Your city sucks! (And so does mine)

It seems the the latest craze amongst entrepreneurs and, in particular, tech “hubs” is to pull out the ruler and compare penises. As someone who’s slept with three of those technology hubs I’m going to tell you that each penis has its own merits and it’s own disadvantages. Allow me to explain.

For the record I’ve lived in three legitimate technology hubs: Seattle, San Francisco, and Boulder. Additionally, I’ve spent a considerable amount of time in Portland. Each one of them had its benefits and detractions. Ultimately, I’m settling down in San Francisco (after moving to it, away from it, and subsequently back 3 times now). Why? It’s simple, despite all of the bullshit that is involved in this incestuous, crowded, echo chamber of a dirty ass city, it is Mecca for nerds. Period. All of the pieces of the proverbial startup pie are here: money, history, talent, schools, partners, clients, press, etc. I don’t have to wait for any part of that ecosystem to grow or blossom. It’s already here and I’m far to lazy too grow or foster any part of those for an entire city.

And guess what? The real Mecca hasn’t moved and neither will the technology Mecca. That does not mean that you have to go to San Francisco to be a real geek or to have a real startup. Anyone who tells you differently is lying to you. Please read that again, they are lying to you. Just ask Michael Dell, Jeff Bezos, and Bill Gates. I hear Dennis Crowley is pretty happy in New York City and Steven Frank is happy in Portland, as well.

So what do I think of each of these hubs?


I lived in Seattle for 3.5 years and dated a girl in Portland for some of that so I’ve spent a considerable amount of time in both cities. I love the Pacific Northwest. The Pacific Northwest is, hands down, the best kept secret in North America. Seattle has a pretty rad technology scene with Microsoft, Amazon, Expedia, Boeing, and Lockheed all calling the area home in one way or another. I’d say, outside of San Francisco, it has the most mature startup/technology scene. New York City might have a legitimate claim to #2 here, but I honestly think Seattle gets left off the map too often in these discussions. It is, as the kids say, legit.

Seattle is seriously where my soul resides. It’s just a fantastic city. If you’re considering Seattle, you should definitely check out Portland as well. Particularly if you like your cities a bit smaller, more bike friendly, and laid back.


  • I cannot stress how cool it is to have a 14,000 foot mountain be an integral part of your skyline.
  • Mild climate where it snows rarely.
  • Close to some of the best skiing in the world. Crystal Mountain, Stephen’s Pass, and Snoqualmi are all within an hour. Whistler is about 5 hours away and Baker is 3 hours away.
  • Near a big body of water.
  • Lots of established technology companies.
  • You will likely never want for things to do outdoors.
  • You will never want for a tasty beer. Nor a tasty wine. I’d say Portland, Seattle, and San Francisco are all equally, per capita, wine crazy with the local vineyards and wineries to back it up.
  • Centrally located between two other fantastic cities: Vancouver, BC and Portland, OR.
  • University of Washington is right in the city and has a good CS department from which to poach.
  • Cost of living is relatively low. A quick look at Craigslist shows 2 bedroom apartments in the city averaging $1700 a month, which is about 30-40% cheaper than San Francisco.
  • This city basically invented the grunge/alternative rock scene. You will never want for awesome shows to watch.


  • I’m not going to lie; it’s gray, in the 40’s and 50’s, and drizzling 4-6 months a year. When I lived there we broke the record by having 38 days straight of rain. The irony here is that Chicago, Boston, and Atlanta all get more precipitation per year.
  • I’m not going to lie; 6 months out of the year it’s sunny and 70. If you like mild weather with no snow and can put up with gloom in the winter, you’ll be just fine here.
  • The food scene is pretty poor. If you’re used to San Francisco, Portland, or New York City you’re going to be pretty bummed out here.
  • The technology scene is largely driven by Microsoft. I hope you’ve sharpened your .NET skills.
  • Public transportation has been pretty crappy for years. It’s getting better, but don’t expect it to be on par with San Francisco, Portland, or New York City anytime soon.


Portland is about 2/3 the size of Seattle and doesn’t have any, that I know of, anchors in the technology scene. My other concerns about Portland, in particular, is that I don’t know what the investing side looks like and that there is no remotely top CS schools nearby from which to poach young talent. Seattle, on the other hand, has University of Washington right downtown and has a pretty well regarded CS program (compliments of Microsoft).

