Sams +$10 Million Portfolio, Money Psychology, and The Decision Register

I realized that wisdom or good judgment is the thing that's most short in supply and the most valuable ... You don't have to be that hard-working or that smart if you have great judgment, if you pick the right things to focus on, pick the right people to work with, pick the right place to live ... If you have poor judgment, no amount of hard work or intelligence really saves you; you kind of screw yourself.

They're like, 'So what do you do for your safety net or whatever?' I was like, you're looking at it ... If I'm still me, I'm safe ... A bond portfolio is not my safety net. My 401k that's locked up till I'm 65—I don't think of that as my safety net. I am my safety net.

My opinion is that most people, if they are trying to make a lot of money, should try to make money through starting a company or owning equity in a company...

Judgment and decision-making is the most important thing you can have. People are terrible at actually honing that. They always say, 'Oh yeah, I learned a lesson.' Really, what was it? Did you did you write down what you were thinking then and what you've learned since? No. You put very little effort into this.

I keep roughly 100 to 200 thousand-dollars in my checking account... Any number above that goes straight into my investment fund.

There's a big difference between smart and wise, and I think that's what we're seeing is basically a lot of smart friends that are not that wise about decision-making. So, they're intelligent, for sure, but they make decisions that don't really make sense if you zoomed out a little bit.

You don't spend the first derivative of money. What most people do is cash comes in from the business, then they spend that money on life expenses. No, no, no. You only spend the second derivative...

As I like to say, I've lost more money than most people have ever made.