- It's generally hot as balls in summer and has already gotten quite cold. Neither of these particularly bother me, assuming A/Cs and heaters are available.

- It's cheap as hell to live here, as long as you live slightly off the beaten path. We're currently living in Medford, a 15 minute walk from Davis square and we pay about $1,400 (or was it $1,200?) a month for an apartment with 3 bedrooms (only two people, but we are gluttons for open space), an "office" (no idea the technical term of this room), living room, kitchen, etc. The building is old as shit and it would cost a small fortune to heat conventionally (hello 1920s oil heating!), but... it's damn cheap.

- The start-up scene is a bit lacking, but there are lots of people here if you look. I probably can't walk into any random Starbucks and run into an entrepreneur, but we're here. We even have a poker night!

- I don't think the pond analogy has any relevance here. With the proliferation of the Internet and a global economy, I'm not convinced it matters where you're located for the most part, especially if you're doing a web start-up. Yes, there are lots more investors in SV, but there are investors here, too -- ones who don't see 900 pitches a day. The investors here all talk about how they want to make Boston investing relevant again.

- And they're proactive about it. They regularly host firm-sponsored events and invite a bunch of interesting companies. We've been to a small dinner party and have a cocktail party coming up. We were even taken out Paintballing by Battery Ventures (Adam Marcus is a great guy, btw) -- that was a profitable day; we got to keep the Battery-stamped masks they provided and ended up taking home 3 cases of beer. We met some interesting companies too, but I was mostly busy shooting VCs.

- Boston as a city is fun and there is certainly a lot to do on the rare occasions we go out. I sure as hell miss all my entrepreneur friends who moved to SF (traitors!), but Dan and I are kept busy enough by the business that I might notice the lessened night-life/culture more if I had more free time.

All that being said, the Pros you supplied for SV are definitely true. We plan to move to SF (Mountain View is pretty dull in my experience, but SF is a great time) when we have more revenue (we did the math; it's a lot cheaper here), but for now I don't really feel like we're handicapped by our location and we're definitely better off than we'd be somewhere like the black hole I come from (Ohio; just threw up in my mouth a little).

I can't speak for your company, but as a business with very low costs and the advantage of not having to immediately and aggressively seek out investment, Boston is the perfect place for us right now. The low cost of living allowed us to become profitable the first month we operated and this type of city allows us to take part in a very diverse (though comparatively sparse) start-up community while supplying plenty of entertainment and cheap/convenient transportation to get to it.

Edit: I should point out that personal preference / taste matters here, too. You might be able to live for a comparable price in SV/SF if, unlike Dan and I, you do not become instantly claustrophobic when supplied with less than twice the amount of space most people seem OK with.

Finally, unless you already have an excessive number of possessions (like a family), moving isn't that serious of a deal and you might find in either location that after 6 months you want to try the other.

would you rather be at an important team in a lesser-known company, or a less-important team in a well-known company

... that's a no-brainer for me. I'd much rather be on an important team in a lesser-known company. By "important" I mean strategic to the business. Such projects tend to be a lot more satisfying, as well as more rational (assuming a basically functional environment). And the lessons they teach are better lessons.

I've noticed two things about less important projects in larger companies. One is that they often get killed before they have a chance to release or gain traction - and it doesn't much matter how successful they are. This is because they're starved for executive support. The other is that they tend to end up in technical ghettos, working on something that seems cool at the time but is divorced from users and the business, and so doesn't have much value.

Food was decent though, especially for a college town. I liked Boston proper much better, but I didn't live there, and as with most cities I'm guessing your enjoyment will depend a lot on exactly which parts you live and work in.In fairness, I may have liked Cambridge better if I lived in Harvard square. I may have gotten sick of it really fast too, idk.

SV is also expensive, though it's probably not much more nowadays. The exception being that you may well need a car there (which is a hell of a lot less painful than having a car in SF or Boston, since parking is free and ample, but still an expense to factor in) whereas Boston has really good public transportation and you can likely do without if you don't mind walking a bit. Your best bet is to just check around on Apartments.com and Craigslist and compare rent for similarly sized units in similar areas if you're concerned about price.

If you're looking for investment for a software startup, or networking that might lead to that in the future, go directly to Silicon Valley. Do not pass go, do not collect $200. Our startup was either the first or second YC company to get a single Boston investor as of this past August. The ratio of SV investors to Boston in YC startups has to be at least 20:1. I hear Boston is pretty awesome for biomed though. I imagine you can find great cofounders in either location, though in Boston you'd have to snag them before they left for SV.

As for your hypothetical, I'd take big fish little pond any day. The pond can grow much faster and larger than the fish. And even if it doesn't, it will almost certainly be more fun and rewarding. Assuming you're normal college grad age, you've got your whole life to be another cog in the wheel. Give yourself a shot of avoiding it permanently.

