I wrote an article about my experience with YC Startup School earlier this year.
At the very end, I mentioned Courtland and Channing along with a feature request:
I really like the concept of weekly updates on SUS. IH Milestones CAN function somewhat like that, but they're public, and it's a free text input, no specific questions. I suggest checking them out on SUS and thinking about whether it makes sense to add a similar feature to IH.
I never got a comment from the IH team. I'm still visiting SUS dashboard every week to enter my weekly update because I really like their format and the simple charts.