the second city is now known as the startup city. >> as most of the city gets ready for the start of school, entrepreneurs of 1871 prepare for chicago's biggest tech event, demo day. >> there's a reason to come to chicago as entrepreneurs. i think there's some geek chic going on. >> sammy is a resident and entrepreneur. now he's ceo of mash.com. sometimes he even plays celebrity matchmaker. >> we know we can find you some great first dates. >> he helps run chicago's digital startups. >> 1% acceptance rate is pretty crazy. >> these startups gear up,