It seems to me like you don't want to be rich so much as you don't want to worry about running out of money. I imagine a lot of people with a decent amount of m

It seems to me like you don't want to be rich so much as you don't want to worry about running out of money. I imagine a lot of people with a decent amount of money feel that way. Personally, I kind of like the hustle and fight at the bottom, but it can get tiring. Money doesn't buy happiness. It only buys you time and the raw materials to be happy. Again, I think your issue might be the thought of losing what you have and that's eating you up. You still have to worry about retirement. You still have to watch your budget. You don't want to have to worry about these things. Obviously if you want to hit 100 million you have to scale big. Since you are afraid of losing money, you would probably need to go a similar route as someone with little to no money. You couldn't hire a bunch of people and you couldn't get into something capital intensive without investors. Going web / app is one way to go. You could hit the scale with little investment. Rather than hiring employees, you would probably need to get someone on board with you to handle the software side of things. You could do a sort of arbitrage. If you want to feel rich, come to the Philippines! On 160K per year (or even 60K) you could do pretty much what you want. If you come up with an idea, you could hire developers for $800 / month. Minimum wage in much of the country is around $6 / pay and a lot of companies find loopholes to hire people for less than that. Maybe go to the mecca of web / apps (San Francisco) and get out, meet people and strike up some conversations. Get a notebook and write down ideas or even just general thoughts. Get that brain working. Creativity is a muscle, it needs exercise before it starts working. Find like minded people. Float the idea of grabbing a sweet party pad in a cheap place like the Philippines or Thailand. Get a maid or two to keep the place clean and cook (or to run to pick up food for you from local restaurants.) Then just build, build, go out on the town and then come back and build some more. You pay for everything (you could probably swing this on just your passive income) and your team gets some sort of stake (maybe even co-founders.) If you need help, hire local developers for cheap. When you have an MVP (and maybe even customers and a solid plan rolling) then come back to SF and pitch to everyone you can. Who knows, maybe you could find some investors and use that money to keep going rather than your own. If it totally doesn't work, go back and try again. Maybe this is naive or not realistic, but sounds like a good plan to me. ;)