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Risk Quotes

Risk is the price of outsized returns. Avoid it completely and you guarantee mediocrity. Take it blindly and you guarantee regret. Risk quotes matter because they remind you that smart risk is a skill: identify downside, cap it, and take the bet anyway. Strategy is not about eliminating risk. It is about choosing which risks are worth paying for and which are not.

"He who will win knows when to fight and when not to fight."
Sun Tzu
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Sun Tzu

Book: The Art of War

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"The idea in anything is to use your technical knowledge, wisdom and love of the game to cut the odds down, to lower the risk."
Robert Kiyosaki
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Robert Kiyosaki

Website: Wikiquote - Robert Kiyosaki (Rich Dad Poor Dad: What the Rich Teach Their Kids About Money-That the Poor and the Middle Class Do Not!)

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"All economic activity is by definition "high risk." And defending yesterday--that is, not innovating--is far more risky than making tomorrow. Innovations and Entrepreneurship (1985)"
Peter Drucker
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Peter Drucker

Website: Wikiquote - Peter Drucker (1960s - 1980s)

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"Innovation requires taking risks that most experts will tell you are foolish."
Sam Altman
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Sam Altman

Interview: The New York Times

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"The secret to being a successful CEO is not having a big vision; it's surviving the struggle."
Ben Horowitz
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Ben Horowitz

Book: The Hard Thing About Hard Things

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"The risk of being wrong is simply the cost of the opportunity to be right."
Marc Andreessen
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Marc Andreessen

Podcast: The Ben & Marc Show

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"The lesson is clear: estimates of causes of death are warped by media coverage. [...] The world in our heads is not a precise replica of reality; our expectations about the frequency of events are distorted by the prevalence and emotional intensity of the messages to which we are exposed. Ch. 13, "Availability, emotion, and risk" p. 138."
Daniel Kahneman
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Daniel Kahneman

Website: Wikiquote - Daniel Kahneman (Thinking, Fast and Slow (2011))

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"There is no instance of a nation benefitting from prolonged warfare."
Sun Tzu
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Sun Tzu

Book: The Art of War

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"“It’s a Texan’s attitude toward risk, reward and failure I’m talking about. It’s how they handle life. They live it big."
Robert Kiyosaki
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Robert Kiyosaki

Website: Wikiquote - Robert Kiyosaki (Rich Dad Poor Dad: What the Rich Teach Their Kids About Money-That the Poor and the Middle Class Do Not!)

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"A management decision is irresponsible if it risks disaster this year for the sake of a grandiose future. p. 43"
Peter Drucker
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Peter Drucker

Website: Wikiquote - Peter Drucker (1960s - 1980s)

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"The best way to manage risk is to move fast. Speed reduces the window of exposure."
Sam Altman
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Sam Altman

Interview: Greylock Partners

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"There are no silver bullets for this, only lead bullets."
Ben Horowitz
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Ben Horowitz

Book: The Hard Thing About Hard Things

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"Every great company started as a high-risk experiment that most people thought was a bad idea."
Marc Andreessen
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Marc Andreessen

Interview: CNBC Squawk Box

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"There is no evidence that risk takers in the economic domain have an unusual appetite for gambles on high stakes; they are merely less aware of risks than more timid people are. Ch. 24, "The engine of capitalism" p. 263."
Daniel Kahneman
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Daniel Kahneman

Website: Wikiquote - Daniel Kahneman (Thinking, Fast and Slow (2011))

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"If fighting will not result in victory, then you must not fight even at the ruler's bidding."
Sun Tzu
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Sun Tzu

Book: The Art of War, Chapter 10: Terrain

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"And in all my years, I have never met a rich person who has never lost money. But I have met a lot of poor people who have never lost a dime…investing, that is."
Robert Kiyosaki
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Robert Kiyosaki

Website: Wikiquote - Robert Kiyosaki (Rich Dad Poor Dad: What the Rich Teach Their Kids About Money-That the Poor and the Middle Class Do Not!)

