The Magic of Idea Math

In mid-2002 I was so depressed I simply ran out of ideas.

Depression scorches the earth of your brain.

I would sit in it at 3 in the morning in the dark. Lord of my crumbling kingdom. Every day I went a little more broke and there was nothing I could do about it. Going broke is very scary.

I would drink to help me sleep. Then I would refuse to wake up. Then the fear would repeat until I fell asleep again.

I pretended to smile at my children. I pretended to smile at my wife.

People say when you pretend to smile it often triggers happiness because you fool your brain into thinking you are happy.

I can tell you: my brain was not fooled. If anything, fake-smiling made me more depressed.

I started to take walks because I was so sick of sitting in the house I was losing.

I would walk through Chinatown and think, “I can just rent some tiny apartment here and work in a restaurant and disappear forever. Nobody would find me.”

I imagined sometimes my old friends wandering into the restaurant and I would serve them.

The thought of that made me happy. Disappearing. Starting over. Maybe I would be a janitor and meet a cute janitor and we would fall in love and live together forever in our tiny apartment.

I would walk from 3am to noon. And then walk again at night.

Walking was the secret trick. It got my blood moving. It got me seeing thousands of people a day. Seeing rooftops where architects went crazy with fun putting on their final flourishes. Relating again to the world.

I started to walk to cafes and bring a book. Then two books. Then three.

I’d bring a book about games. A non-fiction book. And a good fiction book.

One time on the Bowery I passed a restaurant supplies store. I bought a box of waiter’s pads. I started bringing the pads on my walk and writing things down.

I didn’t have any good ideas. Not for a long time. But that’s ok.

The idea was: write a book on “how to win at every game of the universe”.

I ran it by Stephen Dubner who later wrote Freakonomics. He said, “that’s great! You can even make a series out of it. A new book each year.”

But I never did it. Instead I kept coming up with more ideas.

I was buried in quick sand. Ideas were tied together dirty rags that were slowly pulling me out of the quick sand. Or at least preventing me from sinking further.

Eventually one idea turned into a meeting. A meeting turned into a dinner. A dinner turned into a network. A network turned into an opportunity. An opportunity turned into a small amount of money. Then more money. Then I had more ideas.

People say to me, “I get stuck when making the ideas.”

Or they show me their list of 7 ideas and say, “Is this good”.


No it’s not good. Because 7 is the hard part. 8, 9, 10 is where you exercise the idea muscle.

Someone asked Muhammad Ali, “How many pushups do you do a day?”

He said, “I don’t know. I only start counting after it starts to hurt.”

The same thing with coming up with your ideas per day (Yes, I just compared myself to Muhammad Ali).


Take an old idea. One that is big and popular. Maybe million of people love it. Believe it. It’s like a religion. Add something to it.

Example: The Paleo Diet. The idea that you should eat like paleo people because that’s what the human digestive system has evolved over 200,000 years for.

Processed foods are only about 100 years old. An evolutionary blip, hence the reasons for obesity, kidney failure, diabetes, and so on.

Here’s the addition: Paleo people didn’t eat at regular intervals. They didn’t eat three meals a day.

New idea: (today’s paleo + how people really ate 200,000 years ago): “The Multiphasic Paleo Diet: eat at random intervals and vary up the diet considerably (e.g. sometimes eat 1 meal a day. Sometimes 4. Mix nuts, legumes, meats, plants into every meal so nothing can be considered a “breakfast” or “dinner”).


Take an idea that seems impossible. Take the execution. Subtract the reason you can’t.

Subtraction is MONEY. Trust me.

I saw this in a meeting. We were pitching a very wealthy guy. He represented a company worth over $100 billion. We wanted his money.

We wanted a lot of his money. We were hungry for money. Our desire for money was thicker than the air.

He was very blunt. He was like a hammer. He said, “Don’t count on me for a single dime of money.”

The guy leading the meeting on our side was smart. He did Idea Subtraction.

“Take money off the table,” he said. “We don’t want any money from you. That’s covered.”

Then he said, “Assuming we do not need a single dime from you, would you be interested in doing a collaboration with us where we work with your team to see if this is a viable product.”

Answer: The CEO of the wealthy company said, “of course”. Why wouln’t he?

And suddenly we had a joint venture with a multi billion dollar company.

A company that led to millions of dollars eventually being contributed by that company.

Idea subtraction is: have a good idea that seems impossible, find the exact “can’t” in the idea and remove it. See what’s left.

