…And Then I Held A Glass Of Water To Her Lips While She Was Tied Up

I wanted to make money. When I moved to NYC to get a full-time job, I was rich. I was making $40,000 a year. This was a huge move up from my prior salary of $28,300 a year.

I thought I should be able to hire a butler on that kind of money.

I bought a suit. I started looking at nice apartments. I figure I could afford the massive budget of $800 a month, give or take a “few hundred.”

One time, there was an apartment available uptown. I met the real estate guy. While we were checking out the apartment he accidentally dropped his suitcase and about a dozen porn magazines fell out. He apologized while he picked them up and stuffed them back into this suitcase.

I couldn’t afford his fee of 5% of the year’s rent. I had no money other than what was coming up on my next paycheck.

So I lived with my parents which meant I had to get on a bus at 6am and I didn’t get back from the city until about 10pm each day.

Finally, I was hanging around Washington Square Park doing nothing, I met Elias and he needed a roommate. It was just $300 a month. I got the futon and he got the couch. It was one room. The broken shower was constantly running and the kitchen was so bad, I didn’t set foot in it once.

We kept different hours so I was usually asleep when he got home. With a girl.

He and the girl would go into the bathroom and start having sex with her perched on him while the wall pushed back and forth, as if it were ready to burst and they would fall right through. My bed was against the wall and I’d try to sleep, but I’d stay up and listen.

Elias was a strong chess player and made his money gambling chess in the park. His brother Jorge maybe is the most talented chess player in history but never really pursued the game after he was a teenager.

One time I was sick and in the middle of the night, Elias woke me to tell me we were getting kicked out of the apartment.

I decided then and there I needed to make more money.

Nobody had websites then. I thought this was a big problem that I wanted to solve. Everyone needs a website.

My brother-in-law and I did a website for a diamond wholesaler on 47th street. “If you tell anyone you are doing this website,” he said, in his thick Russian-Jewish accent, “I’m going to have to kill you.” People say that as a joke, but he was serious.

And now he’s dead. He was looking for diamonds in an obscure part of Russia and his plane crashed.

Nobody on the street (known as the Diamond District in NYC) was allowed to know that a wholesaler was selling direct through the Internet. We charged $35,000 for that.

My take was $17,500 which I used to pay for a year’s rent at the Chelsea Hotel in NYC.

It was all cash. I gave it to the owner of the Chelsea in a paper bag and he asked, “Are you a drug dealer?” I don’t think he was asking this to see if I should live in his building or not. I think he was just curious.

Then we did HBO’s website for close to $100,000. I was working at HBO and outsourced the site to my brother-in-law. Then we did AmericanExpress.com and LoudRecords.com, BadBoy, NewLine, and Miramax.com and TimeWarner.com and websites for The Matrix, the Wu-Tang Clan, Con Edison, and many others. We were in business.

I worked all day at HBO and then all night at Reset, the name of the company. We got an office, then we got a bigger office. We had big parties.

Maybe five other companies knew how to do websites in NYC at the time and we were the smallest, but I like to think we did the most creative sites.

We did a site called Shoebox. I asked one of my neighbors at the Chelsea, who was a professional submissive, if she would let us photograph and interview her and her girlfriend, a professional dominatrix who was around 7 feet tall and had some sort of extra chromosome that enlarged everything about her and made her constantly lactate.

They came over to our office where we had a big photo studio and they had about 20 pairs of shoes and all of their lingerie. The highlight for me was holding a glass of water up to Maria’s lips when she was completely tied up and thirsty in between takes.

The site was so popular that Con Edison came over and said, “That’s what we want our website to look like.”

Nobody knew what they were doing.

It’s hard to be a first-time entrepreneur. I should’ve made our services into a product, for instance, raised money, and aimed for a big IPO.

Instead we sold for a multiple of our profits. Maybe the only Internet company back then that was profitable. Stupid.

I knew technology, but I knew zero about business. I wish I had just even one mentor then who could’ve told me about the business side of things.

