This is a gambler’s ruin problem. Using the following equation: \[P=\frac{1-(\frac{q}{p})^i}{{1-(\frac{q}{p})^N}}\]
q=0.6
p=0.4
N=8
i=1
P= (1-(q/p)^i)/(1-(q/p)^N)
P
## [1] 0.02030135
Around 2.06% chance that he wins 8 dollars before losing all of his money if he bets 1 dollar each time.
Smith must win each time or lose everything upon the first lose.
P = 0.4^3
P
## [1] 0.064
There is 6.4% chance that Smith will win 8 dollars before losing all of his money if using the bold strategy.
By comparing the probibilities of two strategies, it seems bold strategy has better chance to win 8 dollars before losing all of his money.