DHH: Are you sure you want to be in San Francisco?
37signals.com
37signals.com
The fact of the matter is, there are tons of individuals across the country that make thousands of dollars a month creating websites themselves. They don't seek funding, they either hire a designer/programmer or do it themselves. They don't have a beta, they launch whatever they they are making. They don't have one obscure idea that they think they need to go out and pay $5,000 to form an official company for, but instead have a couple of useful websites that generate money. If they start to make a lot of money, then they'll open a LLC for tax benefits.
On top of that, I'd bet a majority of them have no computer science degree or the knowledge that the hackers here do, which means anyone here can make as much as them since they won't need to pay for programmers.
I think that other cities, like Portland, Seattle, Austin in the US (and maybe Barcelona, Copenhagen internationally) might actually be better places to work.
I wouldn't leave SF, but I grew up here and have family around. If I were starting out, I'd definitely consider other cities.
Most of the programmers I know are now in their 30s with small children. We're trying to figure out how to pay a mortgate and preschool costs that easily exceed $1000/month.
Salaries are high here, and two income families can swing it. But I have realized that high costs are toxic to freedom. Yeah, if you score huge with a startup you'll have enough money be free of the daily grind, but that isn't really in the cards for most of us, even if we take a real crack at it.
I know people who have cashed out of the real estate market in SF and moved to Austin, and they absolutely love it. I think I'd enjoy it there, too. I think that it's probably easier to gain financial independence and start living on your own terms in other cities. And these don't have to be crappy lame places - these are really entertaining places to live. In some ways, I think the cost structure of SF makes it a less entertaining place to be, because people have to make more decisions based on paying the mortgage than doing something creative.
But my wife and I have a huge extended family in SF (parents, grandparents, cousins, nieces, nephews, etc...). I've actually tried to leave, but just I can't do it. And to me, cost is the only problem - if you have the dough, then for a certain type of person, SF may be the most pleasant place to live in the US.
How can you measure the benefits of being around people and businesses that are similar? Its possible to trade stocks anywhere, but why do companies setup in New York or London?
If you don't want to take someone else's money to build your business, then don't. If you lived in Las Vegas would you automatically become a gambler?
37Signals is neither; it's about six people who want the company to remain small and independent. (I have no problem with that.)
First, I'm citing Feedburner to demonstrate that large Google acquisitions don't have to come from the Bay Area. Are you refuting that?
Second, if you ask me to name more Chicago startups, I'll add 37Signals, EveryBlock, Threadless, Inkling Markets, and of course Orbitz.
Third, nobody is arguing that any other city in the US, including Boston, can go toe to toe with San Francisco simply on body count. I am, however, objecting to the argument that in 2008, the only way to be successful in a web company is to be based in the same city as your potential acquirer. I'll guarantee you this: your customers will not give a shit where you're located.
Perhaps. But on the other hand - what value is the opinion of someone who has only ever worked/started-up in SF?
To have a basis for comparison you'd need to have experience both in and outside of the Bay area. Probably multiple places outside of the Bay would be needed for a reasonable basis for generalising.
I live right downtown in Toronto, and while I have a car, I like to walk or bike places. I managed to find a great office that is a 5 minute walk from where I live and it is situated about 500 m from two major subway lines, close to the biggest university and one major college, a hop-skip-and-jump from the museum and art gallery, and countless other great places. I walk out my front door and within 200 m is a great café, a patisserie, a pub, health food restaurant (with food that actually tastes good), etc. I know more of my neighbours here than I did when I lived in a Toronto suburb.
I don't think the key is to live in San Francisco. I think the key is to get the hell out of the suburban hell holes that riddle North America like cancerous spots on an otherwise healthy lung, and find cities in which you can live that offer culture, art, helpful business communities (Google "Toronto BIAs"), understanding government, and diversity with respect to people and industries (e.g., don't live in a one-hit wonder industry city). I can understand that the proximity to the Valley is a huge selling point of San Francisco. You have to remember most of the people telling you to move to San Francisco are doing so because they want to invest in you and they can only do that if they can keep a close eye on you. If you're not looking for investment from those people, then live somewhere else.
I mean, there's some cool stuff coming out of Toronto. Check these guys out: http://www.ideeinc.com/.
I don't think suburbs are the end of the world, especially for people with kids.
You also left out college towns, which can be very nice. While the college town I'm living in now (Laramie, WY) doesn't have the sheer diversity of a major cosmopolitan city, it attracts a healthy selection of smart, interesting people. I can also walk to work in 10 minutes, housing is way cheaper than places like Seattle and SF, and there are mountains less than half an hour away. If you don't need the networking resources of a major city, a college town can be a sweet deal.
