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The Most Important Thing I’ve Learned: Play Every (Interesting) Gig At Least Once

(photo credit: Joe Velz.)

When I first started making this music, a manager type friend told me to “play every gig at least once.” At the time, that advice made perfect sense. We were early into the Spotify era. Live shows and college radio were still the only tried and true way to reach fans in other regions/cities. So I’d save up some cash, book a bunch of shows on a short regional tour, rent a van and go. Of course, I didn’t have the cash to promote the shows and most promoters didn’t either. Unless me and the band had a fan to stay with or made enough cash from a gig the night before for a motel, we’d all be sharing that glorious rental van together.  

To be honest, it wasn’t the van or pennilessness that was the issue, that was kind of the fun of it. But we’d roll into a pub ten miles outside of proper city limits where the PA system was broken and the regulars had no interest in a bunch of half drunk NJ kids with a toy piano singing songs about fire and brimstone. Fans that did show up had to navigate a sub-par experience. Sometimes the house drum kit was playable, sometimes it wasn’t. Sometimes the vocals were audible, sometimes they weren’t. Sometimes the sound engineer was sober enough to mix, sometimes he wasn’t. But we’d play our hearts out, sell a little merch and move on to the next spot. We kept going, but it wasn’t productive or financially sustainable. Morale got lower and lower and the whole thing became, well, shitty.

That’s when I realized it was the quality of the shows that was the issue. It was the approach I was taking to booking and promoting that was wrong. So I started looking at my style and aesthetic and performing in places where it made sense with other artists who made sense on the bill. If that meant bringing my own PA to play in some historic house or library, that’s what I would do. No beer specials. No flat-screen TVs on mute. Just a cool vibe, an interesting concept and high quality performances. From there, I started creating and curating my own events. Collaborating with visual artists, gallery owners, party planners, burlesque dancers, and theater companies to create events that felt special. If you invited me to play a costume-mandatory Halloween warehouse party in Brooklyn I’d play it for whatever you could offer, but if you invited me to play in the corner of a Midtown NYC bar with a $15 cover, I’d pass.

The beautiful thing was that when I started making these decisions, my sense of artistic self solidified, my confidence as a performer and business person increased, and my band was excited to play again. Interesting gigs attract people who love art more than happy hour specials. Those are the people who give a damn and will support you and share your music with like-minded folks.

So for the past several years my motto has been “play every interesting gig at least once,” and if you can’t find one, make one. Every one of these interesting gigs has introduced me to a new incredible collaborator or truly inspired fan. That is by far one of the most important things I’ve learned.

‘Hope And A Hand Grenade’ is out everywhere now, including SpotifyBandcamp, and Apple Music. Shayfer James will be celebrating his EP release show on Friday, March 8, at Rockwood Music Hall, Stage 2 in NYC (9pm show, $10, 21+).

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Angela Mastrogiacomo

Founder of Infectious Magazine & Muddy Paw Public Relations. Lover of passion, ice cream, and books.

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