Early career and professional triathlete

O'Brady moved to Chicago, where he took a job as a commodities trader following the accident. He learned how to walk again, and for a year focused on physical rehabilitation. He began to train for triathlon: swimming, cycling, and running.^[17]

In May 2009 he won a sprint-distance triathlon in Racine, Wisconsin, and in August 2009 he placed 1st overall amateur in the Olympic-distance Chicago Triathlon.^[18] He then placed in the age-group nationals in Tuscaloosa, Alabama, which earned him a position on Team USA at the 2010 World Triathlon Championships in Budapest, Hungary. In late 2009, encouraged by his mentor, financier Brian Gelber, O'Brady quit his job to pursue a career as a professional athlete. With Gelber as a sponsor, he moved to Australia to train in a more temperate climate. O'Brady has since completed more than 50 triathlons, ranging from sprint distance to Ironman competitions.^[15][19]

O'Brady completed Ironman Japan in August 2015, his final triathlon race and placed 6th in the Pro division.^[20]

Endurance and adventurer

Following his retirement from triathlon, O'Brady and his then-fiancée Jenna Besaw created Beyond 7/2, a not-for-profit world record journey to inspire kids and communities to live active, healthy lives.^[2] O'Brady aimed to conquer the Explorers Grand Slam (Last Degree), an adventurer's challenge to climb the highest mountain on each of the seven continents and complete expeditions to both the North and South Poles in world record time. O'Brady and Besaw financed the Grand Slam attempt through sponsorships from Gelber Group, Nike, Columbia Sportswear, and Mountain Hardwear, among others.^[2] The project raised funds and awareness to benefit the Alliance for a Healthier Generation, a non-profit organization that aims to combat childhood obesity.^[21]

O'Brady left Portland on December 25, 2015, flying to Chile and then Union Glacier in Antarctica. In January 2016, O'Brady began the Explorers Grand Slam.^{[citation needed]} O'Brady was joined on parts of his Beyond 7/2 journey by various climbing partners and as a paying client with guides including polar explorer Eric Larsen, Vern Tejas and fellow mountaineer Maria (Masha) Gordon.^{[citation needed]}

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.^[22] 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.<^{[citation needed]}

O'Brady completed both the Bass and Messner lists for the Seven Summits speed record,^[23] climbing Everest, Aconcagua, Denali, Kilimanjaro, Elbrus, Puncak Jaya, Vinson (the "Messner version").

O'Brady is the fastest^[3][5] 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.^[24]

In the summer of 2018, aided by a small support team, O'Brady broke the speed record for the 50 US High Points Challenge when he climbed the highest point in each of the 50 states of the United States in just 21 days, 9 hours, and 48 minutes. While reaching each high point, he invited local residents of all ages and backgrounds to come out to join him in setting a new world record; this piece of the project was coined "The Forrest Gump Effect".^{[25][26][27][28]}

On December 26, 2018, O’Brady completed a solo and unsupported crossing of parts of Antarctica from the Messner start to the beginning of the Ross Ice Shelf by following the South Pole Overland Traverse ice highway.^[29][30] He completed the 932 mile journey in 54 days,^[31] finishing ahead of explorer Louis Rudd who was also attempting the feat.^[32] Peter Wilson has disputed this claim that the trek was unassisted due to the ice highway being groomed and maintained.^[32][33]

In December 2019, O'Brady acted as the first mate in a six-man team on the first man-powered crossing of Drake Passage, the body of water between South America and Antarctica. It took 13 days and 700+ miles in a boat that was 29 feet long.^{[34][35][36][37][38]}

In June 2021, O'Brady summited Mount Everest alongside his wife, Jenna Besaw, completing her first summit of the mountain. ^[39]