Some Startups Need a Second Chance

Last week I wrote about what I called a “probabilistic billionaire.” You create a company with some long-shot idea that will be worth $1 trillion if it succeeds, you convince investors that you have a 1% chance of success, and you raise money at a $10 billion valuation:

This was, of course, too simple. My toy example of a company that was unlikely to succeed, but hugely valuable if it did, was one trying to invent teleportation. But the actual company that inspired the column was WeWork Inc. WeWork never achieved a $1 trillion valuation, and it seems unlikely that it ever will, and its founder long ago moved on to other endeavors. But WeWork still exists. It is bankrupt, sure, but it went bankrupt with a plan to restructure its debts and get rid of its worst leases and try, once again, to make a go of it as an office-space sublessor. That is the sort of modest reasonable business that: