"On average, nothing ever happens for the first time" is an erroneous characterization because it ignores all the times where the predictable thing kept on happening. By invoking the first time you restrict the reference class to those where something unusual happened. But if usually nothing unusual happens (hmm...) and those who predict the unusual are usually con artists as opposed to genius inside analyzers (is this really so unreasonable a view of history?), then he has a point.
"Smart people claiming that amazing things are going to happen" sometimes leads the way for things like the Wright Brothers, but very often nothing amazing happens.
Sure. But then the question becomes, are we really totally surprised without benefit of hindsight? Can we really do no better than to predict that no flying machine will ever be built because no flying machine ever has been? The sin of underconfidence seems relevant here; like, if it's not a sin to try and do better, we could do a bit better than if we were blind to everything but the reference class.
One of the most useful techniques of rationality is taking the outside view, also known as reference class forecasting. Instead of thinking too hard about particulars of a given situation and taking a guess which will invariably turned out to be highly biased, one looks at outcomes of situations which are similar in some essential way.
Figuring out correct reference class might sometimes be difficult, but even then it's far more reliable than trying to guess while ignoring the evidence of similar cases. Now in some situations we have precise enough data that inside view might give correct answer - but for almost all such cases I'd expect outside view to be as usable and not far away in correctness.
Something that keeps puzzling me is persistence of certain beliefs on lesswrong. Like belief in effectiveness of cryonics - reference class of things promising eternal (or very long) life is huge and has consistent 0% success rate. Reference class of predictions based on technology which isn't even remotely here has perhaps non-zero but still ridiculously tiny success rate. I cannot think of any reference class in which cryonics does well. Likewise belief in singularity - reference class of beliefs in coming of a new world, be it good or evil, is huge and with consistent 0% success rate. Reference class of beliefs in almost omnipotent good or evil beings has consistent 0% success rate.
And many fellow rationalists not only believe that chances of cryonics or singularity or AI are far from negligible levels indicated by the outside view, they consider them highly likely or even nearly certain!
There are a few ways how this situation can be resolved:
How do you reconcile them?