Begin with an introductory email. I personally don’t ever read press packets mailed to me, or take phone calls from bands that I don’t know. I don’t care if you draw 2 million people in your home town, I don’t care if you say you have friends in our neighborhood and you can get 50 people to a show…
Booking
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I have earned my living solely from performing and teaching music for the past two years without having to get a day-job! I have found that a lot of the players in college who were considered the best are having a harder time making rent than some of the more determined underdogs. Because I was not the best musician, I had to be REAL and HONEST about what I could offer a venue when booking a gig. For me, honesty has worked better than any trick out there! Hopefully, my experience will help you on your own path.
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If you play the same town every week, you’re over-saturating your market. You need to expand constantly. It’s unlikely to have a decent turnout at an important show if there is advertising for smaller shows in the vicinity that same week.