RISK

Rule No. 1: Never lose money. Rule No. 2: Never forget Rule No. 1.

All I want to know is where I'm going to die, so I'll never go there.

Diversification is the holy grail of investing.

I'm only rich because I know when I'm wrong.

Risk management is not about avoiding risk. It's about understanding it.

Risk means more things can happen than will happen.

Risk is not inherent in an investment; it is always relative to the price paid.

I only invest when the downside is limited and the upside is enormous.

Choosing individual stocks without any idea of what you are looking for is like running through a dynamite factory with a burning match. You may live, but you are still an idiot.

The biggest risk is not being in these technologies when they hit critical mass. Missing the boat is a bigger risk than volatility.

Every day I start by asking: what could go wrong? Not what could go right. That question has kept me alive in markets for forty years.

If you have trouble imagining a 20% loss in the stock market, you shouldn't be in stocks.

If you are buying options on Robinhood without understanding how they work, you are not investing. You are gambling with extra steps.

Leveraged ETFs are not for everyone. They are not even for most people. But when you are right about the direction and the time horizon, they are extraordinary.

I lost six billion dollars in one day in 2000. That experience taught me that the conventional rules of business can destroy you overnight. Bitcoin taught me the alternative.

I have never seen anything in my career with a risk/reward as good as Bitcoin right now.

The key risk is not that Bitcoin goes to zero. The key risk is that you sell it at the wrong time.

When something is important enough, you do it even if the odds are not in your favor.

I knew that if I failed I wouldn't regret that, but I knew the one thing I might regret is not trying.

The biggest risk is not taking any risk. In a world that is changing quickly, the only strategy that is guaranteed to fail is not taking risks.

I would rather be wrong in public and learn than right in private and stay comfortable.

The middle class is the most dangerous place to be. Comfortable enough not to act, vulnerable enough to lose everything.

Insecurity is the enemy of greatness. The more insecure you are, the less risk you will take.

Bulls make money, bears make money, pigs get slaughtered.

The market is always trying to take your money. Your job is to not let it.

I'd rather grow slower without debt than grow faster with it. Leverage amplifies everything — including mistakes.

Planning is important, but the most important part of every plan is to plan on the plan not going according to plan.

The best investors don't predict the future. They prepare for multiple futures.

Volatility isn't risk. Permanent loss of capital is risk. Know the difference.

Rule number one: don't lose money. Rule number two: don't forget rule number one.

If you don't understand it, don't invest in it. It's that simple.

Heads I win, tails I don't lose much. That's the Dhandho framework.

Risk is what's left over after you think you've thought of everything.

The best hedge against bad investments is understanding what you actually own.

Every financial crisis looks obvious in hindsight. At the time, everyone involved thought they were being clever.

If someone promises you guaranteed returns, the only guaranteed thing is that you're about to lose money.

Most financial innovation is just old leverage in a new wrapper.

Fear is the disease. Hustle is the antidote.

When something is important enough, you do it even if the odds are not in your favor.

Failure is an option here. If things are not failing, you are not innovating enough.

We made investing accessible. But accessible doesn't mean risk-free. Those are very different things.

We underwrite every single transaction. That's expensive and slow. It's also why our default rates are half the industry average.

I'm optimistic about AI's potential to solve enormous problems. I'm also terrified of getting it wrong. Both feelings are appropriate.

When you invest twelve minutes and the guy wants a billion, you're going to lose big or win big.