About 230 million Americans live in cities. "City" is a broad term and encompasses everything from Chicago and New York to Des Moines and Topeka. And the larger the city, the more unique its issues are, for good or bad. 

As the third largest city in the country — and the largest between the coasts — Chicago carries with it a lot of baggage. Its population is down almost a million people from its peak, its finances are in ruins, it remains largely racially segregated, and in some neighborhoods violent crime has spiraled out of control. But Chicago also has a lot to offer. It is the second-most visited city in the United States, it routinely tops "best city" surveys (by Condé Nast, Time Out, and Bon Appétit), its architecture is critically acclaimed, its in the middle of an unprecedented building boom, and some of its neighborhoods are undergoing massive changes and development. 

In short, Chicago is a microcosm of other cities. 

Aaron Renn is a Senior Fellow at the Manhattan Institute in New York City where he studies cities and helps craft urban-focused policies. He contributes to City Journal and writes the blog "Urbanophile." Here, he explains how he got his professional start in Chicago, how the city was formative for him, and why Chicago has the best chance to land Amazon's HQ2.

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. 

What differentiates a high growth, high opportunity city, like Houston or San Jose, from stagnant cities, like Chicago or Cleveland? What systems and structures within a city determine its fate?

Chicago is not a stagnant city. It's true that the Chicago region often looks unimpressive statistically, and for the same reason the rest of the Midwest does: the hangover from deindustrialization. However, the Central Area and North Side of the city, as well as some suburbs, are doing very well. The Loop and surrounding areas are among the most dynamic in the country. 

Having said that, Chicago lags the coastal boomtowns in areas ranging from per capita income to venture capital. Part of that is because Chicago is a diverse economy. Diversified positions preserve wealth, but only build it slowly over time. It takes concentrated bets to get rich fast. Or go broke fast as the case may be. Look at what happened to Detroit. Live by one industry, die by that industry. Some of these boomtowns that are too dependent on a single industry may end up running into struggles down the road - even Silicon Valley. Do you want to be the tortoise or the hare?

Chicago does have problems. The first is its severe fiscal problems, which affect not just the city but every level of government in the state. This is going to impose a lot of pain at some point. For some people it already has, as property taxes have been going up. The second is that it lags the coastal cities as an elite, global talent magnet. Chicago is great at sucking in Big Ten grads. But immigration levels have been falling, and it needs more A+ caliber talent too. Third, Chicago's culture is that of the closed network. It's a clout driven town where who you know matters a lot. Outside disruptors aren't necessarily welcome, at least not until they've already become very successful and wealthy. These are the big three things that, if fixed, would propel Chicago to the next level. But again, the core of the city is already doing very well in many ways. So there may not be that much appetite for change at this point.

You mention that Chicago is a closed circuit, clout driven city, and what matters is who you know. I think that a lot of people who are from Chicago, and who might not have lived anywhere else, find that to be entirely natural and would expect most cities to run that way. Can you speak a little about how other cities are organized, and why having an ‘open system,’ so to speak, can lead to success down the road? And can Chicago ever create that kind of open system?

Many cities do not run that way. Silicon Valley is famous for its open networks. In her book Regional Advantage, AnnaLee Saxenian contrasted the open, network driven culture of Silicon Valley versus the more insular, vertically integrated corporate model that predominated in Boston's Route 128 corridor. This network enabled Silicon Valley to clearly eclipse Route 128 to become the undisputed tech center of America.

Similarly, Sean Safford's dissertation "Why the Garden Club Couldn't Save Youngstown" contrasted the social networks of Allentown, PA, which connected many different groups to the ones in Youngstown, OH, which simply reconnected the same people over and over. He concluded that these more open social networks helped Allentown better adapt to the collapse of its steel industry than Youngstown did.

Ask a simple question: can you get a meeting with somebody? I would estimate that of all the people I've ever tried to connect with over my life, around half of people who declined or didn't respond to me were from Chicago. Admittedly, that's not a huge sample, and I did live there a long time. But in my experience, Chicagoans who get a little success have a tendency to adopt a "too cool for school" attitude. 

You also see it in the lack of dissent in the city. During the ill-starred Olympic bid, progressive commentator Ramsin Canon observed, "With big city economies cratering all around him, the Mayor was able to raise in the neighborhood of $70 million dollars to fund the Olympic Bid. At the same time he was able to get everybody that mattered–everybody–on board behind the push for the Olympics. Nobody, from the largest, most conservative institutions to the most active progressive advocacy group, was willing to step out against him on that issue." The City Council has been a rubberstamp committee for a very long time. 

One of the great books on Chicago politics is called We Don't Want Nobody Nobody Sent. A lot has changed in the city since the old machine days, but that mindset still has a hold, and clout is still very much important in Chicago across the board. You're either part of the in-group, or you've got a big problem on your hands.

If getting an investment, making a sale, or even just getting a meeting depend heavily on your connections or having some kind of an in, then outside talent that doesn't already have a big reputation operates at a disadvantage. That hurts Chicago relative to cities where that talent can get the opportunity to shine. I'm not the founder of a company, but it is interesting that it was a think tank in Manhattan that offered me a position, not anybody in Chicago. I suspect this sort of thing happens far more often than people know. 

I think there are some changes happening, particularly with the rise of the tech industry. Everybody understands the need for flexible, dynamic, open, global networks to becoming a strong tech hub.  If a lot more people from outside, particularly from outside the Midwest, started coming, that would help. So would the rise of independent local power bases. For example, imagine a tech founder making a billion dollars on his startup, then becoming something of a maverick who wants to shake up the system.

Regionally, the Midwest is losing people to the South and the coasts. Do you ever see that trend reversing? What can Midwestern cities (and Chicago particularly) do to attract people back?

Nobody has cracked the code on this. If the driving factor really is climate, then there's nothing the Midwest can do. But I do think there are cultural factors in all of these places that can inhibit attraction, as I mentioned above. 

For Chicago in particular, its negative population trends are heavily driven by a loss of black population and a decline in Mexican immigration. Whatever social justice rhetoric you might hear from Chicago leaders, I don't see them clamoring to try to turn things around.

Do you think Chicago has a chance to land Amazon HQ2, and if so, if it’s really something the city should be excited to be in the running for. Would Amazon HQ2 be just as much of a curse as a blessing for the city?

I have said Chicago is the best city for HQ2. It's one of the few cities that could support a company with a headcount of 50,000 people. And there's a fresh pipeline of talent coming in direct from all those Big Ten schools every year. It is affordable relative to the coasts and has a much more permissive real estate development environment than coastal cities. It has a true urban, transit oriented environment that only a handful of other places do. If you look at their criteria, Chicago scores very well. The fiscal problems are a concern, but presumably the city and state would find a way to isolate Amazon from their consequences. (That may be bad policy, but it's the game that's being played).

It will be very interesting to see what city Amazon picks. 

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