Mountain View is very nearly the same price as San Francisco. Because of Google it is among the most expensive places in the valley. I've lived here since we did YC last year, and I've enjoyed it. It's a lovely, quiet, and highly technology focused area, with good restaurants (as long as you like Asian and Mediterranean food), cool little groceries and produce markets (mostly Asian and Mediterranean, but also the Milk Pail which is close to heaven for fans of fresh food), a fantastic library, and even a decent cultural scene (though it is very much white bread small town culture...the performing arts center is excellent for such a tiny town; the massive tax base of the city insures most city services are excellent).

I don't know anything about Boston, but I've heard it's also quite expensive.

I'm paying $2145/mo for a two bedroom rental house a few blocks from downtown Mountain View (with a garage). It's pretty big compared to where most of the folks I know out here are living, but I moved from an even bigger place in Austin, so it was definitely downsizing for me. I've been shopping for a place in SF, and have found that prices are pretty similar for smaller places--$1600-$2000 for a one bedroom (sometimes plus small office) apartment in a decent location.

Salaries in California are enough to make up for most of the higher cost of living, as long as you don't have a strong desire to own your own home anytime soon.

"- Any advice on which of two hypothetical is better: big fish little pond or little fish big pond? Alternatively, would you rather be at an important team in a lesser-known company, or a less-important team in a well-known company?"

How long is a piece of string? We can't tell you what the best work environment is for you. You'll need to try it and see.

Okay, I take back what I said elsewhere on this thread: Boston is considerably cheaper than this. My wife and I had a 2BR, an entire floor of a house with off-street parking, in East Arlington for $1400 a month. A mile walk from the Red Line, on a major bus route. For a cute second-floor walkup 1BR in Davis Square, Somerville -- literally thirty seconds from the Red Line if you run -- I paid $1150.

The funny thing is how living out here in the valley warps your mind about real estate rental (and purchase) prices. When I moved out here I was stunned that I'd be paying twice as much as my mortgage in Austin for less than two thirds the space. Now that I'm out here, I see a place in SF going for $1675, and I think, "Wow, I need to jump at that one! Nah, probably already gone, at that price...why get myself worked up over nothing?"

I'm also probably shopping in somewhat nicer areas than is strictly necessary (in addition to shopping for a bigger place than someone right out of college is probably going to want). I have a dog, and I tend to walk at all hours of the night...it's just a habit I've had for ten to fifteen years, and I think altering it would negatively impact my life, so I'm shopping only in pretty safe areas. And, because my reason for moving to the city is to be nearer to live music, I'm shopping pretty centrally, as well.

You can get a small 1 bedroom place in the $1300 range in both SF and Mountain View. But, that's probably the lower bound, without living in a really sketchy or far out location. I guess that's a big part of the reason most YC founders live with roommates. Splitting a $2700 place three ways works out to a pretty good deal.

And +1 to your strategy of biting the bullet and paying what it costs to be happy, provided you can afford it of course. I'd prioritize keeping the commute short, because that wears on you every day. On the other hand, I used to work in Fremont and live in Fremont, and the commute was nice and short, and rents are decent, but... Fremont? Not such a happening place. At least a 20 minute drive away from all my friends except the one who was my roommate at the time.

So the ideal is probably to live in SF and work in SF, or live in Mountain View/Palo Alto (but not East Palo Alto, unless things have really changed since I left) and work there as well. Or live in Mountain View and work in your spare room. ;)

My current apartment is only a few hundred feet from the Castro downtown and is around $1200 for a 1000sqft 2 bedroom apartment. I'd like to see someone find something like that in SF for the same price.

You got a really, really, good deal. Before I moved out here, I looked at numerous tiny 1 bedroom places that were $1275-$1400 and I considered them unlivable. And, when my rent went up by $150 on the house I live in now, I shopped around again. I'm just not seeing prices anywhere near what you're paying for that kind of space. And, I've been pleasantly surprised to find that housing in the city is not that much more expensive...maybe $100 or $200 more per month, for the locations I'm shopping in.

I will say that I'm now kinda shocked by how ridiculous the paperwork is for most SF rentals. They want huge swaths of banking data. Far more than I had to provide for any other place I've ever lived (even buying a house in Austin wasn't this intrusive). I've talked about the topic with my landlord (who wasn't too intrusive when I moved in here, and has been mostly great and hands off), and he said it all boils down to how hard it is to evict someone in California. Since throwing someone out takes as much several months after they stop paying or do something else against the rules, the property owners do everything they can to insure they never have to throw their tenants out. But, I still find it horribly annoying.

