As the author of five books (and my most recent one entirely self-published), I haven't yet worked out how I feel about this or how to respond. My current compromise is to charge more on the DRM-free LeanPub.

Genuine questions here, not rhetorical or trying to imply anything with them.

Why charge more on a DRM free site? Do you think people buying from there are doing so that they can share the book illegally?

If someone wants to share the book illegally, I would imagine they'll just download it from one of the pirate mirrors out there and not bother paying you at all. My guess is you're probably just reducing the number of people willing to pay the price. Classic supply and demand curve against price.

Where possible, I try not to focus on negative motives. Quite simply, if people see a benefit in DRM-free, why not expect them to pay for it? And there are other platforms beside the two I mentioned – it’s not a choice between DRM-free and (for better or for worse) Amazon.

In case your question was not rhetorical: to folks like me, I view DRM as abuse, because it inevitably leads to me paying for something that I won't end up being able to access down the line. It is in direct conflict with building a library. Having the author opt-in to applying DRM to their books (as you have on Amazon and Google Play, for example) and then expected me to pay them extra so I can actually own the thing I paid for makes me take three steps back from the "Buy" button. I tend to just walk out rather than be treated that way. As a result, I've stopped buying Amazon Kindle books entirely (now that I can't strip the DRM). If I'm paying the money, I'm going to demand control, and if I can't get that control, there will be no transaction.

FWIW, LeanPub for your book suggests $25, and the DRM-laden version is $13.50. That's quite the premium!

I reduced Amazon pricing yesterday for Christmas

Makes sense!

This is silly. You aren't competing with amazon you're competing with Anna. If someone is interested in DRM free they aren't stupid. Take the sale but don't take the piss.

Out of curiosity, what’s the ratio between sales on Amazon and the DRM-free option?

Amazon wins by miles, almost to the point of incomparability. For all my issues with Amazon, that’s fine by me: compared to all other platforms, that’s where the reviews and other forms of social proof are.

How do you evaluate if the DRM is working as intended?

Sales on Amazon are working as intended. DRM there is not a variable I can control.

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Another possible compromise might be to use watermarking-based DRM. Amazon doesn't seem to support it, but other e-bookstores do. In any case, thank you for offering the LeanPub option!