James Altucher
10 min readNov 16, 2020

After I had gone broke the first time, I booked myself into a hotel room. I wanted to spend a day away from computers, away from my phone, away from people, away from THINGS.

I needed to think. I was scared. I had no money left. I had a huge mortgage payment every month. I would default on the next payment. I would never be able to make a payment again. I had one kid and another kid on the way.

Just two years earlier, even a year earlier, I had $15 million in the bank. The night before, I looked at my balance on the ATM machine. I had $143 left. I started to cry. There was nobody to blame. It was all my fault and I was broke.

I booked a cheap room in the St. Marks Hotel. I sat on the bed. My plan was to close my eyes and just think. To meditate on my problem. To try and find balance and stop being depressed, stop being anxious, stop regretting. I was going to sit there all day.

Within five minutes of daydreaming I started crying. I thought of my daughter and how I had ruined her life and she was only two years old. I thought of my dad, how he had a nervous breakdown after he went broke and never recovered. I was going to be just like him.

I started crying about my baby yet to come. She would never know me as a winner. I’d always be a loser.

I felt so bad and I cried all day. I couldn’t stop. I went home that night and my wife asked me, “Did you figure things out?”


— — -


In the history of the planet zero people have woken up and said, “I can’t wait to make James Altucher rich today!”

If anyone calls you and says, “You have to try this amazing deal!” then hang up the phone.

One time my ex-lawyer called me. He said, “talk to this guy. He’s got a thing going on with telecom and Africa.”

I spoke to him. This was in 2005. I can remember pacing back and forth on a subway while talking to him. “Listen,” he told me. “Bill Clinton is interested. George Soros is interested. They are going to come in once we get this round of fundraising done.”

I should have hung up then. What’s going on here? Was Bill Clinton waiting by his phone for this guy to call him and say, “Guess what! James Altucher is IN baby!!” and that Bill Clinton would be breathing a big sigh of relief and say, “Ok then, count me in!”

Of course not! Don’t believe the hype.


I have one mantra when I wake up each day, “I am stupid.” I remind myself all day.

Sometimes I look at a company and I think to myself, “Man, I’m glad nobody else knows about this!” And I structure a deal where I get a huge equity stake because there’s no competition to invest.

Guess what. If there is no competition to invest and you invest, then you are about to lose money. All of it.

Either the entrepreneurs are not good at getting their story out (a bad sign) or their idea is no good (also a bad sign).

If I think to myself, “I’m super smart and everyone else is stupid so I better invest RIGHT NOW!” then 100% of the time I’ve lost money.

I NEVER invest unless there’s someone smarter than me going in the investment.


Don’t invest more than 1% of your net worth in any one deal.

Even if it’s the next Google or Uber, DO NOT INVEST more than 1% of your networth.

Let’s say the deal fails. Goes to zero. No big deal. I just lose 1% of my net worth.

Let’s say the deal is huge. HUGE. 100x. That’s great. On one deal that I can barely remember I just doubled my net worth.

But couldn’t you have made more? Couldn’t you have KILLED IT? Shouldn’t you have invested bigger?

Here’s the secret. No matter how much I invested I would’ve made the same amount of money. Because if it got to be a certain amount I would’ve gotten nervous and tried to sell to whoever would take it.

But the more I invest, the more I could lose.

People say “you should never have regrets”. But I do. I do. I’m happy where I am. But I wish I had been smarter. I wish I hadn’t put 30% of my net worth in 2000 into a device for deaf people to text each other. Or another 20% of my networth in an online marketing company right before that industry blew up.

The day I was forced to move out of my expensive apartment (which was 150% of my net worth with the loan). We were all standing around the elevator. I was carrying Mollie, who was a baby. She was crying. I couldn’t believe this was happening. Everything I worked for was down the drain.

The elevator came. We got in and went down. We drove 70 miles away to a house 1/4 the size of our old apartment. There was a blizzard. I pretended all was ok but it just wasn’t. And it wouldn’t be for a long time.


I had a friend who borrowed $10,000 from me when he needed it. Two years later he had made some money and I reminded him of the loan. “Are you sure?” he said. I said very sure. I said, “Don’t you remember? You were crying when you asked for the money.”

He said he couldn’t remember but he would send anyway,

I never spoke to him again.

Maybe I was harsh. I don’t know. I had another business partner who once called me and needed $1000. His car had been towed and he had been robbed at an ATM machine at 4 in the morning after leaving a strip club. I gave him the money and never spoke to him again after that.

You only have a few opportunities to make a lot of money. You can only do those opportunities if you surround yourself with good people.

What is a good person? It’s not that hard:

A person who listens. A person who is compassionate. And a person who has the courage to take disciplined risks.

What is a loser?

A loser is a victim. A loser wants a short cut. A loser always seems to have unavoidable accidents. A loser doesn’t know where the risks are. A loser compares and despairs. A loser blames and drains.

