The #1 Most Effective Habit

[This was a guest post I did over the weekend at TechCrunch].

There was a girl at the party, Ona, who then started telling me how she met her current boyfriend. She just simply told him she liked him. I was insanely jealous right then of this guy. Here was this beautiful, hysterically funny girl who told a guy she liked him and now he was having regular sex with her.

That doesn’t happen, right? It never happened to me. I sat there nodding, not being able to say anything but thinking, what if she said, “I like you” to me right then. I would’ve been happy. Instead, I got depressed and went to sit on the stairs.

There was another girl there. She was crying.I tried to comfort her by telling her I was an artist. I then asked her why she was crying. Apparently the party was actually her birthday party! I had no idea. I didn’t even know who she was. And she was crying because her boyfriend didn’t show up.

Within a week we were living together. Ultimately it didn’t work out and I did my usual passive thing, which was to move to another city (in this case, NYC), to get out of the relationship.

In Stephen Covey’s Book, “The 7 Habits of Highly Effective People” his first habit is “Be Proactive.” I haven’t read the book. I saw the list on Wikipedia. I WILL NOT buy the book because at this moment it’s the #1 book on Amazon under Motivation on the Kindle and I am #2. How can he be #1 after 22 years? Beating the new, fresh, me! Stephen Covey, I’m coming after you!

But it makes me think – unfortunately he’s dead on. In fact, Being Proactive might be the only effective habit. I read the other six and they all seemed to be corollaries of the  first one.

–          When I started my first company, Reset, I showed my brother-in-law the Internet so he could start learning design for it. And then I hired Reset from my perch at HBO to do HBO’s website. I was insanely proactive in getting the company off of the ground. When I wanted to sell the company I didn’t wait for buyers. I proactively went after everyone who was buying companies in the space. And screw you, Razorfish, for ignoring me.

(Reset’s first version of the HBO website)

–          When I was trading for hedge funds I sent out about 20 emails every weekend to new potential investors. Altogether I probably sent out over 1000 emails. Most of them ignored me. Over the course of a year about 14 allocated money for me to trade.

–          When I started Stockpickr, I spec-ed out the site, had India mock up a few pages, and showed the  CEO of what I was working on. I had spent less than $1000 on it at that point. He wanted to be  involved and eventually it grew into a good business. If I had just said to him, “let’s do a social media business in Finance”, it would not have worked. I would’ve become a consultant rather than an entrepreneur. You have to DO things to succeed. Nobody is just going to give you money. This is why being as proactive as possible is important.

–          Ona was proactive in meeting her boyfriend. He was never going to ask her out. So she told him she liked him and they started going out. She was proactive.

–          Before I met Claudia, I was sending out probably 50 messages a day on dating services. That’s the sheer quantity I had to do in order to meet someone I liked and it worked. And I screwed it up so badly, as I’ve written before. She wrote to me that she was from Buenos Aires and I said, “oh, I’ve always wanted to go to Brazil.” And she wrote back, “uhh, Buenos Aires is in Argentina!” Ugh, what an idiot I am!  I can’t believe she agreed to go on a date with me after that.  But if I hadn’t been sending out 50 messages a day I never would’ve met her. To top it off, I really was hoping Buenos Aires was in Brazil. I would save at least four hours on any plane rides. Oh well.

(Claudia looking very suspicious, minutes after we were married)

–          Whenever I want to guest post in another blog, I write the post first, and then I send it to them, and I ask them if they want to guest post it. It almost always works. Very few times has someone reached out to me and said, “can you write for us.” It’s almost always me proactively chasing it.

Here’s the proactive plan:


–          Proactively list what you want (a spouse, a new job, a new business, a new opportunity)

–          List what the next step is (sign up for dating services, take a yoga class, look at classifieds, spec out your business, decide how you will build your product, contact the people who will build it and get a price from them, ask people if you can work for them, etc.) Make sure the next step is very doable. So doable that you can (and will) do it TODAY.

(I do all my lists on waiter's pads. They are cheap and prevent extended prose).


–          Quickly determine what doesn’t work. For instance, if I went to 100 bars trying to meet women, none of them would work. Similarly, when I set up I set up 10 other websites at the same time. None of them got any traction and I stuck with the one that did.


