I don't think you can automate something that optimizes results on this front. It necessarily involves participation of the kids because that's ultimately the goal of not just giving it to them. There has to be a feedback loop, failure must not mean abject failure, but it must incur a cost to them. I think giving them little chunks while you're alive for them to rusk pursuing endeavors will help them figure out risk and the world without that meaning destitution, a place to go home to when failure occurs, and something they can build on when youre gone is a good approach.