Artist Interview: Ryan Westwood
The ebullient musician on his poignant debut single, ‘By All Accounts’
Ryan Westwood. Courtesy of artist, 2021.
It’s always been challenging for musicians to make a living from their art, but it’s even harder now. As a music fan, it’s enraging to read about how little money artists actually get from all those streams and listens. It’s the main reason I doggedly resist streaming services. And no one is handing out marketing expertise along with a passion for music. I’ve seen how taxing the hustle of selling their music can be for artists. Still, in the current state of the music business, embracing the hustle is the only way for most artists to make a go of it.
That’s why I found Ryan Westwood’s musical journey—a combination of organic personal growth as a musician and intentional marketing strategy—so intriguing. A few days before the release of his debut single, “By All Accounts,” which dropped March 19, Westwood talked to me about how he got to where he is today.
“My whole family is involved in music in some way,” he says. “Nobody has done anything professionally, but I just grew up around music.” His mom plays piano and has tried to teach her children. His sister brought home a guitar and taught him a few chords, and that’s what really clicked for him. “My parents saw I was enamored and bought me a guitar for my seventeenth birthday, and that was the start!”
From Theater to Busking to Burnout
Despite that, music wasn’t his primary artistic passion growing up. “I acted in my first play when I was twelve,” he explains. “I was an actor first, a musician second.” Westwood graduated from St. Ambrose University in 2009. After that he moved around the country for various theater jobs, from Iowa to Louisville, Kentucky, then Chicago.
He’d busked occasionally beginning in college, but while living in Chicago, he tried busking in the subways full time. “It was a really big part of my life for several years,” he says. But it proved to be too much: “I got burned out on music—on my music, on other people’s music. I didn’t see how to make it a career, making ten to fifteen bucks an hour playing for hours.”
So, when he moved to Portland in 2014, Westwood took a hard break from music. “My first few years in Portland I really didn’t even pick up my guitar,” he says.
Ryan Westwood. Courtesy of artist, 2021.
A Fresh Start and a New Style
“In 2017 I started doing some significant self-work,” Westwood says. “I dropped a lot of bad habits, a lot of bad coping mechanisms, and I started to believe in myself. That’s when I started to think, I can do this.” He got back into guitar playing and songwriting in earnest.
A local musician, Jeffrey Martin, became a major inspiration. “He was just a Spotify find that popped up on my radar,” Westwood explains. “I was really smitten first with his lyrics—they’re vivid but leave a lot to the imagination. I started listening to him like crazy, just tore through all his albums. Almost all his stuff is this slow, rolling fingerpicking, so I shifted into figuring out how to fingerpick—before that I mostly strummed—and that shaped my songwriting as well.”
Around the same time, Westwood started watching (“like crazy, compulsive amounts of watching”) videos by Adam Ivy, a music producer and music-marketing guru, about how to be a self-producing musician. In 2020, he signed up for Ivy’s course on music marketing. As a result, Westwood says, “I got involved in this huge community of artists trying to be self-produced musicians.”
COVID-era Serendipity
Of course, there also happened to be a pandemic starting around the same time, which threw a lot of people’s plans into disarray. But in Westwood’s case, it led to an organic development in his music career. “When quarantine first hit, I was encouraged by my housemates to do a neighborhood ‘street sing’ once a week, six feet apart, masks on, outside,” Westwood says. “That was an initial community building machine that I didn’t realize was doing what it was doing—getting my name, personality and brand out there.”
A month or two later, Westwood started doing Instagram Live shows every week. “I think we’re on the thirty-fourth week of Westwood Wednesdays,” he says. “I went from one or two people being there to now ten or eleven people every week. That sounds like small numbers, but it’s a reminder that there are ten or eleven people who want to listen to me every week!”
The synchronicity continued for Westwood. “Mid-2020, a friend started a life coaching business. I signed up to support her and help her test it, but it turned out to be super helpful. I learned a lot about how to make my goals actionable.” Shortly thereafter, he launched his Patreon. “That was really the beginning,” he says.
“I write so much, and I wanted a way to share that consistently with people who were interested in it. Patreon ended up serving as this perfect platform. I’d been playing and writing long enough that I had a pretty solid fan base, but it wasn’t in an organized way, just people I knew and loved that knew and loved me.” Now Westwood writes and records a song a week for his patrons, who number nearly a hundred. “That’s served as a launching pad to allow me the time and money I needed to start recording.”
The Single
On his weekly Instagram livestreams, Westwood is loose, silly, energetic: pulling faces, frequently cracking himself up, answering viewer comments as he reads them, making up songs on the fly. On our Zoom call he’s got a gentler energy, a little introspective. Maybe it’s because we’re talking about his debut single, “By All Accounts.”
The pretty, lilting melody, gentle fingerpicking and evocative lyrics about simple pleasures—”I got a nice fire burning in the fireplace and breakfast on my plate”—give it a comforting air, but at its core, “By All Accounts” is a song about unshakable depression: “I don’t know why I’m sad, I just am.” I mention that the melancholy of the song contrasts with his livestreams and he nods, smiling a little. “There’s a very consistent Ryan on the livestreams and I love him, but there’s a lot of work that went into him. And ‘By All Accounts’ needed to happen so he could exist.”
As an extremely prolific songwriter, Westwood had his pick of songs to record. “I thought for several months, ‘What do I want my debut to be?’ There’s been such a visceral reaction when I share this song with people. People have really reacted to it, even started crying. I thought, this seems to be the one people connect with.” It makes sense because it came from a real place: “It’s a lot about the two-year break when I was burnt out.”
As for the difference between his debut single and his performer persona, Westwood says, “The contrast doesn't bother me. I think at the end of the day, there’s room for all of it. Light and dark both need to exist.” He chuckles, sounding more like Instagram Ryan. “The next song will be big and fun.”
The Future
Westwood’s goal is to record five songs this year and then an EP. He may also start thinking about real-life performances soon. “Reaching out to venues for gigs has always been one of those big scary ‘I could never send that email’ kind of situations,” he says candidly. But the pandemic lockdown gave him time to build up his confidence. “Now that the vaccine is rolling out, I think it’s time to tackle that fear.”
His dream gig, though, sounds like an IRL version of his livestreams. “I don’t know what it looks like exactly, but I’d like to get a monthly group going around a campfire where I play an hour or two of music. Maybe in the same location, or maybe it changes places. That’s something I want to add this summer.”
Even when the world fully emerges from lockdown, Westwood has no intention of changing or scaling back his weekly Instagram shows or Patreon songwriting activity. Connecting with people on a personal level and prolific songwriting are at the core of his success so far, and they’re what he loves about making a living as a musician.
“There are so many things I've learned over the last year and a half,” Westwood reflects, “but one of the biggest shifts was realizing there are so many people who love my music, and that there are more out there who will love my music. It’s like a little relationship; over the course of months or years, you get to love this person and they love you.”
To learn more about Westwood, follow him on Instagram at @ryan.westwood or check out his Patreon.
Watch the music video of “By All Accounts”
Carol Roth. Photo credit: Dan Lee.
Carol Roth is a full-time marketing copywriter and the main music journalist and social media publicist for Adventures in Americana. In addition to studying the guitar and songwriting, Carol’s additional creative side hustle is writing self-proclaimed “trashy” novels under the pseudonym @taberkeley!
