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Comment by bruce343434 | Hacker News Reader

> At Digg, one mentor gave me the savvy advice that the fastest path to financial success was working for four years at three different just-about-to-IPO companies. A surefire way to retire by forty. (This is, for the record, pretty good advice.)

Why is it good advice? What is the context in which it operates?

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Retiring at 40 is not always good. Being able to retire at 40 is of course stress reducing, because you can stop worrying a bit. Actually stopping might not be a good idea: Rates of depression and disease in retired people are not just a function of "being old" -being unoccupied and inactive also play a part.

100%. The converse is true, too. Often, people that carry on working well beyond retirement age, are more happy and engaged than peers who retired. The key thing is having enough time to pursue your own interests and time with friends/family rather than employer owning all your time and energy. Also, if one has the health to work part-time into one's 80s, one doesn't then need huge savings or pension because by, say age 65 when you'd hope all mortgage was paid off, you can live on a half-time wage probably . All depends on maintaining your health though....

At venture-funded startups, a generous portion of compensation will be equity. And four years typically allows said equity to vest fully.

Yea, all you have to do is pick three consecutive winners.

Which is trivial, with hindsight.

Less so in the moment. You could equally well pick three failures, and end up with close to nothing.

Your odds are much better with 3 companies, that one might succeed. Especially if you are joining late-stage startups. But at the same time, your equity package will be smaller, so the exit won't be as impactful.

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