The interesting thing about Naval is that he has a magnetic effect to new listeners and there is a cult-like following. I used to love his early talks and then the more I got to hear him, the more I realized he is just this narciscist rich guy without a shred of humbleness. He has a great sense of clarity in his thoughts and he speaks well. It's a shame really that his character puts me off more than anything else. I'd rather go read original sources with far more insight.
His repeated claims of "I can get rich even if I start over" - yes, Naval, go for it. Give up the name, money and everything you have and try working 2 jobs as a waiter and a nurse, raising kids and keeping your spouse happy while saving enough to go after your investor instincts. The whole thing comes across as out of touch with reality, compassion and thoughtful consideration; instead relies on his survivorship biases as a guiding beacon of life.