Here are some answers. Apparently, he was extremely unpopular in high school. That explains a lot of things:
https://www.therichest.com/expensiv...y-secrets-you-didnt-know-about-dan-bilzerian/
"Dan Bilzerian suggests that his father's legal problems may have shaped his own lifelong
hatred of authority; he has admitted that he hated high school and was extremely unpopular as a teenager. He was often lonely and was widely ridiculed by his classmates after his father was jailed.
Bilzerian had a rootless existence during this period. He moved school twice after Bilzerian Sr. was doing time, quickly finding himself expelled from both due to his outrageous behaviour. Bilzerian carried on this stigma of unpopularity into his military 'career' - his father had won a Bronze Star in Vietnam and Dan felt that he was widely disrespected by instructors and fellow grunts alike for his association to the criminal ex-serviceman."