Are you thinking that you act second every alternate hand?
This is not poker, where you have a rotating button. In blackjack, third base is ALWAYS in position.
Betting minimum to start with is a good strategy.
Once your boss gets to 3750, you must start playing aggressively.
Remember, if he gets to 2500 and bets it all, you're a 57-43 favorite!
If he bets all in with 2500, and you have 2500, clear best play with no surrender would be to bet 1250. If boss wins, you have a chance of winning with a double.
Actually, does someone have the answer to whether it's optimal in this scenario [each has 2500, boss bets all in first to act] to bet 1670 [winning on a blackjack] or betting 1250, to open up the possibility of splitting?