Not only does it have obvious and enormous personal benefits for Jamie, but it's galvanizing for the team to look back and read through just how much has been accomplished in a few months (I'm proudly on Jamie's team, am speaking firsthand).
Unfortunately, if I wrote such a post for the internship I just finished, I'd have to omit parts of it. Even though the company I worked for published a "Diary of a Summer Intern" series throughout the summer. :(
What Jamie did Wrong at Khan Academy
Our backend does much more than just serve static files -- you'd think that we don't have to do much but we keep track of video and exercise progress, summarize progress by user and by coach, provide video recommendations, host a Q&A system with notification support, award badges in real-time while avoiding costly datastore queries, handle mailing lists and email subscriptions, and have support for having a public profile to show off your progress, among other things.
We handle hundreds of requests per second and it's really nice to not have to think about scaling very much -- with any other solution, we'd be doing a lot more system administration.
It's definitely had its ups and downs, but it managed to stay pretty stable when our traffic about doubled when CS launched.
Also, Im not sure I believe statements like "its nice not to have to worry about scaling", although if it is working for KA at hundreds of requests per second, maybe it is an accurate statement
You can read it here (without images, sadly): http://feeds.feedburner.com/JamieWong
Or if you add that feed to Google Reader or some other RSS reader, you should be able to see it too.
Will look into fixing this.