TIDAL was a bad investment. Period. They've had 4 CEO changes in like 2 years. Apple and Spotify have been doing shit behind the scenes to make SURE Jay can't have a seat at the table. He's alluded to this on 4:44 AND in his Rap Radar interview over the summer.
He thought he could come in swinging with that awful rollout making it seem like rich and A-List celebs needed more money (which he has now admitted was a horrible idea), and this whole thing has just really blown up in his face. Especially the "exclusive" war he started with certain artists not giving their music to this or that streaming service.
He has done a great job by slowly getting out of it, though. SPRINT has purchased 33% of the company. And Mercedes will have TIDAL in all of its vehicles starting 2018 as a free streaming service for the driver.
So, he's not stupid by any means. Every investment isn't going to turn a huge profit. It's a gamble. That's business.