I love that he starts with:

But I have to start with a kind of meta-cautionary note:

When you run an active website by yourself, you will come across many opportunities to geek out. This stuff is fascinating at every level of abstraction. But the same curiosity and desire for mastery that helped you succeed as a programmer will now lure you into burning massive amounts of time if you allow yourself to dick around. Every new problem domain will attempt to seduce you with its beautiful, chess-like subtlety. You have to ignore this and respond by playing checkers.

It's a great blog overall if you are interested in the mechanics of a single person web-scale startup.

It's really, really tempting to solve problems you don't have.

I prefer to make problems so that way I can solve the problems I do have.

Considering the blog post is from this month June 2012...

So spending time setting up a data center in the age of AWS is playing chess, where you could get away with AWS and play checkers; isn't it?

What am I missing? (-:

He already has significant scale; running his service on AWS would cost him 5-10x per month.

We pay more for AWS for PandaWhale each month than he pays, and we don't have nearly his scale.

As far as I can tell, Pinboard has never been on AWS. He was leasing dedicated machines before and now it looks like he's "Going Colo."

I'm pretty sure he's just talking about KISS when he says chess vs checkers. Engineers have a strong tendency to over-engineer solutions when in many cases, simple is better. I've certainly been guilty of that myself...