I am currently on a plane to Chicago. Not only have I never been to the city before, but I know a grand total of three people there. Sure, there are people I’ve talked to over the phone and email, but in the end, they could all end up being serial killers. You never really know a person until you work out of their startup’s offices.

Originally, I had the intention of planning everything, down to every single meeting, while I was there. That quickly changed when I told Sarah about the plan. She told me quite bluntly that if I was to do that, I wouldn’t remember a single company. So as that plan went out the window, as did any semblance of a schedule.

While I have a few tentative meetings, and have spoken to a number of people in Chicago who will show me the ropes of the city, I don’t have a plan set in stone. What will I be doing? Well, that’s up to you. I’ll try to remember to post where I’ll be working during the day, as well as when I have a free lunch. It’ll be touch-and-go for a little bit, but this way I don’t have to face the pressure of two weeks of solid meetings, while at the same time making sure to meet any interesting startups.

That being said, please follow me on Twitter so that you’re up to speed on where I am, and what I’m doing. I’ll be there until the 17th, and I’ll be free at most times, aside from when I actually find time to see the city.

I’ll meet with anyone that has an interesting idea, so don’t be shy!

[Image Credit: Shutterstock]