This is the biggest stumbling block for me. Any advice on this particular aspect of it? How do you go about it?
I locate all the venues within a desired radius that do live music. Find out of they do smaller acts, study who they're booking, figure out how to offer something as good or better, call the venue and ask who takes care of live music. At least half the time they just want an email link to demos. I send them to my youtube channel. The other half I go in and meet face to face, play the same youtube videos on my ipad and sell a gig. Getting in takes persistence, but after first performance I get rebooked. Some rooms aren't organized and I end up doing multiple calls after each performance to get rebooked. That gets old. But most aren't that bad. When booking I try to book at least three months in advance all at once.
I tried forming a network with the top soloacts. That was easy when they were really good. Unfortunately most of the top guys stopped gigging or moved somewhere else. The remaining "top" acts are like herding cats. No one calls or talks to anyone. I called several, sent multiple gigs and leads to them, stayed in touch, etc. But it was like trying to develop a relationship with a black hole; everything went in, nothing came out.
Today's solo acts seem far more antisocial and don't network...bizarre. I finally gave up and just collect their websites. Now they do all the work, knocking on doors, meeting, convincing venues to do music, etc. I just surf their calendars, call the rooms, book myself, and it's survival of the fittest or whomever is most popular with the (typically clueless) person that live music was pawned off onto, usually a bartender, or worse, someone who thinks they're a musician, but aren't. 95% of the time I do great in the room because there's only a couple people in the 2+million city I live in that actually do something similar to me. When I don't fit the gig it's usually poor communication of their expectations, or political BS and the person booking music is eventually canned and/or the venue stops live music. Either way, it wasn't meant to be.
I could go on, but the first paragraph says it all.