Ben had thought to work “White Privilege 2” into his Times Square medley performance on Dick Clark’s New Year’s Rockin’ Eve With Ryan Seacrest 2014—“instead of playing ‘Thrift Shop,’ we were going to play that record at the ball drop,” he says—but the song, so full of things to say, wasn’t quite complete. And then “so much was being exposed—with the Grammys, with Iggy, with #BlackLivesMatter” that he had to go back in, again, asking, “How do I participate in this conversation in a way that I’m not preaching, where I’m not appearing like I know it all? ’Cause I don’t know it all. I’m learning every time I have a conversation around the issue. How do I affect change? How do I not preach to the choir? How do I authentically initiate discourse without co-opting the movement that’s already happening? You are constantly having to check your intention as a white person doing any sort of antiracist work.”

Ben recently attended an eye-opening, daylong “Undoing Institutional Racism” workshop. “We were there for six or seven hours and spanned 500 or 600 years,” he says. “It was a crash course on why things are happening right now. It is so multilayered; it goes back so deep. There’s turning points in history that have equated to why police are treating black men the way that they are in America right now. I got a glimpse of that in seven hours, so you’re definitely not going to hear it in a five-minute CNN talking head thing where people have 30 seconds [and] they’re arguing. You almost can’t even engage in the conversation until you do a little bit of homework, to actually have a real tangible grasp on what’s happening.”

He now wants to go big, with plans for a series of town hall meetings built into his next tour; he talks about reaching out to local artists in various cities to participate, citing Meek Mill as a hopeful for Philadelphia. “A concert’s not going to do it,” he notes. “Regardless of the song that I write, or that ends up coming out, it’s not going to do it. It’s going to be a tiny piece. This needs to be part of my life’s work, if I’m going to be authentic in the discourse—not, Let me jump in when I’m supposed to; let me jump out when I want. Because, as a white male, the system’s designed for me to forget this shit quickly after I learn it. It is so easy for me to get back into my place of privilege and forget all of it. And I don’t want to be that anymore. I don’t want to do just enough to get by in the conversation.”

Zach Quillen—Macklemore & Ryan Lewis’ manager and ostensible label head—is giving a tour of Macklemore LLC’s headquarters, situated on the waterfront in Seattle.

They’ve been at this location for just three years, and it’s a noticeable step up from their previous 500-square-foot abode in North Seattle. It’s housed in what used to be a two-level gym. Part of the former weight room has been transformed into an impressive preproduction studio complete with a video editing suite and a sleeping nook larger than most New York studio apartments; the other half serves as a large space suitable for photo shoots and live sessions—an ample serving of Ryan’s guitars are hung up on a wall. Upstairs, where the cardio equipment used to be, there are spacious offices, open cubicles, a private room with a vocal booth, a kitchen, and showers. The building’s other tenant is a storage facility. “That worked out really well for us because we do all of our own merchandising,” says Quillen. “We’re able to do all of our fulfillment here, out of a separate storage space in the building—they have an elevator and a loading dock and all that stuff, so we can handle all of the orders.”

Macklemore LLC—which is a joint partnership between Ben and Ryan—is not a typical label in any sense. “It operates as a label, but it’s not.” Ben says. “We haven’t had to go hire some big shot to turn profit for our company. So, it’s like, let’s keep the team we had when we were in 500 cap venues. And everyone’s grown into their position and evolved and adapted and we continue to push the envelope of what it looks like to be a mom-and-pop business pushing music to the world.” Quillen, a former booking agent for The Agency Group, is listed simply as a manager, but functions more as a CEO—under his purview are the day-to-day operations, including licensing, branding, and interfacing with retailers and Alternative Distribution Alliance, Macklemore LLC’s Warner Bros.-owned distributor, which also handles Fool’s Gold, Matador, Tommy Boy, and many other indies. Radio promotion (which is handled by Warner Bros.), publicity, and non-essential finances are outsourced. “We’ve essentially built a traditional label, but by outsourcing the individual pieces on a work-for-hire basis,” says Quillen.