This is an interesting article. The game itself relies on a 0 expectation, i.e. 50% chance of winning or losing the lower of the two bankrolls. So by definition, this is not a wise bet to do once (let alone repeatedly). In a business setting, you’re looking for a positive expectation or to create one structurally that is repeatable.
It would interesting if the automated game would let you vary the bet size and the payoff so that it gives an advantage to one of the participants to see if there are stable arrangements. As it is, it is mostly a demonstration of the notion of risk of ruin used by gamblers/investors to set bankroll and bet sizes to stay in a game with a positive expectation, but a low rate of payout. One idea would be to try a payout like they use in chess (Elo ratings). If a low rated (bankroll) player beats a high-rated player, the payout is more favorable.
UPDATE: There is now a version that does a redistribution step. https://hackerfactor.com/oligarchy-game.php?soc
