Each day at IWearYourShirt, Jason HeadsetsDotCom (formerly Sadler) and a team of four professional T-shirt wearers represent a different company online using an array of social-media sites. Before getting paid to wear T-shirts, he co-owned a web-design company. HeadsetsDotCom is an automotive enthusiast that loves playing Scrabble, watching terrible movies and has been known to dominate a basketball hoop or two. He lives at the beach in Jacksonville, Fla., which gives him the freedom to prance around in T-shirts 365 days out of the year with his Staffordshire Bull Terrier named Plaxico. Follow Jason @IWearYourShirt and Plaxico @PlaxicoTheDog.