After some excellent insight in a recent email from Jason Calacanis (a VERY sharp and successful startup entrepreneur), I revisited my working hypothesis about folks doing startups.   It’s a bit ironic since I did NOT follow this advice myself, but now it’s too late for me, and I’m doing pretty well.    

I do think Jason and other entrepreneurial geniuses like Mark Zuckerberg  are among the VERY few exceptions to my rule, which is this:

Smart folks should NOT bother with startups.   My “research” is only anecdotal but it’s fairly extensive with respect to  my own online efforts and the many startups and websites I’ve watched over the years, but I think the typical pattern is for smart entrepreneurial folks to invest many years and get only modest returns.    Few – and by few I mean probably less than 10% – are better off with their startup effort than they would be simply working for a big player like Google or Yahoo at 120k per year and saving like crazy.  

For a 25 year old, retirement with a few million can be had in an almost guaranteed way by age 50.    [math is simple here.   A 120k employee can easily save 40k per year over 25 years = 1,000,000. With very modest compounding this will be well over 2 million at age 50.   If you are married you can spend more or save more.

I’m doing pretty well myself as a moderately successful entrepreneur with a few decent websites, but even I’d I’d be much better off had I joined up with Google 10 years back (their stock is up about 1000% as well as paying big salaries.   I’d be a bit better off if I’d joined up with MS or Yahoo 10 years ago [no stock gain, but I probably would have made more money in salary than I’ve made as an entrepreneur).    

The many brighter-than-me folks who have NOT had success with their own startups would be dramatically up after 10 years with a big player.

I think the analogy are the gold miners vs the shopkeepers of the CA Rush of 1849.   Most miners left with little to their name, where the bar, brothel, and shopkeepers did pretty well, building the great state of California in the process.