[3] Previously, he served as the deputy assistant secretary for public affairs at the United States Department of Housing and Urban Development.

In March 2002, he led a rifle platoon into Afghanistan's Shah-e-Kot Valley to engage Taliban and al Qaeda fighters as part of Operation Anaconda—a battle later written about by journalist Sean Naylor in Not a Good Day to Die.

[8][9] From 2007 to 2009, Friedman was a vice chairman and spokesperson for VoteVets.org, a political action committee and non-profit 501(c)(4) with a mission of getting veterans elected to public office.

"[13] In 2009, Friedman accepted a role as the first director of digital media at the United States Department of Veterans Affairs in Washington, D.C.

[16] In March 2014, Friedman was appointed by the Obama administration as the deputy assistant secretary for public affairs at the United States Department of Housing and Urban Development.