Someone asked this on Quora. I answered. I am sorry to say that some of what I’ve written below, I’ve written before. Some of you have read it.

That’s ok. Again, I always say this is what worked for me. Some people might say, “ugh, he’s written some of this before.”

Sometimes I am not 100% original. But I always have to remind myself anyway.

The best advice is 100% autobiography.

So this is my story and maybe someone can benefit or maybe someone can’t. I don’t want to be presumptuous.

This is my answer:

I took out a big life insurance policy and then debated killing myself. Then I lost my home. Then I lost my marriage. I drank a lot. I lost everything. I lost my self-esteem. Or maybe I never had it to begin with.

The IRS was after me. I lost money in a fund I started. I lost all the money in a business I started. I was afraid to return calls. I’d cross the street rather than talk to people. So I lost my friends.

Those were the bad habits.

I can’t speak for others. But when I first made a lot of money (> $10,000,000) I had many bad habits. And I lost 100% of my money. I went broke. I went into exile.

Money doesn’t make you better. It doesn’t really increase your freedom. It doesn’t make you more lovable. It just magnifies what is already inside of you.

And past history is often future character. Unfortunately for me.

But then about the second or third time (or fourth time – who keeps track) I lost money, I was on the floor and I was thinking: what the F?

How can this keep happening to me? I keep making it! Why can’t I keep it?

So I made a list of the things I was doing on the way up. And a list of the things I was doing on the way down.

And it was simple. Don’t buy any self-help guru program for riches. I just started doing every day the things I did on the way up.

I’m about to tell you them. But let me tell another story.

I used the ideas below to make a lot of money starting around 2009 (the last time I went broke. The first was in 2000).

But people kept saying to me, “Easy for you to say. You have money.”

So then, unfortunately, I got some proof.

Bad things always happen no matter what. So a bad thing happened to me. I had a big investment in a public company that was worth millions.

The largest shareholder in the company allegedly (I have to use that phrase) took a large amount of money from the company. Nobody knew. The company went to zero within weeks.

I lost several million.

I found out when, ironically, I was invited to hang out on the set of the TV show, “Billions”. I highly recommend the show.

I found out mid-day and had the rest of the day to go to spend time with the cast and crew and learn how a TV show was show.

Afterwards, when I told the writers what happened they couldn’t believe it. They said I was just as enthusiastic and curious in the afternoon as in the morning.

OK.

But it was in my head. And I said, “OK, now is the time to practice what I always say I did or else I could be in some serious trouble.”

So I did. One year later I can say the results have been startling. The money lost, pretty much made back. My relationships…better than ever. My health…better than ever. My creativity…doing well. My gratitude….I am grateful that my own advice has the best testimonial….once again from me.

Here are the habits I do every day.

Most important – I don’t think about past or future. I just think: did I do these habits today?

That is the only question I ask at the end of the day.

I try to improve 1% each day on:

Physical Health

• sleeping, eating well, exercise (which might just mean…enough movement per day. It doesn’t mean gym time).

Emotional Health

• Improve friendships

• Get rid of the people who put me down or make me feel bad about myself

• Improve my own ability to hold onto my self-esteem rather than outsourcing it to others. It’s hard enough for other people to deal with their own self-esteem, let alone mine.

• Love strangers

• Love my family

• Don’t judge myself too harshly

Mental Health

• Write down 10 ideas a day to exercise my idea muscle. The benefits of this are enormous. I just sent ten ideas, for instance, to a $100 billion company that asked me for them. I build networks, make money, create opportunities, become creativity, because i write down 10 ideas (most of them horrible) every day on a waiter’s pad.

• Write, draw, create, in some way

Spiritual Health

• Simply be grateful every day. Find something difficult to be grateful for. Like a breakup. Or…like losing money.

Note that spiritual health has nothing to do with religion, with meditation, with blah. Only gratitude. Make things simple.

One Question a Day

• At the end of every day ask, “Who did I help today?”

Financial Habits

• The above are the most important habits. If I don’t do those, I’ll never succeed. I’ve seen this over and over. But there are financial habits.

• Never invest more than 2% of your net worth in any one thing. And that includes downpayment on a house. Or college for kids. Or private investments. Or stocks.

• When you invest in a private company…people is more important than idea or industry. Invest with A) someone who has been CEO before of a successful company and B) with co-investors who are smarter than you and C) in a demographic that is trending upwards.

• I keep the rest of my money in cash and I use it to invest in myself. I invest in myself with:
  • experience, education, and stories (I’ll do anything for a good story)

Books 

This isn’t quite a financial habit so I split it out. Read a mix of non-fiction and fiction each day. It doesn’t matter what you learn. Don’t stress it. You’ll absorb.

Books are the way to get a lifetime worth of experiences in just a few days. And you can do that 100 times a year. So (let me do the math), that’s like living 100 years in one year. Or something like that.

Some people say: I can’t do that every day.

I promise you that you can. I really promise this. It’s not so hard.

But I can’t exercise…just do 20 pushups and take a walk around the block.

But I can’t write down 10 ideas a day…it takes five minutes.

I can’t read a book!….Just read 3 pages.

Pull out a calendar. Check the box every day you do all of the above. Make sure you never miss a day.

Oh! Another important habit.

Never, NEVER, blame someone else for your misfortune. That’s similar to out-sourcing your self-esteem to someone else: a boss, a relationship, etc.

The only way someone invented cures, was because someone got sick. Take responsibility for yourself, so you know the future cures. That’s how you live longer and happier in every way.

One more thing I do every day: do at least one thing to get myself out of my comfort zone. A dare a day.

Like writing a post telling you how much money I lost and how I’m proud of it.

Being proud of how much money I’ve lost for others right when I am trying to raise money for another project.

That makes me scared and uncomfortable.

But I want my comfort zone to be as big as possible. So I can live large. So I can help others. So I can be myself. And proud of it.