How’s that for a cherry on top?

Oleksii Sverdlychenko/Shutterstock

The two companies announced today that Yahoo Mail users can now save email attachments to Dropbox and access their Dropbox accounts from within their email. (This doesn’t happen automatically; users have to opt in, and then save each attachment individually. Yahoo previously had a somewhat similar arrangement with YouSendIt.)

Yahoo has some 300 million active users, so it’s a good win for Dropbox, which has 100 million registered users.

And we’ve seen this movie before; it makes sense for startups that are coming into power to partner with underdogs (see: Facebook and Microsoft and search).

Dropbox has emerged as the strongest-positioned consumer technology startup in Silicon Valley, given that it has a clear business plan that actually makes money, is a talent magnet, and has lots of room to grow. (Dropbox gives away two gigabytes of space per user, and charges $9.99 per month for additional storage.) For proof, see the Mailbox acquisition — very few other companies could have won that bidding war by using their stock.

Of course, the Yahoo partnership is not Dropbox’s first validation of that sort, by any means. The company already has key promotions and integrations with Samsung and HTC, as well as a platform on which other people can build.

But meanwhile, back on the mail front, Dropbox still has minimal document-editing tools compared to Google and Microsoft, which both have widely used email services, online storage and online collaboration tools.

But that could change. At a press conference about a new photo-viewing interface earlier this year, Dropbox said that it planned to push away from being a secure personal-storage product to become a service that brings content to wherever people need it.

“We’re moving away from a file system-centric view to a more content-focused view,” explained a Dropbox engineer at the event.

But the photos are sort of disorganized. Maybe it’s not even iPhoto. Maybe it’s another default photo-storage service or your go-to cloud app, like Dropbox.

The creators of a new service called Picturelife think they have a better backup solution.

Picturelife, which has been in the works for the past two years, is coming out of “stealth” mode today, showing off a new-new design and introducing video support in addition to storing photo files. The service is the creation of Nate Westheimer, director of New York Tech Meetup, OMGPOP’s Charles Forman (who dazedly walked into traffic after Zynga bought the casual game company for $180 million) and Jacob DeHart of Threadless.

Last fall, TechCrunch reported that the company raised $4 million in funding.

Picturelife’s approach is to work with all of the key photo apps, cloud services and social networks to allow for easy imports and syncing of photos across computer and mobile. As with most photo-storage services, photo files can be synced over Wi-Fi or by physically tethering a phone or camera to the computer.

But if you want to import an album from Facebook, you can do that, and share photos from Picturelife to Facebook and Twitter, too. Photos can be imported from Instagram, Flickr, DropBox, Tumblr, Foursquare and SmugMug as well, and won’t appear as duplicates in Picturelife.

The app’s search function uses natural-language tech to pull up photos and videos, so you can search by using a specific name or GPS location or just phrases like “photos from last summer.”

Westheimer says the service isn’t meant to replace other cloud-storage services — it’s supposed to work with them, offering a more organized photo-storage service and eliminating the need for local storage or a backup hard drive.

Picturelife costs $7 a month or $70 a year for 100 gigabytes of storage, and $15 a month or $150 a year for 300GB. It works on both Mac and Windows computers, and on iOS and Android mobile devices. The company plans to introduce terabyte options, as well as physical photo printing, in the coming months.

Dropbox had been #326,417 in the queue to buy Mailbox, but skipped to the front by tweeting about it.

– Ross Rubin, via Twitter

Sources familiar with the deal say it was a sizable one for such an early-stage outfit, with a price driven upward thanks to interest from some deep-pocketed companies. GigaOM and TechCrunch both claim that Mailbox was acquired for a price “well over” $50 million, with a significant chunk of stock that pushes it closer to $100 million. Here at AllThingsD, we’re hearing that’s generally accurate, but with a caveat: The stock consideration makes it tough to compute real value. “It’s somewhere in between,” another (cagey) source said of the deal.

