I have been in business nearly all my life. There have certainly been years when I paid no taxes due to losses. Sometimes the losses were “real” in terms of net cash losses. Sometimes they were “conceptual” like deductions caused by purchasing cattle, or perhaps machinery, in one year. I once “lost” a very large amount of money (large for me) resulting from buying stock in a Subchapter S banking corporation. Banks lose money in their early years, passing those losses on to the stockholders in a Sub S, but then make it up (hopefully) later. Sometimes you “lose” a lot from changing asset strategies. But your plan is to make it up later.
I think Trump thinks in terms of the “long view”. Most business people do, or at least should.
Most people are wage-earners, and don’t know what it is to be responsible for a business. Most people, frankly, couldn’t stand living with the stress most business owners have from time to time.