This week on A Waste of Time with ItsTheReal, we welcome singer/songwriter Dermot Kennedy to the Upper West Side! Dermot, who hails from a small town outside a small town outside Dublin, Ireland, talks growing up with intermittent internet, an acoustic guitar, no pop culture references, and the most successful musicians he was aware of being his cousin's cover band. We get into his undisciplined busking career in the streets of Dublin, making just enough money to work for a week in a proper studio, his parents being super supportive of his dreams at 18 years old, the realities of producers taking ideas and credit, how he never wanted to be a local celebrity, and how an Ed Sheeran cover gave him viral success. Dermot recalls his first big break thanks to a video app that brought him down to a Florida convention center, how he didn't want to blow up off of other peoples' music, doubling down on his own compositions, putting everything he had into EPs that didn't go anywhere, how a change of mind led him to release his songs as singles, and walking into a venue in London to a large crowd that found him organically through Spotify. We discuss independent success, how labels and publishers came knocking on his door, feeling like he'd already been through the ringer and what ultimately sold him on Island in the UK and Interscope in the US, and how he's taken the States by storm with clever live rearrangements of his own songs as well as Joey Bada$$ and Kanye covers. All that, plus playing Tiny Desk, recording in Brooklyn and LA, the keys to performing the streets of Dublin, teaching himself piano, the status of his Spotify account these days, some major live gigs he hints at playing in 2020, and so much more!