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.

With that in mind, I don’t think it should be surprising that my finalist cities are the two with the broadest entrepreneurial resources. I’ve always gravitated that way. The only surprising thing is New York’s position as the underdog in this fight. I’m not sure I’ve yet met a New Yorker willing to admit to being anything but the top in anything but, in the world of startups, the Bay Area rules supreme.

New York, NY

What can I write that hasn’t yet been written about New York? I spent two years there after college and there’s really no place like it. I came in as a Yankee-hating Bostonian with nothing but negative biases and left with a wealth of experiences and every intention of returning. New York has the world at your fingertips and a pace to quicken the pulse of the most ardently low-key individual. It forces the naïve to grow fast and keeps the old living like they’re young.

You just can’t beat New York for breadth of experience. It has everything a city could offer. There’s never a reason to feel like there’s something more interesting going on somewhere else in the world because it’s probably happening just blocks away. I always said that if you’re bored in New York City, you’re uncreative or lazy.

The New York startup scene, though, is different. Finance is the big dog in town and startups are a long way down the pecking order. The good thing is that even a relatively small part of New York typically outranks most major cities and that is certainly true here. New York’s startup scene blends a scrappy underdog feeling with the ability to deploy sizeable resources. It seems to straddle the East River, with one foot in Silicon Alley and another in Brooklyn. It is curated and nurtured by groups of very dedicated VCs and organizers who have persevered through the years to bring about the growth we’re seeing now.

Ventures tend to focus on New York’s strengths ““ creative design, fashion, and, more recently, social networking. The recent growth of “Social” technologies combined with New York’s natural population density and education have given it a new and exciting growth opportunity. In the last couple of years, New York has seen significantly higher venture investment and a stronger focus on startups.

For all its entrepreneurial resources, though, New York still offers some of its best opportunities for young engineers and budding business types in finance instead. It’s a lot harder to convince someone to join a startup when they can make multiples of that salary in financial services. I had that gripe about Houston (with energy) and I think the same thing is true of finance in New York. It is slowly changing but the flow of post-web-2.0 engineering talent just isn’t as strong as in the Bay Area.

In the end, there are three personal things that give me pause about returning to New York at this stage of my life.

First, in a similar sort of sense as I mentioned with LA, there is definitely a “keeping up with the Joneses” mentality. There’s a lot of posturing and image that goes along with the high salaries and big egos that dominate finance. There are also a lot of douchebags for the same reasons. I’m not interested in playing that whole game but it is still rather inescapable for anyone living in the city.

Second, New York is a colossal pain in the ass to leave. The city goes on for miles and miles and when you’re done with the city and boroughs you’ve still got sprawl. It’s almost insanity to own a car due to the price and parking concerns so you’re really at the mercy of public transportation. Despite its reputation, New Jersey is a beautiful state but getting out into the woods for some camping or biking or whatever is almost more work than it’s worth. That can definitely lead to some cabin fever.

Finally, I’ve lived there already. New York can never be fully unraveled, but it’s still a place that I’ve lived and worked and played before. That means that there’s not the same sense of excitement and unknown about it that I get when thinking about making the move to somewhere new. I meant it when I said I’ve got every intention of returning, but this may not be the right time.

San Francisco, CA

The foggy jewel of Northern California is rich in culture, experience, and intellectual capital. San Francisco is only the fourth most populous city in California but it has a much larger footprint than that when you consider the incredible resources that are available in the surrounding Bay Area. It’s a city that punches well above its weight class on the global stage because it leverages the full might of Silicon Valley. There is no other place in the US that comes even close to that environment.

Working at a startup is a kind of badge of honor there. Living off of Ramen and rice noodles in a packed little apartment while coding the latest iteration of the next kickass application is a virtue. Major parts of the local ecosystem exist around startups and that’s really cool. Instead of being tucked away fighting for resources and recognition, entrepreneurs have the tools they need to produce”¦ IF they are capable of taking advantage of them.

The Bay Area’s concentration of knowledge, talent, and capital is unmatched anywhere else in the US. Engineers flock there both because they can command robust salaries and because they get the chance to make a real difference and gain recognition for that contribution. Venture capital basically started in the Valley and Stanford is a resource that constantly pushes innovation forward. It is certainly the “big pond” of the startup world.

There are advantages and disadvantages to this setup. The advantage is obviously the presence of top tier talent and resources. Access to peers, mentors, and advisors is unparalleled. One downside is that competition is incredibly fierce. There’s no talent pool just sitting around waiting to jump at the next decent opportunity”¦ people are educated and motived and require a seriously compelling story to climb aboard. There’s a shortage of engineers that is driving a salary bubble which can make it very hard for a young startup to compete. And though there are plenty of exceptions along the way to combat the problem, costs are still higher to start and operate a new company in the Valley than almost anywhere else.

The current environment feels a bit overheated. The advent of Mobile and Social and recent giant exits are resulting in a very Internet Bubble feel to things. Rents are skyrocketing, engineers are in shortage, acquisitions are made purely for talent and lots of capital is flowing to pre-revenue companies. As much as I love the idea of going someplace where there is so much potential opportunity, I am wary of getting burned by trying to keep up with a red hot market. I’m interested in eventually creating long term value not diving into the next hot fad. Unfortunately, the bubble environment can raise the cost of doing so prohibitively high. But, to be honest, I’d still rather get in during a rising bubble than try to grow something new from the wreckage when it bursts.

The ability to leave SF is also a strong point of the city. Northern California is gorgeous and accessible. The whole California coast suffers from over-development but there is still a wealth of unconquered natural beauty within a few hours’ drive in any direction (west gets a bit wet, though). As someone who loves the outdoors, this is a huge bonus. As someone who loves the sun, the San Francisco’s fog is not. The awful climate of the city is a significant downside. Sure, there’s no winter, but there’s no summer either. At least it’s just a half hour drive to get right back into the wonderful heat of the Bay.

In the end, my impressions of San Francisco are based on a lot of assumptions. I’ve been there before but I’ve never spent enough time to really get comfortable in it. I’ve talked to a lot of people who live(d) there, I’ve read a ton of blogs, and I’ve gathered plenty of data on capital funding, startups etc”¦ but in the end and I could be totally off-base on some things and it is still a big unknown. For me, though, that’s a pretty exciting thing.