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.

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

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

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.

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.

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

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

Fear is the disease. Hustle is the antidote.

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

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

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.

Brilliant thinking is rare, but courage is in even shorter supply than genius.

The market is a very unforgiving teacher. If you're wrong about a major technological shift, you don't get a second chance to invest at the same price.

The secret to my success is that I've always focused on the downside. If you protect the downside, the upside takes care of itself.

I always try to avoid losing money. The best investments are the ones where the downside is protected.

Invest in things where, if you're wrong, you can still survive.

Debt is a tool. Used correctly it can enhance returns. Used incorrectly, it can destroy value faster than almost anything else.

The biggest risk in investing is not volatility. It's permanent loss of capital. Those are very different things and most people confuse them.

We're not afraid of volatility. Volatility is just opportunity wearing a scary mask.

Most investors are optimistic because pessimism doesn't sell. We try to see the world as it actually is.

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

It's a tempest in a teapot. We're very comfortable with our positions.

The moment I feel the most vulnerable is when I feel the most comfortable.

Risk is not the enemy. Risk you don't understand is the enemy.

I think the secret is to cut your losses quickly. That's the most important thing. If I'm wrong, I just get out.

We are not in the business of predicting markets. We are in the business of managing risk.

Bulls make money, bears make money, but pigs get slaughtered. And the biggest pigs in investing are people who are afraid.

We think the biggest risk isn't volatility — it's missing the compounding of a great business because you got scared out too early.

We've made mistakes in risk management that we need to address. We were not adequately prepared for the macro environment that developed.

Permanent capital loss is the enemy. Volatility is not the enemy. If you confuse the two, you'll make terrible decisions.

Shorting is the hardest thing in investing. You're fighting the natural drift of markets, and you can be right on the fundamentals and still lose money on timing alone.

Position sizing is where most investors leave the most money on the table. Having a great idea and putting 1% of capital in it is almost the same as not having the idea at all.

The challenge with any quantitative strategy is that the more successful it becomes, the more people pile in, and eventually the edge gets arbitraged away.

Volatility laundering is one of the most dangerous things happening in modern portfolio management. Private assets look smooth because nobody is marking them to market. The risk is still there. You just don't see it until you need liquidity.

Being early in a short is just another way of saying you're wrong until you're right. The market doesn't care about your thesis — it cares about price.

Being early is indistinguishable from being wrong until it isn't.

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

Risk and reward are two sides of the same coin. If you are not willing to take risk, you should not be in business.

In luxury, you never compromise on quality. The day you accept a small compromise, you have accepted the principle of compromise.

The areas where failure is most likely are also the areas where success would be most important.

The biggest risk of all is not taking one.

Amazon was a buy in 2001 at $8. The thesis didn't change when the stock went down 90%. I got the timing wrong but the business right.

Venture capital is a game where you lose most of the time. The question is whether your wins are big enough to cover your losses and then some. Ours have been.

We are in a risk bubble. The risk-taking has been enormous. The valuations have been enormous. And a lot of people are going to get hurt.

The mistake isn't backing companies that fail. The mistake is backing companies that fail for boring, predictable reasons you should have caught.

You have to be willing to be wrong. If you're not wrong often enough, you're not taking enough risk.

The biggest mistake an investor can make is not being in the game. Missing the great companies is far more costly than losing money on the bad ones.

Venture capital is not about being right most of the time. It's about making sure that when you're right, the outcome is large enough to matter enormously.

I think diversification across ideas is a way of admitting you don't have conviction. The name of the fund is intentional.

The cost of missing a great company is much higher than the cost of overpaying for one. Asymmetry matters.

The biggest mistake you can make in a downturn is cutting too slowly. The companies that survive are the ones that make hard decisions fast and then rebuild from a position of strength.

I lost a lot by saying what I believed. I'd do it again. Money you earn back. Integrity you don't.

The short side is never as simple as it looks. You can be right about the business and still lose money for a very long time.

I want to be very aggressive in going after returns. I never want to be in a position where I can lose large.

I have never, ever met a trader who is successful over the long term who doesn't follow stop-losses.

The best traders I know are obsessive about risk management. They think about what can go wrong before they think about what can go right.

The biggest risk is permanent loss of capital. Volatility is not risk. A stock going down 30% while the business remains intact is not a loss — it's an opportunity.

The biggest risk in running a fund is not a bad trade. It is a bad process. A bad process will eventually produce bad trades. A good process will self-correct.

