After listening to DHH speak at Startup School a few years ago I came to the conclusion that for an entrepreneur a "lifestyle business" is a much more probable path to getting rich than the grow-fast-and-flip approach demanded by VCs and angel investors. In retrospect, it seems pretty obvious, but previously I had really only been exposed to entrepreneurship through PG's blog. I had never heard of 37 Signals before.…
Investors want the companies they fund to grow fast, but they don't want to "flip" them. They'd much prefer that they grew into large, independent companies, like Google and Facebook. When companies get sold at earlier stages, it's more often because the founders wanted to than the investors. I would never claim that starting a startup (= a company designed to grow very fast) was the only way to get rich. Anyone can…
The component of your writing I'm referring to is in How to Make Wealth: "If you wanted to get rich, how would you do it? I think your best bet would be to start or join a startup." Your other writings had really resonated with me, and you had described Viaweb's hackers as really risk-averse, so I assumed that I was among the "you" comprising your target demographic. But, having been exposed to other methods of getting rich, I no longer believe my best bet is to start a startup. I would also guess that it is not the best bet of the majority of your readers. It is possible that I am underestimating the prowess of your readerbase, or that you are not writing to the majority of your readers.
I'm happy that you provided an alternative viewpoint at Startup School - I'd love to hear you address the possibility of getting rich via a 37 Signals model on your blog. I know you've mentioned why you don't invest in software companies in order to obtain dividends (despite the fact that people do invest in things like restaurants and banks in order to obtain dividends, and, as an investor, I think I'd rather own shares in a profitable software company than in a profitable restaurant). Maybe you could tie it all together into a blog post at some point. The topic appears here frequently.