We've had a few decades now to observe that the promises of suburbia simply don't hold up. What's sad is that broken families stressed from both parents having to work jobs to hold down a mortgage for the perfect suburban home, consequently eating into the time they would normally enjoy being a family, and epidemics like obesity which are more rampant in suburbia than in many major cities in North America, have done little to get people to wake up to the reality that suburbs suck. But you know what probably will wake people up? High gas prices and an imploding real estate market will.
This TED talk sums up my thoughts on suburbia quite well: http://www.ted.com/index.php/talks/view/id/121
Some suburbs are snotty, overpriced McMansion nightmares. Pass. Others are more affordable. And if you find a suburb you can actually afford to live in, you may not have to have both parents working like crazy to make the house payment. One problem solved. Second, you may have the option of taking control of where you work. If you start your own business, you can often find cheap space in the 'burbs. Or you can work out of some kind of "third space," if you don't need an office.
Don't get me wrong. I'm definitely not defending the cookie-cutter keeping-up-with-the-Joneses traditional idea of the suburbs. Just the idea that you can make a suburb work as a decent place to live on your own terms if you want to.
I grew up in the suburbs and never met anyone who met that stereotype. Suburban homes are cheaper than their urban counter part in terms of floorspace and acreage which is important if you are raising children. I've never met a family where both parents worked in order to afford their home and I'm not speaking of very wealthy people either.
What suburbs offer is a quiet, out of the way place, with lots of room, which makes family life much easier.
Then again, I live in Virginia so I might be confused. There's no distinction between city/suburb/rural county around here, and one never really existed.
I've definitely met those people in Texas.
In the suburbs 15 year olds are still tethered to their parents for transportation. It's ridiculous. Realistically kids are tethered even longer than that as a third or fourth car is not an option for many families. How does it make life easier to be stuck chauffeuring teenagers around for years? Move somewhere they can walk and take public transit from around age 10.
Actually, I still don't disagree entirely, but you did leave out one very important consideration: schools. In many American urban centers the schools are poor, and housing in urban school districts that are good is prohibitively expensive.
So you start looking at suburbs, and the commute is a trade-off you make for the better schools.
Oh, and I wish we could order pizza here -- too far out in the sticks.
I walked to school as a kid, and could walk/bike to my friends' houses until I was 12. Then we moved to the suburbs, and visiting friends had to be worked into my busy parents' schedule -- hence, life got less social.
So, the choice becomes move to the suburbs, home school, or pay up for private schooling of some kind.
Pittsburgh has become a "college town" in some ways. There are several good to very good universities here, and the Oakland neighborhood with Pitt and Carnegie Mellon, has become the economic center of the city in my opinion.
The thing I loved about my visits to SF is that it reminded me of (downtown) Toronto more strongly than any other city I've visited. Great food, friendly people, very multicultural, a lot more easygoing than someplace like New York. Yes, SF is expensive as hell, but downtown Toronto's not significantly cheaper.
If Toronto didn't have the winters it does, I probably wouldn't consider moving. As it is, if SF is a more expensive version of Toronto but without winter and with a larger tech community, then that's a price I'm willing to pay.
San Francisco (and to a lesser extent, Seattle) does a great job of attracting the best and brightest technical people from around the world ... but that doesn't make for a very intellectually diverse set of people (both socially and professionally).
Even though I've only been here for a few weeks, I've been very impressed with just how many very smart, accomplished people I've met that are outside the tech industry -- that all comes from the fact that New York being the city to be in for a variety of fields (finance, media, advertising, fashion)
For me, it's a great lifestyle benefit that I wasn't getting in Seattle.
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.
* 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.
- Public transportation is bad, unless you've ever been to houston, phoenix, dallas, detroit, los angeles, or anywhere else in the US outside of NYC, Boston, Portland, Chicago, or D.C. As bad as it is, SF's public transport is probably the 5th BEST 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.
- Yes.
* 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.
- My office space on Howard street is cheaper than what I would pay on the peninsula or in Chicago. I think I lucked out, though.
* 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.
- uhh... i guess if your friends all work at Yahoo!? I don't really see this unless your friends are all married or dorks.
* 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.
- this is pretty much true.
* 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.
- this is true if your favorite musicians are Jack Johnson or Britney Spears. If you are cool and listen to interesting music there are at least 6 decent mid to large clubs and dozens of smaller spaces. The music scene is better in Manhattan, Brooklyn and Chicago but SF is on par with everywhere else.
* Last call in San Francisco? Earlier than other cities.
