Caleb began his career producing wildlife documentaries in South America and the American southwest. His career in business news began at Bloomberg, where he worked as a senior television producer and was nominated for a 2003 Emmy Award. Caleb then joined CNN, serving as a Senior Producer for The Situation Room, as well as the Executive Producer of CNNMoney.com. He then returned to CNN as the Director of US business news. In 2014 Caleb formed Frog Pond Productions, a digital production and consulting company, and then joined Investopedia in January 2016 as the VP of Content. Caleb is frequently featured as a markets, economic and consumer trends expert on NBC, MSNBC, ABC Radio, Marketplace Radio and Cheddar TV, in addition to markets commentary in his daily newsletters.