Smiley is a journalist and trained lawyer who in May 2017 co-founded the sports betting industry publication Sports Handle, which he continued to lead after the site’s acquisition by Better Collective in June 2019, until August 2023. He continues to monitor the regulated iGaming and U.S. sports betting industries through the lens of a passionate sports bettor and DFS player.

Before that venture, Smiley served as a staff writer for FOX Sports and has contributed to publications including SI.com, New York Magazine, and ESPN, among others. Smiley is drawn to good stories and clean writing and especially enjoys topics involving consumer protection and public policy. He is usually listening to music and does not make plans on Sunday in the fall due to his commitment to watching at least a part of nearly every NFL game.

Smiley currently serves as Chief Content Office for Third Planet, LLC, which owns and operates the websites Casino Reports and Lottery Geeks.