140Love – the Ultimate Dating Service

It was post-Stockpickr, post-my marriage ending, post-me disappearing from thestreet.com and the financial times, post-my worst-selling book coming out (“The Forever Portfolio”) (see the story of that one and how it relates to dating), post the 2008 financial crisis. Post me spending the night at a motel in the middle of nowhere at the insistence of the police. The world was post-apocalytpic and we were now living in the radioactive fallout. No job was safe. No relationship left untouched. I didn’t know where I was living. I didn’t know how long I would live. The sunlight scared me. The survivors tried to put the pieces together. Or so it seemed to me.

I moved into the Chelsea Hotel. I’d leave it rarely, except at night. There was this gourmet hot dog place down the street, now shut down by the Department of health. It was my lunch every day. The rest of the day I’d read or look out the window. When I was a kid I would spend time four blocks away from there at my grandparent’s house. I asked my grandfather once where God was and he pointed out the window, “over there.” I think now maybe he was pointing at the Chelsea Hotel, where I was living.

I was dating. And becoming an expert at it. I tried every dating service. I went out with the former Serbian Olympic Swimming Champion. We met on J-Date. I went out with another woman who was a judge on some TV animal show. We met on J-Date. I tried e-Harmony but I was subhuman for the e-Harmony folks. I wanted harmony in my life.

(J-Date worked well for me. But I never met Sarah Silverman there)

On e-Harmony they make you feel out this questionnaire for what seems like five hours but in reality was probably more like four and a half. And then finally at the end they told me the bad news via a popup. “Our statistics show that people who list their status as ‘separated’ are unlikely to find a stable relationship using our service.’ They DOOMED me. What a mistake that was. Why couldn’t they tell me earlier. Then I would’ve lied. I was ready to get married again. I wanted to meet someone and get married.

I met one girl who fought terrorists for a living. I met one girl who had just divorced a $100 millionaire 20 years older. I met one girl who hadn’t worked in 20 years but lived in a beautiful apartment on the Upper East Side her father paid for. Another girl worked at a major bank and was willing to write whatever check it took for me to get divorced. I met two girls who were identical twins. One or both were lesbians. I liked the lesbian but dated the one that might not have been but she couldn’t handle kids. Plus a friend of mine had gone out with one or both of them and I didn’t like that and he couldn’t even remember. Everything was through dating services. The magic of the internet was amazing. This is why they created hypertext. So we could all finally meet each other.

I’d spend two hours a night instant-messaging, preparing messages, looking at pictures. I wanted to meet someone.

During the day what did I do? Nothing. I had a job still at thestreet.com but never showed up for it. Once a week I still had to do something on CNBC or maybe that was already over. I forget. I sat on a red-ripped chair. I tried to spy through the windows on 22nd Street to see if I could see anyone having sex. I taught one woman how to play poker in the hallway until random drug addicts asked us to be quiet because it was too late. I listened to another woman cry about how I would never be able to provide her a yacht on the mediterannean (I thought it sounded too boring and I would probably get burned).

So I decided to do something new. Something I was truly passionately interested in. Something where I could make a quick 10-20 million dollars because I figured it was that easy. I was only interested in dating. So I figured I’d make an online dating service. I had read about how plentyoffish.com was made by one guy in his livingroom and now he was making one million a month. That could be me. That would be me.

(screenshot of twitter taken November 8, 2006)

Howard Lindzon had showed me a little website, twitter.com, over two years earlier in early 2007. [See, 53 things I learned from Howard Lindzon] You have to try it, he said. “Everytime I take a shit,” he said, “I put the details, size, etc on twitter. Its hilarious. I have about 2000 people following my every shit.” I didn’t really get it. A year later I still didn’t get it. But two years later I was starting to get it. It was useless. But another way to keep in touch with many people who I would like but who would probably never be my friends.

I called up my old buddies in India, the ones who did Stockpickr.com. They, of course, were happy to screw up yet another project for me and charge me as much money as they possibly could while doing so. So I sent them the complete spec of what I wanted. Howard was on board. He had over 100,000 followers so I figured he could help me get distribution.

The idea was: you’d log in with your twitter account. You wouldn’t have to answer any big profile questions. And then people can browse your pictures and twitter feeds and determine if they like you and then send you messages through the service. Also, every day we’d use an algorithm to determine your ideal picks and we’d send you the twitter IDs of your “perfect matches”.

We got some investors excited and got enough interest to raise up to $500,000 or more. One of the investors was the woman who had started the very first online dating service, back in 1995. So we felt like we had a good thing going on. Also other people were interested in getting advice on how to manage their own twitter strategies so we named the company “140 Labs” so it would be more than just dating. It would be…everything! Some ad agency even wanted my help with setting up the twitter strategy for GM’s Volt launch. Why the GM Volt would need to have a twitter strategy was not my business to ask.

One time I was at a dinner. Everyone was saying what they were working on. I said, “I’m working on a dating site for twitter.” I thought everyone would start cheering and clapping. “What a GREAT IDEA!” they would say. Maybe someone would even present me with a trophy. I’m a winner. Then, the guy next to me said, “Wait a sec. I’M ALSO working on a dating site for twitter.” And everyone started to laugh. I turned red. It was as if they all said, “you guys suck.” Or even worse, “James, you suck. Because this guy is going to be the winner.” I tried to patch it up saying, “well, twitter is a big world.” But there you go, two twitter dating sites at the same surprise birthday dinner for Tim Sykes.

