Why does it matter how much $1000 is to you if you can guarantee that you won't lose - which you did just a few comments up the tree? And remember, he said "up to", so perhaps you'd feel more comfortable at $100? Or $10?
"The usual touchstone, whether that which someone asserts is merely his persuasion -- or at least his subjective conviction, that is, his firm belief -- is betting. It often happens that someone propounds his views with such positive and uncompromising assurance that he seems to have entirely set aside all thought of possible error. A bet disconcerts him. Sometimes it turns out that he has a conviction which can be estimated at a value of one ducat, but not of ten. For he is very willing to venture one ducat, but when it is a question of ten he becomes aware, as he had not previously been, that it may very well be that he is in error. If, in a given case, we represent ourselves as staking the happiness of our whole life, the triumphant tone of our judgment is greatly abated; we become extremely diffident, and discover for the first time that our belief does not reach so far. Thus pragmatic belief always exists in some specific degree, which, according to differences in the interests at stake, may be large or may be small." - Immanuel Kant