Also interesting is that someone with such a large and relevant audience on tap couldn't maintain a level of sales that could pay for the font and cloud service

Also interesting is that someone with such a large and relevant audience on tap couldn't maintain a level of sales that could pay for the font and cloud service. That's a huge leg-up on what the average developer can work with. And while their roadmap might've been off, it wasn't insane - you can make a $5 productivity app work. We have an iOS productivity app (at the same pricepoint) of which Gruber was very, very complimentary. We elected to advertise it on Daring Fireball (not cheap) and saw a reasonable return. It's a focused audience for someone with an iOS app. Personally, I think they should've swapped out the font and maybe sold the app to someone who thought they could get it on track.