Weekend in Chicago (Cubs, Roger Creager, Rooftops)

Weekend in Chicago (Cubs, Roger Creager, Rooftops)

Erik, Arvind, and I (all UNC alums) spent last weekend in Chicago. This is my entrepreneur crew. I've worked with both of these guys in the past in entrepreneurial ventures including Preation, MainBrain, Factrivia, and iContact.

We have a lot of fun and categorically bore everyone around us to tears while getting engulfed in business ideas and discussions of what might be. We get together a few times a year for one reason or another. Although we've all talked for years this was actually the first time Erik and Arvind met in person.

We first all worked together on MainBrain back in 2002 while Arvind was still in Sydney, Australia. Erik had the first rooftop gathering of the year which was the prompt for the get-together. His apartment building has an exceptional view of the Chicago skyline about 3 miles south.

Apparently the weather had warmed up the previous week and short notice was provided via email. I left Raleigh/Durham at 5PM on Friday and it was 86 degrees, upon landing in Chicago it was 55 degrees and very windy. As an aside, I left Chicago to go on to Las Vegas for a conference and thus left Chicago on Sunday at 5PM at 52 degrees to then arrive in Las Vegas at 7PM at 88 degrees. It's hard to pack for this.

On Saturday night we saw Roger Creager at Joe's Bar in the downtown after spending the day being tourists. He put on a great show as usual. We took the train down to the river and did Wendella Boats' architectural river tour which was my fourth time on that trip. It was fun as usual, great content, cold as all heck. We also had cocktails at the Signature Lounge at the top of the John Hancock Center when the tour finished.

Of note, the new Trump building is going up nicely and it looks incredible. It's right on the Chicago river and it's very tall. I would love to have a condo in there near the top.

On Sunday the three of us joined the graduating MBA class of Notre Dame on one of the roof decks on Sheffield street overlooking Wrigley Field. We had a great time. Chicago is a great city.