I read this a bit earlier today - I can relate to the fears you get when moving away from being freelance. Looks like it all worked out for him though.
stripe are releasing some of the best UI around at the moment. good behind the scenes info from BDC
Stripe talks to me at every pixel and behavior. Benjamin does there awesome work. It also proves a possibility of great remotely work with a designer. This thing is so often impossible at many companies.
I love the example you mention of your CEO getting in to write code so the letters populated randomly to better reflect a human-quality. SHIT. That is inspiring!
(Edit: Just realized this was a repost - apologies)
Really inspirational for me, that I'll join a new startup next week :)