Craig actively invests in and advises technology start-ups, many of which are founded by military veteran entrepreneurs, through his company, Moonshots Capital, which he co-founded with Kelly Perdew.

Craig is the Co-Founder (along with Joseph Kopser) and former Chief Operating Officer of RideScout, a mobile app that shows users how to get from point A to point B by providing real-time ground transportation information. RideScout was acquired by Daimler (Mercedes-Benz) in September 2014 and recently merged with GlobeSherpa to form moovel N. America.

Craig is also a Co-Founder, with Jason Dempsey and Ken Robbins, of MILLIE, providing military families with information and on-the-ground support to ease the stress of frequent relocations, and Co-Founder of APX Labs, developing augmented reality software for smart glasses to enable the hands-free industrial and commerce workforce.

Before he became an entrepreneur, Craig spent 17 years in the Army, most of that time as an Intelligence Officer serving in support of the National Security Agency (NSA). Craig deployed to Afghanistan with the Joint Special Operations Command where he earned the Bronze Star. He also served as an Assistant Professor of Political Science in the Department of Social Sciences at West Point, NY.

Craig received a B.S. in Political Science from the U.S. Military Academy at West Point, where he was their first Truman Scholar, and he received a Ph.D. in Political Science (minor: Econometrics) from Columbia University. In 2015, Craig was selected by HillVets as one of the 100 most influential and impactful veterans in the United States. Craig was recently selected as a member of the 2016 Class of Henry Crown Fellows of the Aspen Global Leadership Network at the Aspen Institute.

Craig is married to Lawton Cummings, a former Law Professor and television legal analyst. They have two children, Addison (13) and Cooper (11), and reside in Austin, TX.