What you're talking about is a liquidated-damages clause, where the contract explicitly spells out the damages to be awarded in the event of a breach.
The law will vary some from state to state, but these clauses are generally enforceable. Some courts limit their use to cases where calculating the damages resulting from the breach would be impossible or impractical.
But in the United States, along with all other common law jurisdictions, courts generally agree that if the liquidated-damages clause appears to penalize the breach instead of simply compensating for it, it is not enforceable. See, e.g., Ridgley v. Topa Thrift & Loan Ass'n, 17 Cal.4th 970, 977 (Cal. 1998) (“A liquidated damages clause will generally be considered unreasonable, and hence unenforceable under section 1671(b), if it bears no reasonable relationship to the range of actual damages that the parties could have anticipated would flow from a breach.”)
The trillion-dollar damages clause "bears no reasonable relationship" to the damages that would actually result from a breach of a software license, so you can safely expect a court to refuse to enforce it, and limit you to whatever damages you could actually prove in court.
Even if you were to drastically reduce it to "all the money you have, and then some," "all the money you have," "half the money you have," or even " "1 percent of all the money you have," the language still makes clear that the contract is not aimed at compensating for the breach, but rather penalizing the breaching party.
In the end, what you're talking about isn't going to work, because contract law is generally less concerned with penalizing people than with making them whole.
