BILLBOARD LIVE MUSIC SUMMIT Andrew McMahon Talks Playing the Long Game Into an Unlikely Hit & Solo Success at Billboard Live Music Summit

'If I Could Fly, Then I Would Know: The Making of Andrew McMahon in the Wilderness' panel during the 2018 Billboard Live Music Summit + Awards at the Montage Beverly Hills on Nov. 14, 2018 in Beverly Hills, Calif.

The former Something Corporate frontman and his team discussed their strategies for staying connected to the fans and true to McMahon's unique style.

Singer-songwriter Andrew McMahon has had a unique career trajectory among artists of his generation. As the leader of three different successful music projects over the past 20 years -- Something Corporate, Jack's Mannequin and Andrew McMahon in the Wilderness -- he's been able to reinvent himself time and again, all while sustaining a loyal fan base and continuing to write songs that are at once commercial and true to his distinctive, piano-driven sound. That he did it all while surviving leukemia, which he was diagnosed with in 2005, makes his story all the more remarkable.

At the Billboard Live Music Summit on Wednesday (Nov. 14), McMahon joined moderator and Billboard on-air host Chelsea Briggs and members of his team to reflect on his journey from unsigned pop-punk wunderkind to celebrated solo artist. Joining him on a panel entitled If I Could Fly, Then I Would Know: The Making of Andrew McMahon and the Wilderness were McMahon's longtime agent, Josh Humiston of APA; APA's Elizabeth Dixon, who oversees McMahon's tour marketing; Garrett Capone, VP of radio promotion at Crush Music; and Alex Maxwell, national tour promoter for Live Nation. Together, they painted a portrait of an artist who's built his career through forging close connections with his fans, a tireless work ethic and always staying true to himself.

"If there's anything to take away from this panel, as far as I'm concerned, it's that you have to be willing to play the long game," McMahon told the crowd at the Marquesa Ballroom at the Montage Beverly Hills. He pointed in particular to the success of his first single as Andrew McMahon in the Wilderness, "Cecilia and the Satellite," a song he and Capone worked on for months before it broke through to become the biggest hit of the singer-songwriter's career.

"We all felt the song was special," said Capone, "and given the opportunity it would be what it ought to be, which is a massive hit song." To achieve that goal, Capone and his team sent McMahon out a promotional tour that included gigs in everything from barns to conference rooms -- a strategy Capone said the singer was reluctant to embrace at first, though McMahon good-naturedly shot back, "I didn't take much convincing, did I?"

Everyone on the panel agreed that they were fans first, which made it easier for them to rally behind McMahon's career. "I started as a SoCo fan in high school," said Dixon, using the fan nickname for McMahon's first band, Something Corporate. "So it's fun for me now to have Andrew as a client and a friend." Maxwell echoed this, saying she had been listening to McMahon's music since she was 15 and was thrilled when, after leaving her role as talent buyer at the Troubadour to join Live Nation, she learned that McMahon would be her first client. Though the independent-minded artist "had some reservations about Live Nation," Maxwell's obvious affinity for his fan base eventually won him over. "Andrew obviously loves his fans and I wanted to make sure that he knew that we had their best interests at heart."

With Live Nation's help, McMahon has continued to build on the success of shows like his acclaimed performance at Coachella in 2015, when he and his production team unleashed a swarm of balloons that floated over the crowd before bursting and raining down confetti. "That became the model for how to produce our live show -- make this whimsical, make it strange, make it look beautiful," said McMahon. Since then, as he's played larger venues, the artist's repeated message to his team has been: "How do we make the show as big as it can be but still feel intimate?"

Andrew McMahon in the Wilderness' third album, Upside Down Flowers, comes out Nov. 16 on Fantasy Records. McMahon said that after four years of near-constant touring and recording with his band, for this one he hunkered down with producer (and fellow Crush artist) Butch Walker in his home studio and "made a record when no one was looking." "I wanted this record to just be mine," he said. "That's what this album is -- this distillation of this amazing little break I had at home where I didn't feel like I had any pressure on me."

"All of his albums have a personal touch but this one is even deeper," said Humiston, who earlier in the panel told a story of doing shots with McMahon's parents when seeing the then-teenaged singer and Something Corporate, as an unsigned band fresh out of high school, play a sold-out show at the House of Blues in Anaheim.

McMahon, looking back on those early days, said his career since then has already exceeded his expectations, citing the hits "Cecilia and the Satellites" and "Fire Escape" and opening for one of his childhood idols, Billy Joel, as career milestones. "If I had to take my ball and go home right now, I would be like, 'Killer!'" he said. But he's not ready to quit yet.

"As I get further along this road," he said, "I find myself going, 'What's the next thing?'"