Geopolitical events are the most underpriced risk in financial markets because most analysts are economists, not historians.

The Kelly Criterion tells you how much to bet when you have an edge. It also tells you never to bet so much that you risk ruin. Ruin is the only thing you can't recover from.

The question is not whether there will be a financial crisis. The question is how large it will be and when it will occur.

Risk is not the same as volatility. Risk is the probability of a permanent loss of capital. A stock that goes down 50% is only risky if the business is impaired.

Avoiding permanent loss of capital is the first job. Everything else follows from that.

I think about expected value constantly. If something has a small chance of being world-changing and a large chance of failing, the math can still work out.

The opportunity cost of not having Bitcoin in your portfolio is becoming greater every year.

I was the youngest person on the SAP executive board. I walked away from a clear path to CEO. People thought I was insane. Maybe they were right.

We walked away from SMBs entirely in 2022. Fired those customers. Everyone called it suicidal. But you can't be everything to everyone and win.

We dropped out of Stanford after one semester. Our professor said we were making a mistake. Our bank account disagreed.

We built LaMDA at Google. Google was terrified of it. We weren't terrified — we were excited. That's the difference between a big company and a startup.

Google had the technology, the data, the talent, and the money. They just didn't have the courage to ship it. We had nothing except the courage.

I dropped out of Harvard Business School to start a company in South Korea. My professors thought I was throwing away my career. I was just picking a different one.

Yield is just a word for where the money is coming from. And if you don't know where the yield is coming from, you are the yield.

I lost seven buildings in one year. Seven. Most people would have retired. I started planning the tallest residential tower in New York. What else was I going to do — play golf?

I had the building demolished on a holiday weekend because I knew the city would fine me and then move on. They fined me $2 million. The site was worth $100 million. You do the math.

I left BiggerPockets — the most popular real estate podcast in the world — to go all in on my own fund. People thought I was crazy. But I did not build a media platform to stay behind a microphone forever.

I emptied my entire 401(k) to fund Calendly. Every penny of my retirement savings. My financial advisor thought I had lost my mind. That was the best investment I ever made.

Respect the market. It is bigger than you, smarter than you, and it has been around longer than you. The moment you think you have it figured out is the moment it teaches you a lesson.

In the stock market, the money you don't lose is more important than the money you make. Avoiding stupidity is the whole game.

I left Samsung because I realized I would spend 30 years building someone else's dream. I wanted to spend 30 years building my own — even if it failed.

When Silicon Valley Bank failed on a Friday and we had $3.3 billion stuck there, USDC depegged to 87 cents. Those were the longest 48 hours of my life. The government backstop on Sunday saved us — and taught us to never concentrate reserves again.

When I bought UBA, people said I was crazy — the bank was nearly dead. I saw a platform that could reach 20 African countries. They saw a corpse. I saw a sleeping giant.

I was at Lehman Brothers when it collapsed. I watched a 158-year-old bank disappear overnight. That taught me two things: institutions are fragile, and complacency kills. I run Revolut like it could die tomorrow.

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

Through Kima Ventures, I invest in about 100 startups per year. Most will fail. Some will change the world. The math works because the winners pay for all the losers ten times over.

We launched over 100 companies in 100 countries. Most failed. The ones that survived — Zalando, Delivery Hero, HelloFresh — created more value than the failures destroyed. That is the game.

I left a tenured professor position at Cornell to build Avalanche. In academia, that's the equivalent of setting your career on fire. But some things need to be built, not just published.

The best investment I ever made was not a stock or a startup — it was betting on myself when no one else would.

The most dangerous words in business are: this time it is different. It never is.

Quitting medicine was the scariest financial decision I ever made. It was also the most profitable by a factor of fifty.

I dropped out of MIT at 19. My parents were not thrilled. But I had seen enough to know that the idea was better than the degree.

The Power of Broke is real. When you have nothing to lose, you have everything to gain.

My strongest suit is not stock picking. It is risk management.

I learned more about probabilities and risk from playing blackjack in Las Vegas than I ever did in an MBA classroom.

A strong dollar is the wrecking ball for the global financial system. And the wrecking ball is swinging.

I made a lot of money for a long time and then I gave a lot of it back. That is the story of concentrated investing.

If you cannot stomach a 50 percent decline in your investment you should not be in equities.

Margin of safety is not a concept. It is a religion.

Every home in our inventory is a bet. When the market moves against you all those bets move against you at once.

When interest rates moved 400 basis points in a year we were holding thousands of homes. That is what risk looks like in real estate.

