For a bet of $X, the expected value is: (1.5 * X) * 0.5 + (0.6 * X) * 0.5 => 1.05 * X. The ensemble average per round is positive (1.05) and over multiple rounds smoothly tends to infinity with the number of bets. (Definition here: https://en.wikipedia.org/wiki/Expected_value).
The time average for any specific person betting in this game is 0.95 * X (for the reasons you mention) and tends to zero with the number of bets.
So let's go through a few specifics of your comment:
> He actually picked bad numbers. That is a losing bet even on average.
The point of this article is that "on average" is trickier than people tend to assume. There are different ways of taking averages. If you do the expected value calculation and get a positive number, you might (as other comments have said explicitly) expect that a participant repeatedly engaging such a bet would have his wealth trend toward infinity. But, they are wrong (as shown in the article).
> This happens to not show after only 100 trials just because some tiny number of people get really lucky and draw up the ensemble average, but if you keep going, somewhere between 200 and 500 trials, the ensemble average pretty quickly drops below the starting average wealth and stays there, asymptotically approaching 0.
The ensemble average is positive and monotonically increases w/ the number of rounds of betting.