Smoking Crack, Living Large
The worst day in my life as an entrepreneur was … every single day. You sucked the soul out of me.
Like the day I had to fire my sister. Bad.
Or the day that my second biggest client, who owed me a ton of money, simply said he wasn’t going to pay. He represented a $10 billion company. None of his bosses even knew he had hired us to do all this work for him.
Or the day all of our stuff was robbed at a big conference.
It was my fault. It’s always my fault.
When you are an entrepreneur, every thing is your fault. Mistakes are always forgivable, but only if you admit them.
One friend of mine couldn’t admit his mistakes. Now he’s suing everyone who caused him to go out of business. He lives in his car.
Oh, another bad day: when you’re in the middle of selling your company and the only thing you need to close the deal is your landlord’s permission (since there will be a new company on the lease) and he refused to give it unless you give him money. A LOT of money.
Or the day when you release a product and so many people are using it that it crashes and never. gets. up. again. Please computer. Please work.
Or maybe you release a product and nobody uses it. Or maybe you start a business and get depressed and don’t feel like finishing what you started.
Or when you have a crush on one of your employees. What can you do? What if it’s all of your employees? Not impossible to happen. I have a very big heart.
“I never felt this way before,” she said. And that’s the beginning of the end of your company.
I thought I had two choices: job or entrepreneur.
I wasn’t very good at the job thing.
I’ve written many times before why not only jobs are bad, but they are disappearing for various reasons. The “corporatism” that lasted for about 200 years and is now going away.
I don’t blame you if you have a job. I hope you are happy there.
Our brains tell us we are safe. Our brains tell us we are wanted. And the companionship of your cubicle mates is sometimes life-giving.
But here’s what really happens. I suspect this might happen to everyone at some point.
You get “filled up”. You feel emotionally and mentally bloated like you can’t get out of bed. Can’t move. Can’t live. Another day.
Not only does the grass seem greener, it actually is greener. The colors of your life become gray and everywhere else you look seems to sparkle with fantasy.
Whenever I feel that way, I know it means I have to change something. Sometimes big changes, sometimes small.
But entrepreneurship is too hard. I don’t think that’s the right answer either. We glorify entrepreneurs because of charismatic companies that rise up from nothing and change the world. This is great but unlikely to happen to most people.
Here is what the average entrepreneur goes through:
A) You have to kiss ass to get clients.
B) Your initial product didn’t work so you have to figure out how to change or else you immediately go out of business.
C) Raising money is much harder than people think.
D) There is zero security.
Every day you are in danger from competition, clients leaving, top employees leaving, product not working, etc. An entrepreneur risks reputation and poverty every day.
E) An entrepreneur probably has to make 40-50 hard decisions a day.
A GREAT entrepreneur will only make the correct decision 40% of the time. A BAD entrepreneur will be at about 35%. 5% difference.
F) Every day there are unexpected problems that come up.
By “unexpected”, they are so far out of left field there is no way you could’ve predicted them.
G) Many people think entrepreneurship is about taking risk. This is not true. Entrepreneurship is about mitigating risk 24 hours a day. Mitigating risk is very hard.
H) You miss your family. There’s only so many dinners you can say, “I’m sorry honey, I can’t make it today. Something came up.”
I) You have to travel a lot to meet people you don’t like so much.
And most people you have to do business with are people even more scared and nervous than you are.
J) Most businesses fail and then it’s hard to convince yourself to persist long enough to start another business.
Persistence is good but at the moment of failure it’s hard to get up and say “all I need is persistence”.
When I fail, I feel like I’ve been locked inside a refrigerator and I’m afraid nobody will ever get me out. Help! It’s cold in here!
K) You smoke crack a lot.
Meaning: because of a cognitive bias called investment bias, you tend to think your business is better than it really is.
Zero entrepreneurs avoid this. It’s hard to convince them they should put the pipe down for a second. The more passion they had when they started their business, the more crack they are smoking. Passion is not a great thing for entrepreneurs.
L) You think too much about money.
Because you have to pay people, charge people, rent places, buy things, bribe people, sell companies, etc.
