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"I was out in L.A. doing the whole major label showcase and power lunch hustle. It's really just a terrible experience," Dailey says laughing. "You have these people taking you out to lunch, you're sitting next to all these famous faces and they're telling you, 'You're going to be famous.' When all you really want to do is make a great record and hit the road."

Unfortunately, just as things were picking up in the courting Dailey calls "the dance," he was hospitalized with appendicitis. Imagine his surprise when he, with no insurance, came out with a $50,000 hospital bill. Anyone who's ever been sick and far from home can understand what happened next. "I get [out of the hospital], limping about, and I didn't know what to do, so I thought, 'I gotta go home for a little while. I know how to get back on my feet there,'" Dailey recalls. "So I come back to Boston and immediately get a phone call from my manager, 'We're going to make this record on our own.' Originally, he wanted to meet with all these producers back in L.A., people who've produced Neil Young etc. and I said, 'I know the perfect guy to do this album with.'"

That guy was Tom Polce. And in working with Polce, as well as friends who Dailey says, "Are amazing musicians who deserved a crack at it all," Dailey has come up with a collection of 10 tracks that are genuine, intelligent, and show the best of the singer/songwriter genre.

On songs such as the lovely melodic opener "Boom Boom," the genteel "Eliza," the infectious pop-rocker "Bi Polar Baby," and the gorgeous Appalachian folk closer, "Dear Grace," a number usually done a capella live, Dailey shows his eclectic influences, from Tom Waits to early Rod Stewart, while conveying a sound that is fresh and contemporary and, as one reviewer stated, "You hear a long forgotten master being channeled here."

One thing Dailey knew making this record after the experience of his first album, Goodbyeredbullet, was that he wanted it to be a shared experience. And while he clearly can manage on his own, as evidenced by "Dear Grace," he appreciates music as a communal art. "For me I like having a group of people, an ensemble, and getting everyone's energy into this thing I created," he says. "Last time I was more on my own, but I didn't want this album to be that way. It is not as much of a spiritual experience. When you bring in all these different talents and personalities on something that you created and bring it to the next level together, it's tremendous. I remember being in the studio thinking, this is the best thing I've done so far.'"

Working with longtime friends also gave him the opportunity to continue to pay back a Boston scene he is very proud of. That's a big part of the reason the Boston Music Award meant so much to him. "Those bands and artists who win a Boston Music Award are just hard-working Boston musicians," he says. "I haven't seen a person win one of those awards who isn't tenacious and bringing something to the music scene here. So getting that award is a gratifying feeling of accomplishment."

He admits being a little surprised because, like a true troubadour, he took his act on the road, building up a following and dedicated fan base the old-fashioned way by traveling around the country with his guitar. "Sometimes I didn't mingle as much in Boston 'cause I would head out and go tour the country or I'd position myself on the west coast and play up and down the west coast alone for a month and then come home, play a show, then leave again," he says. "So to be out and come home, put out a record, and win an award was a testament to the fact that this is home, this is my base."

Dailey says Back Flipping Forward was definitely informed by his experiences outside of his native city as well. "There are a lot of characters in songs like 'Hollywood Hills' and 'Eliza,' talking about fleeing to Mexico, spinning the tale of something that's definitely not the true life of a guy hanging out in Boston," Dailey says. "That kind of national experience and the traveling, getting your hands dirty on the road, definitely seeps back into your art without even trying."

And while there are specific characters at the heart of those songs, the themes and ideas in Dailey's lyrics hold true regardless of where a track was written. Within such songs as "Eliza," "Good To Me," and "Undone," the ideas of redemption and restlessness play out as if in an early Bruce Springsteen song. In one of the strongest lyrical passages, at the conclusion of "Rise," Dailey sings, "When I grow up/I hope I get the hang of this/I bleed from 6 strings/I let the truth fall from my lips."

It's that commitment to honesty that makes Dailey's rise an impressive one. Here is a troubadour traveling around the country on his own, determined to reach fans through the strength of his music. And now he finds himself, and the album he made independently, signed to CBS Records. Dailey admits he hasn't let himself think too much about being on the label whose famous logo adorned albums by the likes of Springsteen and Dylan, but he does confess it has at least crossed his mind, "It was the label of Paul Simon."

Dailey shares something else with those storytellers, namely an appreciation for the lost art of the album. Because even though the songs on Back Flipping Forward were written in a span covering the past three years, together they represent an album. That unifying theme was important to him. "I sat down with my producer and we picked 10 that just went together seamlessly," he says. "I had a lot of songs on hand and could've thrown a lot more out there, but I wanted to make a nice cohesive record. I wanted to make sure the whole album stuck on the wall, not just a few songs."

With different radio stations around the country having already picked up five or six songs and early press response being very strong, Dailey is finding out that in this case his instincts were right on.