Discussion over the web’s dependency on advertising for revenue has over the years gained more and more attention with the development of various ad-blocking tools and their increasing use in various browsers and operating systems. Most recently, the topic resurfaced when it was announced that iOS 9 would allow ad-blocking applications to be installed by users and also force native apps to use HTTPS for all ads linking to websites or risk broken links. Media organisations and app developers reacted with various levels of concern on the friction between balancing revenue generation with the security of their users data. However, it is a rather blinkered mindset to assume advertising is the only means for income. Instead of settling on a place within this spectrum of how much user privacy platforms are willing to risk, we need to be thinking how to progress new ways for companies to earn revenue while also considering costs to users beyond those associated with payment.