Obst's first recorded live tournament cash came in 2009. At the WSOP, he has cashed 30 times and made seven final tables. After twice finishing runner-up, Obst won his first bracelet in 2017 in the $10,000 Razz Championship, earning $265,000. His largest cash came from a 13th-place finish at the WSOP Main Event in 2016 for $427,000.