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The stage had been Jesse’s home for a decade. He plays around 150 shows a year, from Bonnaroo to the Philadelphia Folk Festival, the 30A Songwriters Festival to AmericanaFest. When the pandemic canceled concerts and delayed the album’s release, he pivoted to performing online and found a strong new connection to his fans, who had helped fund his albums all along. “My musical tribe has always been there for me,” he says with gratitude.
Though recorded in 2019, the songs off the new album click with fans online too. He and his band recorded When We Wander live in the studio, a first for his career. “I wanted to try that Jason Isbell, Chris Stapleton, Neil Young approach to live recording, prioritizing emotion and raw performances over perfection. I loved that experience.” Recorded live, the album resonates especially with the intimacy and community spirit of the online shows.
He also wrote all the music and lyrics this time, instead of working with collaborators, and took a very personal approach, including a look back. “In Spite of You” recalls his stay in a residential facility for behavior modification that traumatized him as a young teenager: “The sermons that you sold me all were fakes.” Yet he emerged to earn a degree from Berklee College of Music, net a five-year staff writer gig on Nashville’s Music Row penning material for major TV networks, and win prestigious songwriting awards. And then to become the singer-songwriter his countless fan know today, who (in the words of Music News Nashville) “bring[s] to mind iconic artist/poets like Paul Simon and Jackson Browne… [with] a performance that touches the heart like only a whisper can.”
Harold’s upbringing in northern Wisconsin was on a small, blue-collar island called Washington Island. Sandwiched between Wisconsin and Michigan, the island is solely traveled to via ferry and mainly by tourists, leading Harold and his mother, brother, and two sisters to be isolated, and spending most of his teenage years playing chords–his dream of making music only being just that.
After relocating to the west side of Wisconsin, near Minnesota, and then back to Milwaukee, Harold worked several jobs in the industry and put together a few bands—but it was nothing like the feeling of making music himself, reminiscing on his upbringing where he was raised by a single mother who encouraged him to sing and play, influenced by bands like Tom Petty & the Heartbreakers and Dave Matthews Band.