Flagged for bogus title. I know it's the same as the title of the linked article, but hypotheticals and predictions ought to be clearly marked as such.
The title was preposterous, and when I saw it I was very skeptical -- but I've seen stranger stories which turned out to be true, so I wasn't completely sure.
To be fair, that's why the prediction is for a $300 buy even though 37signals' revenue is 'only' ~ $8million.
Well, that's why this prediction won't come true. 37signals won't sell to Microsoft barring some astronomical price, and Microsoft won't pay said astronomical price for 37signals.
So, why 37signals? 280 North likewise makes web applications well and their Objective-J model is better for making applications (vs. web pages with ajax) than 37signals' model. 37signals is great, but they don't make competitors for things like Visio or PowerPoint. 280 North is in that arena.
And Objective-J wouldn't be hard to swallow for Microsoft. They'd have to replace the widgets with less Apple-esque ones, but it wouldn't be too hard. And it would give them a base akin to Google's GWT.
Microsoft probably does need to get into the webapp world, but 37signals doesn't compete with Microsoft's lineup and Rails really isn't the toolkit to create a Visio-killer.
I think you're missing the point the author is attempting to make. 37Signals is a well-founded company which has several applications, each generating revenue. It's also well-known. The points which the author purports would make 37Signals tempting to Microsoft do not apply for 280 North.
I tried learning Objective-J when it first came out. It was nice and all but I couldn't shake the feeling of uneasiness that I could be writing this app in Javascript + jQuery.