Meanwhile, GM wanted me to go to Detroit to talk about Twitter. And Jeff Pulver wanted me to speak at a conference about love and twitter. I was starting to feel anxious. I didn’t want to go to Detroit. I felt like I was in the ad agency business again and I gave that up 10 years earlier. And I didn’t know anything about love. What would love having anything to do with twitter anyway. That’s like panties with shit on it having something to do with nudity. I couldn’t waste time going to Detroit and I felt like a fake speaking at a twitter conference about love. What did I know about love? I was in the middle of a divorce. A few months earlier I had to be escorted to a motel by police. That’s what I knew about love.

We launched the site. By this time I had poured about $50,000 into it. Which meant I was being completely ripped off somehow. A site like this should cost no more than $4000. But I was off my game, off my practice. I had a lot of things on my mind. In order to succeed in business it helps to avoid these 9 ways to fail. I probably had eight of the nine happening to me on a regular basis. I had no chance.

People started to sign up. But it wasn’t fast enough. Howard tweeted it, I tweeted it.  We got about 100 signups. Then about 10 more. Then maybe 8 more. What’s going on? Why not faster? Why weren’t the servers going down because they were loaded with so many signups? And then it hit me: twitter is not anonymous. Look at this screenshot of these initial signups. Most of these signups were just friends but the point is: you can see their names. Dating services are mostly anonymous. They are like onions. You unwrap one layer at a time. First the mystery, then the sweet taste, then the identities revealed. Until finally you start crying.

So that’s ok. I could be a dating service and maybe sell it to another dating service while I raise the money and build other twitter ideas since I now had twitter skills. And I could also be an agency. And I can make twitter games. And I wanted to buy a site called tweetizen. And…And…And…I could do everything. I could be THAT twitter guy.

Some money got wired in from investors. On the day the next $500,000 was supposed to be wired in I woke up shaking. Physically shaking as if the bed was vibrating. I didn’t want to do it and my body was telling me. I couldn’t take the money. I couldn’t put that $500,000 in the bank. Not worth it to then devote years of my life to this idea. I felt like I was going to vomit.

The whole thing was just a bad idea. I wired back the money that had been sent in. I emailed everyone else: “don’t wire.” The whole thing is off. Some people wrote back. “Why?” they were all set. They really wanted to wire even though I was telling them no.

I never responded. Josh Stylman, a well-respected entrepreneur, even wrote to me, “after all of our meetings I at least expect you to answer me why you don’t want the money.” I never spoke to him again even though we have many mutual friends. I feel guilty about that. I’m afraid to run into him in the street. I just didn’t have an answer. My body was just shaking too much.

I shut it all down. The site itself lasted until about a week ago when Amazon’s cloud finally shut it down. I don’t think anyone found their true love on there. But it had been hard work and I needed a rest after that. Sometimes your head hurts so bad from all the people you disappointed, all the money you spent, all the energy that you wasted on a project that slipped away. It reminded me of the first date I ever went on.

When I was at the ripe old age of 17. It was in some summer program at a college (that was my definition of “summer vacation” during college. I let her cheat on my tests in Economics 101. Everything seemed so new and exciting. We saw the movie “Cocoon”. We sat and made fun of all the other first dates. We had ice cream afterwards. We walked. That movie was so sweet, Sophia Lee said to me. But without the use of computers I had no chance. Despite “Cocoon” being ‘so sweet”, Sophia Lee didn’t fall in love with me. And to this day I’m really upset that Sophia Lee never even spoke to me again.


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Oh, I totally forgot. I have some lessons I learned from this experience.

A) There are a million dating services. You have to work really hard to market them. I had no idea.

B) Twitter is not enough to build a business. Its been two or three years since then and only one twitter-related business has been sold. Tweetdeck. And it was sold to Twitter. So who knows?

C) The worst thing I did: dont’ be one of the “cool” kids. All of the pizzazz was happening around the tech meetups in NYC and it was all twitter twitter twitter. So I wanted to get involved in the mix. I wanted to be one of hte cool kids. I wanted to be the coolest. At the age of 41. I took the “cool kid” stuff and mixed it with my passionate interest: dating. What did I get? I got a new wife and a bad business.

D) If something is not working, shut it down. Start over. Don’t take the money. Else you become a slave, just as bad as the slaves in the pencil factory.

E) I had too many partners. Before the business had even started I personally had less than 10% of the company. I’m always in favor of giving up equity but this time I gave up too much to too many people for too little. I was doing deals left and right for a business that didn’t exist. Too much.

F) What I should’ve done. Built the site for $4k with no help from anyone except India. Skip all the hip cool meetups. I should not have spoken with anyone about it. Launched it. Got some signups. Seen if it worked. And if it didn’t, flipped it right away for peanuts to match.com or whoever.

But you know what: it all worked out for the best. I was only interested in dating while I was dating. And, after that, I found much better things to do with my time.

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