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"An organization belongs on a sick list when promotion becomes more important to its people than accomplishment of their job they are in. It is sick when it is more concerned with avoiding mistakes than with taking risks, with counteracting the weaknesses of its members than with building on their strength. But it is sick also when "good human relations" become more important than performance and achievement. p. 93-94"
Peter Drucker
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Peter Drucker

Website: Wikiquote - Peter Drucker (1930s- 1950s)

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"You have to be willing to look stupid to take a risk that actually matters."
Sam Altman
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Sam Altman

Interview: Lex Fridman Podcast

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"The risk of doing nothing is often greater than the risk of doing the wrong thing."
Ben Horowitz
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Ben Horowitz

Interview: PandoDaily

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"Calculated risk is the hallmark of a professional builder, whereas blind risk is for amateurs."
Marc Andreessen
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Marc Andreessen

Essay: The Techno-Optimist Manifesto

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"Many unfortunate human situations unfold [...] where people who face very bad options take desperate gambles, accepting a high probability of making things worse in exchange for a small hope of avoiding a large loss. Risk taking of this kind often turns manageable failures into disasters. Ch. 29, "The fourfold pattern" pp. 318-319."
Daniel Kahneman
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Daniel Kahneman

Website: Wikiquote - Daniel Kahneman (Thinking, Fast and Slow (2011))

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"He who knows when he can fight and when he cannot will be victorious. This is the essence of calculated risk."
Sun Tzu
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Sun Tzu

Book: The Art of War

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"If you are going to build the Empire State Building, the first thing you need to do is dig a deep hole and pour a strong foundation. If you are going to build a home in the suburbs, all you need to do is pour a 6-inch slab of concrete. Most people, in their drive to get rich, are trying to build an Empire State Building on a 6-inch slab."
Robert Kiyosaki
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Robert Kiyosaki

Website: Wikiquote - Robert Kiyosaki (Rich Dad Poor Dad: What the Rich Teach Their Kids About Money-That the Poor and the Middle Class Do Not!)

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"The better a man is, the more mistakes will he make - for the more new things he will try. I would never promote a man into a top level job who had not made mistakes, and big ones at that. Otherwise he is sure to be mediocre. p. 147"
Peter Drucker
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Peter Drucker

Website: Wikiquote - Peter Drucker (1930s- 1950s)

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"In a startup, the risk is usually that you'll fail to make something people want, not that the tech won't work."
Sam Altman
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Sam Altman

Essay: Startup Playbook

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"Wartime CEOs often have to take risks that would seem insane in peacetime."
Ben Horowitz
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Ben Horowitz

Essay: Peacetime CEO/Wartime CEO

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"The market is the ultimate risk. You can have the best team, but if the market doesn't exist, you fail."
Marc Andreessen
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Marc Andreessen

Essay: Why Software is Eating the World

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"A recurrent theme of this book is that luck plays a large role in every story of success; it is almost always easy to identify a small change in the story that would have turned a remarkable achievement into a mediocre outcome. Introduction, p. 9."
Daniel Kahneman
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Daniel Kahneman

Website: Wikiquote - Daniel Kahneman (Thinking, Fast and Slow (2011))

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"The opportunity to secure ourselves against defeat lies in our own hands, but the opportunity of defeating the enemy is provided by the enemy himself."
Sun Tzu
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Sun Tzu

Book: The Art of War, Chapter 4

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"There is always risk, so learn to manage risk instead of avoid it."
Robert Kiyosaki
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Robert Kiyosaki

Website: Wikiquote - Robert Kiyosaki (Rich Dad Poor Dad: What the Rich Teach Their Kids About Money-That the Poor and the Middle Class Do Not!)

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"Risk is the price you pay for the opportunity to change the world."
Sam Altman
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Sam Altman

Speech: World Economic Forum

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"Hiring for lack of weakness is a mistake; you must hire for strength."
Ben Horowitz
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Ben Horowitz

Book: The Hard Thing About Hard Things

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"You have to be willing to be misunderstood if you're going to do anything new or risky."
Marc Andreessen
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Marc Andreessen

Podcast: The Ben & Marc Show

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"He who wishes to fight must first count the cost."
Sun Tzu
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Sun Tzu

Book: The Art of War, Chapter 2: Waging War

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"It is what you do not know that is your greatest risk."
Robert Kiyosaki
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Robert Kiyosaki

Website: Wikiquote - Robert Kiyosaki (Rich Dad Poor Dad: What the Rich Teach Their Kids About Money-That the Poor and the Middle Class Do Not!)

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Why these quotes matter

Risk is inherent in every strategic move. The key is to take calculated risk, not random risk.

How to apply them daily

List worst-case outcomes and design a cap for each. Prefer asymmetric bets where upside outweighs downside. Diversify risk across multiple small experiments instead of one massive gamble.

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"Risk is not reckless when it is measured. It is how you buy leverage." Explore more quotes from Quotes For Motivation.