1. He didn't have the best voice.
2. His song writing to me was unoriginal and simplistic.
3. He was selling something I already had and didn't need from him nor could I relate to his version of.
I grew up surfing and spending much of my life on or near the beach(NJ, Puerto Rico, San Diego, Mexico, Florida, Portugal, Hatteras) and still do to this day and my perception of such a life differs vastly from the typical "parrot heads".
But he certainly parlayed his "brand" of a certain lifestyle into a money making machine.