Chicago startup extravaganza

Last night I had the pleasure of being a judge at a start-up competition/meet up put together by MidVentures here in Chicago. 25 local start-ups were chosen to be in the running for some cash and prizes, and several in addition to that just came and set up tables anyway. Myself and the other judges (the founders of GroupOn and OpenTable, a Google executive, the founder of an options trading house, and a VC partner from OCA Ventures) got to walk around for 3 hours talking to all these start-ups, then compiled our scores to come up with a top 5, and ultimately our top 1 after hearing the top 5 pitch to the crowd for 3 minutes each and answer questions from the judges.

Some random thoughts I wrote in my moleskine on my train ride home after the event:

• These were mostly early stage companies, so lots of people bootstrapping vs. having taken funding. Being largely bootstrapped ourselves, I obviously have a lot of respect for this approach but also recognize it's a tougher road.
• Because of all the bootstrapping, lots of focus in the start up pitches about how they're going to make money, customer acquisition costs, etc. There was no "we'll figure out the business model later."
• Related, I didn't meet a single team who was trying to use advertising as a primary revenue model.
• Disappointing number of founders lacking the actual skills to build and design stuff themselves. Lots of business people "outsourcing" the technology development.
• I saw very few name tags of people from big companies in the area. No Boeing, no Motorola, no McDonalds, no Kraft. Maybe they were there, but from this and other evidence I've seen, there seems to be a disconnect between the entrepreneur community and big Chicago business which is unfortunate. I think those companies would have been interested in some of the companies there last night.
• Lots of discussion about the lack of respect Chicago gets as a start up hub even though some incredibly successful companies got their start and operate here. Time to get over it though and just keep pushing ahead - there were over 400 people that showed up last night which is testament to the promotion job MidVentures did but also for the enthusiasm that already exists locally.
• The influence of Paul Graham and a few other luminaries we all read is pretty evident. Heard many "just trying to get to ramen profitable" quotes.

The winner, by the way was g2.fm.

Other start ups I saw that I really liked:

• Rent Monitor - Beautiful management software for landlords
• JoeMetric - Mobile platform for conducting market research
• Genlighten - Outsourced genealogy research using qualified librarians all around the US
• Give Forward - Personal campaign software to raise money for medical expenses of sick relatives