While the obvious answer to that would seem to be "no," if you manage to set up one of Mr. Singer's "I'll bet you I can win eight of 10 sessions" wagers with an individual prone to making foolish wagers, then I guess (with that caveat), the answer could be yes. You could win the sessions bet while losing. You could lose the sessions bet while winning. Or you could "middle it" by winning both the sessions bet and making a profit on the vp machine.