In the video, in the continuous version the game never end and highlight the "loser" strategy.

When you are behind the optimal play is to make a gamble, which most likely will make you even worse. From the naive winning side it seems the loser is just doing a stupid strategy of not following the optimal dichotomy strategy, and therefore that's why they are losing. But in fact they are a "player" doing not only their best, but the best that can be done.

The infinite sum of ever smaller probabilities like in Zeno's paradox, converge towards a finite value. The inevitable is a large fraction of the time, you are playing catch-up and will never escape.

You are losing, playing optimally, but slowly realising the probabilities that you are a loser as evidence by the score which will most likely go down even more next round. Most likely the entire future is an endless sequence of more and more desperate looking losing bets, just hoping to strike it once that will most likely never comes.

In economics such things are called "traps", for example the poverty trap exhibits similar mechanics. Where even though you display incredible ingenuity by playing the optimal game strategy, most of the time you will never escape, and you will need to take even more desperate measures in the future. That's separating the wheat from the chaff from the chaff's perspective or how you make good villains : because like Bane in Batman there are some times (the probability is slim but finite) where the gamble pays off once and you escape the hell hole you were born in and become legend.

If you don't play this optimal strategy you will lose slower but even more surely. The optimal strategy is to bet just enough to go from your current situation to the winning side. It's also important not to overshoot : this is not always taking moonshots, but betting just enough to escape the hole, because once out, the probabilities plays in your favor.