All this being said, Portland is a fucking fantastic city with a lot of great benefits. I think if you’re considering Seattle you have to consider Portland.


  • This is a lovely 580,000’ish person city which is exceptionally bike friendly. You can bike across the main city center in 15 minutes top, which is pretty great.
  • The food scene here is, per capita, top notch.
  • BEER! BEER! BEER! Oh man, with McMenamins, Deschutes, Full Sail, etc. all calling this place home you’ll basically never run out of new brews to taste.
  • Not only is it less than an hour from the Goonies rock and the Pacific Ocean, but a couple of giant rivers flow through it.
  • Portland didn’t want to be left out of having a mountain be in its skyline either. Mt. Hood is much closer to the city than Mt. Rainer so, despite it being about 3,000 feet shorter, is much more imposing on the skyline.
  • All of the things I said about the great outdoors in Seattle applies here.
  • Same goes for skiing. If you like boarding and skiing, you’ll find plenty of friends in Portland.
  • Great public transportation.
  • Rent on a two bedroom apartment will come with about a 20-30% discount over Seattle as well.
  • Also has a great music scene.


  • Everything I just said about Seattle’s weather can be equally applied here.
  • Portland has a higher chance of snow in the winter. It’s not surrounded on two sides by mountains and doesn’t have the same water barrier that Seattle has. As a result, Seattle gets snow once every 3-4 years and Portland gets a mild flurry or two every year or two.
  • No decent CS departments to poach talent from.
  • No real anchor technology companies feeding the ecosystem and I don’t believe there are any big players in the investment scene there.


I moved to Boulder to start SimpleGeo. Mainly because I could move and Matt couldn’t. There’s really no better way to describe Boulder than as a laid back college town nestled in the foothills of the Rocky Mountains. This is not a real city by any means, but does have some of the big city amenities thanks to all the rich white people that live there.


  • The technology community there is growing like a weed. While I can’t really point to a single anchor company, there is a pretty impressive investment ecosystem with Foundry Group and TechStars there.
  • If you like hiking, biking, climbing, kayaking, etc., then you’re gonna love Boulder. The great outdoors isn’t just close by to Boulder, it’s literally at your footstep. I very much loved opening my back patio door to hear the Boulder Creek rushing by in the spring.
  • Speaking of biking, I can’t imagine any other city of 90,000 people in the US being more bike friendly than Boulder. My leisurely bike rides from my apartment along the Boulder Creek bike path were just stunning.
  • Despite being such a small town there’s some pretty spectacular food.
  • If you do NOT like skiing or snowboarding you probably shouldn’t even consider Boulder. Seriously. Vail, Breckenridge, and Beaver Creek are all within 3 hours.
  • University of Colorado is a legitimate CS school. Tons of eager talent lurking around. The drawback is many of them, such as Dave Morin, get lured to other technology hubs.


  • Due to zoning weirdness, rent and real estate in Boulder is actually pretty expensive for a city its size. I’d make a wager that it’s as expensive as Seattle, if not more so. Particularly when it comes to purchasing. Rent is about on par with Portland and Seattle.
  • I really yearned for hardcore technology while I was in Boulder. A lot of the technology scene was very much focused on creating consumer applications. I’m a big infrastructure, big data, big scale kind of guy and often felt out of place in that scene.
  • It’s fucking cold. Don’t believe one ounce of that bullshit Brad Feld or Andrew Hyde tell you about mild winters and 300 days of sunshine a year. The sun doesn’t help one bit when it’s -10 and there’s two feet of snow on the ground.
  • It’s tiny. 90,000 people does not make a real city.
  • It’s predominantly filled with rich white people. The kinds of people who have $1m condos in Boulder as their second or third homes. If you like your home to be a melting pot, Boulder is not for you.
  • Music scene is kind of bunk. Good shows swing through Denver on occasion, but Denver isn’t exactly easy to get to from Boulder.

San Francisco

All told I’ve spent almost four years living in San Francisco. I’ve moved here three times (2000, 2007, & 2010) and have finally given up on attempting further departures. What I find so amazing about San Francisco is that I simultaneously love it to death and want to strangle it at the same time.