That Dropbox was able to best such rivals in a bidding war is an impressive feat, and one that speaks to the company’s momentum and its valuation, which these days hovers between $4 billion and $5 billion. Not nearly as impressive a feat as the one Mailbox just pulled off by fetching well over $50 million for a nascent, unproven business, though.

“After spending time with Gentry, Scott, and the team, it became clear that their calling was the same as ours at Dropbox — to solve life’s hidden problems and reimagine the things we do every day,” Dropbox said in a blog post. “We all quickly realized that together we could save millions of people a lot of pain.”

The 14-member Mailbox team will report to Dropbox headquarters in San Francisco next week.

The Mailbox app launched only a little less than a month ago, where it gained much attention for attempting a new take on the way users access email on their mobile devices. Beginning with the iPhone and Gmail, Mailbox allowed for different ways of accessing email, including resurfacing a message after a few days or hours, and color-coding organization. Users were also prompted to swipe in different ways to carry out different actions.

However, the company had trouble dealing with demand, with many would-be users downloading the iPhone app but unable to use it while they waited for their turn to be let off the list. Some 1.3 million people made “reservations” to sign up for the app. Even without letting all of those people in, Mailbox is already delivering 60 million emails per day, the company said.

Mailbox explained in its own blog post on the acquisition, “We can’t wait to put Mailbox in the hands of everyone who wants it.” And of Dropbox: “They’ve got a ton of experience scaling services and are experts at handling people’s data with care.”

As with any sort of startup like Mailbox, the business model immediately came into question: How was a small email app supposed to start generating revenue?

The answer, it seems, is clear — now it doesn’t have to.

(Image courtesy of Revenant/Shutterstock.com)

BYOD is pervasive whether enterprise decision-makers have embraced it or not. In fact, research by Harris Interactive reveals that 81 percent of employees already use personal devices at work. BYOD is an affordable way for connected, data-driven employees to work around the usual hassle of IT, and next-generation smartphones and tablets offer them invaluable productivity and file-collaboration applications. So, for all of its advantages, why does BYOD cause more and more anxiety within organizations, particularly since using mobile devices in the enterprise became standard decades ago?

The big IT dilemma with tablets and other personal devices is data protection, plain and simple. The days of company-issued BlackBerries are long gone. Now, as privately owned tablets and other personal devices log on to corporate networks and exchange company files, it becomes harder and harder for IT departments to guarantee the accessibility, availability and protection of data stored outside the “four walls” of their own infrastructures.

Data is moving between secure corporate servers and unregistered personal devices, and even into third-party storage services like DropBox, which makes it difficult to protect sensitive information and leaves it vulnerable to corruption — or worse, leakage to malicious hackers or fraudsters. Corporate data obtained through tablets and smartphones — including employee information, text messages, emails and confidential documents — is incredibly valuable for cyber criminals, and incredibly damaging to organizations and their customers. The threat of mobile data leakage is very real, and a recent Forrester survey found that nearly 40 percent of professionals were concerned about security on their devices.

Despite these risks of personal device use, the enterprise shouldn’t push back, but instead should plan and adapt by instituting new policies that make BYOD not only a productivity driver but a seamless and secure way to create more interconnected workplaces. That means the role of IT must change. IT must become an enabler, and ensure data is secure and available, regardless of where and how it is stored and accessed.

Shockingly, research by technology advocacy group ITIC found that 71 percent of businesses that permitted BYOD had no specific BYOD security or support policies. However, there are immediate steps enterprise decision-makers can take to create businesses that are primed for accommodating personal tablets and other devices without sacrificing business continuity and security. The first measure is to put in place policies and procedures that account for personal devices accessing the company network. These should include regular security audits to ensure mobile-related vulnerabilities are addressed and up to date. Additionally, business continuity plans should be updated to reflect BYOD realities. For example, employees should have an easy way to report when their devices are lost, so that IT can block access to company networks and wipe sensitive data clean.

