I've played over 500 shows in 40 states and have booked nearly every show myself (I'm still DIY). I started, though, in my (former) hometown of Minneapolis. Before ever leaving the state (of Minnesota for those struggling with geography) I had chalked up about 30 local shows.
From the moment I made the decision that a performing songwriting career was to be my life (mid-freshman-year of college after giving my dad a near heart attack) I began playing out as much as possible. I made a local goal: sell out the Varsity Theater.
The Varsity Theater is a 700 person capacity venue in Minneapolis just off the University of Minnesota campus. Nearly every band that has toured through Minneapolis has played it at some point. I lived a block from it when I decided to make music my life. I'd walk by it every day from the sub shop I worked at and salivated as I passed the 40 foot tall marquee with a hot touring act's name in lights.
In one year, I not only played the Varsity Theater, but filled it. And two years later I sold it out.
Before even thinking of touring you need to figure out how to conquer your local market. It sounds a little aggressive to say conquer, I suppose. Hipsters would say "simultaneously satiate the collective consciousness of the city." But I say conquer (because it's a true battle � and hipsters are assholes)
You have to figure out early on what your niche is going to be. Everyone has one. I started with the University of Minnesota (of 40,000 students). Hardly a small niche, but a niche nonetheless. I was part of that community so I understood the hot coffee shops, Greek houses, dorms, the grassy mall, the union, had friends at the newspaper and on the ultimate frisbee team and so forth. I took a blanket approach and plastered the campus with posters for every show � just to get my name out there and begin the conversation. I also started playing every possible venue on campus (in coffee shops, dorm lounges, bars, open mics, music venues, sorority lounges�yup, frat houses�bro, and�elevators (that's another story). Eventually everyone started to take notice.
One person seeing a poster or a Facebook ad or a YouTube video won't get them out to your show. They have to be hit from multiple angles and from multiple people.
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