Mortgage lending is a rate-sensitive business. When rates double your business does not halve. It falls off a cliff.

Central banks have created the largest asset bubble in human history. When it pops the consequences will be generational.

Smart contract risk is real. One bug could cost billions. We audit everything. We run bug bounties. We still lose sleep.

The greatest risk is not taking one. I have applied that to basketball business and tequila.

Portfolio resilience is more important than portfolio optimization. Prepare for multiple scenarios not just the most likely one.

Megathreats. Climate change. AI displacement. Deglobalization. Debt crises. The world faces more simultaneous risks than at any time since the 1930s.

If proprietary models win and open source dies our business dies too. We are all in on open source AI.

I think the main quality you need in running a newspaper is a stomach for risk.

The trouble in America is not that we are making too many mistakes, but that we are making too few.

The opportunity is always greatest where others see the most risk.

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

The most dangerous words in finance are: this time is different. The second most dangerous: it can't happen here.

All bubbles end badly. Every single one without exception.

Doing what everybody else is doing at the same time that everybody else is doing it is a formula for disaster.

Crypto is volatile. Get used to it. If you can't handle a 50% drawdown, you don't deserve the 500% upside.

Poker taught me more about risk management than any finance textbook ever could.

I like buying companies that have low debt. I don't like businesses that owe a lot of money.

Conservative investors sleep well.

The four most dangerous words in investing are: this time it's different.

The riskiest thing we can do is just maintain the status quo.

The market rewards conviction. The market also destroys overconfidence. The line between them is thin.

Leverage is a tool. In the right hands, it builds fortunes. In the wrong hands, it destroys them.

I stopped publishing short research. The risk-reward changed. When a subreddit can organize a squeeze against you, the math doesn't work anymore.

The greatest risk in investing is not volatility. It's doing something stupid because you panicked.

I've made money and I've lost money. I'd rather be in the game losing than sitting in the stands watching.

When you're old like me, the thing you regret is not the money you lost. It's the deals you didn't do.

I've never had a safety net. That's why I run so fast.

Complex systems don't fail gradually. They fail suddenly. The snowflake doesn't cause the avalanche — the mountain does.

The worst thing that can happen to you is you go broke. I've been broke. It's not that bad.

Leverage in crypto is just a tool. Used correctly, it amplifies returns. Used incorrectly, it amplifies destruction.

Credit investing generates more consistent returns with less downside than equity. That's why Apollo shifted.

I was in the room when LTCM nearly destroyed the global financial system. I learned that nothing is as safe as it looks.

The 2022 downturn tested our model. Defaults rose. We tightened underwriting. The core idea is still sound.

One regulatory decision in one state can affect millions of users. We live with that risk every day.

Insurance is about pricing risk correctly. Better data means better pricing. Better pricing means better business.

I quit my hedge fund job to make YouTube videos about math. My family thought I was insane.

The greatest risk is not taking one. You miss 100% of the shots you don't take.

The biggest risk is being unwilling to take any risk at all.

The greatest risk is playing it safe. Mediocrity is the real danger.

Rock and roll and venture capital have more in common than you'd think. Both are about taking risks on something new.

I put $27 million of my own money into that whiskey. If you won't bet on yourself, why should anyone else?

Diversify geographically. No single country should hold your entire fortune.

I left a CEO job to make angel bets because I'd rather be in the arena than the skybox.

Employee number 30 at a company worth $65 billion. The lesson: join rockets, not safe bets.

$710 million to challenge the most valuable company in tech. We knew the odds.

I quit my job making laser printers to build a fusion reactor. My wife was surprisingly supportive.

I quit a law firm in Africa to figure out how to make eggs without chickens. My parents thought I'd lost it.

Risk more than others think is safe. Dream more than others think is practical.

We nearly ran out of money in 2015. If we had raised one month later, DoorDash wouldn't exist.

I came to this country with nothing. That gives you a very different relationship with risk — when you've already lost everything once, starting over isn't as scary.

Everyone told us we were crazy to start a bank in Brazil. Five banks controlled everything. But that's exactly why the opportunity existed.

In 2008, we had seven billion pounds of debt and the world stopped. I thought I'd lost everything. We negotiated with 230 banks and survived.

Facebook offered us $3 billion. We were 23. Everyone said we were stupid to turn it down.

The Eagles were nobodies when I signed them. Guns N' Roses were a mess. Nirvana was underground. I back artists, not sure things.

In Russia in the 1990s, there were no rules. You either figured it out or you disappeared.

