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.