Corner Office: Island Records President David Massey on His Hot Streak of Hits, Betting on Shawn Mendes

Adam Krauss
President of Island Records David Massey photographed in his New York office in 2014 by Adam Krauss.

The label exec on his hot streak of hits (Iggy Azalea, Kiesza), learning from his mom and betting on Shawn Mendes.

The history of the music industry may yet be written by David Massey, 56, who has filled 35 volumes of his diaries with experiences that go back to swinging London. In 1962 his mother, Marion, began managing fledgling pop star Lulu, and he grew up “absorbed with the business,” he says. Massey started out managing Wang Chung in 1982, transitioning to the label side (and trading London for New York) in 1991, when he became vp A&R at Epic, and counted Oasis among his first signings. In 2007, he left Sony for Universal and a chance to run his own label, Mercury, expanding his portfolio in 2013 to include president of Island, where he signed Avicii and brought Iggy Azalea to Island Def Jam. In April, the two labels split, and Massey, married with a grown son and daughter, has quickly established Island -- which has a staff of just 28, but works hand-in-hand with the Republic radio promotion team -- as home to a diverse group of newly minted hitmakers: Kiesza, whose debut single, “Hideaway,” topped the U.K. singles chart (it moves to No. 53 on the Billboard Hot 100 dated Sept. 27); Tove Lo, whose “Habits” is a top 20 alternative radio hit, and has topped the Hot Rock Songs chart for four weeks; and 16-year-old Vine sensation Shawn Mendes, whose first EP entered the Billboard 200 at No. 5.

What did you learn from your mother?
Everything. She took me everywhere with her. My twin, Stephen, who loved football, went with my father to matches. Hanging out with my mom was the greatest training. I remember in 1967 being at home and her getting calls from lawyers -- “ ‘To Sir With Love’ is No. 7 with a bullet ... it’s No. 3.” I became fascinated by the whole process of the Billboard charts. I grew up with Lulu almost as a sister -- she lived with us when she first started, and she was 15, about Shawn’s age. It makes me very comfortable with young artists, because it’s how I grew up.

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You went to law school, then decided to become a manager.
When I graduated it took me some time to come to terms with the fact that I wasn’t going to be a politician and a high court judge, but I would end up like my mom. I met a band I really wanted to manage, Wang Chung, and I said to her, “How am I going to raise this with them? I’ve never managed before. I’m 22 years old, they’re all 28.” She said: “Keep talking to them, and eventually they will ask you to help.” And that is what happened.

What made you leave management for Epic Records?
Wang Chung split up and these producers I managed called Jolley & Swain split up -- they produced all of the Bananarama hits, Spandau Ballet, Allison Moyet. [Then-senior vp domestic operations] Michele Anthony called me in April of 1991 and said, “We want to create a creative environment out of Sony, and we want people who haven’t done A&R before coming in fresh.” It felt like the right thing to try. I thought it would be a two-year process; I did not intend to stay.

But you did for 15 years. What made you move to Universal in 2007?
That jump was driven by [then-IDJ chairman/CEO] L.A. Reid and Steve Bartels. Getting into the Universal system and learning from L.A., who I saw as the best A&R person in the business, felt like an opportunity not to be missed. It did prove to be a difficult road.

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Why?
My first week, I went over to L.A.’s assistant and said, “Can we fix a time for me to come and see L.A.?” She looked at me like I had two heads. “You just walk in and talk to him.” It was a culture shock. Fifteen years at Sony, which styles itself as the Harvard of the music business, or it certainly did when I started, into the rough and tumble of IDJ.

The recent separation of Island from Def Jam -- how did that come about?
IDJ was created as a cost-saving device. It was a shotgun marriage between two cultures for pragmatic reasons. What is going to be clear at the end of the year is that both the newly formed individual labels are going to benefit liberally from it. Def Jam is killing it with Iggy, which we started together, and they’re going to have a very interesting fourth quarter. And Island is reinvented as this nimble, almost boutique-level label that wants to do fresh, innovative things.

Island signed Shawn Mendes, who had built his following on Vine. Can you judge an artist in six-second clips?
His stats are remarkable, so there’s a response to him that is truly organic, but it was really nothing to do with the stats. I would’ve signed him within three minutes of him sitting down in my office. I knew for sure. I’m hearing the new songs that he’s writing, and he’s got the troubadour quality of an Ed Sheeran but he’s also got that populist across-the-board, across-the-nation feel of someone like Taylor Swift.

You’ve reunited with Nick Jonas. He appeared recently on NBC’s Today, as well as in a couple of gay clubs. He seems to be rebranding himself.
Very much so. I signed him as a solo artist when he was 10, and the initial vision for Nick was a soulful kid. When the Jonas Brothers decided to split, Nick and I had a conversation the next day. We have this soulful contemporary direction -- it enables him to use his falsetto, and there’s groove and warmth to it. Playing in gay clubs is all about widening the audience, and the gay audience is a tastemaker audience who recognize great music.

What’s your management style?
Collaborative, but assertive. I work 24 hours a day, and if you’re going to work with me I’m going to need you to commit like I am. But our team is so inclusive. Everyone knows what’s really going on, and there’s a sense of no hierarchy but there is structure. It’s very organized. I believe leadership is important. So I want to be focused and decisive and calm at all times.

This article first appeared in the Sept. 27th issue of Billboard.