Remove the obstacles.

Another example: “I wrote a book but CAN’T find a publisher”.

That’s ok. Self-publish.

Or, “I have an idea for an app but CAN’T program.”

That’s ok. Go to and for about $600 you can outsource to a good programmer.


Today I wrote down ten ideas that could be the outline for a book.

Tomorrow I’ll write down ten ideas for each one of those ideas.

The next day I’ll write down ten ideas for each of the ten above.

Then I fill in the blanks between all the ideas.

Then I have a book. If you are lazy, you can even outsource to the last part of this.

Idea Exponentials can leads to a book being written in five days.


I wrote an article that was very popular called “10 Reasons to Quit Your Job”.

So then I wrote “10 Reasons to KEEP Your Job”.

I wouldn’t contradict myself (although there is nothing wrong with that. The aliens won’t care after they invade us) but I would suggest ways to be an “intrapreneur” within your workplace so you can stand out and maybe create multiple streams of income WHILE you are at your job.

I was an intrapreneur before I was an entrepreneur. Negative ideas are more realistic.

Idea negatives challenge me to be open-minded. Challenge me to carve out new space in the world.

Challenges me to break rules. Challenges me to see multiple sides of something that is beautiful.


Taking one idea and replicating it. Scaling.

Example: let’s say I write successful advertising for a local dentist. The ads double his business. Now I have a track record.

I can go to every dentist (maybe not in the same town) and say, “here’s what I did for this dentist. For $X I can do it for you now.”

So you take the same idea and multiply it many times. Then you can even multiply that. Sell, “here’s how I made a million dollars helping dentists” in a webinar.

Amazon is a great success at this. They sold books online. They said, “this works, so now what other industries can we be the backbone of all ecommerce for.

Shoes, flowers, food, music, movies, etc.”

Then they said, “we built the computer infrastructure to handle millions of requests. Now we can resell that to all industries.” And that became the Amazon Cloud Services.


This is critical for business.

Peter Thiel is an excellent example with PayPal.

PayPal was initially a way for people to pay for anything they wanted by using their Palm Pilots.

Well, nobody has Palm Pilots anymore.

And it was hard to educate everyone in the world to accept payments electronically.

So he divided and divided again until PayPal became THE way to pay for any items bought on Ebay, a tiny tiny company at the time.

Their entire focus was Ebay, they became a monopoly (even beating Ebay’s internal competition) and then expanded from there.

First divide so much that you are a monopoly, then build.

When I was building my first business, we made websites for companies. But it was hard to call any company and convince them they needed their websites.

We first focused on record labels and movie companies. We divided our idea down into a niche we could dominate. Suddenly we were THE guys for the entertainment industry.

We divided further. We were THE guys for gangster rap websites.

Then we expanded and did larger and larger websites.

And, of course:


When the Fugees, an already popular rap group, combined rap with the BeeGees song, Stayin’ Alive, it was only a mediocre song. Go listen to it. It’s ok. Not great.

But because it was one big thing combined with another huge thing, it became a huge hit.

Idea sex is hard to fail. When you take two good ideas and merge them into one.


People say it becomes “10,000 hours to be world class”.

But if even I (I wish I could capitalize “I” even further”) took a hip hop beat and sang the BeeGees song “Stayin’ Alive” I can make it a hit. In just ten hours.

It takes 10,000 hours to be world class at any ONE thing. It takes 1000 hours to be world-class at an intersection. It takes 100 hours to become world-class at the intersection of 3 or more things.

I keep telling Claudia to create “Tango Yoga”. Heck, I’d take it just because of the name alone.

Which reminds me: Gotan Project. A great band. They took an electronic beat, combined it with tango music. Created hit after hit. Are they Argentinian? No. They are French.


People say “Execution is everything”. I can tell you it isn’t. If you can’t come up with ideas, then you’ll never be able to come up with execution ideas.

When I had an idea for a website once (2006) the next thing I did was come up with “10 ideas for pages on the website”. Then “10 things on each page”. Then “10 ways I can execute on this”.

All of these were subsets of the initial idea.

Eight months after that list I sold the company.

St. James Place.

If you want to win at Monopoly, own St. James Place.

I like to think they named it after me. But the reality is: when you get thrown in Jail, it’s the place you are most likely to land.

Atlantic City + Capitalism = Monopoly.

And in Scrabble, it’s good to know that “QI” means “life force”.

Don’t forget to just play.

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