- except it is the same as Los Angeles, Portland and Minneapolis, an hour later than Seattle and Boston, and about the same time as when most bars in Chicago now close. If you want to stay out really late your only choice in the US is Manhattan.
* Weather? Choose between "brown" or "wet".
- more like "cold and windy" or "not quite as cold and windy"
* Streets? Laden with human feces and garbage. Am I being hyperbolic? No.
- it sounds like someone's office was close to 6th and Market. SOMA is slimy in parts but gentrification happens and the poo is mostly confined to a few select corridors these days.
Poopy streets to avoid: 6th between Market and Folsom and associated side alleys. Capp between 15th and 17th. The tenderloin bounded by turk, mason, leavenworth and o'farrell.
* Compared to Chicago, Seattle, Portland, Atlanta, or Boston, San Francisco is filthy, both in a "civic pride and basic hygiene" sense, and in a "methadone clinics spewing out mentally ill homeless people contributing to a desperate humanitarian crisis" sense.
* What areas are walkably friendly got that way by gentrifying and bleaching out the culture and neighborhoods from the city. Live in San Francisco? When was your last block party? Can you name your neighbors?
* Strong indie music scene? I guess it depends on what you like --- you could caricature me as a Pitchfork fan. Admittedly, comparing to Chicago, most other cities save New York and Seattle are going to suffer. But go read JWZ's blog about the DNA Lounge and form your own conclusions about how vital and diverse San Francisco's indie venues are.
* If your friends all work at startups, a big chunk of them live in the South Bay, which means you will rarely see them, because facing a 45 minute commute (that's without 101 traffic) at 12:30AM is a strong deterrant to an impromptu night at a bar.
* Your office on Howard Street --- presuming it's a real office --- is not cheaper than what you'd pay in Chicago. Let's compare notes. You first.
I'm skipping the good stuff about San Francisco. Leaving aside the benefits of being surrounded by product managers and QA team leaders, which is a dubious benefit, let me get in:
* You have 7-day-a-week access to solid Dim Sum.
* You live in the US capital of fresh water aquarium suppliers.
* On any Friday or Saturday you are 30 minutes, a cooler, and a couple of logs away from a bonfire on the beaches south of San Francisco.
* If your car can handle, the drive to Half Moon Bay is pretty awesome.
I'm assuming most of the readers here don't have kids. I have two. We won't get in to how much worse the city is going to be for you if you're trying to raise a family.
- I agree with that, I guess. SF is pretty psychotic.
* What areas are walkably friendly got that way by gentrifying and bleaching out the culture and neighborhoods from the city. Live in San Francisco? When was your last block party? Can you name your neighbors?
In my neighborhood the block party is in September but the SOMA block party is in a couple of weeks. I know all the people who live in my building (there are only 5) and three of my good friends live on the same block.
* Strong indie music scene? I guess it depends on what you like --- you could caricature me as a Pitchfork fan. Admittedly, comparing to Chicago, most other cities save New York and Seattle are going to suffer. But go read JWZ's blog about the DNA Lounge and form your own conclusions about how vital and diverse San Francisco's indie venues are.
- JWZ is grouchy because he was hoping to open up an industrial club but instead has to cater to asian gangsters coming up from Daly City. The scene he is into (industrial dance music) was never big enough to support a club the size of DNA and pretty much died out entirely 10 years ago. Everyone who was into it is now 40+ and doesn't go out anymore. I will admit that I don't go to many shows but the bands that I like (Autechre, TV on the Radio, Cornelius, are a few shows I've seen) seem to play here as often as anywhere else. The LOCAL music scene isn't that awesome, IMO. Most people are trying to be DJs rather than be in bands.
* If your friends all work at startups, a big chunk of them live in the South Bay, which means you will rarely see them, because facing a 45 minute commute (that's without 101 traffic) at 12:30AM is a strong deterrant to an impromptu night at a bar.
I guess that would be true. However most of the friends I have at startups work at startups in the city.
* Your office on Howard Street --- presuming it's a real office --- is not cheaper than what you'd pay in Chicago. Let's compare notes. You first.
We pay $8850 for 9000 square feet. Pre-wired, server room, and physical workspace in the basement (part of our product involves creating physical prototypes)
* JWZ is certainly not a good trendspotter, but you're providing a parody of his experience. He's not complaining that nobody cares about VNV Nation; he's complaining that he can't get permits to host 18+ shows (why do you care? Because lots of touring acts won't book 21+ shows), and chronicling the demise of one music venue after another.
* You are getting a fantastic deal on office space; you're paying approximately what we're paying for finished office space in the Loop (we have a smaller space; our company is split evenly between Chicago and Manhattan).
