Depends on the ESPP, no? The one ESPP I had was pretty nice: the shares were offered at a (double-digit, percentage wise) discount of the lowest share price at

Depends on the ESPP, no? The one ESPP I had was pretty nice: the shares were offered at a (double-digit, percentage wise) discount of the lowest share price at either the beginning or end of the purchase period. That effectively guaranteed a profit of at least the discount (more or less).