Tell me about your background. You grew up in small-town, southern Indiana, lived in Chicago for about 20 years, and now you live in (and love) New York City. When did you first fall in love with cities? Is there something about cities in particular that you find fascinating?

I love cities like only someone from a town of 29 people can. I did not know I was a city person until I moved to Chicago after college in 1992. For a lot of people, college is a great time of personal discovery, transformation, and exploring new possibilities. That didn't happen for me in college, but it did in Chicago. Chicago itself was a massively transformational influence on my life. I owe my love of cities to Chicago and the experiences I had there.

You go by "Urbanophile" online, which translates to "lover of cities." What attracted you to cities enough that you wanted to make a career out of studying them? What does "studying cities" look like, exactly?

I actually registered the urbanophile.com domain name back in 1997. I picked it because the name I wanted was already taken. Yes, even back then it was tough to get a good domain name. So I just made up the word. But I guess I would have already have described myself as a city lover at that point in time, obviously.

I never planned to make a career out of cities. I actually started off publishing the blog The Urbanophile on the blogger platform at the tail end of 2006, using that title as a pseudonym. I didn't even put my own name on it. I was working as a consultant at Accenture and doing the blog as a hobby because I thought - correctly as it turned out - that I had insights to share on cities that nobody else was saying.

Two things made me rethink what it could be. The first is that somebody sent me a link to a competition the Chicagoland Chamber of Commerce was running for innovative ideas to boost public transit ridership in Chicago. I entered that competition and won, beating out 125 other entrants from around the world. I collected a $5000 prize, but more importantly the great PR team at the chamber managed to get a big story about it in the Chicago Tribune that included a picture of me on the cover above the fold.

This had a couple of effects. First, when your boss picks up his newspaper in the morning and your picture is on the cover, that raises questions. Secondly, once one newspaper wrote about me, other newspapers considered me a credible source to use, so I started getting featured in the press. My boss was very congratulatory about this, but I realized that a growing media profile was probably not consistent with staying at Accenture, which was always a firm that frowned on extra-curricular activities.

The other thing is that high ranking government officials started to email me asking to connect to talk about issues they were facing.

These converged to make me think I might be able to professionalize this. So I ended up leaving Accenture to see what I could do with it.

Fast forward to today and I am a Senior Fellow at the Manhattan Institute, a think tank based in New York. I do a few things. I write policy papers with ideas for cities and states. I also write articles for our in-house magazine City Journal, as well as other publications. I speak to various groups around the country on topics like economic development. And I meet with local leaders and others such as reporters to help them think through their problems.

Chicagoans like to compare their city to New York, but New York doesn't give much thought to Chicago. From a Chicago perspective, is it even a comparison worth making? And why, in your opinion, is Chicago often saddled with an inferiority complex vis-à-vis New York?

I actually don't know the origin of Chicago's second-city inferiority complex. That would be an interesting article or book to read.

I think it's natural for Chicago to compare itself with New York. When Chicago was a rising metropolis in the late 19th and early 20th century, leaders believed it was destined to pass New York and become the premier city of the country. That didn't happen, but with Chicago's stunning growth in that era and unparalleled industrial might, it wasn't a crazy idea.

Chicago and New York superficially resemble each other at a lot. Both have forests of skyscrapers in dense central business districts, elevated trains, extensive commuter rail systems, taxis, etc. Both have fabulous, globally significant cultural institutions.

So in some sense, what other city would Chicago compare itself to?

The reality is that the two cities are very, very different. Chicago definitely needs to be looking at the marketplace to see what other cities are doing. But that marketplace is much, much bigger than just New York, so fixating on that one city isn't necessarily productive.