Aug 29, 2013 ยท 2 minutes

Remember AIM? The service formerly known as AOL Instant Messenger was -- how would the service's core demographic say this? -- "hella popular" just a few years ago, and not just among the teeny-boppers who inspired that sad excuse for a sentence. Some, like Josh Bryant and Levi Nunnink, used the tool to collaborate and create a virtual office for their design and development work.

The only problem, besides the burning desire to include an emoticon with every message and replace vowels with numbers, was that AIM sucked at sending files. So the duo decided to create Droplr. The service began as a side project meant to make it easier to share design mock-ups; it has since become a six-person company dedicated to improving the file and image-sharing service full-time.

"Droplr was always something we weren't sure about. But the growth we saw and the revenue we had coming in from Pro changed that," Nunnink says."The ideas we had for it and the growth we were seeing really demanded that we either pay attention to it full-time or stop iterating on it."

Many services promise to make it easier for people to share files. There's Minbox, Hightail, and CloudApp. There's newly-improved sharing features from Gmail and Dropbox. And there are many messaging applications that promise to make it easy to send messages, images, stickers, and other communications. So what makes Droplr different?

Well, to hear the company tell it, it's Droplr's age. The service has been around long enough to attract many devoted users who continue to use Droplr even though all of those other services are available. And that means introducing new features, such as the freshly-launched Droplr Draw, that customers have been asking for for months.

Droplr Draw allows Pro users to annotate images before sending them on a probably-horrifying journey through the miracle that is the modern Internet. Or, put another way: It's Skitch, the annotations tool acquired by Evernote in 2011, but with purportedly better sharing features.

"The thing that Skitch has never done, and that we feel we really do well, is sharing," says Nunnink. "Skitch doesn't have the same power that Droplr has in taking that image and getting it from A to B."

Nunnink says that Droplr would like for new users to sign up because of Droplr Draw, but that's not the tool's main purpose. Instead, it was keeping Droplr's existing user-base happy with the service despite the increasing competition -- fitting, given Droplr's history.

"I guess [Droplr's transition from a side project to a business] really started with user demands. It was getting to the point where users were asking for features, and it was turning into something that was more than a side gig or a project," Nunnink says.

Droplr has been bootstrapped and grown via revenues brought in through its Pro service, which costs $5.99 per month. Nunnink and Ryan Andrews, Droplr's CFO, say that recently "some things have changed" on the funding front but declined to elaborate.