I grew up with nothing. No parents, no money, no connections. Everything I built came from taking chances others wouldn't.

I dropped out of USC to run Box from a dorm room. My parents were not thrilled. They're fine now.

I've always been a contrarian. The problem with being a contrarian is that sometimes the crowd is right and you're the fool.

The biggest risk is the one you don't know you're taking. Most investors are concentrated in ways they don't understand.

Luna was supposed to be a stablecoin. A stablecoin going to zero was not in our risk models.

We believed crypto was going much higher. Why hedge something you believe in?

I opened my first electronics stall with $1,800. My entire life savings. If it failed, I had nothing. So I made sure it didn't fail.

Concentration is wonderful when it works. When it doesn't, you learn why diversification exists.

I wrote my PhD thesis about why EV companies fail. Then I started one. You could call that confidence or insanity.

I went $53 million into debt to follow my dreams. You have to be willing to lose everything to gain everything.

I've always played my best when I've played bold. That applies to golf and to business.

I don't regret the risks I've taken. I regret the ones I didn't take.

I've made some bad bets. But I've also made some great ones. That's the nature of being aggressive.

You can't win a major by playing safe. You have to go for pins other guys won't.

I backed a 23-year-old who wanted to kill music piracy by giving music away for free. Everyone thought we were insane.

We invested in SpaceX when it had zero successful launches. That's what frontier investing looks like.

The first dollar into a startup carries more risk and more reward than any dollar that follows.

Avoiding big losses is as important as capturing big gains. Over 40 years, the math proves this beyond any doubt.

Every entrepreneur needs to be comfortable with a very high level of uncertainty. If you wait for certainty, you'll never start.

The markets have the capacity to do things that regulators cannot anticipate. Sometimes that is a feature. Sometimes it is a catastrophic bug.

Risk is not the enemy. Mispriced risk is. If you understand the risk better than the market, you should take it. If you don't, walk away.

We tell girls to play it safe and do everything right. We tell boys to be brave and try things. Then we are surprised that men dominate every risk-taking field.

The best insurance decisions I have ever made are the risks I declined to write. Saying no is the most underrated skill in underwriting.

I left school at 16 to race in Europe. Most people thought I was crazy. Most of the best decisions of my life looked crazy at the time.

I play football with joy. I make business decisions the same way. Not every decision will be right — but all of them will be mine.

Concentrate your energies, your thoughts and your capital. The wise man puts all his eggs in one basket and watches the basket.

Liquidity is the one thing you can't buy when you actually need it.

Due diligence isn't a checklist. It's a relationship. You have to understand how someone thinks under pressure, not just how they perform in a bull market.

I'd rather take a big loss on a trade I understood than a small loss on one I didn't.

Models tell you what should happen. Markets tell you what is happening. When they disagree, trust the market.

Discipline beats talent. I've seen brilliant traders blow up because they couldn't follow their own rules when it mattered.

In a crisis, the only thing that matters is liquidity. You can be right about every position and still go bankrupt if you can't meet margin calls.

The army taught me one thing that Harvard didn't — how to make decisions when you don't have all the information and the consequences are real.

I grew up in a housing project. The thing about starting with nothing is you're not afraid of losing it.

Leverage is a tool that makes smart people feel invincible right up until the moment it destroys them.

The biggest risk in investing is the risk you don’t see coming.

I’d rather miss a move than get caught in a bad one. There’s always another trade.

209% in one year sounds amazing until you realize it means I was taking enough risk to lose 100%.

Losing $1.8 billion of someone else’s money teaches you things about risk that no MBA program ever will.

The London Whale wasn’t a mystery. The positions were so large they were distorting the market. You just had to be willing to stand on the other side.

When the government changes the rules in the middle of the game, there’s no hedge for that.

Taking over Steak n Shake at 31 was either the bravest or the dumbest thing I’ve ever done. The stock price says it was the former.

Climate change is the biggest investment opportunity and the biggest threat of our lifetime. You can’t separate the two.

In biotech, one FDA approval can make your decade. One FDA rejection can ruin your quarter. That’s the game.

I didn’t go to college. I went to the futures pit. Turns out, one of those teaches you more about risk.

I was homeless at 18 and sleeping in my car. That kind of experience either breaks you or gives you an unfair advantage in understanding risk.

Selling my car was the first real bet I made on myself.

The biggest risk in my career was not joining Alibaba. It was staying comfortable at a job that paid well but would never change my life.

The Zozosuit was my biggest failure. But I would rather fail trying something nobody has done than succeed at something boring.

