We noted yesterday that Box rejected an acquisition offer significantly higher than its $550 million valuation. The company making the offer hasn’t been named, but just last week Chip Hazard reported that Dropbox rejected a $800 million take-over bid from Apple. What’s going on here?

Both Box and Dropbox, along with other services like Sugarsync and Syncplicity, offer the ability to not only store files in the cloud but also to sync files between the cloud, desktop/laptop computers and mobile devices. Each provider offers client applications for multiple platforms, including Windows, OSX, iOS, BlackBerry and Android. If Apple really is interested in Box and Dropbox, I’m guessing it’s to shore-up iCloud’s syncing capabilities. Syncing is a non-trivial technical challenge and both Box and Dropbox have proven technology and experienced teams. If Box and Dropbox aren’t in play, keep an eye on Sugarsync, which has been getting some serious analyst love lately and also features device management capabilities.

I should also be careful to point out that it could well be Apple didn’t bid on either Box or Dropbox. All parties are mum at this point. And I have no reason to think it was Apple that made the Box offer other than the report that it also tried to acquire Dropbox. VMware, which has been on a software-as-a-service acquisition spree lately and has provides Box with Active Directly integration, is another candidate.

But if it is true that both companies declined big acquisition offers, was it a wise move? Venture Beat’s Matthew Lynley wrote that the rejection “isn’t necessarily a bad move for a hot company like Box.net, because it could suggest the company is desirable and attract other, richer offers.”

However, it reminds me of Foursquare’s rejection of Facebook’s rumored offer and GroupOn’s rejection of Google’s $6 billion takeover bid. Check-ins are sounding a lot less sexy these days, and Foursquare competitor Gowalla recently pivoted. Meanwhile GroupOn’s IPO is troubled, to say the least. It may have been wiser for these companies to have taken the cash when it was offered.

Still, with Microsoft’s cloud storage offerings (SkyDrive for consumers and SharePoint 365 for enterprises), Amazon’s tk, Apple iCloud and Google Docs, it’s hard not to question the wisdom of the decisions. And with the RIAA gunning for file storage/sharing services, the legal backing of a major corporation should come in handy.

On the other hand, some thought it was crazy for Facebook to turn down a $1 billion acquisition deal in 2006 (Facebook was recently valued at $80 billion). Unlike Foursquare at the time of Google’s offer, Box and Dropbox have business models and revenue. And unlike GroupOn the companies’ services aren’t necessarily easy to replicate.

And Box, which is more enterprise focused than Dropbox, has integrations with other document storage systems like SharePoint, Google Docs and Documentum. It’s been focusing on offering a better experience, especially mobile, than out of the box enterprise systems. It claims 60,000 customers, including some big names like Proctor & Gamble. That’s a good place to be.

Services Angle

There’s huge interest in cloud file storage right now, and especially in companies like Dropbox and Box that can help users access files from mobile devices. And Apple really was interested in Box, it could say something about Apple’s enterprise ambitions. iCloud is expected to include a Google Docs-style hosted version of Apple’s iWork applications, so it could be getting ready to take Microsoft, Google and Box head-on.