Is there truth in it?
Yes and no.
When a contractor, sole proprietor or Owner operator makes their quarterly payment they are currently not required to take into account the penalty from the healthcare law if they do not have health insurance. However, the quarterly payments made count towards the total annual taxes due to be paid in the beginning of 2015 and the penalty would be attached to that final number.
Something to consider is that by attaching the penalty to the quarterly payments made throughout 2014, that the amount of money to be paid out next year during tax season would be substantially lower than if the penalty were to be taken out then. This is an option that I would guess that Matt Drudge has elected to take. Yes he is paying the penalty - no he doesn't have to.
How does it affect me as an Owner Operator?
Well, if you have healthcare by now then it does not affect you at all. However, if you don't then you too can choose to pay your penalties out with your quarterly payments like Matt Drudge or pay them at the beginning of 2015.