DHH: Are you sure you want to be in San Francisco?

I'm surprised that noone's really talking about money here. The Bay Area has one of the highest costs of living of any city in the country. That means its going to take that much more of your time to work, to make money, and to live. If you're spending your time working to live, that means you're not using that time to work on your projects.

Right now I'm taking a culture hit. Living in Worcester, MA certainly doesn't put me at the center of startup culture, but Boston and Providence are close enough. I can take the bus/train and find myself surrounded by technically oriented people. A low cost of living in this town is what allows me to work less and affords me the free time to work on my projects. To me, this time to work is alot more valuable.

(Oh, there is culture in Worcester. You just have to dig. :)

It depends on the fields you're interested in. Seattle feels just as diverse as NYC to me, just in different ways.

If you're into finance, advertising, and fashion, NYC is hard to beat. Seattle, OTOH, wins big at mountain climbing (we have mountains nearby), aviation (we have Boeing nearby), and martial arts (we have Japan nearby), for example. It's also a hotspot for medicine, microbrews, and certain kinds of music.

I've been to NYC a few times, and if you're into the things they do well, I'm sure it's heaven. But if you're not, it's just another big city where people talk about boring things like finance and fashion.

This is really personally my remaining annoyance with News.YC. Too often, people either agree with a submission, or they disagree with a submission. There are too few posts per day that critically think about what is being discussed.

In this case, I don't remember seeing one post about following a combination of strategies at once (if there were a couple of posts, that doesn't make the situation any less sad.) Making a smart product, having a strategy to grow, and offering a free viral version as well as a paid version that pays your bills is the way to go! In fact, having an abundance of free customers will increase the chance you NEED investment, not just the fact that VC's will be more interested. They're more interested because they know you will need money!

If you have a paid version that pays your operating costs, and gives value, you can keep working on your startup indefinitely. It's also another way to get VC's interested. But except in this case, you logically won't be a little bitch. Instead of having to fake confidence while your cash flow has brought you down to nothing (more likely below nothing), and the only reason you're getting a good valuation is because there are many, many VCs around, and they like that you went to Stanford or something, you will instead be in a situation where you proved people will pay for your product and you don't really need to time selling your company or getting investment in the right cycle of the economy. So which option is better? Whichever one is better at the time! That's what DHH has been saying. If he actually needed investors for a venture, I'm sure he would surely take the money he needs. But he doesn't, so he doesn't. There's no wrong way.

But he's wrong because Silicon Valley gives you that option to pursue VC's in case you need to, and the quality of life seems to be among the best places in the world. And it's sure better than living in the middle of nowhere. And it's great that you can meet cool people and ask them feedback about your apps without receiving questions like "why are you doing a startup" (because working for most companies is a rip off), "wow you must be rich" (people think it's rich people who do startups), and "can you fix my computer" (no explanation needed.)

I like YCombinator's approach, where one can launch and see what happens for a few months before figuring out the best steps -- more angel funding, VC funding, multiple VC funding, selling, quitting, changing an idea, or even having a paid version.

Give me a break. I lived in San Francisco for a bunch of years, starting after my first company got bought out --- I've experienced the city both totally flush with cash and living paycheck to paycheck. Allow me to retort:

* Public transportation in the Bay Area is a shambles, and, in particular, getting between any two points in the (tiny) city of San Francisco involves interaction with the worst bus system in the country.

* Housing is spectacularly expensive, which, in hacker teams, simply means you're going to be living in half the space you have now, with no amenities.

* Office space in San Franscisco? I already spent the modifier "spectacular", so let's go with "catastrophically" expensive, meaning: your office won't be in the city, it will be in San Mateo, which despite its relative proximity to the city, will still be an hour and a half commute. Unlucky enough to wind up in Santa Clara? I was. My commute from SOMA often exceeded two hours each way.

* Half to 3/4s of your friends are going to live in the South Bay. No matter where you choose to live --- San Francisco or the suburban Mallhalla of the South Bay --- you are going to be 45 minutes to an hour away from anyone you want to visit.

* An ongoing dispute between the dispatchers, the city, and medallion owners keeps taxicabs artificially scarce, so that you are going to wait 20 minutes to catch one on Folsom or downtown.

* There isn't one good place in the city to see a show, but that doesn't matter, because your favorite band skips San Francisco.

* Last call in San Francisco? Earlier than other cities.

* Weather? Choose between "brown" or "wet".

* Streets? Laden with human feces and garbage. Am I being hyperbolic? No.

Almost any other city in the country, save Los Angeles, can lay a better claim to being a destination for long-term lifestyle companies than San Francisco.

Winter in Chicago isn't that bad. Do you think "wow, this is great weather" every day during the winter? No. But the spring, summer, and fall is very enjoyable.

The problem with Chicago is that there are no other hackers around (all the tech people work for banks, and end up being as interesting as you'd imagine), and there are no 24-hour coffee shops, at least not near me.

Chicago is a good place to be if you want to be alone. I guess it's "a big city" but it sure doesn't feel like it at times.