Despite his success, every show could be one of Matt Nathanson's last.
"It's rad to be able to make enough money to live off of, that's awesome," Nathanson said. "To be able to play music for a living is the shit, it's the quintessential part of it. And I feel like I'm constantly trying to spread the word more, as much as I can."
At the same time, Nathanson is fearful of failure.
"I still have this insecurity part of 'pretty soon its going to be over, no one's going to come to your shows,' and it's always in the back of my head," he said. "So every time I write a record or play a show I'm trying to win the prize fight. I'm like, 'This is it. These people are never coming back if I suck.'"
Such is the mindset of Nathanson, who played a show at the 9:30 club on Oct. 29. He is at a place in his career people do not normally talk about - just past the crossroads. Recent career decisions, most notably signing with Universal, has hopefully given Nathanson a bit more peace of mind. The attendance at his shows has gotten better, and the audience more familiar with his work.
This helps, because when Nathanson is on stage, how he judges his show is based on the connection between himself and his audience.
"It's all about connecting at the base level," he said. "If we played like shit, but we had a really good connection with everybody, that makes a show fantastic. I feel like the shows when I walk off stage and I'm bummed that they didn't go well, it's because I feel like there's still a distance between the crowd and the stage."
On stage, it is clear that making the connection is what Nathanson strives for. He is extremely crude and loves sex jokes, but something about his boyish charm allows him to be extremely brazen but never really offensive. Another mechanism he employs to draw an audience in, even if they are unfamiliar with the music, is covers. During the show he covered Ashlee Simpson's "Pieces of Me," Rick Springfield's "Jessie's Girl," Paul Simon's "Diamonds on the Soles of Her Shoes," R.E.M.'s "Losing My Religion" and Ozzy Osbourne's "Crazy Train." But his music is the real draw. He sings every song like he never tires of them. His songwriting seems to be the most critical element to being a musician.
Nathanson's songwriting is very cathartic.
"When I write I write from a very internal place," he said. "When I think a song is done, when I feel like I've done all I need to do, I always try and take it a step further. Short stories are a great example ... you can always say it more concise: you're trying to hold onto the thread or the spark that drew you to it in the first place but you're trying to articulate it in the best possible way."
His insight and meticulousness is evidence of a man who started from scratch. After attending a New Hampshire boarding school, his college experience at the University of Southern California at Clairmont was life-changing.
In New Hampshire his passion for writing music was uniquie, but in California he entered "an artist community where everybody created." He cites his peer influences at the time, including Ben Harper, David Linley, the Mountain Goats and Tommy Jordan. From these artists and his subsequent work, he learned "you have to create your own identity" and "digest your own influences ... You've got to be smart enough to navigate your way through."
His show is reflective of this self-awareness. When he's on stage, he is always in control. The band is very well orchestrated. Sometimes they try to pretend that they have not rehearsed the cover they are doing, but it is just too seamless. He is equally comfortable with his band as he is playing solo acoustic.
And this kind of control has allowed him to stay true to himself. Evidence of this was his switch to the Universal label. Nathanson allays the fears of those who are quick to say that big labels usurp control.
"The Universal thing is very much not really an issue ... I picked the producer ... the players ... the songs and photography," Nathanson said. "It's more distribution-wise; it gets out to a larger group of people and there's this potential that it could be a big thing."
Touring is part of this distribution, and has been a big thing for Nathanson, who spends a lot of time on the road.
"When I'm writing or recording a record for a long time, I can't wait to get back on tour," he said. "Then when I'm on tour, and I'm out for, like, fucking three years I'm like 'I can't wait to write.'"
His songwriting is paramount. He describes his favorite song as "always the last song I wrote. I say, 'now that - that's the closest I've been.'" He is even going to start working on his own process.
"My output is so slow," he said. "The next couple months after we're done with this tour will be the first time that I'm going to try to write every day. ... Maybe there'll be this fucking wild surplus of stuff and it'll be really neat. In my dreams I have this wild overabundance of songs."
The way of life Nathanson is experiencing now will probably set the tone for the rest of his career. It is now about that time that Nathanson is experiencing the pressures that come from making your career music. Back when he was doing open mic nights at USC, he probably never thought he would have a downloadable Matt Nathanson buddy icon.
But he also probably never thought he would tour with the likes of John Mayer, Train, Howie Day, OAR, Maroon 5, Guster and Five for Fighting. Fame and fortune would be nice, but the connection is tantamount, and he always strives for the song that makes him "feel like I've done something cool"