For ten summers, beginning in 2010, Sampson attended Gordie Sampson's four-day Songcamp in Ingonish, Cape Breton.[3] He moved to Halifax in 2011 and began playing in local clubs and bars while attending university.[4] In 2014 he independently released his debut album No Pressure No Diamonds, which was co-produced by Gordie Sampson, Dylan Guthro and Carleton Stone.[5][6]
Sampson contributed to Classified's 2016 single "No Pressure", featuring Snoop Dogg; this song was awarded Song of the Year at the 2017 East Coast Music Awards.[1][7] Also in 2017 a music video which he co-created with the band Port Cities was nominated for a Music Nova Scotia Award.[8]
Nova Scotia-based Sonic Publishing offered Sampson a publishing administration deal in 2019; he was the first addition to their newly created publishing division, Sonic Entertainment Group. Sonic Publishing also administers works by Adam Baldwin, Alan Doyle, Dave Sampson, Matt Andersen, and Matt Mays.[9]
On October 4, 2019, Sampson released his new record All Types of Ways, recorded in Nashville with fellow Cape Breton native, Gordie Sampson.[1] In October that year he was awarded his first gold record for his work Classified's "No Pressure", and also was one of five prize-winning finalists in the RBC Emerging Musician Program.[10]
Sampson has also co-written with Gordie Sampson, Donovan Woods, Alan Doyle, Matt Andersen, Neon Dreams, and Caitlyn Smith.
On April 16, 2022, Dave Sampson played live in the town of Sydney, Nova Scotia.[9]