However, policies and procedures aren’t enough to resolve data protection concerns in the BYOD era. It’s also important for enterprise decision-makers to seek out simple and comprehensive data solutions that help integrate personal device use and traditional IT, without complicating workflows for their employees. These include mobile device management (MDM) systems, which help IT regulate devices accessing corporate data, and central management tools that monitor all devices connected to the network. Additionally, employees need access to enterprise-friendly file-sharing, storage and collaboration tools, so they aren’t motivated to seek insecure, third-party alternatives like DropBox. Storage, backup and business continuity solutions should all be aligned with BYOD to create a seamless IT environment.

The advantages of BYOD are undeniable. For example, a recent CDW poll found that 84 percent of professionals experienced improved multitasking using tablets, and gained more than an hour in productivity benefits. If tablet and personal device use in general is such an asset to the workforce, enterprises must focus on making BYOD secure. The implication for IT and all enterprise decision-makers is clear: Data must be available, accessible and protected, regardless of where, when and how it is accessed. With that in mind, IT can keep calm and carry on as the tablets come marching in.

Scott Crenshaw is Senior Vice President of Strategy and Chief Marketing Officer at Acronis, a Woburn, Mass., company specializing in data availability, accessibility and protection solutions for physical, virtual and cloud environments.

I was so delighted to get your instructions last week on how to delete pictures from my iPad but it doesn’t work for me. I can check off the photos I want to delete and the red delete button does comes up — but it doesn’t delete. It’s dimmed. Any ideas on how to get it to work?

A:

I apologize that my answer last week was incomplete. You can only delete photos in the Photos app on an iPad if they were either taken on the iPad, received on the iPad via email and saved to the Camera Roll, or loaded using the iPad USB or SD card camera adapters. If the photos were synced to the iPad from iTunes on a computer, they can’t be deleted on the iPad. This is almost certainly why your delete button isn’t working. Apple says it bars such deletion because synced pictures are considered to primarily exist on the computer. If you want such synced pictures off your iPad, Apple says you have to go into iTunes and turn off syncing those particular photos or albums to your iPad, or turn off photo syncing entirely.

Q:

How do you create a new photo album on an iPad and get the pictures in the order you want?

A:

To do so, first use the Edit button, select multiple photos, and then use the “Add to…” button, add them to a new album and name the album. Once the photos are in the album you created, you can arrange them by hitting the “Edit” button again and dragging the photo thumbnails into the order you prefer.

Q:

I’m looking for a very light laptop to take on the road. Would it be possible to use an 11-inch MacBook Air on the road while using a PC in the office? All my files are on Dropbox or Evernote. Can I run Office apps like Excel on a Mac and modify files on both the Mac and PC?

A:

Yes. Microsoft makes a native Mac version of Office that uses the same file formats as the Windows version. And Dropbox and Evernote are available and access the same content on both platforms. Most other common file types, like JPG photos, MP3 music and PDFs, work interchangeably. And the MacBook Air is an excellent thin and light laptop. It can even run Windows itself — and the Windows version of Office — if you choose.

Email Walt at mossberg@wsj.com.

Image copyright Pakhnyushcha

These days, it seems as soon as some new technology begins to gain traction, VCs and journalists herald the arrival of a new technological order. While these predictions often end up being true eventually, many of us are left aggravated that the status quo sticks around for so long. Perhaps no such case is as true as with the cloud. The cloud has, without question, resulted in truly revolutionary benefits to enterprises and consumers, but it always seems to be presented in a very autocratic way: Stop what you are doing, and do things a new way.

Enterprises are obviously the first to accept such requirements. As long as this new solution offers a material benefit to their business, the smart companies will rapidly adopt it and put it to work. Conveniently, they are also quite willing to pay for such benefit, should it be real. This is critical, because consumers hate paying for things, so someone has to underwrite the commoditization of new technology. This is essential to understand because, contrary to what is marketed to consumers, the cloud is expensive.

