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He started his label just as the music industry was beginning its struggle with illegal downloading

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Ten years ago, Jeffrey Remedios left his job at Virgin Records Canada to start a business – his own music label called Arts & Crafts. At the time, the music industry was starting to undergo massive changes. Digital music was in its infancy but illegal downloading was beginning to affect the business. Needless to say, people thought he was nuts. “My parents thought I was crazy for leaving a full-time job to start something new in an industry that was falling apart,” he says.J.P. Moczulski/The Globe and Mail

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One of the artists signed to Arts & Crafts is Canadian singer-songwriter Feist, seen here performing in August of 2012. Mr. Remedios’s big idea when he started Arts & Crafts was to create a partnership between artists and the label. He wanted to manage the musician, own the publishing rights to the songs and act as the person’s record label. That “360 deal,” as it’s called now, is becoming more common, but it wasn’t the norm 10 years ago.NTB SCANPIX/Reuters

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Musician Moby, seen in the Arts & Crafts office in Toronto in August of 2013. Mr. Remedios began experimenting with digital releases and other non-traditional ways to promote music. A big part of Arts & Crafts’s success came about because the company was willing to try new things. One of the biggest challenges Mr. Remedios faced was illegal downloading. Whenever he would send advance music to reporters, retailers and other people who needed copies before the release date, it would invariably end up on a file-sharing site.Gloria Nieto/The Globe and Mail

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Another artist signed to Arts & Crafts is Australian singer-songwriter Sally Seltmann, formerly known as New Buffalo.Cybele Malinowski

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Amy Millan is also signed to Arts & Crafts. Mr. Remedios has experimented with giving away music for free. One of his artists, Timbre Timbre, released a record in mid-2009, but Mr. Remedios says it wasn’t doing as well as he had hoped. On Halloween he put the album on his site and allowed people to have it for nothing. Nearly 40,000 people downloaded it, he says. Soon after, album sales picked up and touring opportunities opened up for the band. Giving away the record enabled people to listen to it and talk about it, and that broadened the fan base, he says.Yan Lassalle

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Bell Orchestre, one of Arts & Crafts’s bands, once toured with Arcade Fire. Arts & Crafts celebrated its 10th anniversary this year, and while the industry looks a lot different than it did a decade ago, Mr. Remedios says it’s an even scarier place than it was when he started the label. It’s harder than ever for artists to make a living, and now that anyone can release music online, musicians have a more difficult time getting noticed.Delphine Bally

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Mr. Remedios’s company is still innovating, he says. Most of the chances he and his artists have taken have paid off. He has 33 employees and offices in Toronto, Los Angeles and Mexico, and he’s confident that he’ll still be putting out music 10 years from now. Most importantly, though, his parents no longer think he’s making a mistake. “They’re super proud of me,” he says. “They don’t think I’m crazy any more.”J.P. Moczulski/The Globe and Mail

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