Well, rich is relative, of course. But, I take in about 200k in passive income / year. My house is paid for, and while I budget for 120k / year in expenses, it's actually more like 60k. So, the rest just compounds. (Once you have everything, it's hard to find things to spend money on.)

At my first job, I made 30k / year. And, that sort of set my standard of living. I bought my first house in early 2000s for $250k which increased my cost of living. But, I made it back in increased equity. But, everything else went into investments. I maxed out my 401k with index funds. Non-401k investments went into a mix of technology stocks.

As for The Dude lifestyle. Well, I'm mid-40s. I smoke a lot of weed. Hang out with my friends. We make bad music, art, and comedy together. I bike a lot. I chill under the sunset. I still like to make software, and I'm still relatively good at it, but I have no interest in interviewing nor competing with today's hungry all-stars. So, I just abide.