–          If you want a new job, proactively go out and get another one. Preferably freelance : think about what you do best, and then do it for three paying customers. Contact 30 customers and ask what simple services you can do for them that they would be willing to pay for. Three of them will respond and now you can quit your job.

–          If you want to raise money: Contact 100 VCs or angels and share with them your business. If they all say “no” then build up for six months, send them all notes on your progress EVERY MONTH, and go out and raise money again six months later. If you have no progress then start a new business. It didn’t work.

Another example: when a book publisher once  rejected me, I wrote back to her saying that I fit perfectly with her list, describing how I could publicize the book with the different branches of her own company, I would make all changes she wanted, I would work with a co-author, etc and wouldn’t you know it – she published my book that she had rejected. It was an easy book to write (my co-author did a lot of the writing) and I got an advance and made money. It never would’ve happened if I hadn’t researched her and proactively chased her down.


–          If you want publicity, write your own publicity. Write a guest post for a popular blog. If you want to go on TV, contact the producers of shows and give them ten ideas of what you can talk about and why they should pick you to talk about them. Example: I have no credentials in politics but I wrote a post about a year or so ago for the Huffington Post on who the possible third party candidates could be. Next thing I was on five radio shows talking about it. Suddenly I was a political expert.

Another example: In 2002, I wrote Jim Cramer an email with the subject line: “10 ideas for articles you should write”. He liked the ideas I wrote in the email. But he said, “Why don’t YOU write them”. And that began my financial writing career.


–          If you want health, proactively get it. You know when you are putting bad stuff in your body, when you’re not sleeping enough, when you’re not exercising enough, when you’re letting short-term pleasures get in the way of longer-term gratification . Proactively make sure that when you’re 80 you’re not stooped over and suffering.

(don't forget to exercise)


–          Of course one way to make more money is to spend less. Cut out the biggest expenses in your life. Even rent or mortgage. It’s no crime or shame to move someplace else. I’ve done it repeatedly when I’ve needed to. That’s how you live happier and longer.


–          If someone is making you angry how do you be proactive? That’s easy. Ignore them! Don’t try to fight them. You’ll never win. Do you think you are going to win an argument against a friend, parent, or boss who hates you? Of course not. Ignore them until they stop hating you. Now that entire problem is gone.


–          So today, write down the five things you want and what the absolute very next step is to getting those things (if you want to start a business, for instance, write down some ideas for businesses and how you can realistically start them within the next month). If you’re at a loss, here are my suggestions and it goes along with the Daily Practice I recommend:

– write down 2 goals for what you Physically want out of life and then how you are going to get those things incrementally accomplished TODAY.

– write down 2 goals for what you Emotionally want out of life

– write down 2 goals what you Mentally or Creatively want out of life

– write down 2 goals for what you Spiritually want out of life and how you can go about getting those things

(I did beat out Covey for about 15 seconds. Click here if you want to buy it and get the promotion I describe).


You can come up with a lot of reasons for not proactively beginning something. Excuses are easy and I get it. But how about take a ten day diet from excuses. You can get back to your “I can’ts” 10 days from now. If I said, “I can’t start Stockpickr, I’m running a fund of hedge funds.” then I never would’ve started it and sold it nine months later. If I said, “I can’t self-publish – nobody will buy it” then I never would’ve had for 15 seconds the #1 best selling Motivational book on Amazon’s kindle store, BEATING OUT Stephen Covey’s crappy little book.

After I was dating Sue for two years (the girl whose birthday party it was in the beginning of this post), I went shopping for an engagement ring. My friend, Peter, went down to the main store in Pittsburgh with me. There was an emerald ring that looked nice and it was $700. I was shaking. That was a lot of money to me.

There were so many pretty girls walking around the store and I fell in love with all of them. It was an honest and sincere love I felt for every woman walking around. I wanted to marry them all. Right then. And had lots of babies with them.

Later that night I came home and told Sue I wasn’t ready to get married yet. A year later we were broken up. Probably the most effective habit: Don’t be proactive about the things you don’t want to do. Else you’ll die.




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