I think the biggest takeaway for me from this is how he had the power to, and actually said, "no" to feature requests. This has definitely been a problem for several projects that I've worked on.
I think that's the hardest part. Generally you say know even when it's technically possible. Hell you probably know exactly how to do it, just not in the timeframe you have. Learning to keep your ego (I can do this) from getting in the way of what's best for the product and the business is the hardest lesson a good developer has to learn IMHO. It's the programmers version of crossing the chasm.