We also wanted to try out different ideas. While we were running a website business, we also tried to be a rap label, a producer of TV shows, and even a tea company.

We found a rap group we liked and almost signed them, but lost interest.

About half the companies we worked with had employees who asked for bribes in order to throw business our way. “Bribe” is a strong word. Sometimes it was more subtle. “Favor.” Nevertheless, we always paid the bribe.

Humiliation was common for me. I’d fly out to California to pitch Jim Carrey’s agent about doing his website. “This is going to be HUGE!” his agent said. “You HAVE to go to a party with us later tonight.” And an hour later I would call for directions to the party and the agent would say, “Wait, wait, wait a sec. Who is this?”

Another time I hired someone to be CEO while I was still working full-time. He’s a good guy but I didn’t understand how to make a deal. He wanted 10% of the company that would vest in six months. In six months and one day, he took his 10%, quit and made a sitcom for MTV.

Water under the bridge. We’re good friends today.

We felt like we were the wild west. Rappers with guns would stroll into our offices. Trent Reznor would hang out throwing around ideas for the Nine Inch Nails website.

Miramax executives would scream at me over the phone if one pixel was out of place on their logo. One day we spent the day tasting different teas. We wanted to pitch Honest Tea, but it didn’t work out.

Clients would get shot and killed at awards ceremonies in the music industry. HBO one time wanted to buy us but that’s when I had to admit that I was at both places and had to quit working at HBO.

My first day on the job, I cried because I had no idea what to do and people stopped returning my calls after I left HBO.

Then we started getting calls to get acquired. One guy said, “I don’t know a hamburger from a website but I know that a stock with an Internet company is going to go up.” He was from a company that manufactured burn gels and they wanted to buy us so they could put “.com” at the end of their name.

I went on a vacation to Paris. There’s a restaurant at the bottom of the Eiffel Tower. The guy sitting next to us was celebrating. He had just sold a chain of Papa John’s pizza stores. When I got back to New York, he kept calling me and wanted to invest. Maybe he would’ve been my smart investor, but we never took in any money.

Eventually we sold. Eventually people realized that it doesn’t cost $75,000 to make a three page website about Dennis Miller. Eventually the entire web design business went bankrupt as an industry before it reinvented itself as “full services” in the Internet space.

I didn’t know what to do after we sold the company. I felt totally lost.

I had money and it seemed lonely sitting in a bank account. So I bought a house. I rode helicopters every week to Atlantic City. I made a lot of new friends who all wanted something and none of them speak to me anymore.

I played poker every night for 365 straight days. “Ingrid says hi”, Brian Koppelman, the writer of Rounders, wrote me the other day. Ingrid was usually in charge of the Mayfair Club, the best poker club in NY in 1999. Portrayed by Famke Jannsen in the movie.

Every day was a mask to fool someone into having a relationship with me. Into doing business with me. Into not firing me. Into buying my company.

When I actually had to “be myself,” I went broke and lost all of my relationships almost instantly.

I no longer even speak to my partners in the business, all of whom are blood relatives. I was drinking, gambling, running businesses into the ground, spending, and betraying.

I could say, “I wish someone had given me advice” during this time but perhaps many people tried to.

I wish I could say, “I listened” but I honestly didn’t have the ability to listen. I didn’t even know what listening meant.

Listening is a more difficult skill than “Doing”. Because you know the difference between “done” and “not done”. But there’s no line that tells you whether you listened or not.

This is the entire reason why the self-help business is a scam.

There’s absolutely nothing that could’ve helped me. I would later lie down in the street and pray for a car to run over me while my baby girls were upstairs playing.

I wish I could re-live the entire experience. Like the blizzard of 1996 when we all went to work at midnight to finish a website and it felt so good to deliver. Or when I was scared I’d have to fire everyone because I lost a big client and didn’t tell anyone.

Now when people ask me what I would do differently I always say the same answer, “I wouldn’t change a thing.”