O'Brady became the fastest person (male) to complete the Explorers Grand Slam (Last Degree) when he reached the summit of Denali in Alaska on May 27, 2016, and set a new speed record of 139 days. He bested the previous male record of 197 days set by Richard Parks in 2011. O'Brady is the 36th person to complete the Explorers Grand Slam (Last Degree) and the current record holder. O'Brady completed 10 expeditions in total to fulfill both the Bass and Messner lists.
O'Brady is the fastest to complete the Three Poles Challenge, an adventurer’s challenge to reach the North Pole, the South Pole and the summit of Mount Everest. He began the challenge in Antarctica on January 10, 2016, reached the North Pole on April 19, and summited Mount Everest on May 19, 2016.