You are asking HN ... as a community we are pretty biased toward start-ups. In many ways you seem ideally set up for technical leadership in a start-up. [1] Y

You are asking HN ... as a community we are pretty biased toward start-ups. In many ways you seem ideally set up for technical leadership in a start-up. [1] You have led teams creating key portions of really successful tech. [2] Money is not a concern for you. This means that you have "infinite runway" to initially explore ideas as long as it is software oriented. This also means that you have the luxury of delaying or being picky about taking on investors. [3] Real business problems - you get to choose [4] Risk, reward - although you are unlikely to succeed, you might be one of those who succeeds, either in building a nice sustainable business worth a few million or maybe even create a high growth "unicorn." In any case you will almost certainly stretch yourself in many different ways.