Seed investing is about buying lottery tickets where you have read the research and know the odds are better than everyone thinks.

I bought an airline for one ringgit. People said I was crazy. Those same people now fly AirAsia.

I dropped out of Stanford at 17 because I thought I could build something that would save millions of lives. The jury is still out, but I'd make the same decision again.

Build from a position of financial strength so you never have to make a decision out of desperation.

If you want to win in sports, you've got to be willing to take a risk.

The key to long-term survival and prosperity has a lot to do with the money management techniques incorporated into the system.

I made my money by selling too soon.

I keep my losses small and let my profits run. That is the whole secret.

I never argue with the tape. If a stock goes down, I get out.

The worst thing you can do is miss a major trend. Missing the bus is worse than being on the wrong bus.

The shale revolution didn't happen because of big oil companies. It happened because of wildcatters like me who were willing to take the risk.

If we get AI right, it could be the most beneficial technology in human history. If we get it wrong, it could be the most dangerous.

The default outcome of advanced AI is not good. We have to deliberately steer it toward good outcomes.

Junk is a state of mind, not a state of credit.

Biotech is the only industry where one molecule can change everything. That is terrifying and exhilarating in equal measure.

The biggest risk in a family business is not the market. It is internal conflict. Manage your family, and the market becomes manageable.

Islamic banking is not a restriction. It is a discipline that protects both the bank and the customer from greed.

Any investor who ignores geopolitics is not an investor — they are a gambler who has not yet lost.

We do not view volatility as risk. Risk is the probability of a permanent loss of capital.

Africa is not a risk — Africa is the opportunity that others are too afraid to see.

Every business cycle reaches its peak. The investor who ignores this will be reminded by the market.

Without a command of probability theory, you are just a gambler in the dark.

The riskiest moment is when you are right. That is when you put on too much weight, get overconfident, and lose discipline.

The fundamental law of investing is the uncertainty of the future.

The only investors who should not diversify are those who are right 100% of the time.

Distressed investing is not about being ghoulish. It's about pricing risk better than everyone else.

I would rather lose one-third of my shareholders than lose one-third of my shareholders' money.

The greatest risk is not volatility. It is the permanent impairment of capital.

The key to investing is not predicting the future. It's buying assets at a discount so large that even if you're wrong about the future, you still win.

Risk is not knowing what you're doing.

Investors who confuse short-term market movements with long-term fundamental risk make very expensive mistakes.

A quantitative model is only as good as the discipline to follow it when it tells you something uncomfortable.

Market crashes don't come out of nowhere. The warning signs were there in 1987. The question is whether you're looking for them.

When long-term support levels break, the chart is telling you something that the fundamentalists have not figured out yet.

The chart tells you what market participants collectively believe. You ignore that at your own risk.

Once you've won the game, stop playing.

Diversification is the only free lunch in investing. Everything else has a cost.

I saw the Hainan bubble from the inside. When you see speculation that wild, the only smart thing to do is take your money and leave.

The best deals I have ever made were in markets that other people thought were too risky to enter.

A currency devaluation is painful for every business in Egypt. The question is not whether it hurts — it is whether you have built the company to survive it.

Seed investing is a game of being early and being right. You will be wrong a lot. The key is to be spectacularly right a few times.

I bought a store with borrowed money and a lot of nerve. That is still the best business plan I ever wrote.

The biggest risk of all is not taking one.

India's biggest risk is not poverty. It is the weakening of the intermediary institutions — the NGOs, the journalists, the universities — that stand between the citizen and raw state and market power.

It was a calculated risk. Every big bet looks crazy before it works.

The Lakers are bigger than any one player or coach. We have to protect the brand while still taking risks.

Transitions are either your greatest risk or your greatest opportunity. You choose which one it is.

A leader who is afraid of failure will not take bold action. Bold action is what separates transformational leaders from managers.

The SVB weekend showed that USDC is resilient. It de-pegged briefly and recovered. That stress test proved more than six years of smooth operation ever could.

I am always frightened. Fear means you are doing something that matters.

The film business is unlike any other I've been in. You can have the right story, the right talent, the right marketing, and the audience still decides. That humility is a good lesson for any investor.

In the oil business, you learn quickly that not every well comes in. You accept uncertainty as part of the equation before you ever turn a drill bit.

You can't be in this business and be timid. Pipelines take years to permit and build. You commit, and you execute.

You cannot build a ten-billion-dollar piece of infrastructure unless you are willing to look completely ridiculous for a very long time.

