Mayor Emanuel: What’s the name of this deal? 

A Drink With.

This is an actual deal? It’s not just like made up for this?

Usually we have a drink so next time, they’re on us.

Do I have a skeptical look on my face? I can’t believe you guys make money for this. That’s great. [Turns to Assistant Press Secretary, Caroline Weisser] Why did I study Hegel and Kant in college? And they came up with an idea that’s more productive than my idea?

What excites you most about Techweek and Chicago’s tech community? 

It’s really the amount of energy here and how big it is this year. I have the context from last year when I came and gave a speech and it’s exciting because the energy here is reflected by the amount of energy that happens year-round, not just this weekend. We are actually grabbing everyone’s attention as a city with the new inventions and the companies. You have GrubHub and a lot of other companies that are filing for IPOs and talking about their acquisitions. It’s not an accident that what used to be local-level funding is now attracting coastal. Seriously, now they have to have offices here just to stay on top of it and that tells you anything you need to know.

Do you order off of GrubHub?

I don’t have to, I just call them. No, but seriously, yes I do! 

Where do you think we’ll see Techweek 10 years from now?

Well, there’s no longer going to be the SXSW. Techweek will be the Midwest mecca.

Your days are jam-packed. Name one thing you can’t start your morning without doing.

I always exercise, seven days a week. I can give it to you, I’ve been doing this for 30 years. [Three days during the week] I swim a mile and bike four miles. [Two days during the week] I bike 25 minutes on random, level 14 and do 15 minutes on the elliptical. [Then on my off days from the gym] I’ll go to a private yoga class or I will run 3.5 miles.

We’re exhausted just thinking about it. Are you a coffee drinker?

I’ll have a Big Shoulders Coffee on [certain days] because it’s right near the gym.

You’re quite regimented. It must come with the job.

I have bizarre little things. I could tell you just how [regimented] I am but, never mind.

Who is one of the first people you go to for advice?

You know, that depends.

On the situation?

Yeah. I mean, if it’s political I talk to my friends who have been with me like David Axelrod, Paul Begala, James Carville, John Cooper, Stan Greenberg, my whole staff. It’s the people who have been with me and I’ve been with them for years. If it’s about friendships or things like that, obviously I go to my wife. I’ll also talk to her about office stuff. I’m fortunate because if it’s on policy I’ve called on the president, the former president. The good news is I have many options.

If you could have a drink with anyone, who would it be?

I already have it! This is all I care about, this question right here. I’m only doing this interview for this question!

The anticipation is killing us.

Abraham Lincoln. Really, I’ve got like 6,000 questions for that guy.

Did you see the movie “Lincoln”? 

Yeah, I saw the movie “Lincoln” and right now I’m reading “Gettysburg: The Last Invasion” which is probably the fifth book I’ve read on Gettysburg. I can give you Antietam, I can give you Bull Run, I can give you Vicksburg Campaign.

And you still have time to read books! You’re superhuman.

I read a new book every three weeks. Every three weeks I finish a book.

What do you think Lincoln would drink? Set the scene.

He would probably have a bourbon and I would have a coffee because I’d want to stay awake for the interview. He’d have had a more stressful day. He’d be on his 11th general and I’d have only one police superintendent. [Laughs] No, but don’t you think? I mean, think about it…

We get Lincoln as an answer often.

Who else asked for Abraham Lincoln?

Scott Kluth. Lincoln must be popular in the tech community.

You know why? I’ll tell you why. Here’s my guess. Now seriously, successful people are only successful because they’ve actually learned something from failure. The reason Abraham Lincoln was the greatest president was because for every one of his failures he discovered something, he learned something and he was able to apply it in the next situation. And as entrepreneurs, they have to fail before they succeed.

That’s the perfect ending to our interview. 

Good luck on your venture. Because I love this idea … But if you guys edit any of this out, I swear!


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