My first night in my first apartment in NYC I woke up with cockroaches everywhere. I went to the bathroom and the entire floor was swarming with them. I panicked and screamed because I was a little baby and never saw this before.
My only piece of furniture was a foam futon. I had a garbage bag next to the futon that had all of my clothes in it, including my one suit. The next day the landlord got rid of the cockroaches somehow. Magic cockroach solution.
I never wanted to go home. I was too lonely there.
I would stay up late playing backgammon and chess with all the Greek guys at Steinway Billiards. Astoria had two types of people: Greeks, Hispanics, and me.
I loved all the girls. I would write my phone number down on two dollar bills that I would leave as tips for waitresses. I wanted all the waitresses in Astoria to call me. I would’ve married and had children with any of them.
None of them called. I always left my HBO number where I was the lowest ranking “Junior programmer analyst” although if you called and listened to my voicemail message maybe you would’ve heard, “this is James from HBO”. I needed to work all of my advantages. $2 bills, no fear, and HBO.
I would read Wired magazine and other tech-related magazines at all the cafes, maximizing my exposure to waitresses. Maybe they would think I was interesting somehow.
And I would take notes. If there was a new technology, I’d list things I could do with it. I’d list things HBO could do with it.
Eventually, because of the Internet work I was doing at HBO, other companies would call me and ask, “what do we do with this Internet thing?” Nobody had a website then. Most companies figured there was no need for a website.
It was all basic. With HBO I asked them, “why don’t you do original shows on the web just like you do original shows on TV?”
With JP Morgan I asked them, “Why don’t you let customers see their balances via the website?” With a clothing catalog company I asked them, “why don’t you let people design their outfits and then hit order for the whole outfit?”
For a diamond selling site I asked, “Why don’t you let people see the certified GIA certificate of the diamond so they know it’s real?”
Greeks have three types of backgammon. I learned them and would play all night. Sometimes they’d take out the chessboards and then I’d play them all simultaneously. I never had so much fun in my life and I had no money, nothing going on, no girlfriend, no nothing.
Then afterwards I’d take a walk with Nick, who was the only other good chess player there. “I have Hepatitis C,” he told me one time. “I’m just waiting until I die. There’s no cure.”
He was a good-looking guy but was afraid to have a girlfriend. “I don’t want to put anyone through what my final days will be like.” Every day we’d take walks for hours. He was my first real friend in New York.
I asked more questions. To a record label I asked, “How about we put videos on the CDs of your artists?” To Warner Brothers, “How about we make a game on the website based on The Matrix?”
There was a strip club next to my apartment building. I would go there rather than go home. One girl gave me her pager number but when I called her the next day I didn’t know how to leave a message after the beep so I got embarrassed and stopped going there.
Maybe she would’ve been my wife and had my children?
My friends from HBO would start coming with me to Astoria after work to play backgammon and chess and pool and have coffee and hang out with all the people who were my new friends.
It was a party every night. People from Astoria. Recent arrivals from Greece. My programmer friends from HBO. Coffee, games, laughing.
I kept thinking of questions with no answers. Companies finally said, “can you answer that for us?” and they would pay me to answer. Then they’d pay to have the answer implemented.
And they would pay more and more and I hired people and I got very busy and I had deadlines and clients and money and stress. I sold that company, started others, kept asking questions. My stomach began to hurt and it took about 15 years for the hurt to go away.
And in those 15 years I made it a point to start off every meeting asking questions. If you can’t be curious about a client, you can’t solve their problems. If you can’t break them out of the comfort zone then there’s no reason for you to be in the room. THE ONLY REASON you exist in those meetings is to be curious about their problems.
Every date I went on, every client meeting I had, every morning just for the fun of it – I wrote down questions, I asked questions, I was curious.
I practice EVERY SINGLE DAY: how many questions can I ask today?
There aren’t any answers. There are infinite answers to each question. But the more questions you ask: the wider your comfort zone becomes. I call this comfort zone compounding.
Questions punch holes in the comfort zone. Questions turn serious into fun.
If you are sincerely curious about the other person then their “mirror neurons” will make them insanely curious about you and they won’t even know why. This is science. This is the secret.
This is how I build businesses. This is how I build life-long relationships. This is what worked for me.
One day I moved away from Astoria and I don’t think I’ve ever been back. Nick’s probably dead. But I bet everyone is still playing games and laughing. and somewhere in Astoria there are hundreds of $2 bills with my phone number on it.
That was the last time I was able to say, “This is the best time of my life”. Until now. Until the moment I posted this.