In business having money and a forceful/persuasive nature can work well. In the gambling world, not so well and yet these same people never really learned their lesson because another often positive trait in the business world (ego/pride) meant they couldn't accept losing in the casino world. Sad really but the reality of a lot of it.
First, 99.999% of bac players do not know how the fk probabilities work on such game.
For that matter all those geniuses who sell their invincible systems for $49.99 or $49.999 do not know probabilities either. They'll tell you every shoe is beatable for many units or that after 3-4 shoes you'll surely be ahead of many units; it's like they are telling you the rain is stoppable or elicitable by tribal dancing or by human efforts.
Second, for every bet we'll win, being $5 or $50.000, we'll expect to get a $5 or $50.000 losing bet.
Actually losing bets are always $5 or $50.000, winning bets are slightly worse than that.
If we win 10 hands in a row, we must expect the same opposite 10 losing sequence and it's very important to win and lose nearly the same amount on those specular probabilities.
In reality 100% of bac players will lose a lot more on losing sequences than what they win on the same lenght winning patterns.
Third, under normal circumstances the game is so whimsically produced that we have no means to predict when W/L sequences will equal or deviate from the "norm" besides some complex patterns that need many parameters (and time) to be fulfilled.
Too deviated outcomes are dangerous for opposite reasons: illusion to be a genius from one part or to be unlucky from the other, but they are just the reflex of probability world. Casinos do not win more money than math expected because we are unlucky but because we try to be more right than expected by raising our finite wagers into a virtual endless bankroll
Now tell Al's friend to try to get the money back by one unit profit per every 2-3 or more shoes dealt and you know the answer.
Maybe he can manage to set up his standard bet to $5.000 or $10.000 but he won't do that. He thinks to do a lot better than that by guessing and hoping for the best.