He managed to win 100k from the little he was able to summon up courage with.
What's the best way to overcome the problems of uncertainty and hesitation when determining an amount to wager?
I agree with this being hesitant could make or break you, but whatever the outcome is I don't think you should be hard on yourself cause its gambling, anything could have happened, always stick to a particular amount and don't go beyond it no matter how tempted you are to do it, if you normally stake 5 dollars on a bet and if that's what you are comfortable with do not stake higher, and even if the outcome goes in your favor, don't regret that you didn't stake higher cause you might be tempted to do so next time..you probably might not be lucky on your next try
I think on the contrary, hesitation is failure, hesitation means we do not trust our own decisions, and cannot come up with the best plan. In Op's story, if those 3 people lose, the story will turn in a different direction: they will feel lucky because they didn't bet everything they had. That means they failed their plan from the start by not making the best decision.
The solution to this problem is that if we feel hesitant and cannot make a final decision, we should not participate in betting or let others decide.
In addition, not only in gambling, if we often hesitate and do not make decisive decisions in life, we will always live in regret and regret.