Buying lottery tickets is the extreme end of the spectrum. It's not for everyone. It's not for 99% of people probably. But if you're Andrew Whittaker or Geraldine Williams or Harold and Helen Lerner, it turns out that you can do better than the guys patiently working at startups.
The expected value of working on a startup is positive. The social value is also positive. And I don't think anyone would argue that, on the margin, you can't do something extra to raise your odds of winning disproportionate to the extra contribution.
So lotto tickets appear to be a terrible counterpoint.
Explaining jokes is usually an unsatisfactory business for everyone involved, but:
What's in question is not the value of working in a startup rather than doing nothing at all, but the value of working in a startup relative to the sort of business that DHH founded. So far as I know, it's an open question whether that is positive or negative -- whether you look at the founder's own interests, or those of society, or the amount by which the founder's extra skill and efforts can improve the chances of success.
Of course I was not suggesting, and do not believe, that founding a startup is exactly like buying lottery tickets. I was suggesting that "for such-and-such people, identified in hindsight by the fact that they were very successful, founding a startup appears to have been a tremendous success" -- which I took to be the point PG was making -- is a poor argument for the superiority-for-some-people of founding a startup over founding a "lifestyle business", since there may be no good way to know in advance which people they are, and it may largely come down to luck.
(Which is not the same as saying that there's nothing at all you can do to help your chances of success. Rather, what making a heroic effort does might be to move you from the "almost certain to fail" category to the "quite likely to fail, and some tiny chance of huge success" category, after which it's a matter of luck. And it's perfectly possible -- and I don't profess to know whether it's true -- that on the whole you're likely to do better in a "lifestyle business" in a startup even in that second category.)
My point was that lotto tickets are a bad decision that works out well for some people. Starting a startup is a good decision that works out poorly for some people.
It's just not helpful to draw the comparison; it's like hearing someone say they like a comedian, and then pointing out that John Wayne Gacy was a popular party performer. The fact that distribution A contains outliers from Distribution B doesn't mean that A and B are even roughly comparable.
1. The relevant question is not "startup versus nothing", it's "startup versus lifestyle business". How do you know that choosing a startup in that context is a good decision?
2. I wasn't claiming that startups and lottery tickets are at all the same sort of thing. I was making a point about saying "X, Y and Z founded startups and it worked really well for them": that just isn't good evidence that startups are good in general, or even for any particular (however rare) sort of person, unless you can say what's special about X, Y and Z other than that their startups happened to succeed.