I have always believed that the greatest risk in this business is not drilling a dry hole. It is failing to lease the land before someone else does.

You have to go where nobody else is willing to go. The greatest discoveries are never made in comfortable places.

Climate change is not a risk for the future. It is a risk for right now, and it will reshape demand for every commodity we produce.

We arrived in Los Angeles with no money, no return ticket, and an agreement that if the show flopped we would disband. We had nothing to lose — and that is exactly the right state of mind for doing something that has never been done before.

The biggest risk isn't concentration — it's owning mediocre businesses. If you know what you own, concentration is not risk. It's conviction.

After taking risks and drilling a lot of dry holes, when it looked like all hope was lost, I'd find something that kept me going.

Your life will also be fluctuating and you will die of a heart attack. If you really lose sleep over it, maybe the best way is to keep the money in the bank.

No one could have planned for a world where every ship had to stop at once.

We have success and sometimes we have failure. And sometimes if I see no failure, I wonder if we didn't push it enough.

I was 25-26 and at that age, you had no fear of failure. You felt you could do anything.

We are in the business of backing outliers.

I enjoy dreaming, I enjoy building, I enjoy the ambiguity and uncertainty of creation.

Fail fast and spend as little money as possible to get your ideas validated.

At the start there was no expectation. We had nothing to lose.

When you are young, your ability to take risks is very high.

One of the huge attractions of Arista was that it was small and entrepreneurial.

Don't be afraid to fail.

The biggest risk I face is illiquidity. We still have a lot of capital calls coming in.

You'd better do your homework and do all of the testing beforehand so you know what you will do.

By choosing stocks with a substantial difference between price and value, a wide margin of safety is created. The lower the purchase price relative to value, the lower the risk. Contrary to popular belief, by decreasing risk, this method increases potential reward.

The most important thing that you need is rule of law so you have a predictability in the restructuring process.

Deutsche Bank is too big to fail. We think management has a good handle on it.

We don't use lots of leverage, the industry doesn't. The liability structures are very long tailed.

Life is millions of combinations of probabilities that are interdependent, hard to predict.

Trading is injurious to your wealth. If you are smoking you may die in 20-30 years whereas by trading, this may happen the very next day.

As long as there is diversification among high-quality companies, the risk of permanent capital impairment is minimal.

I am not afraid of my portfolio companies failing. I am more afraid of them not trying something ambitious.

I would rather back a founder ten years too early than a company that is already obvious.

One big hit can carry a company for a decade, but it can also make you afraid to try the next thing.

A crisis is the worst time to be a broker and the best time to start a firm.

There are failures with integrity, and there are failures without integrity.

When you jump, the net appears.

You need to be greedy when everyone is careful. We did 10 times more investments in 2022, when a lot of people were not investing anything.

If every deal worked, you wouldn't be in venture capital. You'd be in luck.

It's okay to wait it out. As they say, live to fight another day. But you have to live so that you can fight again.

You should take the investment risks since you can afford them.

We are fighting a war for our future.

In finance, risk management is really the bottom line.

This is why we say that Ethereum's complexity may be a curse.

In any case, it's time to seriously consider what measures we can take if the situation deteriorates.

Volatility does not scare me. Missing the important networks does.

Being early means being alone and uncomfortable for a long time. That is where the returns are.

Concentration is a double-edged sword. When you are right it is glorious. When you are wrong there is nowhere to hide.

Conviction only pays if you can hold through the pain.

The biggest risk in crypto is not volatility. It is where you keep your assets.

If you would not roll up your sleeves and help a network, you probably should not own it in size.

The real risk in crypto is not a price drop. It is backing a network nobody ends up using.

Being early and surviving the swings is the price of catching something before everyone believes.

Poker did not teach me to gamble. It taught me bankroll management. Do not go broke.

It was terrible at the time, but in hindsight it turned out to be a blessing in disguise.

I would never, as a hedge fund investor, invest in a blackjack player. But I've made a lot of money investing in casinos.

Midway through last year, I think the music had stopped, but some people were able to keep on dancing for longer than others.

You have to be willing to look wrong for a long time in this market. Conviction without patience is worthless in crypto.

In crypto, concentration is how you win and how you get hurt. I would rather own a few things I deeply believe in.

In DeFi, the code is the law. That is the whole point, and also the scariest part.

I have been a stock broker for all my life. I have seen all the crashes, financial crisis, where really, it is only a paper loss. Just make sure you are not jammed with cash flow.