I had to get over 100 prostitutes to like me in five seconds or less.

I didn’t do this because I wanted to sleep with them. I did it because it was my job.

For about 2.5 years I had a job that I created for myself. I had to interview people at three in the morning on a Wednesday night and find out what they were up to.

If someone is out at three in the morning on a Wednesday night, there is usually a reason. And usually not a good reason.

Why three in the morning? Because one time a girlfriend kicked me out of her house at three in the morning. “Any guy would be better than you!”

I left. And when I walked outside I was surprised how vibrant and exciting three in the morning was.

I wanted to find out what was going on. I wanted to talk to all the interesting people.

But I was too shy. I couldn’t do it. I could only watch. So I made it my job.

I was a computer programmer at HBO. I pitched to them, “just like you specialize in original programming for TV, you should do original programming for the web”.

I pitched a web show “III:am” about what goes on at three in the morning.

In three years I probably interviewed 1500+ people.

Every week I’d take the top four interviews and put them on the “world wide web”.

One thing was always true: NOBODY wanted to talk to a random stranger like me at three in the morning.

And I was scared and shy every time we started.

Here’s what I did: