And a musician’s life is anything but easy — something James discovered when he was nine years old and living in Michigan. “I wanted to play trumpet in the sixth grade, and after two weeks of it, the band teacher told me that the trumpet wasn’t for me and maybe music wasn’t my thing,” James recalls. “And I was completely devastated, crushed, because I always loved music.” But the next day, his mom bought him a guitar, and the impact of the rippling strings beneath his fingers was immediate. “Since then,” he says, “I knew that’s what I wanted to do.”
By seventeen, James was hustling, loading his plate with work as a freelance sound engineer in production and performing professionally with local bands. He took on every opportunity, from rock-and-roll concerts to political rallies, growing his production résumé with steadfast determination. “It’s such a tough thing to break through as a musician,” he says. “Rather than having a normal day job and going the conventional route playing guitar on the side, I tried to immerse myself in the industry from high school on.”
Constantly hungry for more gigs, James kept an eye on local Craigslist pages. In 2010, after his move to the San Francisco Bay area, James stumbled on an ad he felt was created especially for him: “It was for an 18- to 24-year-old guitar player, and it listed two influences: Larry Campbell and Dave Rawlings, who were two players that I really like that a lot of people maybe don’t know,” he remembers. He responded to the ad and auditioned at the listed address: the house of Grateful Dead bassist Phil Lesh’s youngest son, Brian Lesh.
“I wasn’t a Deadhead. I didn’t grow up listening to the Grateful Dead or anything, and I’d never been to a house like that before,” James says. “And they had a grand piano in their basement. And I’d never seen a grand piano in a house at that point.”
Playing with Brian Lesh marked the beginning of a pivotal chapter in James’s life. “Whenever [Brian] was home, we’d play gigs, and Phil would always come to all our little gigs at bars in the Bay Area, and I got to know him a little bit,” James says. “He was always super supportive.”
Phil Lesh opened a music venue and restaurant called Terrapin Crossroads in the Bay Area in 2012 and offered James a gig as a production assistant, occasionally calling on him to play with Lesh’s Terrapin Family Band at the bar. “So that sort of evolved into me being in his band for ten years,” James says.
In the middle of that decade-long stint, James became Phil Lesh’s manager for the Fare Thee Well tour, in which surviving Grateful Dead members Bob Weir, Bill Kreutzmann, Mickey Hart and, of course, Phil Lesh, celebrated fifty years of the seminal jam band. “It’s a bit of a wild ride, crazy to think about,” James says, reflecting on his experience organizing multiple stadium shows that attracted more than 70,000 people each. “We went all over the world playing together, and then I met my wife, who lives here, and that’s what brought me to Denver.”
He met his wife, Megan Baldwin, in 2018 after playing at Red Rocks and Ophelia’s Electric Soapbox for the first time with Phil Lesh’s band, and Baldwin had just become the vice president of Edible Beats, the restaurant group that owns Ophelia’s. “She was talking to me about how [Ophelia’s] was looking for somebody for [the booker] position, and I did so much of that in Terrapin,” James says. “I think she was jokingly saying one night, ‘Oh, you should do it,’ and I was like, ‘That’s an interesting idea.'”
James has been a booker at Ophelia’s since the fall of 2021. He stages such acts as Shamir Bailey and DJ LTJ Bukem and organizes events like Y2K dance parties and free brunch shows. “He is an instrumental piece of our team,” says Brian Butler, Ophelia’s general manager. “He caters to all genres, which is what we stand for.” James books a combination of national and local acts, bringing big talent to Denver while curating the local music scene.
“I love that room so much,” James says. “Ophelia’s has a special place in my heart and history.”
Every now and then, James still finds time to perform, bouncing between local Denver acts and nationally known artists. In 2016 he met breakout bluegrass star Billy Strings at the High Sierra Music Festival in California, and after a Strings performance at the 1STBANK Center this past February, James and Strings hosted a post-concert show with Andy Thorn at Knew Conscious in Denver. James even has a few events scheduled for August: He’ll be playing at Ophelia’s with Everyone Orchestra, acting as the musical director at Conscious Alliance’s annual benefit and performing at the Gerald R. Ford Amphitheater in Vail.
But what never fails to astound James is how one nondescript Craigslist ad accumulated into a lifetime of experiences. Everything, from the 1909 Steinway Grand in James’s studio — the same piano he saw at Brian Lesh’s house back in 2010 — to the commemorative statue marking the date of his first Red Rocks show, can be traced back to the day he clicked on that ad.
“I don’t have a huge blood family, but the connections that were made at Terrapin are some of the strongest lifelong friends that I’ll ever have. That ten years was a really special thing to be a part of — a super unique moment in time that brought so many great people together,” James says. “I can’t imagine…it would’ve been a totally different path if I hadn’t seen [that ad].”
Ross James and Everyone Orchestra, 9 p.m. Friday, August 18, Ophelia’s Electric Soapbox, 1215 20th Street. Tickets are $30-$37 and can be purchased here.