I don't intend to use this as a platform for just relinking to other blogs but, given the context of my recent posts, in this case it seems rather appropriate. In an archived essay, Paul Graham brings up some very insightful things about the characters of ambitious cities that I couldn't write any better myself. In particular, he talks about the subtler messages that cities send and why that is so important for choosing the right one. Check it out:

http://paulgraham.com/cities.html

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If you've read through my thought process in the previous posts then I don't think it comes as much of a surprise that my compass will guide me to San Francisco. Since I was young, I've always felt a westward pull. Maybe I'm just a product of effective marketing but there's always been something romantic and attractive about following the sun over the horizon towards the glittering majesty of the Pacific Ocean. I felt it even just moving from New York to Houston"¦ it is this idea of excitement and opportunity that springs from the very thought of West. Yes, I agree, I probably played far too much Oregon Trail in elementary school (curse you, typhoid fever, for all the Abigails and Johns and Marys you took from me along the way!) but I just can't help the feeling.

Despite the seeming inevitability of my eventual shift to the west coast, I think I'm doing it for the right reasons. I've always preferred being the small fish in a big pond because that means bigger opportunity and an accelerated chance to climb the learning curve. The Bay Area is where that opportunity resides. I am excited to surround myself with intelligent and motivated people looking to change the world in all kinds of interesting ways. I'm excited to be immersed in new cultures, technologies, and experiences every day. I can't wait to ride through the redwoods, explore wine country, and consume some world class seafood.

Sure, I'm not thrilled about the fog, the cost of living, or California's absurd regulatory and tax systems. Those are the necessary evils in all this. There are downsides to living anywhere and I think they're hardly insurmountable (please remind me of this when I bang my shins on the corner of my bed because it's only 6 inches from the wall in my 150sqft studio and I slipped on an empty Cup-O-Soup container). There is just so much opportunity and creativity and energy out in SF that, for me, I don't think it could happen any other way.

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The finalists in this whole process can't lay claim to the kind of general perfection of San Diego or Austin but their flaws come from a place of unmatched opportunity. New York and San Francisco are sister cities in many ways. They are the first and second most densely populated in the US. They are hubs of cultural diversity on their respective coasts. Most importantly, they offer the kind of breadth and depth of entrepreneurial opportunity that it is difficult to find anywhere else.

Penn was one of those annoying colleges that actually required you to write a unique essay just for them. Schools of that ilk were the bane of my upper year in high school, during the college application frenzy, but I am glad I put in the extra time. I'm not going to say that it was anything particularly brilliant, but I wrote about how important it was that Penn had a huge variety of options in their curriculum. At the time, it was just another essay and I really didn't think too much about it. Two years into school there, when I began my transition towards finance, those options became critically important. I finished with an engineering degree but my push into the Wharton world is what landed me at Bank of America and put me where I am today. I am hugely thankful to have had that opportunity available to me.

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The NVCA publishes an annual VC yearbook using MoneyTree data. I put together a chart of total VC investment by region for each of my 8 choices. I'm not sure anything about it really surprises me... Silicon Valley dominates while New York and Texas are trending higher.

Similar data comparing tech- or internet-specific financing echoes the same trends. Likewise if you filter for only early stage or seed startups.

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The final four cities are, frankly, all places that I really want to live in. At this point it is less about finding reasons to not move there as it is finding reasons why it's better to live in a different city on the list. The following two towns round out my list of three "Places I've Never Heard Anything Really Bad About" list. They are awesome, they're beautiful, there's almost no downside but"¦ they just aren't quite the right place for me right now.

Austin, TX

Texas is awesome. I'm going to write a post about how much fun it is to live in Texas. The hub of that awesomeness is Austin. There's an active and fervent university culture mixed with a strong focus on music and the arts. Living in Austin is affordable and culturally diverse. Nestled at the corner of Hill Country, there are phenomenal opportunities for everything from lake sports to horseback riding to biking to motorcycling. It's got youth and energy.

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I cut the list of potential cities in half based on the criteria I outlined before. Unfortunately, that means some great candidates didn't quite fit the bill.

Boston, MA

I love Boston because I spent 16 of my formative years in the "˜burbs just a half hour outside of it. I am and will always be a Boston sports fan (Go Pats, go Sox.). Thoughts of the illogically twisted cobblestone streets of Beacon Hill, street performers in Quincy Market and the smell of Italian food in the North End fill me a with a warm, fuzzy, nostalgic feeling. There's a certain energy to the area that comes from the presence of so much intellectual firepower in the local secondary schools and universities. In terms of engineering talent and entrepreneurial culture, it scores top marks. The city is active but not prohibitively expensive. New England is a gorgeous place to live.

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I'm leaving Houston and going"¦ somewhere. I have the advantage of portability in my lifestyle - there's a lot of crap to sell and that sucks but I'm not faced with kids in school or a spouse with a rooted career. That means the world is my oyster so I need to figure out where to go. I've made a list of the most feasible cities and fleshed out my criteria for choosing among them.

By necessity, there will be some pretty sweeping generalizations in this process but this is a high level analysis so don't get all up in a twist about it if I'm missing the "underlying subtlety" or "charm" of a particular place.

Cities in the Running:

Austin, TX

Boston, MA

Denver, CO

Los Angeles, CA

New York, NY

San Diego, CA

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Why am I leaving Houston? The easiest explanation is that I've got "happy feet" and I'm allergic to staying in one place for too long before getting the urge to dance away. It's a bit more subtle, though. I've got personal reasons and professional reasons for moving on.

Houston is the third or fourth (depending who you ask) largest city in the US but it feels a lot like a small town. I'd even call it the "largest small town in America". Perhaps that's a result of its complete lack of zoning laws and aggressive expansion of city limits or the fact that tumbleweeds could be blowing across downtown Main Street after 5pm on a Friday and no one would be there to see them. It's a city without a strong sense of its own culture "“ it tends to attract young professionals who are at a middle point in their lives and looking to eventually move on. It's a big small town in the middle of hundreds of miles of flat, featureless countryside.

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