Due to his success as a high-stakes online player, he appeared on multiple seasons of GSN's High Stakes Poker.

Galfond is originally from North Potomac, Maryland and attended Thomas Sprigg Wootton High School and the University of Wisconsin–Madison.

The final table featured a number of well-known professional players including Phil Hellmuth, Daniel Negreanu, John Juanda, Kirill Gerasimov, Johnny Chan, David Benyamine, Brian Rast as well as online star Adam 'houdini' Hourani.

[11] Galfond finished in 18th place at the 2006 World Series of Poker Circuit event in Grand Casino Tunica, earning $22,895.

[14] According to Galfond, he chose “OMGClayAiken” as the antithesis of the “macho” screen names that are prevalent in online poker in hopes that other players would be embarrassed to lose to him.

The first six challengers were Bill Perkins, Brandon Adams, Chance Kornuth, Dan 'Jungleman' Cates, and online poker players 'ActionFreak' and 'VeniVidi1993.'

In addition to the money won or lost on the poker table, Galfond and his challengers had large side bets that they were competing for.

[25] In October 2020, Run it Once was one of several entities named in a $330 million defamation lawsuit brought by poker professional Mike Postle.