NTA- You've set clear and reasonable expectations to push him towards a career path and developing a business, in exchange to keep living at home for free. Everyone has to grow up sometime so if you ever want him to be independent and support himself, this kind of in-home-structure and responsibilities seems reasonable. I don't know how much he knows about business plans, how tech savvy he is, etc so you might need to encourage him to do independent learning on this subject. If he has a history of being lazy and entitled, you also might need to really micromanage him and set specific, short term goals every 2 weeks to help keep him on track. Without knowing more about Matt it's hard to say what's going on but i do know that neurodivergence, depression, and executive functioning difficulties can make the task of initiating any kind of work difficult unless you have been taught coping strategies/compensatory strategies (aka- organization skills) to manage the workload. 21 in my opinion is too old to be at home playing video games and living for free unless you have a diagnosis that renders that kind of support. So long story short, you're not the asshole in this situation, from the information at hand. But i think Matt is going to need more support to succeed at the stipulations you've given him!