"John's eyes don't close, and so he's been losing a lot of sleep," explains Adam Shearer. "And that is really bad." Shearer, frontman for local folk-rock band John Weinland, is detailing some of the more gruesome side effects of songwriter John Vecchiarelli's recent surgery. He's also explaining how Vecchiarelli says he doesn't want help paying the medical bills and why more than 25 Portland artists are coming together to help anyway.

The longtime host of the White Eagle's open mike—an event singer-songwriter Laura Gibson describes as "the first community [she] felt in Portland"—Vecchiarelli has affected the careers of countless artists as a careful, considerate soundman and an oftentimes voluntary booking agent. Shearer says, "He is the guy who knows everybody and is making things happen, but isn't trying to get any attention." Despite Vecchiarelli's huge community of friends and accumulating debt—he has sold every type of instrument he owns, save one of each—Vecchiarelli was wary when Shearer originally approached him about a benefit show. "He said, 'No way,' and raised his voice," explains Shearer. The full-time musician, who is being financially supported by his longtime girlfriend—a server and freelance photographer—was finally convinced by singer-songwriter Rachel Taylor Brown. "[My friends] were giving me crap about it," Vecchiarelli explains. "They said, 'Look, you're being selfish in not letting us do it.'" Now he says, "It's going to save our asses."

Vecchiarelli's first surgery, which removed a benign mass from his right sinus cavity about a month ago, was partly covered by insurance. But getting the money for a second, reconstructive surgery that aims to correct the placement of his right eye is, in Vecchiarelli's words, "going to be a fight." The 45-year-old folk singer says that as a punk-rock kid, "I didn't even think about that stuff. I didn't expect to make it to be as old as I am now." But these days he's looking to the future hopefully: "I'll need glasses in the end, but I like my hearing more than my sight."

"John and I had a stern heart-to-heart about taking care of your communities," says Shearer. That conversation—paired with the fact that Vecchiarelli wasn't comfortable being a beneficiary without giving something back—led to the creation of musicianhealth.org, a resource for musicians to learn more about health-care options. Scott Garred (of Super XX Man) says, "That totally sounds like John; push it as far away from being a personal matter as possible." The site—designed by Shearer and donated by Portland-based online record store and distribution company CD Baby—launches the day of the benefit and will feature musicians' consumer reports posted in a blog-type format. Vecchiarelli will develop the mission statement and ultimately fill the role of administrator.

It hasn't been easy, but Vecchiarelli has come to terms with the idea of so many people helping him: "If one person in the audience says, 'Wow, that's a drag, and it's a good thing John had insurance; maybe I should look into that,'" he explains, "then it's totally worth it."

Super XX Man, John Weinland, Laura Gibson, Pete Krebs, Rachel Taylor Brown and many more play John Vecchiarelli's benefit Sunday, Oct. 22, at the Doug Fir. 8 pm. $10+. 21+.