The brothers began working on music at the age of 12 where their focus was hip-hop where they created beats for local artists such as Yukmouth. The name Hippie Sabotage was inspired by their father’s initials H.S. They initially started in the indie genre in 2005 and gradually entered the electronica genre. They continued to venture into creating hip-hop musical beats for Chicago artists like Alex Wiley and C Plus. They progressed into making electronic music, after which they headlined several music festivals such as Lollapalooza, Bonnaroo Music Festival and Electric Zoo.

The brothers released their own material in 2013 with their EP Vacants followed by The Sunny Album in 2014. Ellie Goulding posted the remix “Habits (Stay High)” with the brothers and Tove Lo, which resulted in world-wide attention, hitting number one that year on Billboard‘s Next Big Sound chart. They later released their third EP Providence in 2016 followed by their EP Options That year, the brothers refused to exit the stage and assaulted a security guard after experiencing technical difficulties at What the Festival in Portland, Oregon.