In my opinion his startup career and failures have nothing to do with the fact that (he thinks) he is unemployable. He (like many others) just doesn't want to

In my opinion his startup career and failures have nothing to do with the fact that (he thinks) he is unemployable. He (like many others) just doesn't want to play the "leet code white board" interview game, nor wants to play along and pretend to be super excited about some foolish cult-like startup only to receive less money. You can argue that the interview questions don't make sense, but in the end, if you decide you don't want to play the game and master the tech interview, then you will have less options.