It's expensive. Difficult for commuters, even if you live in the city, just to get around. It's style over substance, and it attracts brogrammers, not "bright young talent", which can exist anywhere.

The guy grew the company 5x. I don't think attrition is the issue.

I assume he left because it wasn't his company anymore, it was run by the board. If the board can override his will as CEO and accept losing the CEO over office location, that by default means the board did not really value him. I would expect that hurts. Some things you can't prove with data, these are subjective decisions that fall into the realm of a CEO's responsibilities to look out for his team. It wouldn't be so far fetched to believe that Yishan felt that the board did not allow / trust him to do his job.

It's almost certainly not really just about office location.

"cool, fun, sexy"? It's a disgusting place with a corrupted government and 40 years old development policy and an even older infrastructure. Fun, sexy? How about not being able to find a single coffee shop open after 9:30PM on a freaking Saturday near Market St?

Any real world class metropolis like Hongkong, Shanghai, Tokyo or New York would blow SF out of the water in the "cool, fun, sexy" department.

I happen to agree with everything you just said, but by American standards, it’s… well it’s in the top ten, I guess.

Compare Hong Kong, Shanghai, Tokyo, or New York City to Daly City and then tell me where San Francisco falls on the scale.

I moved to SF from my college town of Springfield, Missouri. It's a town of 150k people surrounding by the rural Ozarks. Obviously, there's nowhere near as much art, music, comedy or "culture" as in SF, but it's immensely easier to get around, and much more convenient to do normal errands like buying groceries, household items, etc. And don't even dare compare rental and home prices. I certainly won't claim Springfield is a "better city," and I don't know exactly what criteria you have in mind, but for day to day life it's far more convenient.

This is what people overlook when they trash the Midwest or "flyover country". I guess they may think it's cool to ostracize people who live in "Provo, UT" (which is nice, by the way) because they don't go to enough art festivals, but the business of day-to-day living is much less complicated in those places. If you just want to raise a family and go do simple recreational things together, your life will be immensely bettered by not living in a high-population urban district; you'll have a lot more money and a lot less headache. Image-obsessed twenty-somethings, like the ones often employed by tech startups, may think it's cool to ostracize suburbia and ignorantly claim that no one with "real talent" will want to live there, but most of them will be singing a different tune as they enter their 30s and try to live an actually significant life.

Market street is not a very vibrant part of the city. Nevertheless:

http://www.yelp.com/search?find_desc=coffee&find_loc=San+Fra...

SF cool, fun, sexy? Have you ever been there? I found it dirty, scary, and smelly.

Yeah, that sounds like a better description of my 3.5 years here. Of course, don't tell any of the SF-lovers exactly where you live, because they'll just blame your experience on you not living at exactly the right block. Live in Soma? Oh, that place has no night life. Live in the Mission? Oh, you're too close to the BART station. Live in the avenues? Too far away from the city center. And so on.

Well, it's a city a lot of people like but certainly those adjectives could be applied to just about any good-size city--and it's why a lot of people also don't really like cities period. I'd add that, if your experience with SF is going to a show at the Moscone or elsewhere nearby, that general area (Market, Tenderloin, etc.) is definitely less nice than much of the rest of the city. But it's also fair that SF, for a variety of reasons, also has more street people of various sorts than most cities do.

Honestly I loathe the place. Not for any of the reasons you just listed. (“scary”? SF??)

I was born in New York City, grew up in L.A., started a company in SF, and live in Chicago, but the only place I've ever been held up at gunpoint was in San Francisco at 4th and Mission.

You got stuck up in front of Denny's?

That sounds like bad luck. Within San Francisco, 4th and Mission seems like one of the less likely places to be held up at gunpoint since it's so busy.

I mean you were on Mission street. I raise an eyebrow to the "loathsome gentrification" stories that pop up pretty regularly.

What are your reasons, out of curiosity? I'm a reasonably-sized guy, so I rarely feel personally scared, but I don't have to look far to see some really sketchy situations.

"dirty, scary, and smelly"...Have you ever been to the East Coast? I would say SF is on par as far as dirty and smelly goes. Scary? I think it's pretty underwhelming but I come from NYC/Philly/Baltimore area so that might bias my viewpoint.

That's what makes it cool, fun and sexy.

So is every world-class city.

And yet plenty of "bright young talent" seems to do just fine in the rest of SV. "Demands" is overstating it a bit.

One could say the same thing about the mandate to move to SF or lose your job. Not everyone wants to live in the city. You might call suburbia a hellhole, but some of us see the city that way, particularly given its cost of living.

"Suburban hellhole?" It's important to realize that many people hate cities, and would much rather live in suburbs. Why are there so many huge suburban areas around (most) large cities in the US?

You have to contextualize those demographic moves.

The post-war American suburban drive was in large part driven by economics and policy. Mortgage subsidization from the 30s with the Home Owners' Loan Corporation and the GI Bill in the 50s made loans available to mass consumers, while the HOLC's discriminatory redlining policy and the deindustrializing of cities (driven chiefly by lowered shipping costs) caused dense urban areas to become less desirable.

Mixed in with this you also had suburban-oriented urban planning (lots of highways, little public transit investment), brand new car driving infrastructure, low energy costs, lots of cheap land to expand to and in the 70s and 80s rising urban crime.

If you were looking to live somewhere, you had lots of incentives to prefer the suburbs. Today, most of these trends (energy cost, crime, job markets) have changed course.