Boston is cheaper, but I'm not sure I'd say significantly cheaper. 1BRs start at about $1200/month here - I've heard that the minimum in Mountain View is about $1500/month. With roommates, you can get a room for $700ish/month in the Davis Square area, which is about on par or a little less than Mountain View. Gas prices are a little lower (talking pennies, though), restaurant prices seemed a little higher in Boston (though maybe my friends just took me to inexpensive restaurants in Mountain View), and I didn't get a chance to check out stores in California.

You can save a ton of money here by living away from the major subway lines. A friend of mine has $400/month rent (3 roommates) in Brighton because he's at the end of the Green Line, which is frigging slow. Another friend had $450/month (1 roommate) in a gigantic 2BR on the Newton/Watertown border. I looked at rents in the Teele/Inman square areas in Somerville; they're about $200-300/month less than equivalent apartments in nearby Davis/Harvard squares, because they aren't directly on the subway line. If you need a car anyway, definitely consider living in one of the areas that's not well served by public transportation - you'll make up for it in rent.

The suburbs also have lots of greenery, particularly once you get outside the 128 belt. It's not like suburbs elsewhere in the country, all strip malls and parking lots laid out on a grid. Typical towns in the Boston area have one or two major roads running through them, residential roads branching off them, and lots of unused space because none of the roads are straight. We're on an acre of land, extending about 500 feet back from the road, and when one of my dad's friends from Cupertino visited, his son said "Wow, you live on a park."

Driving in Boston sucks. Whenever possible, I drive into Alewife and take the subway in.

The diversity in the Boston area is a major plus. It's likely that you'll have normal friends here, the kind that think that yet another social network is just a burden and not an opportunity. There's a significant tech population, but it's not like everyone lives and breathes technology.

As for the startup scene: there's an important cultural difference between Boston and the Bay Area. In Boston, the expectation is that you'll work for an established company for 10-20 years, pay your dues, and then start a company. When I talk about startup founders I know, West-coasters seem to assume they're my age - no, most of them are parents of friends or older coworkers I've worked with.

This has been changing a bit recently, because of the general trend of younger people starting companies and the large college population in Boston. But it still seems to be the expectation among investors. Maybe someone who's sought funding more recently could comment, but when my cofounder was testing out investors, many of them seemed very skeptical. Encouraging, but not willing to part with cash for a couple guys 2 years out of school.

Lastly, I'd encourage you to go far from home. I didn't; actually, I moved back home after college, since there were no shortage of jobs in my field close to where I lived, and I could save up cash and use it to fund my own startup. Which is good, it gave me options and let me do stuff I wouldn't otherwise be able to - but now I'm looking to move out to Silicon Valley, precisely because it's on the other side of the country.

My wife worked as an admin in a startup for 2-3 weeks in Cambridge, and hated the job, hated the commute, hated the culture so much, she quit her job and went back to school to finish her video production degree. She had hoped it was like her job working at US Robotics/3Com, but it was very, very different.

The thing that we really struggled with in New England was the "Townies" and the culture. There really are two different classes of people in New England:

   *"Townies" (people born and raised in the towns of New England)
   * "Gownies" (People who move to New England to go to good schools and then settle in and work white collar jobs or get their grad degree and leave).

So, where you live in Boston-land is important. I think that if you're living in the East Side of Providence, or Harvard Square in Cambridge, it can make all the difference in your social life. It's really hard to get a vibe about that until you've lived there. Each town has a distinct flavor, and a distinct attitude towards outsiders. Choose wisely.

Silicon Valley: I've almost lived here longer than anywhere else I've ever lived: 3 years. And, I'm not planning on moving anywhere in the near future. I really like it here, and I'm not moving away unless I have to. That's never happened to me ever before. (I've moved over 25 times in 35 years.)

The people are great. The chance to meet other people and make friends with others that are doing the same things is astounding. I started http://hackersandfounders.com as a meetup group, and it's doubled in size every month but the last. There's just a ton of hackers interested in founding businesses here.

That means a ton of emotional/cultural support that you really can't put a price tag on. Services are also really easy to come by: like it's really easy to get groceries delivered, getting a maid is rather inexpensive and very much worth it. Prepared foods can be outsourced pretty easily using something like Dream Dinners or Dinner A'Fare. You're never very far from really cool things if you need to take a day trip and get away to recharge the batteries.

And finally, housing. If you're considering moving to SV, you really should take a look at renting a house with someone. We live in San Jose, and we split rent on a 4 bedroom, 2 bath house for $2k. Not only do we have a ton of space and a back yard, we turned the formal living room into the startup office. Not bad, when my friends are paying $1700 for a nice one-two bedrooms in an apartment complex. And, you're away from the fun cultural stuff of San Francisco, but it's only a 75 minute drive without traffic, Mountain View is 30 minutes away, and a bunch of restaurants, coffee shops, movie theaters and a FedEx/Kinko's are 3-4 minutes away. Pretty ideal for a startup if you ask me.

