Datadog's $65M/year customer mystery solved

In my career, I have found that this is not usually the question to ask. I am very confident that I could put together and support a solution that does everything I need Datadog to do and has direct costs far, far lower. However, this would also consume a noticeable fraction of my time, both in predictable ways (maintenance, feature adds that I decide I need), and in unpredictable ways (oh no it’s down).

I believe a much more useful question to ask is just “is this the highest and best use of my finite attention and time?” It is much easier to find $100,000 a year of budget than it is to find an additional $50,000 worth of skilled[1] developer time.

[1] This skilled part is critical because if you have some flunky create your “SaaS alternative” you are in for an even worse time.