From 2007 through August 2010, Gross was a senior editor at Newsweek, where he wrote the "Contrary Indicator" column.

"Before joining Newsweek in the spring of 2007, Mr. Gross wrote the "Economic View" column in the New York Times, was a contributing writer to New York, and contributed regularly to magazines such as Fortune and Wired. From 1998-2007, Gross served as the editor of STERNBusiness, a semi-annual academic magazine on economics and management published by the New York University Stern School of Business".

For Newsweek Gross wrote the weekly "Contrary Indicator" column. He also wrote a twice-weekly "Moneybox" column for Slate, which also appeared on Newsweek.com.

In September 2010 it was announced that Gross was joining the staff of Yahoo! Finance. In an early Yahoo Finance column, Gross was identified as "economics editor and columnist".