to be fair a friend of mine made one of the first flashlight apps on iOs and made a tidy sum out of it.

I think the question really is about how well you hit your timings. You can have held bitcoin but sold it went it hit $5k or less. You can have a technical advantage in a given field but somehow waste it (dead startup, serious illness) and lose your timing. Nobody knows what the right timings are, but I think the OP is pushing for a more consistent risk investment strategy and setting up the timings to raise the floor significantly at the cost of losing some of the best possible ceilings.