There are a lot of people here defending working for porn sites. I'll play devil's advocate. (Or the opposite? Whatever.) In general, being associated with porn is a problem.
In hetero porn, tons of the models or performers or whatever are said to be involved because they were sexually abused when younger. Doing porn requires a certain numbness and if the performer doesn't have that when she starts, she will. It's just a very sad situation. A lot of people, including me, would never get involved with it, and consider money made there to be tainted.
(I know nothing about whether the same is true for gay porn.)
A hookup site isn't like that. Although there might be "numb" people participating, they aren't being exploited / selling themselves so there's just a different feel. But you never know where your life might take you. Sometimes very uptight people are gatekeepers to something you really want. You shouldn't let that possibility control your life, but on the other hand you shouldn't give up those unknown future opportunities for nothing. This job would at least have to pay more to make up for that.
Yes, the new bankruptcy system tries to eliminate that option for people making more than the average. It's an extremely bad reform, as it hits higher income people trying to take risks and build businesses.
Here's what to do if you're caught in that: decide to declare bankruptcy, then figure out a way to establish a six month period with your income below your state's average. Quit your job, stop paying yourself a salary from your company, whatever. If you've got to feed a family, make a mortgage, pay for your kids college tuition and otherwise support an above state average lifestyle for people you love... I don't know. Consult a good bankruptcy lawyer, and if they don't have a solution for you, ask them directly for a recommendation of a lawyer who will help you to beat this system.
Derek, you did great work in creating that wealth and everyone here is happy to see you enjoying some of it. But please consider re-writing this to something more truthful - fewer words emphasizing your altruism and spartan lifestyle (?) and more words talking about the tax advantages and forced spending discipline that this smart plan gives you.
The title, for example, shouldn't be "Why I gave away my company to charity". You didn't do that. (Which is good! That would be crazy.) How about, "Why I willed my estate to charity."
I'm an atheist and a confirmed sexual libertine but those ads pissed me off too. Too tacky even for the Superbowl, which is saying something.
Much worse, though, was the ad for some damn NBC crime drama which showed some pretty young girl falling into the hands of a serial killer, then showed him burying her in a shallow grave down by the river or something. Yet another show about fear, pain and misery.
You have too rosy a picture of what your high school classmates were doing. They were mostly wasting their time. What you're calling "dating girls" is better described as "chasing girls", and they were mostly unsuccessful.
You need, at most, a bit of moderation. Don't try to be normal - normal sucks.
Hmmm. I want to hear from some great programmers who are often here on HN. Do you guys type quickly? Paul Graham and Patrick Collison, are you speed typists? How about Ryan Davis and Jey Kottalam? Suggest some more great hackers, too.
"We are undergoing the Paris-ification of America. The snobbish French always thought Americans were nuts to let Washington, the capital of the country, and New York, the capital of the world, turn into hellholes. Why build public housing projects in the middle of your great cities for riff-raff? The French elite, no fools, kept beautiful Paris for themselves. They warehoused their African immigrants out in the bleak suburbs, where every night is Car-B-Que night."