Have a chat with him on what motivates him. Is he seeking attention, approval or is he generally curious about understanding and breaking things? As others hav

Have a chat with him on what motivates him. Is he seeking attention, approval or is he generally curious about understanding and breaking things? As others have mentioned, things are better when he is on the straight and narrow. If he doesn’t want to work for a company, he can work for himself and consult / sell his expertise for companies that are willing to pay top dollar for finding serious securirty issues in their products and services. Finding a mentor (as has been mentioned) will go a long way. Someone that had been trouble for himself and others - but decided to go on the straight and narrow - and basically provide and educate with various choices and consequences (both good and bad).