Your question seems a bit too general to give a good answer without anymore context. If you are talking about skills for a specific job or industry, then following and talking with industry experts is enough. If you are talking about trends to help with your own business, then obviously it depends on what your business is :)

Either way message me if you would like to chat in more detail on this.

Read Hacker News.

Go out and meet people - and make friends with people who you think are smarter than you. There is a logic that you are the average of the five people you spend the most time with.

Talk to those friends constantly.

If you always chase after skill sets, certifications, you will be operating at relatively the same curve as everyone else who is doing the same thing. And that's good. But, if you truly go for things that truly challenge your thought process, thinking, and framework beyond an academic sense - things that other people can't copy, you will end up a better founder, a better CEO, and a better person as a whole.