So all of the kaleidoscope dreams you start with get exchanged into something you can put in a cash register.
It was never about money, you say, until it becomes all about money.
I’m not saying this is your business. But this is, more or less, the average entrepreneurial experience. To survive being an entrepreneur you have to constantly be solving all of the hard problems above.
Not impossible. But not always fun. And mostly not lucrative.
Around 2009 I realized I couldn’t do it again. I had started many businesses. Almost all of them had failed. Some of them had done very well. But those were the most painful.
Meanwhile, I was getting a divorce, most of my family didn’t speak to me, I was gaining weight, I was drinking too much, and I was unhappy.
I told one friend I was gaining weight. He wrote back, “Damn, I saw you a few years ago and it wasn’t good. I can’t even imagine what you look like now.”
I was really scared. I thought, how can this be happening to me again. I would ask strangers in the street why everyone seemed depressed all the time and they would just look at me.
I started to do what I always did to get out of this situation. What I call my daily practice. Focusing every day on improving just 1% my physical emotional mental and spiritual health.
Here’s what happened first. I stopped regretting the past. This was a huge relief. The past is a black hole. You get sucked in and it feels like there is no way out.
Some people say that in the middle of a black hole you can find a way into another universe. I don’t know if this is true. It wasn’t true for me. I kept getting lost in the dark on my way to that other universe.
“Improving 1%” doesn’t really mean anything. But it helped to think this way. I wasn’t trying to be a mathematician. “1%” sounded like a good amount to improve each day.
Within about six months it hit me. It was an Aha! I realized I didn’t need to be an entrepreneur to make money.
In fact, better not to be. Better not to staple myself to a single idea. “One idea” will control you. But “100 ideas” and you are the master.
There’s a saying “stand next to the smartest person in the room”.
Harold Ramis stood next to Bill Murray and the rest is history. Steve Jobs stood next to Steve Wozniak. Sergey Brin stood next to Larry Page (or vice versa) and so on.
I got rid of all the people in my life who were no good for me. Everyone who tried to take.
Then I found all the people smarter than me. A lot smarter than me. Because “a little smarter” is hard to tell. They had to be 10 times smarter than me. This is difficult because why would they want to be around me?
I worked really hard at finding the things I could help them with. Some people, for instance, are brilliant scientists but don’t know business. Some people know business but don’t know marketing. Some people know marketing but don’t know technology. Some people make money, but don’t know how to be happy. Some people are happy, but have no friends.
I ended up as an advisor, board member, tiny investor, writer, friend, to some of the smartest people I’ll ever meet in this lifetime.
And not in any one field. In fields ranging from biotech to energy to tech to employment to information products to entertainment to every field.
I tried to become good at giving all of these people ideas. Or helping in any way I could. I swept the floors and cleaned the toilets. And sometimes it worked.
Knowledge will give you power and lets you start a business. But the only way to rise above the mess is to have character. Character earns you respect. Respect is worth more than anything else.
I read the other day that the “average multi millionaire has income from at least seven different sources”.
If you have a job you’re stuck with just one source. So that’s out. And if you are an entrepreneur with a straightforward business model it’s probably just one source of income. Too risky!
I started meeting people in so many different fields and started generating income from so many diverse interests that I was able to mix and match.
I’d introduce people who were from totally different fields. I learned from one field things I could apply to other fields. When I made money from one area, I could invest it in another.
And so on. It took time. I went from dead broke to actually stimulating my brain being involved with so many smart people. To feeling like I was helping them save the world.
I’m not very smart. I was thrown out of graduate school and I was honestly the worst student there. I barely graduated college. I barely graduated high school. The people I met became my school.
I used to fall for all the myths: rise up in your job and get promotions, become an entrepreneur, develop a great product, it’s not the goal its the journey, etc etc.
The most important lesson I ever learned, the only thing that continually saved me from bankruptcy, is to find the smartest person in the room and stand next to them. And figure out how you can help them.
So now I’m going to call the smartest person I know and see how I can help her. My 12-year-old daughter. 
