"I dropped out, and I'm proud of it!"
After a couple of years touring upstate New York in a duo with his musician brother, the singer/songwriter/multi-instrumentalist decided it was time to break up the act and head to the Big Apple to pursue a record deal.
Even then, DeGraw couldn't sit still long enough to wait his turn at an early open mic at Wilson's restaurant and nightclub in Manhattan. Instead of going in and waiting his turn, he called ahead and lied that he had a gig later and just had to go on as soon as he arrived.
He got his prime slot, left his card at the door and went home.
The ruse paid off. The next day, club owner Debbie Wilson called DeGraw and booked him weekly for the next two years.
Using her connections, Wilson got him in front of James Diener, J Records senior VP of A&R/marketing. Diener, in turn, got DeGraw into label chief Clive Davis' office for a personal audition, putting an end to a bidding war for DeGraw's services.
His debut album, Chariot, has been on the charts for more than a year, and with the August release of a raw re-cut of the album, appropriately titled Chariot Stripped, he's still climbing.
During the same period, Podell Talent Agency chief Jonny Podell had him moving from the opening slot of three-act bills to headliner status at clubs like House of Blues, Irving Plaza and La Zona Rosa to hone his live show. In between were 20 dates opening for another slow-but-steady riser, Maroon5.
"The album's been a steady build, and I convinced the label to let me re-cut the album into more of a raw record," DeGraw said. "People who like my music are also the kind of people who like to hear more raw recordings than the original record was.
"So, we went back in the studio and took two and a half days to re-do the whole album. We just hung mics around the room, with the players in the same room with me, and we just played through. It's a more true way for a songwriter to say, 'Here are our songs' to somebody," DeGraw explained.
With the release of Chariot Stripped, DeGraw is blowing up on the charts. And his live show has also seen vastly increased numbers since Podell got him started on the college circuit opening for Sister Hazel last year.
"James (Diener) called and told me that he had somebody very special and he thought that I might feel the same way, and I did times 10," Podell told Pollstar about seeing DeGraw perform for the first time.
"I went to see him at Joe's Pub in Manhattan. I think (DeGraw and Wilson) appreciated my enthusiasm. I really thought I had the next big thing, somebody very special," Podell continued.
"It didn't hurt that Clive Davis felt the same way. I've always said, over 35 years, that Clive Davis knows; all the rest of us just guess."
With a client roster that includes established stars like Van Halen, Alice Cooper, and The Allman Brothers Band, and launching a new company after splitting with Evolution Talent in July, Podell didn't need to take on an untested newcomer. But DeGraw was different, the veteran agent said.
"I think agents, overall, hedge their bets. Overall, they have many, many clients and they all bet a certain number of them will hit. In Gavin's case, I didn't feel like I needed anybody else. I was that sure that between us, we could go all the way," Podell said.
Wilson was bowled over by DeGraw, too. She sold the restaurant, became his manager and guided him through the process from signing a label deal to recording his first album.
"When I met him, he was so young; he'd never really even been in a studio before," Wilson told Pollstar. "But the raw talent was so obvious and undeniable, I couldn't believe he hadn't been signed or developed by somebody at that point.
"I think the business is such now that so few people get it. And Clive really gets it. Being able to be signed with Clive was really what I wanted for Gavin and what I'd hoped for from day one."
DeGraw got the full treatment from his new boss, too - including a pre-Grammy Awards showcase last year for a roomful of industry execs and artists that the 25-year-old had only been able to admire from the distance of his radio. He was entertaining artists like Carly Simon, Aretha Franklin and Prince, all of whom he cites as influences.
"That was scary. If that building would have crumbled, there would have been no more music industry," DeGraw said. "You're in front of some of your idols or people who created the industry that you're in, and you want to satisfy them. You want them to love you like you love them. It was spectacular and terrifying."
DeGraw is currently out on a headlining tour, selling out many of the same clubs he'd performed in as a supporting act just a year ago, and where Podell says he'll probably remain as long as the demand keeps growing - and that could be a while.