Josh Weinstein: art is how creative people make sense of things.

Before starting his San Diego life in 2009, while he was still living in New York City, Josh Weinstein released a new album every three years. But nearly 15 years passed before he released his latest album this past September, titled Mind the Gap. “There’s more variation in the newer stuff,” Weinstein says. “I went farther in all directions than I went on previous albums. There’s stuff that’s a little bit out of the ear, and a little bit crazy. I wasn’t afraid to push crazier. Then the stuff that’s kind of sweet and tender, I dove right into.”

Weinstein had notched sonic victories, things like receiving airplay on almost 300 stations worldwide and being licensed by MTV after his 2009 album Love and Alcohol earned critical praise. So why did so much time pass before he released any new music? “I certainly thought the ‘every three year’ trajectory was going to continue. I came to San Diego from New York for a PhD program with two kids. Between the combination of raising kids and trying to finish my academics, it wasn’t an opportune time to make another album. Then, I had a crisis of, like, does it matter what music I make? Particularly, with kids and in the midst of a struggling marriage, the idea of writing songs — even though that’s one thing that gets you through all that... I probably had a crisis of confidence about whether anyone would care what I had to say.”

Albums or no albums, Weinstein says he never stopped creating. “Even in what I thought were the down years, when it came time to list the songs, I ended up with over thirty songs that I thought were recordable. There’s a bunch of stuff that I didn’t even put on that list. There’s never been a version of me, as long as I’ve been alive, that hasn’t been writing songs. I think creative people make sense out of things that happen through their art. Getting to say something in a song is how I can deal with difficult stuff.”

With Tom Waits-like poetic prose and sound baked in, and co-production from local star Jeff Berkley (Berkley Hart), Mind the Gap is stacked with 24 songs. “And I probably cut about eight or nine more,” says the reloaded songwriter. “That’ll be another album.” He notes that it doesn’t always take expensive equipment to record quality sound. For a lot of the songs, he simply pressed the record button on his iPhone to capture his vocals. “Whatever range the iPhone augments fits my singing range and voice well. When I would make my demos at the piano, I would often like the way my vocals sounded in that demo better than my home recording set-up with expensive microphones.”

Since Weinstein’s previous album in 2009, the way we consume music has changed. CDs and cassettes are now novelty items. True, vinyl is timeless for the junkies, but we’re mostly a global population of streamers. “When you’re younger and producing albums, there’s some pressure to show quantifiable returns from them. Now, for me, streaming is the ideal format, because there are no barriers anymore between producing music and allowing people to hear it. Even back in 2009, I had a strong sense of what a CD meant in the long term. I have friends who’ll complain about streaming revenue, and I’m thinking, ‘Are you crazy? We’re independent artists, and everyone everywhere in the world can hear every song we make, good or bad.’ It’s pretty incredible.”

At the Music Box on July 14, Weinstein will be celebrating the release of Mind the Gap and also the 20-year anniversary of his first collection of material, released in 2003. Alongside Weinstein will be local guest stars Chloe Lou, Ariel Levine, The Brothers Burns, Jeff Berkely, Johnny Vernazza, and Gregory Page. “I don’t want anybody to be taken for granted, but I literally just asked them to be a part of it,” he says. “I’ve played on a couple of Gregory’s albums, and I consider him a friend. They’re honoring me by doing this. I’ll be playing stuff from all my albums. I’m really excited. It’s a bunch of stuff I haven’t done in a while. It’s going to be friends of mine singing, and guys I haven’t played with in a long time.”