If your business is regularly in a “bind” then depending on exactly what that bind is perhaps you should not be in business. If the problem is simply irregular cash flow then do what other businesses do to cover that problem: get a line of credit from a bank or other commerical lender where you can borrow money when the cash is tight and then repay when the cash becomes flush later. If the problem really is poor profit margin then you may simply be in the wrong business or not the sort who should be running a business. You should never need your employees to contribute back to help your business out of a “bind.”
The exact details of what you propose to do matters, but you certainly run the risk here that you either violate the laws against illegal gambling or violate the laws on employee pay. I strongly suggest you consult an employment law attorney in your state to discuss your idea before you implement it. If you do something that ends up being illegal that could really cost you.

