Assuming this kind of wager is more likely in a nightclub with drunk people (that brought party money) then a regular bar.

Gotta pay expensive drinks for you and homey to not stand out and appear massively sus,

May take a while to find a good target, depending on the crowd size you only have one shot to smooth talk your way into it.

In the meantime your spending time, possibly gas finding new locations. Local employees will catch on also if you do it too often the same spot.

In the end gotta split the profits with your partner

Might be above minimum wage but far from big money.