"Public transportation in the Bay Area is a shambles". Well, you have me there. On the other hand, it sucks in most other large metro areas as well. NYC is the only real exception.
DHH meant the Bay Area and the SV, not San Francisco proper. "San Francisco" is what outside people call the Bay Area because they don't know better.
Housing has been spectacularly expensive everywhere in the US for some time now. We pay a premium for living in a place unlike any other, chock full of natural beauty, culture, and iconoclastic innovation. We also get paid more, and it more or less balances out.
"you are going to be 45 minutes to an hour away from anyone you want to visit" -- that's called life in any big city.
Taxicabs? Say it with me: Bay Area. Not "San Francisco."
"There isn't one good place in the city to see a show" -- the (world-famous) Fillmore, the Great American Music Hall, Slim's, Bimbo's 365 Club, Bottom of the Hill ... that's just off the top of my head, and only in the City. And why would your favorite band skip a metropolitan area of ~13 million people?
"Weather? Choose between 'brown' or 'wet'" -- you know that is not true. Not even close. SF has some of the most amazing, mild weather in the world.
"Streets? Laden with human feces and garbage. Am I being hyperbolic? No." Actually, you are indeed being hyperbolic. There are places in SF, like every major city, where you will find homeless living. There are places in SF where I would be willing to eat off the sidewalk. And we're talking about the Bay Area, not SF alone.
Hmm? Not my experience in three east coast cities.
Oh, and there's that wine country about 45 mins. north.
So, yes, you have French Laundry (if you count it), and NYC has Per Se, and Chicago has Alinea. Panise vs. Masa vs. Charlie Trotter. If you're a normal person, you're going to run out of places to get 7 courses prix fixe in the Bay Area before I run out of them in Chicago.
Everything else is subjective. You have Mission taquerias. We have Frontera. Yank Sing vs. Arun's. Anything in San Francisco vs. Hot Dougs.
Call whatever city you want "the top restaurant city in the US". Nobody is moving from Chicago or NYC to San Francisco for the food.
Name someone who has moved from NYC or Chicago because the restaurant scene in either didn't match up to San Francisco. I'll take your word for it that that person exists.
There is also very expensive housing (second after manhatan), and potential of earthquakes, but compare to Boston and most of the South is much much better.
And I agree, transportation is kinda sucky. I find myself using a car, even within the city.
BTW, not everybody works in Southbay or peninsula. I actually do work in emeryville (east bay), and the commute is about 25-35 mins, depending on traffic.
But, also many young startups are choosing SF and not peninsula to start up. The problem to find cheaper place will come only when the startup grows a lot, and you really need a lot of space.
And yet, PG is eerily silent... does YC cater to people following the 37sig model? If one decides to stay a private company, how do investors ever make back money?
This probably stems from my naivete, but how do investors make money if a company has no intention of going public or being acquired?
37signals is not for sale now and probably never will be. We like what we're doing too much and are more than comfortable with just the simple financial success of a profitable business making dividends.
Again, doesn't mean that our way is the only way. I'm just trying to do mine to encourage others to see it as a viable alternative to the funding -> sell out route.
This is why medieval venture investors were willing to back sea voyages but not factories. In a sea voyage everyone got liquid at the end of each trip, and it was very clear what was on each ship.
I'm not suggesting of course that 37 Signals would take advantage of investors. I'm just explaining why, structurally, venture investors are not interested in dividends.
For people who are just interested in building a business, not searching for an exit, the traditional VC is just not a relevant option. 37signals is amongst those people.
http://osdir.com/ml/culture.people.kragen.journal/2007-09/ms...
I've lived in Taipei, Los Angeles, LA suburb, east San Jose, Cupertino, San Diego, Pendleton, Lejeune, and now back in Cupertino with constant visits to San Francisco and I can honestly say... it doesn't really matter where you live.
Learn as much as you can. Make as many friends as you can. And make sure you always have a WiFi connection.
In my case, I'll ultimately be more successful starting out here, than I think I would have in the Bay Area.
If you're going the "DHH path" (profitable lifestyle business, limited outside investment), it probably doesn't matter much.
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.
However, if I was, I'd say:
Draw a 50 mile radius circle around Stanford. Get a list of all consumer startup acquisitions in the last 2 years. Put a pin in the map for each acquisition. (This is straight from the mouth of Ron Conway, so apologies to him).
Rinse/repeat for VC investment (which is nearly required for any consumer startup)-- it turns out that VCs tend to invest in Valley companies (because that's generally who they can meet face to face).