IMHO, you're right on all counts about the pros and cons. I don't have recent data, but my impression is that Boston rents are not significantly cheaper (as they would be in, say, Alabama); savings will come from transportation costs. You can live without a car in Boston. Living without a car in Silicon Valley will make you feel like a second-class citizen. Obviously, Boston is closer to your folks if you're from NY.

If I were going to do a startup, and was able to honestly utter the phrase "I lived in SV for a while and loved it"... it's very hard to argue with Silicon Valley. Yeah, it's a monoculture, but it's a monoculture designed around what you're trying to do. Aspiring screenwriters move to L.A.; aspiring musicians move to Nashville; aspiring software wizards move to Silicon Valley.

But the most important thing is: you can change your mind. More than once. Pick the job that seems the best and don't sweat it. Sample Boston for a year or two if you want and make the move to SV later.

The problem is time. I live in Bedford, and while it's technically possible to get a bus+subway from here to the financial district, it takes about an hour and a half. That's compared to 35 minutes driving (no traffic), ~55 minutes driving (with traffic), an hour driving to Alewife then taking the red line in, and an hour and a half for biking to Alewife and taking the subway in. Not much point.

Commuter rail is similar - it's like 1.5-2 hours to take the commuter rail from Concord to Porter and then transfer to the red line. Might be a bit better closer in to the city, but commuter rail coverage is a bit spotty - it's faster to drive to Alewife from Bedford than it is to get to the nearest commuter rail stations in Concord or Lincoln.

I had planned on taking the Lowell train to Boston after I moved to NH, but that was when gas was $3.50+ a gal and it would have cost me $25 for gas round-trip. Commuting on the train would have added about 2 hours a day to my commute vs driving in.

My work allows me to be very flexible with my schedule, so I've been driving in later to avoid rush hour and leaving work after 8pm. With gas less than $2, it costs me less to drive in than it does to take public transportation, plus saves me 2 hours a day.

Time = Money (or sanity, at least).

While Boston is cheaper, it's not that much cheaper. I think you'll probably do slightly better off depending on the offer you get. (I currently live and work in Mountain View)

Startup-wise Boston seemed pretty sparse compared to the Silicon Valley. That was definitely part of my decision (not just where to work, but as you say, networking, conferences to go to, etc).

I still think little fish, big pond is the better way to go. It gets frustrating otherwise and limits your growth. Important team in a less known company also is much better for career and personal satisfaction.

I'll be honest, weather also greatly influenced my decision. Also what's your move going to be like? Getting all my stuff across the country was yet another reason for me to stay in the SV.

I personally actually much prefer Boston city and the general vibe of Boston, but career-wise I decided SV was better.

I lived in Boston for quite awhile and experienced a bit of the startup scene there. Bay Area beats it hands down. Boston/Cambridge isn't a bad place to be, but my experience has been that the diversity doesn't give you any benefit. Most of the time I was there and doing startups, I felt removed from where the action was really taking place. There's not a lot of momentum there. I'm a strong believer that the people you surround yourself with and who you let influence you have a big impact on your mentality/success.

The price difference in terms of rent/everything else is negligible if you want it to be. As long as you don't need to be in a certain location to make you happy, you can live quite cheaply.

In terms of your job offers: You need to consider what you actually want out of the job. Most likely the real difference is not so great, so the actual consequences of your decision don't really matter. If you are just out of school, you should be focused on opening doors and making connections. But don't put so much emphasis on this one decision -- it's not like you are going to be there 20 years. For all you know, you could be there 6 months and realize that you want to do something else or move.

Whichever you choose, make a concerted effort to try to learn from and appreciate the different social norms of your new home. I didn't do all that I could/should have once, and I regret it.

I guess there are local buses at either end. Emphasis on guess, however, since everyone I know in the Valley commutes by car, except for the truly diehard fifteen-mile-a-day bicycle commuter I used to know. Obviously she wasn't commuting from SF.

Both Palo Alto and Mountain View are extremely friendly to commuters. SF is, too, but it's quite a long way away. That's not to say I don't know a lot of people that make the SF to MV or PA commute. A huge percentage of Google and Facebook employees live in the city. Though Googlers have a shuttle service, with WiFi, so they don't generally take Caltrain.

But, I agree. Commuting sucks the life out of you...even with a train, spending two hours each day in transit just wouldn't be worth it, to me.

And then it's cool for a short period of time, but pretty soon days fade into weeks and every time you dread it, especially when you realize its 45 minutes each way. Suddenly you're spending 10% of your waking time (which is like 40% of your free time) commuting and before you know it you're looking on Monster.com/eHarmony again.

Just a cycle I've observed many times that seems to occur with 100% frequency, though oddly I've never had either a job or girlfriend who was over 15 minutes away.