Can a loser change? Yes. Can you change a loser? No.

I was a loser.


I couldn’t rent an apartment a few years ago. The head of the building called me and said everyone who lived there had to meet me first.


“There’s an irregularity.”


“You don’t seem to have a credit score. Have you never owned a credit card?”


So I had to ask them why it was so abnormal to have never been in debt? Why was I the strange one because I didn’t owe money. He didn’t really have an answer.

They finally let me rent the apartment. But I had to put six months down in advance. They didn’t trust me because I never borrowed money before.

6) NOTHING ILLIQUID: houses, art, etc

Almost everything you want to buy is worthless. Think about it. Art? Sure, some twisted group of people decided to hold art auctions and drive up the price of a piece of paper with a drawing on it to a hundred million dollars.

People pretend art has value. It does. Sort of. 200 years from now, the aliens will dig up our remains and see a painting with a price tag on it: They paid $200 million for that!? Hhahaha!

Just hold on to your cash.


I always keep as much as I can in cash. I don’t make money on cash. Interest rates are near zero. But, for me, I buy peace of mind. I can sleep. People say, “Make your money work for you!”

Don’t make your money work for you. Just let it rest for a bit. It’s ok to rest. If it works for you, you have to think about it. I’d rather think about other things.

The worst thing I did in the Financial Crisis was invest and trade pretty heavily. Not because I won or lost money then. But because I thought about it too much once I was doing it.

Life is pretty hard already. Pandemics, global uncertainty, tens of millions of jobs have been lost. Industries are changing. Don’t make life more complex.

Why make life so difficult when there are many things to do to make it easier.

(this is a real $100,000 bill)


Most people just focus on one skill: making money.

They figure once they make money it will be easy to keep it and grow it.


There are three skills: making it, keeping it, growing it.

I knew how to make it. But it’s not pleasant to make it and then lose it — over and over.

You’ll learn to keep it and grow it if you follow this checklist.


You need all aspects of health to make money.

In “Choose Yourself!” I wrote about my “Daily Practice”.

You can’t make money without, every day, working on your physical health (eat, move, sleep well), emotional health, creative health (10 ideas a day), spiritual health (simply avoid trying to control the things you can’t control.

If you are getting divorced, expect a year or so of your life to be taken from you. If your business partner is getting divorced, then expect him to be not partner material for the next year or two.

Every day ask yourself, what did I do to improve my physical health, my relationships, my creativity, and my stress. Ask yourself, “Was I the hero in my story today?”


In 2000, I was mentally ill. I had millions of dollars from selling a business but in my head, I was dirt poor. It’s a cliché but somehow I didn’t like myself, I had this hole inside of me that was not fulfilled by the money.

I thought I needed to have 10x the money in order to be happy. THEN I would finally be happy and satisfied.

I took big risks and invested as much money as possible into a ton of deals. Everything I touched went to shit. It all went to zero.

I didn’t know this basic rule: Risk is more important than opportunities.

Once you find a good idea or a decent opportunity, the goal is to not make as much money as possible, but the goal is to every day reduce risk.

Always ask, “what is the worst-case scenario?”

Divorce. Disease. Depression. Business failure. Economic cycles. A one-year deal might turn into a five-year deal. A trend might not work out. Etc.

80% of the time, the worst case happens. Deal with it.

After you deal with it, ask again, “what is the worst-case scenario?” Repeat.

Don’t forget Warren Buffett’s two rules:

  • 1. Don’t lose money.
  • 2. Don’t forget rule #1.

I forgot those rules. 20 years ago I didn’t even know those rules. I wish JUST ONCE I had:


I wish I had found just one person to ask what I should do with my money.

And I wish that magical person had said to me: “Don’t do anything right now. Wait. Enjoy life a little bit. Travel. Learn. Do a project just for the fun of it. Get excited about something you’re passionate about.

I wish someone had sat me down and told me what I’ve told so many people in the years to come: Just put all the money in the bank and don’t change ANY part of your lifestyle. Don’t buy things, don’t invest things, just keep the money in the bank for at least one year.

Let the money marinate your soul for a little bit.


If you don’t respect money, it won’t respect you.

Failure is not a badge of honor. Going broke sucks. And it’s hard to make money. It’s actually harder to make it after you’ve made it and gone broke.

One time I saw an astrologer. I told her I couldn’t get over my depression until I had made all of my money back. She told me to grieve it as if it were the loss of a loved one and then move on. She was wrong. It felt much worse than grieving the loss of a loved one. I am upset I wrote that but it’s true.

Another time I saw a psychiatrist. He said what can I do to help you? I said the only thing that can help me is if you give me a check for a million dollars.

He laughed and said, “I have a feeling that won’t help you very much.”

I don’t know. Maybe it would’ve helped me a little.



James Altucher

For some reason, I’ve turned myself inside out and all my guts have spilled onto my blog. One day I’ll run out of stuff but not yet. http://bit.ly/2blmiaG