talent discovery show and see where you fit in against others in the world who have the same dream.
4) Always do your best when you are performing and be ready to walk through a door if it opens.
I don't know where you live - but there are probably people doing what you want to do in your area making music in churches, clubs, local commercials, community theater, and such. Find them. If there isn't a music business of some kind where you can develop relationships, you may need to go where they are.
In any case, good luck in your pursuit.