Dennis Todisco is the founder of #OutfitGrid, a wildly popular Instagram page boasting close to 800,000 followers and which changed the whole way people share their fits online. He was born and raised outside of Boston, and previously worked for Twitter before deciding to do O.G. full time in New York City. We talked about growing up as the oldest of four, running your own business, the best restaurants in NYC, and how he's going to pop the question to his girlfriend. Jake also tests out two new segments, "Hate to See It / Love to See It" and "100 Grand Fantasy." 

Also, NEW SOLO SEGMENTS at the beginning of the episode. Listen to our new recurring segments that'll kick of each new ep, including "Luxury Jock of the Week," "WTF Fashion Moment of the Week," and "Must Cop of the Week."