People are buying and creating unbelievable amounts of content daily, driven by photos, personal videos, music and movie purchases. Movies and personal video have gone from standard definition to high definition — potentially going to ultra-high definition, if CES is any indication — and the trend is clearly moving more toward online purchasing. Music downloads surpassed CD sales two years ago and, even in light of successful streaming services; online music sales continue to grow year over year. Digital photography and videography have also surpassed their physical counterparts. Indeed, photos and videos are no longer things you take only on vacation or on special occasions. Smartphones have enabled us all to shoot photos and video all day long, for even the most mundane reasons. All these devices are continuously increasing resolution, and thus file size.

Gartner estimates that the average household had roughly one terabyte of files by the end of 2012, with that forecast to grow to approximately 3.3TB by 2016. At the same time, it is estimated that people will have, on average, 5.8 Internet-connected devices per person by 2015. There’s no doubt that people will continue to spread more and more data across more and more devices, based on these trends. If these predications are even somewhat accurate, the assumption that the cloud will be able to affordably accommodate all consumer data is difficult to accept.

Cloud storage is not built from hard drives bought off Amazon.com on the cheap. Indeed, whether it is the consumer cloud or the enterprise cloud, cloud storage services are enterprise-grade through and through. “Enterprise-grade” might as well be synonymous with “expensive.” That pricey storage is made up of enterprise-grade hardware, and kept in an enterprise-grade data center. Every step of the way, it is managed by an army of smart people, who are generally well paid. Let’s not forget local and geographic redundancy. The result is that while cloud storage is able to reduce its price slowly over time, consumers are increasing their storage demands on a near-geometric scale. Thus, while consumer cloud services may have a free tier to give consumers a taste of the benefits, virtually none of them offer enough storage to accommodate all the average person’s data. If some company were to cobble together all the necessary Web services to offer this, perhaps built off of Amazon Web Services or Microsoft Azure or something similar, it would cost nearly $1,000 per year in storage alone, and, of course, there is much more to all this than just storage.

The result is “cloud fragmentation” — users are putting subsets of their files into a litany of separate cloud services. Sometimes this is driven by the amount of free storage, and other times this is driven by an optimization of media type (e.g., documents versus videos). This fragmentation, however, increases complexity and becomes a burden to manage. I often have to think about whether a given document is in Dropbox, Google Drive or SkyDrive. My photos are spread across Flickr, Facebook and Instagram. Some videos are on Vimeo and others on YouTube. Of course, these are only a very tiny fraction of my more than 900 gigabytes of files. This complexity is something I refer to as “cloud overload,” where the number of cloud solutions I have has me scratching my head to remember which one I use for what, or to share with whom.

Why would consumers choose to do this? Price. The free tiers of most cloud services are indeed quite alluring. The marketing is great. The benefits are clear. It is the price that’s unacceptable. To mitigate that, consumers do all they can to extract benefit from the free tiers.

This is a clear divergence between consumer demand and technological reality. Cloud storage is too expensive for consumers to purchase for all their data, so they don’t. The result is user data getting spread across an array of primarily free solutions that fragment features by media type or value proposition (e.g., sharing, backup, etc.).

Occasionally, we see enterprises underwriting technological development that does not lead to the technological maturity and commoditization consumers require, at least not very quickly. This is, without exception, the case with the “consumer cloud.” Consumers require simplicity, convenience and affordability. The consumer cloud is built from services, including storage, sharing and device/platform interconnectivity. We’ve seen many companies emerge as tremendous successes; however, the products that define this space are themselves defined by their compromise in regard to consumer demand and expectations. Changes in user behavior (e.g., stop doing what you normally do, and do it a new way) are the friction that slows ubiquitous adoption. Furthermore, high cost ultimately makes such products, even when widely adopted, niche solutions.

Still, cloud services offer such unbelievable benefit that no one would argue that there is not demand. The question is less about what benefit can be derived from the consumer cloud; rather, it is how it should be delivered.

So, what solution have savvy startups begun to offer? It’s what is increasingly known as the “personal cloud”: A way for users to access all their files, on all their devices, all the time. And best of all, it’s affordable.

