I had a conversation yesterday with two friends. Neither one is technical at a developer level, but both are long-time Mac and iPhone users. They know their way around the platform.

My first friend, we'll call him Ted, said he was having trouble with his iPhone. His photos and videos had grown to take up nearly 10GB of storage space. And with a only a 16GB iPhone, his phone was very nearly out of room. He wanted to know how to backup his photos off his device but still be able to access them when needed.

He assumed there was an Apple-centric way of doing this. He figured he could just buy more iCloud storage space. He was shocked when I explained to him that the only user-friendly solution I know of is Dropbox. I told him that even if he bought more than the default 5GB of iCloud space, he'd still be limited by his on-device storage limits. iCloud only backs up what's currently on your phone. If you delete photos and videos from your device, they're similarly deleted from your next iCloud backup.

I walked him through how the Dropbox app works. Install it on your phone, sign up for an account, and the app periodically uploads everything in your camera roll to your Camera Uploads folder in your Dropbox. Once uploaded, you're safe to delete them from your device - freeing up space. Then, you can either use the Dropbox app to browse your photos or a dedicated Dropbox photo app like the wonderful Unbound.

Ted thought that idea sounded like a great one and was all ready to sign up. But then I told him the catch - the free Dropbox plan only offers 2GB of space. He needed at least 10GB, which I said would cost $99 a year.

He was dumbfounded. In an age where seemingly every online service is free, why should he have to pay for Dropbox? I tried explaining the value it added and how much I loved the service, but he just couldn't get past the idea that this was a service that Apple should be offering as part of owning the phone. I couldn't really disagree with him. It does seem like a problem Apple should be solving, but they're not.

With all that said, my other friend Larry chimed in. He said he wasn't worried about his photos and videos because he was backed up. I asked if he were already using Dropbox or paying for one of the larger iCloud storage plans. He said "no, I bought the larger 32GB iPhone so all my data is backed up with Apple."

This time I was flabbergasted.

He went on to explain that all of his data was safe because of iCloud. I let him finish and then had to break the bad news to him that iCloud only works for the first 5GB. Once you go beyond that, none of your data is backed up unless you're a paying customer. Apple, through all of their flashy marketing around iCloud and promises of it "just works", has convinced a large set of non-technical users that their most precious data, their photos and videos, is safe when it's actually anything but.

This is exactly that problem that I'm writing about in my book. I'm desperately trying to preach to users that the data you hold so dear isn't being handled by Apple. If you lose your phone, in most cases, your photos and videos go with it. And as I talk to more and more people about this problem and explain to them how things actually work, so often I'm met with incredulous stares. Not that they're surprised or outraged about their data not being safe, but at the sheer audacity that someone would suggest they need to pay for their data's safekeeping.

In person and in my upcoming book, my goal is to make a solid case that your data is most definitely worth the measly $9.99 a month Dropbox charges. My sister was absolutely devastated when her iMac's hard drive failed without a backup. She mistakenly thought that her (at the time) iPod's photo cache served as a full backup of her photos. I can still remember the awful look on her face when I explained that her four years of high school photos along with the first year of her college photos were reduced to nothing more than 160 pixel wide thumbnails.

Apple never marketed to her that her iPod Photo backed up her memories, but she still mistakenly assumed that. But now we're in an even worse situation where Apple really is marketing to users that all of their data is safe. I can only cringe at the thought of how many customers go to a genius bar to get a replacement phone and are told "just sign into iCloud and all your data will be restored" only to find out that's not the case.

My mom meticulously archived and organized our family photos into dozens of albums when we were growing up. All those albums and film development cost real money. It was an investment. The idea that everything online should be free has created a pernicious entitlement culture where users are unwilling to pay a little money to safeguard their most precious digital memories.

It's a terrible situation and one I'm trying to correct with my book this Summer.