Ask HN: sick + not passionate, generally fucked up. thoughts?

I graduated from Stanford in 2005. Since then I have had a great run in founding a company, getting funded, and we are a profitable start-up with 11 employees. Our revenues are in the 11-12MM range and I own a very large percent of the company. I didn't really want to have a co-founder but I did recruit a friend early on with whom I built the product, but he owns 8% (not a lot), and other employees own 1% and some later employees own 0.5%. The VC that funded us is great friends with my dad(which helped, also my dad initially bankrolled some of the setup costs), and we were profitable before starting so it all worked out in my favor, and however selfish it may sound, we ran with good salaries after getting funded, and I had started alone, so I didn't want to split equally. Also my friend didn't mind as he was/is drawing a good salary.

I am a run of the mill person (financially secure childhood, went to a good school, went to a good college, and have a good company that is probably going to grow around 10-20% over every year) meaning that I never really felt that I decided anything for myself, and I guess I am having a midlife crisis? but really I am just sick of my life and I have no idea what I am doing. Over the last year or two I managed to take some extended 2-3 week long breaks because before that there was a lot to do, so I guess I tried remedying it using breaks where I would not be connected to tech and just go hang out at the beaches of south America. It definitely gives me a clear head, but I am unable to think and decide clearly.

Over the last year and a half I have thought a lot about killing myself and have decided that I am not brave enough to carry on with something like that, but I really have no passion and some of what Tony Hseish (Zappos Guy) talks about in Delivering Happiness (book) really resonates with me. But I have more problems. Also on the outside I think I appear extremely happy and perfect but I guess I am more insecure and have started having self-worth issues.

I had a really great & happy childhood. Was bullied some in high school & was also a bully (went to a boarding school and really it was part of life, and wasn't something major or life altering). I experimented a bit with my bisexual-ism with consent of-course but it was merely part of growing up in an all boys environment. Anyway had a great college experience, blessed with 'good looks' genes, was in a popular fraternity, got laid a lot, and well experimented a lot with some random fantasies that I think I can somewhat attribute to an all boys boarding school upbringing. I don't drink much and have been smoking pot since 12 when I went to boarding school. I guess I turned out pretty well on the outside, but I think that I may be a rotten person. I know this and yet I am unable to do anything about it. I am generally not a good person I guess, I used to shoplift and still do on occasion, and some years ago I figured that I may have kleptomania, but I haven't really been diagnosed with it. Also I have always cheated on tests/exams if possible. I am usually nice to people / girls but I haven't had a stable relationship ever despite having a sexual relationships with many. I possibly see a lot of myself in the max tucker? but I don't sound like a jerk or brag about stuff (despite of what i am doing here).

Growing up I had no idea what I wanted to be, I just knew that I wanted to be extremely rich, and have all the shebang that comes along with it. Now I have a company that is generating a significant amount of revenue and healthy profits too, My parents were entrepreneurs and they are pretty wealthy but I wasn't aware of all that much at the point. I guess now I am not sure whether I want to be extremely wealthy (attainable in 7-9 years: 100MM, just an arbitrary figure I have, used to be much higher, but honestly that wasn't realistic) or just cash out now by trying to sell and settle for a lesser amount which would still be significant, plus hopefully inheritance later. This initial get rich scheme was fueled by all the "Sydney Sheldon's" that I read in high school and some other lewd literature, and at one point I seriously considered becoming a criminal. Growing up, 'The Godfather', 'Scarface', and of late 'American Gangster', 'Blow', 'Lord of War' have been my favorite movies. I have also read extensively about organized crime over the world.

Anyway I have these really sick fantasies which I also had as a child for some reason and I can't get the grip on how they started. Going to a small "rules enforced" all boys school and then being let loose on a college campus with good looking girls with whom I had little or no interaction growing up may have been a likely cause.<p>Anyways I guess I am just venting out to this community that I have been fortunate to learn about from about depression, and start-up stuff, and other random things. I shared some of my fantasies with a close friend like some months ago, and he said that he was disgusted and told me to see a therapist. Long story short, my first therapist was a female and we ended up having some adult fun, and then I went to see this other guy and he was like you should try and fulfill some of these and see how you feel after? so strike three, I went to this famous guy that wrote a book about hypnosis and has published papers about how that provides insight into childhood that may affect current behaviors and that also wasn't a really helpful session. The third guy did however say that I have a mild alternate personality. I don't want to go into much detail about what these feelings/fantasies are so as to not offend people, but just a fyi: they all involve adults and mostly female adults but are outright weird/ and to some extent sick and involve controlling? behavior and other dark stuff. I am sane enough to control these thoughts but there are times that my mind races and I enjoy having these thoughts and realizing in retrospect that they are not normal/acceptable/legal in some cases. Also, I fear that I might be slowly become the person that I am in my thoughts specially given the financial freedom that I am afforded by being lucky.

<p>Idk why I am putting up this rant, but it just feels to get it off my chest? and hopefully I can get some advice? Also I am mildly on a marijuana high so sorry if some of this sounds incomprehensible.

<p>temp email: xequalsxplusone@gmail.com / if you'd rather just email me. Thanks.