Herb graduated from Santa Clara University with a Bachelor's degree in communication. He went on to attend Columbia University Graduate School of Journalism receiving an M.S. in journalism.  
Prior to CNN, Herb was a defense reporter at POLITICO, where he wrote about the Pentagon, Congress and defense industry political influence, and did a stint as author of the "Morning Defense" newsletter.  
Herb was also a national security reporter at The Hill and a Washington correspondent for the Minneapolis Star Tribune, where he covered the short-lived presidential campaigns of former Minnesota Governor Tim Pawlenty and former Rep. Michele Bachmann.