Look For What You Know Well
The Startup CTO's Handbook is posted on Hacker News. It's a big chunk of text and it's difficult to figure out what to read and not. No escaping opprtunity cost. User tptacek offers a neat litmus test to evaluate the quality of content quickly:
tptacek (hackernews):
One way I try to get my head around things like this is to skip to a section I understand deeply and see what they said. Here, the claim is made:
Don't try to get a compliance certificate at the last minute. Preparing for and conducting an audit such as for PCI DSS or SOC 2 from start to finish is a lengthy process, ranging from six to twelve months for most startups. Starting early and maintaining compliance is cheaper than starting late and doing rework.
This is basically the opposite of the advice I would give a startup. SOC2 attestations in particular are easy to get, and are a waste of money to obtain preemptively before there are purchase orders on the line for them.
There are things you should start doing early that lay the groundwork for attestations, but you should be doing them anyways, even if you never plan to get a SOC2 (and if a big-ticket customer never demands it, you shouldn't SOC2). That's stuff like setting up single sign-on and having protected git branches; simple best practices.
The other option is to look for recommendation from people you trust. HN scores are a proxy of just that.
Related by JenniferRM (lesswrong):
... my book reading heuristics generally require three independent suggestions before I start taking a book seriously.
A cheaper trick was to search the Stanford Encyclopedia of Philosophy for Bovens, Hartmann, and Williamson which lead to a nest of articles, some of which mentioned several of them. I listed and prioritized them using ad hoc scoring (points for mentioning each person and a good title). Hartmann jumped out because he had wider ranging interests and was tapped to co-author the encyclopedia article "Models In Science". To reduce the trivial inconvenience of starting to read, I reproduce the suggested reading list with my ad hoc numerical priorities right here:
There is also the attempt at compiling The Best Textbooks on Every Subject. I like this one as the recommendations are from people that have sampled multiple books - and they are required to explain the reasons for the relative ranking.