A few months ago, I went to pick up a computer for a friend at the Apple store and had to wait for 45 minutes while memory was installed. While I waited, I listened to conversations of people coming in to ask technical support questions at the "Genius Desk."

In the 45 minutes I was there, every question asked was about getting around iTunes’ Digital Rights Management (DRM) for legitimate and legal reasons. Every answer was a "sorry" and a shrug.

Here’s an example: "I have a desktop computer, a laptop computer, and an iPod. My laptop broke and you guys just gave me a new one. Now I can’t copy my music over to the new computer." That iTunes users has every legal right to copy the song onto their new computer but the DRM won’t let them do it. What are the chances of someone that spends $200 on iTunes music files and gets locked out from their own legally purchased files by DRM goes back to buy more songs or re-download the ones they lost? Very low. They’ll buy a CD or just go download those songs on a P2P network they know is secure or unmonitored.

In response to this, iTunes’ DRM has become more permissive but it’s not enough — nor can it be. Ultimately, iTunes is competing with P2P systems and ad-hoc systems of swapping amongst friends. The RIAA is wrong in their characterization of the fundamental difference between these systems: the difference is not one of price — the price can (and will) get cheap enough that very few people will care. The core issue is one of software failing to respect its users by privileging the desires of outside interests (in this case the RIAA and its member companies) over its users’. The users get screwed and they won’t come back.

Here’s another example. The last three times I’ve introduced the concept of Free Software to folks, they’ve asked if Mozilla, which they use, is Free Software. Mozilla has taken off in the non-Free Software crowd in large part because of its ability to do pop-up blocking and some related features. Mozilla is doing something that Internet Explorer doesn’t and they’re sick of IE.

Nothing is stopping Microsoft from adding this functionality to IE. In the absence of patents, Free Software shouldn’t assume it can "out innovate" well-funded proprietary software (which seems to be one claim of the Open Source camp); functionality can and will be copied. The reason Internet Explorer can’t compete with Mozilla is that Microsoft places the desires of some (their executives, their executives’ friends, their shareholders, advertisers, pop-up-makers, Hotmail users, the RIAA and the MPAA) over the desires of their users. Microsoft chooses to not incorporate functionality that their users want.

The mistake that both the RIAA in demanding DRM and Microsoft in designing web browsers that don’t block pop ups are making is that they’re taking their de facto monopoly for granted. Their software is annoying — or worse — and as long as viable alternative exist, a growing number of people will turn to them. At some point, things will tip. As people become aware that there are alternatives, these monopolies will be eroded. Ultimately, they will be dismantled. The incumbents, chained down by deals and alliances and promises made to advertisers, recording industry executives, shareholders and their ilk, will find themselves unable to react in an appropriate or timely manner. Free Software is already poised to capitalize on this.