Weiss is a native of New York City. He graduated from Northwestern University with an MS in journalism in 1982. He was an Associated Press reporter in Toledo and Columbus, Ohio. From 1998 to 2005 he worked for The Blade. In 2005, he was deputy business editor of The Charlotte Observer. In 2008, he was correspondent to the Charlotte Bureau of the Associated Press.
With Kevin Maurer. No Way Out: A Story of Valor in the Mountains of Afghanistan. Berkley, 2012. ISBN0425245268
With Kevin Maurer. Hunting Che: How a U.S. Special Forces Team Helped Capture the World’s Most Famous Revolutionary. Berkley, 2013. ISBN0425257460
With Michael Sallah. The Yankee Comandante: The Untold Story of Courage, Passion, and One American's Fight to Liberate Cuba. Lyons Press, 2015. ISBN0762792876
The Heart of Hell: The Untold Story of Courage and Sacrifice in the Shadow of Iwo Jima. Berkley. 2016. ISBN978-0425279175.
With Chris Wallace. Countdown 1945: The Extraordinary Story of the Atomic Bomb and the 116 Days That Changed the World. Avid Reader Press / Simon & Schuster. 2020. ISBN978-1982143343.
Previously the Pulitzer Prize for Local Reporting, No Edition Time from 1953–1963 and the Pulitzer Prize for Local Investigative Specialized Reporting from 1964–1984