23-year-old, Philly-bred singer-songwriter Jesse Ruben freely confides that he’s done a bit of “obsessing” over his second album, The Ones That Matter.

Not that such anxiety is evident on the highly accomplished disc, the follow-up to Ruben’s self-released 2008 debut, Aiming for Honesty. Adding full-band accompaniment to his lush, soulful pop-rock, Ruben also stretches impressively as a writer on The Ones That Matter, achieving a near-novelistic sense of character and setting on finely hewn tracks like “A Lack of Armor,” “Bleeker and Sixth,” and “Unbreakable.” His relentless attention to detail pays off handsomely.

He makes no apology for meticulously fine-tuning all aspects of his work and presentation. “Every time you create something you have an opportunity to say something new – or at least something honest,” he says. “I take that opportunity seriously.”

Ruben’s expansive and deeply compassionate point of view has resonated strongly with an ever-growing audience, whom the performer has cultivated with virtually nonstop touring and persistent online networking; as a result, he’s sold some 5,000 copies of Honesty on his own.

He often receives emotional messages from fans declaring that his songs have crystallized their feelings, commemorated milestones in their lives and even helped repair broken bonds. “One woman wrote to me and said she and her daughter didn’t get along, but when she drives the girl to school every day they listen to my music – and it’s the only time they don’t fight,” he marvels. “The songs I wrote in my basement helped her relationship with her daughter. How could I ask for more than that?” Indeed, his compositions have connected so powerfully with listeners that several cover versions have been posted on YouTube.

Such moments of connection helped inspire the title of The Ones That Matter. Ruben had compiled a list of some 80 candidates, but it was in the aftermath of the recording process that he realized what the disc should be called.

“I was on an epic road trip,” he remembers of this epiphany. “I realized that as much as this album is about music, it’s ultimately a representation of who I am – and all that amounts to is all the incredible people I’ve surrounded myself with, and the places I’ve spent time, and the stories and jokes that came out of those experiences with those people. That’s when I understood that the only logical name for the album was The Ones That Matter.”

Recorded during a record-breaking snowstorm in Charlottesville, Virginia – where producer Chris Keup (Jason Mraz, OAR, Parachute) and partner Stewart Myers (Mraz, Lifehouse, Rachel Yamagata, Mandy Moore) have their studio – the disc afforded Ruben a chance to fully appreciate the devotion of his pals. “I had some of my best friends in the world come down to help me finish the record,” he relates. Other players on the disc include drummer Brian Jones (Mraz, Yamagata, Moore); and keyboardist Daniel Clark (Ryan Adams, kd lang, Moore). Meyers handled bass on several tracks.

The profound gratitude Ruben felt upon finishing the album snowballed in the coming days. “I wanted the title of this record to express my thanks to everyone who mattered – not just my friends who worked on the record, but their friends. The people who gave me a couch to crash on, made me dinner, drove me to the train station. Everyone who came to my shows, and walked up to tell me what the songs meant to them. I’m thanking them all with this record.”

Ruben’s story begins in the heart of a musical family. His father and grandfather were both professional musicians, performing at weddings, Bar Mitzvahs, corporate events and other gatherings in Philadelphia and its environs. Ruben recalls watching in awe as his dad’s band rehearsed rock, pop and R&B hits. He began taking piano lessons, but lost interest during his adolescence. “I had told myself I couldn’t play guitar because that was my dad’s instrument,” he notes. “Then I realized how stupid that was.” His father bought him a cheap guitar with the promise of a better instrument if he made progress; the guitar felt right in Jesse’s hands, and by age 16 he was writing songs.

The artist cites singer-songwriters like Paul Simon, Joni Mitchell and James Taylor as his greatest influences, but also admits a fondness for the standards penned by Cole Porter and the Gershwins. While he’s loath to compare himself to his idols, he says he takes courage in their stories. “Paul Simon wasn’t always hailed as a genius,” he points out. “At first, he was a 20-year-old kid with a guitar who dreamed up these incredibly ambitious songs. Realizing that helped me give myself permission to write what I wanted to write.”

He only applied to one college: Berklee College of Music in Boston. His first year there was a struggle, as he plunked out rudimentary solos in guitar classes filled with fusion-shredding virtuosos. But once he was able to focus on songwriting, Ruben blossomed; regular gigging soon followed. “By the time I graduated,” he points out, “I was on the road pretty much every weekend.”

As a live performer he racked up odd experiences like playing backyard barbecues, singing at a daytime Sweet 16 party, and even serenading a couple of fans on their anniversary (he showed up in their kitchen with his guitar, at the woman’s bidding, to surprise her boyfriend). The gigs gradually got bigger, and soon Ruben was paying his rent with engagements across the East Coast – becoming adept at getting around by commuter rail, booking cheap flights, promoting his shows and maintaining contact with fans via Facebook, his blog and the comments on his YouTube video posts.

The online community also came in handy when he was recording his debut album. “I had no money, and five of my friends held a Facebook fundraiser for me,” he reports. “They presented me with a giant check for $2,500 on my twenty-first birthday.” And though elements of this initial effort seem distant to him now, Ruben credits Honesty with giving him a leg up in building his audience; in addition to the brisk sales of his debut, he continues to enjoy rapturous fan feedback about its songs.

Upon graduating from Berklee in 2008, Ruben was already living out of a suitcase in his battle-tested Toyota. “If I had my choice, I’d be touring all the time,” he volunteers. “I love the lifestyle – sleeping late and getting up and driving and playing and meeting a bunch of people and doing the same thing the next day. I love not having to worry about cleaning my room or doing dishes; I’m cool with living out of a suitcase; I’m just working toward the day when I can trade the Greyhound for a bus of my own.”

“I’m staying out of New York for a while,” Ruben sings in “A Lack of Armor,” although that self-imposed exile may soon be coming to an end, as the singer-songwriter plans a move to the Empire State from his temporary base in Nashville. But for the time being, Ruben’s true home is the road – where he’ll no doubt continue to touch lives, have offbeat adventures and add new names to the ever-growing list of The Ones That Matter.