Not all things in life are quantifiable (you know, things like justice, love, or your experience of the color purple), but the proverbial "entrepreneurial bug" is not one of them.
As a corollary to a well-known math problem called the two-envelope paradox, it is perfectly rational for an individual to want to start one company after another and expect a higher reward after each iteration, even if the expected outcome associated with each of these endeavors is completely random (as I would argue is the case every time you start a new company)! To understand that mathematically, this is how the two-envelope paradox works (taken from the latest analysis of this paradox on PhysOrg.com):
In the two-envelope paradox, a player must choose between two envelopes, one of which contains twice as much money as the other. The player can open the envelope they choose, and then they have the option of switching envelopes. The other envelope, of course, has either twice the money or half the money as the first envelope, but the player does not know which.
It may seem that, since a player has a 50-50 chance of choosing either envelope, they have an equal chance of gaining or losing money whether they decide to switch or keep the original envelope. However, probability theory seems to confusingly show that it’s always better to switch.
For example, say the first envelope you pick has $10, so that the other envelope has either $20 or $5. Then you can calculate the expected value (i.e. the probability-weighted sum of the possible values) of the second envelope, assuming that each possibility has a 50% chance: (0.5 x $5) + (0.5 x $20) = $12.50. Since $12.50 is more than $10, it makes sense to switch. No matter which numbers you use, you always get an expected value for envelope two that is 5/4 higher than the value for the original envelope: if c is the value of the original envelope, the expected value of the second envelope is (0.5 x [0.5c]) + (0.5 x [2c]) = 5/4c.
This counter-intuitive mathematics can explain very well why so many first-time entrepreneurs try again, regardless of the success or failure of their first attempt. And why it is perfectly rational for investors to expect a higher payoff from a not-so-successful serial entrepreneur than a first-time entrepreneur.