Just a little more than two weeks from today, on Sept. 2, Box CEO Aaron Levie will host BoxWorks, the company’s biggest pep rally of the year. There’s a nice line-up of all-stars keynoting — Jim Collins, author of Good to Great, Disney’s Jeff Katzenberg, LinkedIn’s CEO Jeff Weiner and Aneesh Chopra, former CTO of the United States.

And then, of course, there’s Levie himself. Not only is he Inc. Magazine’s Entrepreneur of the Year, but he’s also got celebrity-like status in Silicon Valley. Never mind his Hollywood connections to the likes of Ashton Kutcher, who invested in Box, and Oscar winner Jared Leto who reportedly visited the company earlier this year.

But There Are Big Problems

What’s less likely to be out for display are Box’s miserable finances, its delayed IPO and talk of increasing competition from industry giants like Microsoft, EMC, Google, Citrix, VMWare, Amazon and fellow Sync and Share startup Dropbox.

Though you certainly don’t see Levie sweating in public, he has to be feeling the heat. Consider that one year ago analyst Forrester gave Box the pole position in the Enterprise File Sync and Share (EFSS) space, by last month Gartner tagged it as the third of four leaders in its Magic Quadrant for EFSS.

Levie would, no doubt, argue that he’s thrilled with Box’s placement, especially because it is the only “cloud-only” provider in the Leaders quadrant. And while that’s certainly an achievement, cloud-only may not be what Enterprises want at this point in time. Consider that, according to a reliable source, shortly after GE chose Box as its EFSS solution, the conglomerate’s managers got push back from some powerful users who refused to put all of their files in the cloud.

This problem is being solved by adding a second vendor’s services, which GE already uses, into the mix. But the fact that a company who wants to be on the edge couldn’t go with Box as a standalone may be proof positive that, at this point in time, a cloud-only play, regardless of how good it is, isn’t a single best solution. Especially when there are more highly rated options like EMC Syncplicity and Citrix, which are hybrid, available.

Hedging Bets

Whether Box can remain viable as a “cloud only” solution is something that would-be customers and investors will likely scrutinize.

Or maybe they’re already doing that. Especially if what Heather Sommerville of the Mercury News reported is true.

Referring to Box’s most recent round of funding in July, she indicated that at least one of Box’s newest investors is hedging its bets. She wrote:

Under the terms Box agreed to as part of a $150 million investment this month, the company must go public by July 2015 at a value of no less than $20 per share or it will be on the hook to pay penalties to investors."

Box a Leader, But Not THE Leader

But this isn’t Box’s only pressure where timing is concerned. Dropbox, which didn’t have much of a business offering until now, is beginning to catch up. (Watch for news tomorrow.) So is Microsoft. And EMC’s Syncplicity and Citrix’s ShareFile both out-ranked Box (qualifiers were “completeness of vision” and “ability to execute”) in Gartner’s Magic Quadrant that was released last month. It’s worth noting, too, that neither of these giants is sitting still. EMC Syncplicty lowered its prices and increased its storage allotments late last week.

Box’s other competitors are making strategic moves as well. Fellow MQ-dweller Accellion, which was hell-bent on private cloud-only before last week, is now available on Google Drive for Work and Microsoft’s OneDrive. Not only that, but they’ve also taken on a self-service sales strategy, which Box also uses, on their kiteworks for teams offering.

And then there’s AirWatch, which VMWare bought earlier this year. They have what is probably one of the strongest mobile plays in the industry. And it’s only recently that they started (General Manager John Marshall wanted to have the time to get the integration right) to show up VMWare’s price sheet. But now that they’re there, VMWare’s massive, red-hot sales team will be selling their wares and, Box competitor, Secure Content Locker is one of them.