Bennett attended Washington University at St. Louis where he doubled majored in Economics and Finance and minored in Mathematics. An accomplished student, Bennett earned Dean's List and received the John M. Olin Prize for Excellence in Economics (prize for best economics honors thesis). He graduated summa cum laude with a Distinction in Economics in 2012.
While in college, Bennett was the Co-Founder and COO of BandScramble, a musical online social networking platform that connected musicians to bands in a comprehensive online community. He was an Emerging Markets Trader at Goldman Sachs and an Associate at Techstars before become the Co-Founder and SVP of Product at Bluecore, a customer behavior data firm. The company has over 200 major retailer clients across the electronics, automotive, and apparel industries with brands such as Nike, Gap, and Staples using their service. They have raised $28 million in capital from investors such as FirstMark Capital and Georgian Partners.