Besides all of this technology talk, the reason I love San Francisco so much comes down to two things: the weather and how outright fucking weird this place is.


  • The weather is dramatically better than Boulder, Seattle, or Portland. No hints of snow and, outside the actual city, it’s basically 60-70 and sunny year round. During the winter months, and near the water, San Francisco has a tendency to be on the cool side and rainy at times. All-in-all, though, the weather is pretty great. Of course, it’s a hell of a lot better in LA as Chris Lea constantly reminds me.
  • Basically every single major venture capitalist in technology in the US is either headquartered here or has major operations out here. The place is literally awash in capital. The flip side of this is that almost any idiot can get his stupid idea funded.
  • Two of the most prestigious universities in the world, UC Berkeley and Stanford, are within 30 minute drives of the city.
  • San Francisco, and the valley, are home to basically ever major consumer internet company in the world. The area has been completely overrun by nerds for the most part.
  • The art scene in San Francisco is amazing. It runs the gamut of photography, installation art, the Burning Man scene, Maker scene, etc.
  • Possibly the second or third most famous wine country, outside of France and Italy, in the world.
  • There are sandy beaches on the Pacific Ocean within the city limits and easily within biking distance.
  • The food scene here is fantastic. Outside of LA and San Diego, I’ve never found a city with burritos like this.
  • Pretty fantastic music scene.
  • It’s a major hub for many international carriers. If you want to get to Asia quickly and cheaply, it’s a great option. So is, of course, LAX.
  • Pretty fantastic, yet dysfunctional, public transportation.
  • San Francisco is filled with some of the most wonderfully weird, eccentric, accepting, creative, intelligent people I’ve ever met in the world. There is no other city I’ve visited that has such a high per capita of weird. I love this.
  • I’m not sure if you’ll find a better place to get a tattoo. So many fantastic artists to choose from. I mean, fucking Ed Hardy helms the scene here and many of his proteges are following in his footsteps.
  • Have you driven down Highway 1? Have you seen the Redwoods? Stunning.
  • You can surf inside the city limits.


  • This is, hands down, the dirtiest fucking city I’ve lived in. Nobody else is even close. You can walk down the sidewalks of the nicest neighborhoods in the city, the ones with million dollar mansions, and there will be human feces on the sidewalk. The flip side to this is that they’re creative poops, such as the one my girlfriend recently spotted inside of a banana peel.
  • It’s an excruciatingly expensive city. Decent studios start at $1500 a month. Two bedroom apartments, which you’ll share with a roommate, will likely start in the $2800 to $3000 a month range.
  • San Francisco, being the epicenter of technology, is just as equally filled with snake oil salesmen and wannabes. In fact, there’s a term for the wannabes: wantrepreneurs.
  • This is an echo chamber. There is no counter balance to what you’re working on really. Everyone thinks everything is fucking amazing or a pile of shit because Arrington or Kevin Rose said so. This leads to a lot of self-masturbation.
  • Seattle, Boulder, and Portland make San Francisco’s beer scene look paltry at best.
  • I honestly can’t describe how terrible the traffic is here. 280, 80, 101, 880, 580, HWY 1, and 680 are all four lane highways and all are completely gridlocked during rush hour. It’s fucking terrible.
  • You literally can’t escape technology. There are fucking Farmville signs along the major highways. I find it extremely difficult to get way from the tech scene without physically leaving the city.
  • Despite what some people might tell you, this is not a very bike friendly city. The cabs and MUNI drivers have been in a decades long competition to see who can kill and/or maim the most bikers.
  • It’s an absolute nightmare to get to anything that resembles the mountains you find in Boulder, Seattle, or Portland. During peak season it’s not unheard of to spend 5 hours in the car getting to Tahoe.
  • The city government is terrible on so many levels.


I very much enjoyed my time in the Pacific Northwest and would recommend checking out both Portland and Seattle. I’m slightly biased towards Seattle because I prefer bigger, denser cities. I didn’t like Boulder at all due to the cold climate and small size of the city.

As a result, I’m sticking with San Francisco, despite poop filled bananas, because it’s a big, dense city filled with a bunch of weirdos who love building great technology.