How much $ is needed to never have to work again?

[Ludanto]

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I had a friend a few years back whose company stock options ballooned to the point that he asked his father (a VP of finance at a major company) how much he would need to retire at 25 and live the same lifestyle his parents did. I'd describe the lifestyle as the upper end of middle class. Nice 4 BR house in the 'burbs (no McMansion), new Lexus every 4-5 years, travel and dining out at a reasonable rate. Assume married and children at some point. His father's answer was "5 million".

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This is very interesting. I wonder what HE meant when he said he wants to retire. I would be very interested in what his assumptions where that need to be fullfilled before he can say he 'is retired'.