Regarding the relevance of Tim Ferris: I'm not overly familiar with his work, but from what I do know, he's very well known for writing best-selling books on applying a scientific method to life improvement. That's what this app does, but puts a nice interface and layer of gamification over it. If Tim also has the tech company exposure as mentioned in the article, why would he not be a valuable advisor? At least on paper, his credentials seem very relevant.
Regarding the manual input of readings, I'm not diabetic, nor do I have anyone close to me that is, so purely an outsiders perspective here. The limitation of cable transfer of data is that 1. You have to support X number of testers 2. You have to support X number of phones 3. It doesn't encourage you to monitor your variations throughout the day. The end result is probably diminished user experience and a much smaller addressable market.
If you watch their demo video, the process to enter your reading is very simple. It will remind you if you're being slack and rewards you if you add information beyond just the reading. For example, you can take a photo of your meal, and make notes on how you're feeling. Presumably the more that goes in, the more value you get out.
