Jay, alongside industry competitor and CardRunners professional Taylor Caby, featured in a Forbes Video Network documentary[1] that explored the world of online poker-coaching as an emerging business in 2007.

The DeucesCracked brand was founded in January 2007 with Rob Cole, Joe Tall, Chris Vitch, Chuck Danielsson, and Jay Rosenkrantz as the executive officers.

On 9 July 2009, DeucesCracked hosted a fund-raising Connect Four competition and auction, raising money for the Lili Claire Foundation.

In November 2009, Jay's co-star and poker professional Dani Stern joined Deucescracked as an executive producer after leaving a rival training site, PokerSavvyPlus.

The show included strategy discussion and an interview with a prominent member of the poker community; several members of the site have featured as guests, as have other notable players including Tommy Angelo, Matt Flynn, Terrence Chan, Andrew Robl, Justin Smith, Dan Harrington, Cole South, Phil Galfond, David Peat and Bobby Hoff.