Personal cloud services for consumers give users the ability to have all their data on all their devices. While not a consumer platform, Amazon Web Services (AWS) provides a good model, since it delivers truly groundbreaking cloud services within a fairly simple service approach. Personal clouds are somewhat analogous to AWS on a consumer level. New personal cloud services have started to build inter-device connectivity into the operating system of your devices, which is conceptually similar to AWS-like services being built into your own computing devices. The result is that instead of users conforming to some new product’s requirements for you to get value, it conforms to the user’s own behavior.

Products like this are technically challenging to build, because they must integrate deeply into some other platform/device; in fact, they often augment it so that the device or operating system itself works in a new way (e.g., as a part of a personal device ecosystem). The result, however, is that consumers are offered a solution that accommodates their demands — one that is simple, convenient and affordable. These services can be cheap or free for any amount of data, whether you have 2GB, 2TB or 2PB, because they are leveraging your own devices to create your cloud and not hardware located in and across multiple data centers.

We all can be overzealous about predicting the future at times, so it is important to take stock of the present. The cloud is producing some of the biggest benefits to enterprises and consumers since the inception of the Internet itself. It is shepherding a variety of services and products that enable content sharing, distribution and access. While enterprises may reap the most advanced benefits of this now, it is obvious that the consumer versions of these technologies are compelling and exciting. The opportunity for companies to innovate is often not measured in features, as much as user experience. This is the unrealized opportunity within the consumer cloud, and the direction so many companies are taking to build the next set of products to affect our lives.

Today, DropBox announced some enhancements for its business-oriented Dropbox for Teams service. The big one is the creation of a new administrative console that gives managers the ability to keep track of all users signed in to a company’s Dropbox account, and to also control what they can and can’t do, how much space they’re using, and what devices they may be using.

If you’re a typical Dropbox user, you probably use it to share files between your home and office, or to quickly share with people you do business with outside your company or with lots of people on your team. In this way, Dropbox has sort of snuck in the back door of large companies where it is used, and has recently fully embraced that with Dropbox for Teams. The service is in use in some capacity by people at more than two million businesses around the world.

The company said the new features are part of a stronger strategic push to make Dropbox more enterprise-friendly this year. It has got a long way to go versus Box, which has been aimed at the enterprise since day one.

The new features include photo albums, quick previews for PDFs and other documents, and easier sharing to Facebook, Twitter and email. All of them are specifically for the Web version of Dropbox, and all are expected to be released to all users within the next month.

This isn’t anything that’s going to make anyone’s jaw drop. But the thrust of the features speaks to a larger aim of Dropbox to be less of a secure personal storage system, and more about bringing content to wherever people need it, said Dropbox’s Chris Beckmann, who is product manager for Web and photos.

“We’re moving away from a file-system centric view to a more content-focused view,” explained Ramesh Balakrishnan, the company’s engineering lead on photos.

So, for instance, Dropbox previously hadn’t had a notion of a photo album. In the new system, once photos are grouped together into an album, Dropbox understands them to remain that way, no matter if the files are moved around or subsets of them are shared elsewhere.

These small moves that Dropbox is making to improve the way it handles content show how far the company has to go. For instance, there’s no way to navigate photos besides scrolling through them in chronological order. And within the document previews, there are no editing tools.

YouSendIt, the file-sharing and enterprise collaboration company, said it had bought a small startup called Found Software that helps users find and discover a wide range of data across many devices and cloud services.

The Campbell, Calif.-based YouSendIt, whose newish CEO is former Yahoo and AOL exec Brad Garlinghouse, said it had found a “cloud-nostic platform” — no, really, it did coin that term — to increase the mobile capabilities of its services.

YouSendIt did not disclose the price it paid for San Francisco-based Found, which was co-founded by Stephen Brady, Vijay Sundaram and John Mitchell. They will all join YouSendIt.

But the acquisition does give the company some differentiation in search and discovery in the fast-growing data storage and sharing space, as it seeks to compete with powerful rivals from Dropbox to similar offerings by big companies like Google.

I talked to Garlinghouse about this, as well as why he went to YouSendIt, and how it might be rebranded going forward, in the video below: