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It's an abomination on so many levels.
If your team is comfortable with Microsoft's stack, why force them to learn Java/python?

Well, they other options are open. So it might make sense. :P

Microsoft's stack adds a not-insignificant cost to a 3-4 person bootstrapped startup's budget.

Up to you whether or not you're getting enough of a productivity gain to justify it.

Visual studio express editions are free and a windows vps is cheap.

Even if you decide to spring for the full developer licenses you are looking at less than a week of a developers salary for some really good tools.

During one of the podcasts I believe Jeff stated that he was able to get free copies of the most expensive version of Visual Studio from a friend at MS.
If you are a startup you can probably get Microsoft's software for free.

Talk to one of their technology evangelists, they love seeing cutting edge companies building their business on MS.

Anand Iyer, http://blogs.msdn.com/aniyer/, can point you in the right direction.

Jeff Attwood and co that built it are used to .Net/MS/Visual Studio development, so for them the cost was probably small compared to the cost of switching stacks + tools.
The MS stack also has lots of good tools which can help speed up development.
Hey, everyone, let's use this content-free comment to vote on how much we like ASP.NET!
Take a look at the html source and see if you think it's an abomination.
I don't. Why should I?

Also, you may want to peek at the HN HTML source.

.. At least they didn't use Visual SourceSafe.
With what was Stock Overflow built?
As long as we're being pedantic:

With what was Stack Overflow built?

:~)

It's probably not the stack I would pick and my initial reaction is always to gasp when I see startups built on Microsoft, but...

- ASP.NET can scale, if you do it right. Aside from Microsoft.com/MSN, which don't really count, MySpace uses it (though they upgraded from ColdFusion, which wasn't much better) and Plenty of Fish, the web's largest dating site, uses it too: http://www.plentyoffish.com/about_team.aspx These are probably all larger than the most successful Rails sites.

- ASP.NET MVC isn't a horrible programming model. Forget the abomination that's normal ASP.NET with its funky events. If you've used another MVC framework like Rails or Cake, you'll feel right at home.

- Microsoft's startup program gives startups the early software for super cheap: http://microsoftstartupzone.com/

- It's all about getting v1 out and releasing early and often. If your team grew up on Microsoft, are you really going to make them all learn a new framework? If you do it right and prove out your idea, you can always rewrite later.

Also, lot easier to find programmers if you're in .net or java. One might argue about the quality, but certainly the supply is much larger.
"my initial reaction is always to gasp when I see startups built on Microsoft, but..."

What would you recommend that career Microsoft developers use for their startups?

Maybe just have static html pages, web services, and jquery for Ajax. Use whatever you want for the web services (Python)
I didn't like stackoverflow.com UI.