The point is-- It's way easier to get funded in the Valley (I'm raising money in the Valley and Seattle right now, so I'm speaking from a bit of experience).
And the data seems to show that it's easier to sell your company if you're in the Valley (which is the only realistic path to liquidity for founders/investors). Even if the data didn't confirm it, it makes SENSE, doesn't it?
Meanwhile, the elephant in the room here is that you aren't going to be acquired by Google, in the same sense as you are not going to win the lottery. There's a get-rich-quick mentality behind web startups that is totally not borne out by the numbers, and it cuts both ways: unrealistic hubris that infects judgement (for instance, by moving teams out of comfortable environments to San Francisco), and devastating emo temper tantrums at minor setbacks, like not being accepted into YC.
His point seems twofold: 1) The availability of funding in the Bay Area tempts people to take it whether they need it or not, and 2) The competition for top talent is stronger here than anywhere else.
The first point, on funding, is news to me. Yes, the availability of VC here is correlated with more Bay Area startups being funded. It doesn't mean that your startup will automatically be funded just because you're located here - the competition for funding is as strong as the competition for talent.
I meet people doing self-funded startups all the time. The differentiator is whether you want to be the next Facebook vs. traditional profit model. Yes, the funded web-2.0-ish startups get most of the press here, it doesn't mean that no one is doing it another way.
Yes, the competition for talent here is fierce. Right now I'm looking for a CSS expert, no programming required, and even that is nearly impossible to find. However, I know I will find someone sooner or later because I'm located in SF. I shudder to think how hard this would be if I were in St. Louis or something, or even a less tech-centric city like Chicago. A few weeks ago I needed an expert Flex hacker to help with something I'm building, so I just called up my friends until I found one. Try doing that in the midwest. Also, I'm at the kind of small, traditional-profit-type company that DHH so admires.
Hackers move here because SF is the best place on earth to be a hacker, and that fact mitigates in your favor when looking for talent.
I just moved to SF from Boston. I think more people understand startups in the Valley, making hiring with equity displacing cash more of an option.
I also think my startup's success will heavily depend on distribution and business development deals. That makes moving to a concentrated area more important.
The Peninsula (Palo Alto, San Mateo) and the South Bay (Mountain View, San Jose, Santa Clara, Sunnyvale) are home to the popular web sites used around the world.
The issues you would deal with living in SF differ pretty dramatically from the ones you'd deal with living anywhere else in the Bay Area. (Except the expense, which is bad everywhere.)
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. :)
I have an uncle in Worcester, and I visit it once and a while, and I think it is really boring.
edit: I guess I should have added the ";)" JUST KIDDING!
[I live in SF bay area and work in VC funded startups]
I mean life is not just 37 signals? At some point in time, he has to come out and do another startup. Is he setting himself a trap of doing a very narrow set of startups?
I think this mentality is a big part of what's wrong with the startup culture in the Bay area. This notion that it's inevitable that you have to work for a long string of companies, better not get too attached to any one of them.
Jason and I intend to make 37signals a company that'll last for 20 years. Maybe we won't succeed, lots of businesses fail, but that's at least our goal.
It's a sad state of affair where such a simple goal is looked upon with suspicion and disbelief.
People are naturally risk-averse -- moreso than pools of capital would prefer. Capital wants to maximize expected return, and will smooth out the variance by diversification, rather than trading away raw expected return for stability.
Along the lines of start small, regional and expand. It's easy to differentiate yourself as a regional online application. Anywhere else.
Set up shop near a college with a strong tech program.
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.
I've worked for two startups here, both successful, and know of plenty more. And of course, "Feedburner Feedburner Feedburner 37Signals".
Should there be a monthly meetup for people like us in Chicago? Absolutely. I set one up for security people (http://www.sockpuppet.org/chisec) and it's been pretty successful --- at least, if its spinoff (http://www.citysec.org) is to be believed. If 40 people will show up each month to swap drinks for infosec stories, surely more would show up to talk about Social Networking for Pets.
In the words of 37signals -- and Dr. Phil -- get real. Winter is hell in Chicago, summer is a pressure cooker, and fall and spring are tolerable for a few days.
"Isn't that bad" is relative. Weather in the Bay Area is amazingly good. One of three mediterranean climates in the world. There is no comparison.
You are entitled to your opinion, but I disagree. It's just the weather; if that's the defining feature of your life, try to do something more interesting :)
DHH generalizes wildly in this rant -- usually an indication of anger and jealousy rather than reason.
Afford? DHH is not rich.
And this doesn't really have anything to do with cost. 37signals is a multi-million dollar company and we (including the founders) could certainly afford to move to San Francisco.