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.

Unfortunately, two factors hold be back: 1. I. Hate. Winter. I’ve lived through enough winters to know that I don’t ever want to see another slush season. It’s personal. 2. I’ve moved on. I guess it’s that same intangible push that causes people to leave their small town and seek their fortunes in the world. Boston will always be a part of my life but, for whatever reason, I am resistant to the idea of going back.

Denver, CO

Denver is the only city on the list that I have never been to. It is famously beautiful and has an almost 70% sunshine probability (yep, it matters.). There are really only 3 cities that I’ve never heard anything truly bad about and this is one of them (the other two are still in contention). I know it’s not exactly the same, but I’ve been considering Boulder, CO in the same thought process as Denver (they’re just 30 miles apart). Boulder has a tight knit and growing entrepreneurial community and consistently ranks as one of the happiest cities in the US. Both towns are meccas for outdoor enthusiasts and the lifestyle is, by all accounts, sublime.

There’s just something that feels a bit too isolated about setting up life in the middle of the Rockies. It’s not doubt a perfect place for many people to found their lives and businesses but I really feel the pull of the coasts for their bustling activity and easy access to resources.

Los Angeles, CA

I had to include LA on the list because I couldn’t dismiss out of hand the largest and most diverse city in beautiful California. It is a town with a lot of opportunity and a lot of problems. On my visit there a year ago, I was struck by the care and beauty that went into every shop and restaurant. The coastal beach towns are gorgeous and glamorous and I could actually see myself plunking down there someday in the future.

That day is not today, though. Traffic is god-awful, the air quality sucks, and the cost of living is absurd. It’s close to beautiful beaches and hills but good luck getting to them. There is a ton of professional progress going on in LA but there is such a “keeping-up-with-the-joneses” culture that I can’t ever see myself bootstrapping a startup in that setting and I can’t ever see myself living there if money is a factor.

Seattle, WA

Seattle has a scrappy entrepreneurial scene and an outdoorsy culture. The Northwest is gorgeous and by all accounts I’d probably love the area for the three-to-five months of the year that it isn’t cold or rainy. There is a lot of great engineering talent up there and it’s always been a hub of technical development. I just don’t think it’s an ideal cultural fit for me because, though I certainly exist comfortably in the down-to-earth crowd, I am looking for a place that will really provide a full spectrum cultural experience.