LEFT TO RIGHT: John Shepski & Chad Lanning of Fluff & Gravy; Ben Hubbird & Casey Jarman of Party Damage Records; Jared Mees of Tender Loving Empire.

"I COULD PROBABLY count on one hand how many people are making a living running their record label in this town," says Jared Mees of Tender Loving Empire.

Most Portlanders don't realize what it takes to run a small record label—they might imagine a funhouse with fire spinners and a PA system blasting local hits. In a city enamored with the DIY complex, Portland has become a haven for people starting their own recording projects, and they're all working very hard to make it work. It's not easy, and as Josh Hughes of heavy music label Eolian Empire affirms, "Nothing makes money."

It isn't always a rewarding job, either. "It's mostly a lot of rather menial, boring work," says Ben Hubbird of Party Damage Records. "Sending lots of emails, packaging and mailing lots and lots of records." It's also easy to spend a lot of money and time on projects that don't take off. Sometimes you spend so much of your own money that you have to steal a box of wine, as Hubbird told me he did. "I'm going to hell," he adds.

Aside from the work on their hands, label owners—no matter how small—are constantly hounded by people trying to get a piece of them. There are publicists, packaging companies, and designers who want you to use them in your business. Not to mention all the musicians that come knocking at your door. No small record label can take on every musician they want to, but that doesn't keep them from getting asked.

Every label has its own way of handling this. Hughes explains Eolian's checklist: "One is that they are a great live band, two is that they have their own thing going on, three is that we like hanging out with them, and four is that they mostly have their shit together."

Andrew Sloan and Mees of Tender Loving Empire similarly describe their selection process. "Andrew fills up a Super Soaker with paint," says Mees, "then I stand there with bands drawn on my hands and my feet and my chest. He proceeds to shoot me with the Super Soaker and the band that ends up with no paint on them wins."

"If I just squirt him in the nuts, it means no records that year. That's it," adds Sloan.

In their short time in the business, John Shepski and Chad Lanning of Fluff and Gravy Records have learned the importance of lining up priorities. They explain that you have to have your press and touring happening at the same time, or you won't see the success you're looking for. It's something they didn't realize going into the label, and they feel that some of their best press came at a time when they wish their artists had been on the road, so fans would come out because of it.

It's a sad truth that labels are having a hard time making any money at all. As CDs become less popular, things are changing, with the rise of downloads, streaming, and the revival of spinning vinyl records at home. Several of the labels I spoke with explained how huge streaming, in particular, has become—to the point where it is now one of their biggest pieces of income. Lanning says you have to "embrace it or fall behind." Shepski adds that you can't opt out of it unless you're big enough to do so.

Naturally, one of the biggest reasons for Portlanders to start labels is to promote their own music. Then a friend asks them to put their record out, too, and suddenly they're running a label. A familiarity with the music industry from a musician's perspective—or music writing, in the case of Casey Jarman of Party Damage—helps at least offer perspective on what kind of work needs to be done to succeed. Tender Loving Empire even put out books and other merchandise along with their first music releases, but Mees eventually realized he had to focus on one thing and do it well; music won.

Meanwhile, Sloan explains that the only thing holding Portland back as a music haven, ironically, is the lack of larger labels. Without any local powerhouses, it can be hard for other Portland labels to get national attention. As such, it's vital that labels build up a local audience as much as possible and send their bands out to meet the country face-to-face.

While this all sounds daunting, there are rewards beyond money. All of the labels I spoke with are happy in their positions putting out fantastic artists and working on their projects. "I'm totally addicted," Lanning says, explaining that he will sometimes get up at 2 am to see how many fans watched a video or saw a post online. He says every time he signs a new artist, it's like "a videogame where you gain a new power."