Michael Arrington, the loudmouth founder and former editor in chief of TechCrunch, is famous for investing in the start-ups that his blogs would then cover. Although he no longer runs TechCrunch, he was a partner in two investment funds during his tenure and now manages his own, CrunchFund. In other words, even when he is not a direct investor he has connections or interests in dozens of companies on his beat, and his insider knowledge helps turn profits for the firm.

— Ryan Holiday

Ryan Holiday Quotes

Any dangerous spot is tenable if brave men will make it so,” John F. Kennedy.

— Ryan Holiday

There’s a quip from the historian Will Durant, that a nation is born stoic and dies epicurean. That’s the sad truth Boyd was illustrating, how positive virtues turn sour.

— Ryan Holiday

If you cannot reasonably hope for a favorable extrication, do not plunge deeper. Have the courage to make a full stop.

— Ryan Holiday

Action and failure are two sides of the same coin. One doesn’t come without the other.

— Ryan Holiday

The perceiving eye is weak, he wrote; the observing eye is strong. Musashi understood that the observing eye sees simply what is there. The perceiving eye sees more than what is there. The observing eye sees events, clear of distractions, exaggerations, and misperceptions. The perceiving eye sees “insurmountable obstacles” or “major setbacks” or even just “issues.” It brings its own issues to the fight.

— Ryan Holiday

You have to believe you can make a difference. You have to try to make one.

— Ryan Holiday

He who fears death will never do anything worthy of a living man,” Seneca once said. Alter that: He who will do anything to avoid failure will almost certainly do something worthy of a failure.

— Ryan Holiday

Hate defers blame.

— Ryan Holiday

If we only did what we were sure of, if we only proceeded when things were favorable, then history would never be made. The averages have been against everything that ever happened – that’s why we call it the mean.

— Ryan Holiday

Doing the right thing almost always takes courage, just as discipline is impossible without the wisdom to know what is worth choosing. What good is courage if not applied to justice? What good is wisdom if it doesn’t make us more modest?

— Ryan Holiday

Socrates had a mean, nagging wife; he always said that being married to her was good practice for philosophy.

— Ryan Holiday

The old doctrine that submission is the best cure for outrage and wrong does not hold good on the slave plantation,” Douglass wrote. “He is whipped oftenest who is whipped easiest, and that slave who has the courage to stand up for himself against the overseer, although he may have many hard stripes at the first, becomes in the end a freeman, even though he sustain the formal relation of a slave.

— Ryan Holiday

Silencing the noise around them, they could finally hear the quiet voice they needed to listen to.

— Ryan Holiday

Stop looking for angels, and start looking for angles. There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there. When people ask where we are, what we’re doing, how that “situation” is coming along, the answer should be clear: We’re working on it. We’re getting closer. When setbacks come, we respond by working twice as hard.

— Ryan Holiday

But the reminder here is that no matter what happens, no matter how disappointing our behavior has been in the past, the principles themselves remain unchanged. We can return and embrace them at any moment. What happened yesterday – what happened five minutes ago – is the past. We can reignite and restart whenever we like. Why not do it right now?

— Ryan Holiday

What good is wisdom if it doesn’t make us more modest?

— Ryan Holiday

We shy away from writing a book or making a film even though it’s our dream because it’s so much work – we can’t imagine how we get from here to there.

— Ryan Holiday

A person who lives below their means has far more latitude than a person who can’t. That’s why Michelangelo, the artist, didn’t live as austerely as Cato but he avoided the gifts dangled by his wealthy patrons. He didn’t want to owe anyone. Real wealth, he understood, was autonomy.

— Ryan Holiday

Take a step back, then go around the problem. Find some leverage. Approach from what is called the “line of least expectation.

— Ryan Holiday

Nobody is born with a steel backbone. We have to forge that ourselves.

— Ryan Holiday
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